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Roger Simon, Politico's chief political columnist, has been a respected name in American
journalism since the 1970s — and an authoritative voice in American politics for just as long.
After the historic contest between Hillary Rodham Clinton and Barack Obama finally came to an
end in June, Simon launched an intensive effort to get behind the scenes — and to the bottom —
of what happened and why.

He interviewed scores of well-placed people at all levels of both campaigns, many of whom have
been sources of his for years. This project, which Simon named "Relentless" to reflect what he
saw as the animating spirit of Obama's remarkable campaign, is the result of Simon's two years
of reporting on this campaign, and decades of observing political personalities in action.
– John F. Harris

Introduction: The path to the nomination

By: Roger Simon
August 24, 2008 09:09 AM EST

In the summer of 2006, Patti Solis Doyle offered David Axelrod a job. Hillary Clinton was running for reelection to
the Senate and Solis Doyle was her campaign manager, but everybody knew Clinton was soon going to run for
president. And Clinton wanted Axelrod onboard.

Axelrod was a highly experienced and successful political consultant and just what Clinton needed. But he
declined. Presidential campaigns were mentally taxing, physically exhausting and emotionally draining. There
were easier ways to make a buck.

Unless. “I wasn’t planning to work in a presidential race,” Axelrod told me, “but if Barack might run, well, he would
be the only guy to cause me to get in.”

It was not impossible. As early as November 2004, even before his swearing-in to the United States Senate,
Barack Obama was having conversations about the possibility of a presidential run in 2008.

The conversations were very preliminary, however, just a toe in the water. And Hillary Clinton was not worried.

In May 2006, Clinton herself had interviewed another experienced campaign consultant, Steve Hildebrand, but
had turned him down. The time was not right. And she had plenty of time. But it would prove to be a costly
mistake. A few months later, Steve Hildebrand would play a key role in persuading Barack Obama to run for

Hillary still was not worried. She would put together a great campaign team, a Dream Team. It did not turn out that
way. “Happy families are alike,” Leo Tolstoy famously wrote. “Every unhappy family is unhappy in its own way.”
The Hillary Clinton campaign was an unhappy family. I was told by Clinton campaign staffers that Mike Henry, the
deputy campaign manager, stalked Clinton headquarters in Ballston, Va., with a baseball bat in his hand. I was
told that Patti Solis Doyle stayed in her office watching soap operas and refused to return the phone calls of
governors, members of Congress and Bill Clinton. I was told that there were suspicions that Mark Penn, the
campaign’s pollster and chief strategist, “cooked the books” in presenting his polling results. (All denied the
accusations.) It was that kind of campaign.

In the very beginning, the Obama campaign felt it would have to do everything right in order to beat Clinton. The
mere thought of running against her was intimidating. “We thought we had to be almost a perfect campaign to
win,” David Plouffe, Obama’s campaign manager, told me, “because she was so strong.” The Obama campaign
would not turn out to be a perfect campaign, of course. No campaign is. But it didn’t need to be.
Months after Hillary Clinton announced in January 2007 that she was running for president, her campaign was still
disorganized, inept and, in a word used over and over again by her top campaign aides, “dysfunctional.” One of
those aides said: “I don’t think we knew what a political operation was. It was the weakest I have ever
experienced. It was dismally weak.”

The campaign would improve as time went by, becoming more coherent, better planned and much less arrogant.
But by the time it improved, it was already too late. Barack Obama had wrapped up the nomination, cleverly,
skillfully, relentlessly. Always relentlessly.

Both campaigns made mistakes. But whenever Obama suffered a setback, he always had a Plan B ready, waiting
and often already under way. “It was a game of chess, and we thought methodically,” said Axelrod, who would
become Obama’s top strategist. “We took a pawn here and there.” In the end, it would be enough. In the end, the
pawns would create a king.

Presidential campaigns have grown so vast and complex, with so many moving — and sometimes clashing —
parts that few candidates feel they are actually in control. But, in the end, they are responsible.

Solis Doyle, Clinton’s presidential campaign manager, who was later replaced, said, “I would not make any major
decisions without her. She was very hands-on.”

Howard Wolfson, Clinton’s communications director, said Clinton “assembled a team that she had a lot of
confidence in and let them operate and implement, but she was certainly involved in setting the overall strategic
direction of the campaign.”

In the end, Hillary Clinton might not have gotten the campaign she deserved, but she got the campaign she

It was a campaign that had many people who were knowledgeable about media and messaging but who never
got the math, those tricky little rules that led one candidate to victory and the other to defeat. “Ninety-five percent
of the campaign staff didn’t know the rules,” a top Clinton aide told me. And the 5 percent who did felt nobody
ever listened to them.

Obama’s campaign was proud not only of what it had but also of what it lacked: drama. When David Plouffe, the
campaign manager, ordered that all the printers be set up to print on both sides of each page, that was
considered a dramatic moment at headquarters. (Hey, figure it out: You use half as much paper that way.) The
twin-stall unisex restroom at Obama headquarters (with posted instructions reminding men to lift the seat) might
have been considered dramatic, but nobody seemed to mind much. There were certainly tough moments during
the campaign: the unexpected loss of the New Hampshire primary, the incendiary remarks of the Rev. Jeremiah
Wright, Obama’s comments on small-town Americans becoming “bitter,” and the mishandling of the Ohio and
Texas primary campaigns, to name some.

“But one of Barack’s strengths is that he is never too high and never too low,” Axelrod said. “He doesn’t pump his
fists in the air and whoop when things go well, and he doesn’t holler when they don’t.” His staff was remarkably
like him in temperament.

“We had a job to do, and we did it,” Axelrod said. “The experience of this campaign has been an absolute joy, but
we had a few challenges that looked very, very significant — Rev. Wright was one — but we kept our heads and
moved on.”

Inexorably, grindingly, relentlessly, they moved on.

This series is based on the interviews that I conducted with 25 staff members and advisers to the Obama and
Clinton campaigns after the end of the primary season. It is an in-depth, behind-the-scenes look at two campaigns
that were strikingly different in temperament, planning and execution. The Barack Obama campaign, as this
article will show, was hoping for a quick, knockout punch of Hillary Clinton but was already calling superdelegates
in March 2007 just in case the campaign became a drawn-out battle. The Clinton campaign would not wake up to
the importance of superdelegates for months and, in fact, would have more basic problems. “We didn’t have a
superdelegate strategy?” said Terry McAuliffe, Clinton’s campaign chairman. “We didn’t have a pledged delegate

The Obama campaign did not prepare just for its victories, but, just as importantly, it prepared for its defeats: It
had a careful plan in place to keep Clinton’s delegate victories to the narrowest margins possible. Virtually all of
the Obama top staff understood the math that would lead to the nomination. Hardly anyone in the Clinton
campaign did. Obama secretly began his general election campaign before the primaries were over, quietly
moving staff and resources into key November states well before Hillary Clinton conceded defeat.

The Clinton campaign could look back on a number of paths not taken: The campaign seriously discussed having
Hillary apologize for her vote in favor of the Iraq war, but she never did so. And Bill Clinton, against the advice of
top staffers, who felt he was “delusional,” insisted the campaign make a serious effort in South Carolina because
of what he considered his strong relationship with black voters.

Although the Clinton campaign would improve and Hillary would do better in the latter part of the primary season,
by then it would not matter.

In North Carolina, a few weeks before the end, Tom Vilsack, the former governor of Iowa and a Hillary supporter,
sat in the back of a car with Bill Clinton going from event to event. It was the end of a long day, and Vilsack
remembers the former president looking for any ray of sunshine amid the gloom, anything to have made the
joyless campaign worthwhile.

“Even if she doesn’t win, they will know Hillary better and like her better,” Bill Clinton finally said. “She’s a complex
person. They just didn’t know her. If you know her, you just love her.”

© 2008 Capitol News Company, LLC

Part One: The improbable plan

By: Roger Simon
August 24, 2008 09:15 AM EST

In May of 2006, when Hillary Clinton was publicly running for reelection to the U.S. Senate, she was also secretly
interviewing potential staff members for the presidential race that she would launch the following year. One
person she interviewed was Steve Hildebrand.

Hildebrand, a political operative from Sioux Falls, S.D., had run two Senate races in that state, had been political
director of the Democratic Senatorial Campaign Committee, and, most importantly, had run Al Gore’s successful
Iowa caucus campaign in 2000. Hillary did not have a lot of people around her who had presidential campaign
experience, let alone Iowa experience, and Hildebrand was an expert on field operations — the nitty-gritty, down-
in-the-trenches skills of staffing and targeting voters and getting them to the polls.

But Hillary took a pass on Hildebrand. Later, some in her campaign would talk in anguished tones about their
missed chance to hire him. And with good reason. Just four months later, Hildebrand would make the four-hour
drive from Sioux Falls to Indianola, Iowa, to attend the Harkin Steak Fry, an important annual event sponsored by
Sen. Tom Harkin. Barack Obama was the keynote speaker. Hildebrand had never seen Obama speak in person
and, in fact, had not seen Obama’s dramatic keynote speech at the Democratic National Convention in 2004 on
television. (None of the commercial networks had carried it live.)

Hildebrand, who had heard a political speaker or two in his life, was blown away by Obama’s steak fry
performance. “I drank the Kool-Aid; I saw the magic,” Hildebrand said. “I saw how he interacted with people after
the speech. They were just clamoring to be around him.” Hildebrand rode with Obama in a van to the airport, and
Hildebrand talked about the excitement and emotion he had just witnessed. “What does this all mean?”
Hildebrand asked.
“I am not sure,” Obama said.

Hildebrand drove the four hours back to South Dakota, and as soon as he got home he started calling and e-
mailing people. “For 3½ months, I was spamming people with Barack Obama clips,” Hildebrand said. “That’s how
fired up I was. I was a freak. There were 30,000 to 40,000 new friends a night on this Facebook page for him. I
would sit with my laptop in my living room in Sioux Falls and just keep refreshing. I was the oldest living person on
Facebook.” (He was 43.)

But that is not how Steve Hildebrand changed history. Hildebrand, who later joined the Obama campaign, was the
person who told Obama — insisted! — he should run for president. David Axelrod, one of the people closest to
Obama, had resisted doing that. “I never told him he should run,” Axelrod said. “Anyone who knows presidential
campaigns has to be reticent to urge someone to run. As a friend, I wanted him to make a decision he was
comfortable with and not regret it after a year or 18 months. Hildebrand was the one who most strongly urged him
to run. And Barack didn’t even know Hildebrand!”

Hildebrand said that it was not an easy sell. Obama had just gotten to the Senate in January 2005. And now, in
the fall of 2006, he was supposed to run for president? “It was almost a guarantee he wasn’t going to run for
president,” Hildebrand said. “It wasn’t the time. Four years down the road, he would run for governor of Illinois or
president. As to running for president in 2008, he hadn’t done a lot to prepare.”

But by November 2006, the talk of Obama entering the presidential race grew serious. “The evidence that this
was going to be a change election was manifest,” Axelrod said. “Mark Penn [Hillary’s chief strategist] sees
microtrends; he doesn’t see macrotrends. That was a macrotrend.” In November 2006, a Gallup Poll showed that
67 percent of Americans were not satisfied “with the way things were going in the United States.” (By July 2008,
the number would grow to 81 percent.) Hillary Clinton could be challenged and beaten because the people
wanted, in Axelrod’s view, not a replica of the old Washington ways, but a remedy. There were more and more
people who hated traditional politics, the influence of special interests and the paralysis that came when
politicians cared more about party dogma than about achieving results. When experience meant the same old
Washington ways, the Obama people felt, experience was going to be a minus and not a plus. “Obama’s whole
candidacy was the closest thing I have seen to a draft in history,” Axelrod said. “We were led there by young
people and people who wanted something new.”

But wasn’t it, to use one of Obama’s favorite words, a little audacious for him to run with so little national
experience? Wasn’t it even presumptuous? Maybe. “But very few candidates suffer for having run too soon,”
Axelrod said. “Many suffer from running too late and waiting. This was the year that matched up with what he

In early November 2006, Axelrod and a small group of Obama insiders, including Hildebrand and Axelrod’s
partner, David Plouffe, met with Obama and his wife, Michelle, at Axelrod’s consulting office under the El tracks
on North Franklin Street in Chicago to talk about an actual campaign. Obama knew what he didn’t know. “Give
me a mock-up of the schedule for a week so I would know what it looks like,” he said. “Give me a schedule for a
day. How often will I see Michelle and the kids?”

“He had never been around this,” Hildebrand said. “He wanted to talk about Iowa and New Hampshire and what
those states would be like and how to organize there.”

Plouffe said: “The jury was out whether we could get together a credible campaign against the most powerful
machine in our party. But we didn’t have the stifling pressure of expectations that we would win. We were all
intrigued, it could happen once in a generation, but generally people think about running for years. My assumption
was a presidential run was worth looking at but was improbable.”

Obama listened and thought about it. Another major meeting was held in mid-December, plans proceeded and
Obama gave the final green light in the first week of January 2007. “OK, let’s run,” he said. “Let’s try to win. Let’s
put our chips in the middle of the table and see how we do.” When he had been in the Illinois Legislature, Obama
had been a regular at low-stakes poker games in Springfield. Now, however, the stakes were going to be very
high. Nobody runs to be humiliated, and the Obama insiders had to turn into an actual staff and started making
plans quickly.
“One reason we won is we didn’t have a playbook on the shelf,” Plouffe said. “We were making it up as we went
along.” But they made it up quickly and always with options in case one set of plays did not work.

The first thing the staff did was get the candidate ready for the meat grinder he would soon be fed into. “One day
we did a rapid question and answer session with him, so he would know what was coming,” Hildebrand said. The
staff wanted to prepare him, in other words, not only for increased media scrutiny, but also for the opposition
research that Hillary and the other candidates would produce to use against him. “We asked him questions about
his personal finances, the votes he took in the Senate, things like that,” Hildebrand said. “He was really good.”

Did Tony Rezko’s name come up? I asked. (Tony Rezko was a close associate of Obama’s who had already
been indicted and would later be convicted of fraud and money laundering.)

“I think Rezko’s name came up,” Hildebrand said.

Obama’s main concern, however, was whether his campaign could compete with the Clintons (they were almost
always viewed in the plural by Obama and his campaign), both financially and organizationally. “They will get the
traditional support, and where does that leave us?” Obama asked. The Obama staff crunched numbers and
decided it needed to raise $12 million in the first quarter of 2007 to run a credible campaign. But there was a
problem. “Our first plan only came up with $9 million,” Hildebrand said. “Obama didn’t have a national fundraising
base. We didn’t know how nervous people [i.e., potential contributors] were going to be about him going up
against Hillary and Bill. And John Edwards had the trial lawyers.”

As it turned out, Obama did just fine. In fact, he did better than just fine. In the first quarter of 2007, Obama raised
$25,791,503. Clinton raised $26,054.569. True, Obama had come in second, but the political world was stunned.
Suddenly Obama looked like more than a guy who could give a good speech. He looked like a contender.

“People in our campaign were in shock that Obama raised what he did,” a top Hillary adviser said. “It belied our
arrogance that nobody else could meet her on the field of battle.”

© 2008 Capitol News Company, LLC

Part Two: Looking like whiny babies

By: Roger Simon
August 24, 2008 01:00 PM EST

Obama campaign organizers drew up plans, lots and lots of plans, and always a budget for how to pay for what
they were planning. They even planned for things that few people — including few people in the Hillary Clinton
campaign — even knew about. In March 2007, only a month after Obama announced, Hildebrand came across
two people in the Obama campaign offices he had never met before: Mike Robertson and Myesha Ward.
Robertson was calling members of the House and Senate and Ward was calling members of the Democratic
National Committee to lock up their votes as something called “superdelegates.” Hildebrand was baffled. “Just to
throw myself under the bus, I remember meeting them and wondering, ‘Why do we have them on the payroll?
What is that about?’” he said.

The Clinton campaign had nobody on the payroll to call superdelegates in March 2007. “People didn’t know about
superdelegates,” a high-ranking Clinton staff member said. “Nobody figured it out. They thought it was all about
winning states and not delegates. That was Penn. He was always talking about national polls, he was
preoccupied with them. He stressed electability, that she could win in November.”

By May, the Obama campaign was working out a detailed strategy for the entire campaign. At the first meeting,
30 people met in a conference room in Obama’s campaign headquarters, a vast floor of a skyscraper in
downtown Chicago. On one wall was a meticulous pencil drawing of the Obama family and through the floor-to-
ceiling windows was a view of other skyscrapers and a green sliver of Millennium Park, one of the most beautiful
(and audacious) parks in America. It was a headquarters that clearly had a sense of place: Chicago.
Hillary Clinton’s headquarters was in a former Immigration and Naturalization Service building in Ballston, Va.,
that had been retrofitted for use as a political headquarters. Her campaign had insisted on a “stand-alone”
building (though it never filled more than three of the five floors) and had signed a lease through March 31, 2009,
which would have been more than two months past her planned inauguration as president, at a cost of $107,000
per month, according to one source. There was no sense of place — it could have been any suburb anywhere —
and the staff joked that there were still holding cells for illegal aliens somewhere in the building. It seems like a
small thing, but the Ballston headquarters rankled some in the campaign, especially younger staff members who
wanted the Hillary Clinton campaign of 2008 to be like the Bill Clinton campaign of 1992.
“There was no sacrifice required to work for her,” one of her staffers said plaintively. “It was a sacrifice to work for
Bill Clinton and go to Little Rock. Everybody wanted to be James [Carville] and Paul [Begala] and George
[Stephanopoulos], and that’s not who we were. We were a D.C.-based, bloated campaign with people who were
with her because she was the safest bet and we paid the most and hired the most and she was the most likely
nominee. And at headquarters, we were all just worried about getting shivved in the shower.”

The Obama campaign, on the other hand, was low on drama but high on the drudgery of campaigning. It was
mapping out the essentials for a national campaign, which Hildebrand listed as: “What is the ballot access for
each state? How do you win? What are the demographics that make it better or worse for us? What is our
support? What is her support?” The strategy for Iowa, a state Obama considered crucial, had already been
discussed earlier in the year, but now real plans were being made for Super Tuesday, Feb. 5, when 22 states
would hold contests. And it was going to require a sacrifice from the staff: It was going to require moving.

“At one point in midsummer, we closed down field and political operations at headquarters and moved people to
the Feb. 5 states,” Hildebrand said. “We were the earliest to staff up and open offices there, and the first six states
we staffed were caucus states. That was a strategic decision.” The Obama campaign liked caucus states, which
place a high value on organization. This was a little counterintuitive considering Obama was good at mass rallies,
which are the bread-and-butter events of primaries, and Hillary Clinton, it was assumed, was going to have the
superior campaign organization. So how did the Obama campaign actually expect to win caucuses? “We decided
we were going to be better at it,” said Jeff Berman, director of delegate operations for Obama. “I am being very
sincere. Would the Clintons devote the time needed to court caucus voters? We would.”

Berman also felt the caucus states favored Obama politically. “There is a history of progressive activism in caucus
states,” he said. “The question is not just whether they are caucuses or primaries, but what is the culture? Some
caucus states were outside of Hillary’s political orbit. They were in the West, the Great Plains, the Rocky
Mountains. Hillary’s strength tended to be more East Coast and West Coast.”

The Clinton campaign feared and loathed caucuses, where people had to show up and vote all at the same time.
Most caucuses also banned absentee or early voting. The Clintons, who had not complained about caucuses in
the past, now saw them as the embodiment of evil. “I talked to Hillary in Nevada [a caucus state] before an event,
and I thought venom was going to shoot from her mouth,” one of her staff members said. “She hated caucuses:
They underrepresented the working poor, her supporters had jobs to go to, they were waitresses and day care
workers. ‘We should have fixed the rules! The caucus system skews to the wealthy!’ she said. But the bottom line
is, the rules are the rules, and you can’t not compete because you don’t like the rules. We looked like whiny

Seven of the Super Tuesday contests were caucuses, and Obama would end up winning every one of them
except American Samoa.

The Obama campaign, it should be pointed out, did not actually foresee the future; it merely prepared for it. It did
not know the campaign would get down to a state-by state battle. The Obama campaign, like the Clinton
campaign, looked forward to winning a political struggle, not a delegate struggle. “We wanted to win Iowa and
New Hampshire for a one-two punch and then Nevada and South Carolina,” Berman said. “We were all prepared
for those four. That was Plan A. But if Plan A doesn’t work, what do you do next? I had planned it out through
June 2008.”

Which turned out to be a good idea, because Obama’s Plan A failed. He did not win the first four states. He lost
New Hampshire and Nevada. “So we had to go back to work, and we had to win it another way,” Berman said.

In late July 2007, long after the Obama campaign had not only devised a plan for the primaries and caucuses but
had even begun sending people to crucial Super Tuesday states, the Hillary Clinton campaign held a three-hour
Sunday “retreat” for the entire political staff in Ballston.
The meeting was designed to show off the political and field operations, and Michael Whouley, who had played a
key role in John Kerry’s 2004 primary campaign, had flown in for it, even though he was not on the staff. Whouley
had become a legend in the party when Kerry referred to him as “the magical Michael Whouley” after he saved
the Kerry campaign in Iowa. Whouley’s comings and goings were so closely watched in political circles that a
major blog reported he had gone to Iowa to start campaigning for Hillary. (Which was inaccurate, as it turned out.
Whouley never went to Iowa. A crucial meeting about Iowa that Whouley did attend was actually held in Chicago,
in part to keep Whouley from being sighted by all the reporters who were in Iowa.) Also at the Virginia retreat was
Guy Cecil, who would eventually become the national political and field director the Clinton campaign, a fortunate
choice since he was one of the few people in the entire Clinton campaign operation, as it turned out, who actually
understood the rules of delegate selection in the Democratic Party.

Though some in the Clinton campaign were quite pleased with the campaign’s messaging operation -- Hillary
would be the candidate of experience and strength -- some of those in attendance at the retreat felt the campaign
was lacking something: an actual plan to win the Democratic nomination for president.

“It was eye-opening,” one person in attendance said. “The political and field operations were dysfunctional. There
was not enough staff, the staff that existed was too junior, and there was no plan. There was no political or field
plan on how to win the nomination.”

“It was totally f***ed up,” another said. “There were growing pains, and they had to up the talent level of who was
supervising these kids.”

For the Clinton campaign, it would be a long, tough slog. “It was joyless,” one of her top advisers told me. “It
wasn’t a happy campaign even when she was winning.”

“We assumed they knew what they were doing,” one of Clinton’s top fundraisers said of the campaign’s political
operation. “They didn’t know jack.”

To the outside world, it did not look this way. The top headline on the Drudge Report on Oct. 4, 2007, was:
“Clinton has 33-point lead.” But that was based on a public poll. And the public, to say nothing of pollsters, is often
the last to know.

A longtime Clinton staff member said: “I have been around Hillary for years, and nobody should have been
shocked. Her team has been dysfunctional for years. It was called a juggernaut, but it was a joke. What shocked
and saddened us was that it took her down. We hoped that she would be bigger than her organization.”

© 2008 Capitol News Company, LLC

Part Three: Lost in Hillaryland

By: Roger Simon
August 24, 2008 09:18 AM EST

In the spring of 2007, several confidential discussions were held within the Hillary Clinton campaign to have
Clinton admit that her vote to approve the Iraq war had been a mistake and to have her apologize for it. It made
sense. The Democratic Party was solidly against the war, and many voters had gone to the polls in November
2006 to elect a Congress they hoped was going to end the war. The other Democratic candidates in the race who
had voted for the war — Chris Dodd, Joe Biden and John Edwards — had all said their votes in 2002 to authorize
the war had been wrong. Only Hillary was holding out, and Barack Obama was hitting her hard for it, saying that
he (who, lucky stiff, had not been a senator in 2002) had opposed the war from the beginning. His attack was a
dagger at the heart of her central message: Hillary was the candidate of experience? Yeah, the kind of experience
that led her to vote for a disastrous war.

But Clinton continued to stick to the line: “Knowing what we know now, I would never have voted for it.” Which she
repeated only when she was forced to address the issue at all. On “Larry King Live” in April 2004, however, she
had said: “No, I don’t regret giving the president authority, because at the time it was in the context of weapons of
mass destruction, grave threats to the United States, and, clearly, Saddam Hussein had been a real problem for
the international community for more than a decade.”

On Feb. 11, 2007, the day after Obama announced for the presidency in Springfield, Ill., he flew to Ames, Iowa, to
say that those who voted for the war should have known better. “Even at the time, it was possible to make
judgments that this would not work out well,” he said. Those who envision Iowans only as bucolic growers of corn
or raisers of hogs don’t know Iowans. Democrats there, especially the activist Democrats who tended to turn out
for the caucuses, were decidedly against the war.

Unfortunately for Clinton, the presidential campaign season began in Iowa. But when she flew there in late
January 2007 on her “announcement” tour (she had actually made her formal announcement on a video), in her
first, hourlong town meeting, she did not mention Iraq once. She mentioned ethanol twice. She was asked about
Iraq everywhere, however. She had gone to Democratic Party headquarters to meet with party activists before the
town meeting, and she got asked about her voting for the Iraq war right away. “There are no do-overs in life,” she

Some on her staff now wanted a do-over. Why not? How hard would it be to say, “Sorry. Mistake. I am only
human. Let’s move on.” And her sticking to her (blazing) guns on Iraq was having a financial impact. While
Clinton’s fundraising was going well, it was expensive fundraising, much of it done by direct mail, one of the most
expensive forms of fundraising there is. (The cost of paper, printing and postage adds up fast.) Obama was
raising his millions on the Internet, which was cheap. Why couldn’t Hillary do the same?

“We tried,” Terry McAuliffe, her campaign chairman and chief fundraiser said. “But we had a 60-year-old woman
who voted for the war. That’s a fact. The online community is very liberal.”
“There was plenty of discussion in the spring of 2007 about her apologizing for her war vote,” a top aide said.
“But she didn’t want to apologize because she didn’t think she had made a mistake. And from a political
standpoint, apologizing would have been inconsistent with her strength and experience message.”

Strength and experience was the message that Mark Penn, Clinton’s chief pollster and chief strategist, insisted
would carry her to the White House. The Obama campaign was delighted with it. It made her look like an
incumbent, and America was very tired of its chief incumbent, George W. Bush. “For whatever reason, they chose
to run Hillary as the consummate insider in an election that was all about change,” David Axelrod, Obama’s chief
strategist, said. “We might have won anyway, but the contrast worked in our favor.”

There was another problem with Hillary saying she was sorry. “Apologizing would have been especially difficult for
a female candidate,” the top aide said. “It would have made her look weak and vacillating.”

A high-ranking staff member said: “We considered saying the Iraq war vote was a mistake, but that was quickly
swatted down. Mark [Penn] did not believe in it. And we always had to keep an eye towards the general election.
In a general election, her support for the war would have been great.” This was, however, a classic case of not
keeping your eyes on the prize: The Clinton campaign was already looking forward to the championship instead
of worrying about winning the playoffs.

Some in the campaign worried constantly that Hillary would not look tough enough, would not look “manly”
enough to be the first woman president, if she admitted she had actually made a mistake once in her life. But the
evidence showed she looked plenty tough already. “Ironically, our early research found the Hillary attributes that
tested the highest were masculine,” a high-ranking Hillary staffer said. “The attributes were ‘tough, ready, strong.’”
The highest attributes for Edwards and Obama, Hillary’s campaign found, were “empathetic, sympathetic, cares
about me.”

Some might look at those results and say: Hey, those Obama and Edwards attributes are pretty appealing, and
maybe we need to warm Hillary up a little to latch onto some of those. But that is not the way Hillary’s campaign
saw it. “For the last 16 years, she had been portrayed as the caricature of a tough bitch,” the high-ranking staffer
said. “So we decided her image should be: ‘Let’s roll up our sleeves and get to work! Maybe she’s a bitch
because she’s competent!’”

Maybe she’s a bitch because she’s competent? That kind of thinking (if that is what it can be called) was
emblematic of the tension in the Clinton campaign between those who wanted to stress her “masculine” qualities
(strength, experience) and those who wanted to stress “feminine” qualities such as warmth and humanity and the
fact that she was a mother, daughter and wife. Those who fought to emphasize her human side would always
point to New Hampshire, where she teared up, showed emotion and won. It seemed so obvious: Emotion equals
victory, and competent bitchiness equals defeat.

Guy Cecil, on the other hand, who played a significant role in the New Hampshire victory, always felt Hillary’s
emotion got too much credit. “The moment she teared up had impact,” Cecil said, “but you don’t come back from
13 points down by tearing up. There was an efficient, hardworking and stable operation in New Hampshire and
not a lot of drama.”

That was a minority view, however. Top people in both campaigns felt Hillary had won New Hampshire because
she teared up in at the Cafe Espresso in Portsmouth, N.H., on Jan. 7 when meeting with undecided voters. She
had been asked how “as a woman” she faced each campaign day. “It’s not easy, it’s not easy, and I could not do
it if I didn’t, you know, passionately believe it was the right thing to do,” Hillary said, her voice catching. “This is
very personal for me. It’s not just political. It’s not just public.”

The moment led the ABC, NBC and CBS evening newscasts.

“We went to her,” a top Clinton communications aide said, “and we said: ‘Look, you showed your human side in
New Hampshire and it worked. So let’s keep doing that.’”


“And she still didn’t want to do it,” he said.

But why?

“Because she wouldn’t do it!” he said. “There was a lot of water over the bridge, and she wouldn’t go there.”

“Water over the bridge” was code for The Thing That Could Never Be Mentioned in the Hillary Clinton campaign,
and that thing was Bill’s affair with Monica Lewinsky. If Hillary was going to open up and get all warm and fuzzy,
she was going to have to do it by giving interviews showing she could be human and emotional. But she didn’t
want to open herself up by giving such interviews, and -- understandably, perhaps -- she did not want to revisit
some of the most emotional (and awful) moments of her life. Switching from talking about serious issues (which
she truly loved to do) to talking about human stuff (which she wanted to keep private) was just an invitation for the
press to ask her about Monica. And if one thing was crystal clear to Hillary and her campaign, it was that the
press was the enemy. Period.

I asked Howard Wolfson, her communications director, if, from the very outset, the Hillary campaign thought the
press would be hostile.

“Yes,” he replied.

And was the press hostile?

“Yes,” he replied. (And he insisted that my question and his answer be quoted in exactly that manner.)
The negative attitude toward the press had greater implications than just hindering Hillary’s ability to show the
warmer side of her personality. It affected, in the views of some, the way she staffed the entire campaign. Many of
her top people had little or no real experience in presidential campaigning. (Patti Solis Doyle, the campaign
manager; Mike Henry, the deputy campaign manger; and Howard Wolfson, the communications director, had
never worked in a presidential campaign in any significant role. On the Obama campaign, David Plouffe, the
campaign manager; David Axelrod, the chief strategist; Steve Hildebrand, the deputy campaign manager; Jeff
Berman, the national director of delegate operations; and Robert Gibbs, the communications director, all had
significant presidential campaign experience.)

In a Washington Post article in late July of this year by Lois Romano, a source close to Hillary quotes Hillary as
saying she was “disappointed” in Solis Doyle (who was replaced as campaign manager in February 2008). “I put
her in a job she was incapable of performing,” Clinton is quoted as saying. “I’m out here killing myself … thinking
a process exists, and no one said, ‘The emperor has no clothes.’”

Which begs the question: Why did Clinton, who had known and employed Solis Doyle in top jobs for years, give
her the campaign manager job in the first place? Why, in fact, did a smart political operative like Hillary Clinton put
together such a poorly functioning campaign staff?

“Loyalty,” Wolfson said, “was very important to her.”

People were hired by Clinton because of their absolute loyalty to her. And Clinton was, in fact, told the emperor
had no clothes. She was repeatedly told by staff members that there were grave problems in her campaign. Three
key Clinton staffers in three separate interviews told me they had informed Hillary Clinton directly that the
campaign was having serious problems and was not being managed well.

A top aide to Clinton told me: “I was walking her back to her office in [the Russell Senate Office Building] from the
Capitol, and we were crossing Constitution Avenue and I just said to her: ‘You have a staff both here and in the
campaign that don’t feel empowered, and we have lost our edge and aggression and live in fear of screwing up.’
She was furious. It was the most tense conversation I’ve had with her. ‘This is not what I wanted,’ she said.”

The aide continued: “She was extremely upset. And the first thing she did was call Patti and say, ‘Fix it.’ Patti
called my boss and said I should ‘shut the fuck up.’ That is verbatim. The staff loved me for it when word got
around. But Patti’s way of fixing things was to tell the whistle-blower to shut the f*** up.”

Actually, however, it was Hillary who blew the whistle on the whistle-blower, as she would do repeatedly.

A top Hillary strategist told me: “The one time I complained [directly to Hillary], I got told by Patti, ‘Don’t ever go to
her again about [these] issues.’”

Another Hillary staffer said: “I did have a conversation with Hillary by e-mail about things not getting done.” Hillary
asked him some questions, but word soon came down the pipeline for him to shut up. “It was not appreciated that
I was e-mailing her,” he said.

Solis Doyle was very protective of Hillary, but she was also very protective of herself. Terry McAuliffe, Hillary’s
campaign chairman, had advised against hiring Solis Doyle. Bill Clinton, according to a source close to both Bill
and Hillary, also advised against it and wanted Hillary to hire Paul Begala, one of Bill’s 1992 campaign aides, for
the job.

But, with certain exceptions -- like Penn, who had worked for Bill in the past -- Hillary wanted to stay away from
hiring the Friends of Bill (until the campaign got in trouble and then she had reached out to a few of them). “She
had an inexperienced staff, but the concern was that she had to run as her own person and not as Bill Clinton’s
third term,” an aide who worked for both Hillary and Bill said. “She felt his operation and culture didn’t fit her. As
first lady and in her Senate office, she had a very female-centric, matriarchal environment. He is more
freewheeling and less structured.”

To put it mildly. Solis Doyle had coined the term “Hillaryland” to describe Hillary’s female inner circle. The term
caught on, and many stories were done about it. But some were unimpressed, feeling that the Hillaryland talent
pool was shallow for a major presidential campaign. An influential member of Congress, who was being wooed
furiously by both Clinton and Obama, was invited to meet with the people of Hillaryland. He declined. “That’s OK,”
he said. “I’ve already seen ‘The Vagina Monologues.’”

There was another reason Hillary did not want to have more Bill Clinton people around her. She felt his people
were the kind of people who leaked to the press, and she would tolerate a lot of problems -- like a nonfunctioning
campaign -- but she would not tolerate leaks. “There was more indiscretion in Bill’s world about talking to the
press,” an adviser to both Bill and Hillary said. “Bill’s people leaked all the time.” But this was because Bill’s
people viewed the press as something to be used, not stiffed. They knew that by building bridges to the press in
the good times, those bridges would exist in the bad times. (And Bill Clinton would come in for some very bad
times.) Also, quite frankly, the members of Hillaryland were sick of hearing about how Bill did things.

“As the campaign kicked off, there was a conscious effort to not have him out there,” a high-ranking Hillary staffer
said. “We used him strategically to raise money. I called the question of Bill the ‘Circus Factor.’ People would ask:
‘How do you deal with Bill?’ We didn’t have a good answer, because we didn’t know. The Clintons didn’t have to
decide, and they hadn’t discussed it and they didn’t want to. They decided it was not a decision they had to deal

The discussions about the Hillary campaign within the Hillary campaign were so prolonged and intense that some
felt the campaign was overlooking something: Barack Obama.
“The crowds he was drawing in 2007 should have scared the shit out of them,” said Bill Daley, who had run Al
Gore’s presidential campaign in 2000 and had been Bill Clinton’s secretary of commerce but now was backing
Obama. “They should have been asking: ‘How do you take this guy out?’”

In fact, Obama was not a perfect candidate. He had vulnerabilities. Though Obama was inspirational on the
stump, he could also be very cerebral and intellectual and did not radiate warmth the way some presidential
candidates (like Bill Clinton, for instance, or Ronald Reagan) did. And Obama aides grew concerned that where
Obama most liked to show his intellectual side was during debates, which they knew had more to do with theater
(and combat) than with debating. “He would give not just answers, but show both sides and why he was right,”
one of his aides said. To break him from that habit, his aides abandoned the usual debate prep involving mock
debates -- aides taking the parts of Hillary and John Edwards, standing behind lecterns in a mock studio -- and
just fired questions at him around a table. It was designed to drive home one lesson: Ignore the “debate” aspect of
debating; in fact, ignore the other debaters as much as possible. “We wanted to sharpen his answers irrespective
of what others were saying,” the aide said.

And Hillary could have tried to be warm to contrast with Obama’s cool. But when the Hillary campaign tried to
make her a little warmer, she either balked or the result was a disaster.

In September 2007, some top Clinton staffers arranged for her to appear on the season opener of NBC’s
“Saturday Night Live.” One said: “We told her doing ‘SNL’ would be a way of showing she was being a good sport
and letting her hair down. I pushed her, and Howard [Wolfson] pushed her. But she didn’t want to do that shit.”
Not until her campaign was in trouble, anyway. Obama appeared on “Saturday Night Live” in November 2007, but
Hillary didn’t do the show until March 2008, after losing several key races.

Why did the Hillary campaign seem blind early on to what would later become apparent? “The rationale for her
candidacy was inevitability,” one aide said. And when you are inevitable, you don’t have to get everything right
because you are going to win anyway.

Bill Daley, who thought that deep down Hillary was a better candidate than her campaign was able to show, also
thought that the Clinton campaign wildly underestimated Obama, in part because of his race. “He’s black, start
there,” Daley said. “When was the last time a black guy pulled this off? Well, never. A black guy in the Senate
only three years, who had never done anything in their opinion? They felt he was just a pretty boy. They had a
bloated campaign and no strategy.”

“Hillaryland was about Hillary,” Daley said. “By the time they focused on him, it was over. He was credible, he was
real, and they couldn’t stop him.”

© 2008 Capitol News Company, LLC

Part Four: Amid the corn

By: Roger Simon
August 24, 2008 09:19 AM EST

It was going to be all about Iowa. The caucus that would not die. The Iowa caucus had gained national attention
in 1972 as an oddball little contest for party insiders, and now it was a monster rally. The rules had been designed
to keep tourists, i.e., regular voters, away: It was always held on a winter’s night, everybody had to show up at the
same time and stand around for hours, and there was no secret ballot. Only a very small universe of party
activists used to attend, and it was meant to be that way. It was a party-building event for insiders and by insiders.
But that was before presidential campaigns went on steroids with large staffs, enormous budgets and massive
targeting operations.

One day in October 2007, Paul Tewes, Obama’s Iowa state director, asked Mitch Stewart, his caucus director, to
find the person the Obama campaign had contacted the most in Iowa. The caucus was still three months away.
“He found a person we had contacted 103 times,” Tewes said. “By mail, phone and door-knocking.” One hundred
and three times! Why didn’t the guy turn off his phone, weld shut his mailbox and put a “Beware of Dog” sign on
his front door? Because this was Iowa. And even people who didn’t vote in the caucus were very, very proud of
living in the state where the presidential race began. And, by the way, after 103 contacts, the guy was still
officially listed by the Obama campaign as “undecided.” That’s Iowa, too.

For public consumption, the word that defined the Obama campaign was “change.” But privately, especially in
Iowa, the word the campaign was most proud of was “relentless.”
Call, mail, door knock, organize. Contact everybody, whether that person had ever voted in a caucus or not. If it
moved, hand it a leaflet. If it didn’t move, push it and hand it a leaflet. The candidate understood the stakes. “If I
win the Iowa caucus,” Obama told Bill Daley early in 2007, “I can get the nomination.”

In its early days, the Obama campaign had only one standard. “Front and center for all our decisions on spending
money and time was: Would it help us win Iowa?” said David Plouffe, Obama’s campaign manager. “If the
electorate of 2008 was going to be similar to the electorate of 2004 [in Iowa], we were going to have no chance.
The Holy Grail was to fundamentally alter the electorate.”
The campaign went after everybody. Democrats who had never gone to a caucus before; independents and even
some Republicans were invited to every event. And Obama skipped some sacred Democratic events and dinners
so he could hold his own events. “We weren’t worried about party events, because it was such a narrow
universe,” Plouffe said. Some Iowa Democrats howled, and Obama got some bad press because of it. Plouffe
didn’t care. “One of the most important words in politics is ‘no,’” he said. “We said no to a lot of things that would
dilute our focus, including events and speeches the other candidates attended. But we needed to get the support
of a lot of people who wouldn’t pay $25 to attend a dinner.”

Young people, for instance. Especially young people. Tewes estimated that by mid-December, more than two-
thirds of the high schools in Iowa had Obama chapters. Going after the youth vote was not audacious. What was
audacious was assuming that young people would actually show up on caucus night. It was a political axiom that,
in the end, young voters always let you down.

But the Obama campaign dovetailed his outreach to young voters into its general message of change. Sure, kids
didn’t vote. In the past. But give them a reason to vote, give them a pathway to a political campaign and a
politician they could believe in, and they would become the change they longed for. In Iowa City, Obama had a
13-year-old precinct captain. She was too young to vote for Obama, but she was not too young to seek votes for
Obama. “Who could say no to a 13-year-old?” Tewes said. And she was a good bookend to the Obama precinct
captain in Burlington who was 93. (Who could say no to a 93-year-old?) The Obama campaign also had 40 to 50
precinct captains who were Republicans. “Some thought that would turn off Democrats, but I found Democrats
loved it,” Tewes said. And everybody, even senior staff, had to go door-knocking at least once a month. (Door-
knocking can be a misery. It’s wearying, it’s either too hot or too cold, and some people really do have Beware of
Dog signs. And dogs.)

When Plouffe came to Iowa, he would work the phones. And he didn’t always like what he heard on the other end.
“It was late December, and Edwards was polling very high and taking over our twos,” Plouffe said. (Campaigns
rank voters from one to five, a one being the most likely to vote for you and a five being the least likely. A two
would be a voter leaning toward you.) “Edwards had energy at the end, and that was nerve-racking. So I decided
one night to call some of our twos. And I got four people for Edwards in a row! That was the most stressful 15
minutes of the campaign. But, in the end, we held onto 80 percent of our twos.” Which was a high percentage.
Campaigns usually count on getting only about 60 percent of their twos and 80 percent of their ones.

Edwards was always a concern in Iowa -- and not just to the Obama campaign. Initially, the Clinton campaign
also thought he would be the man to beat. Edwards had come in second in Iowa in 2004 and had been
campaigning in the state virtually ever since. “We all understood Edwards would be in our lane as a ‘change’
candidate,” David Axelrod said. “Had the [voting] universe been the same, Edwards would have won. Edwards
was good in the prescribed universe of existing caucus-goers, but he didn’t go outside the lines.”

Edwards’ message of populism, of sticking up for the forgotten and ignored against the elites and Washington
insiders, was a potent one, however, and Axelrod was worried that Hillary would adopt it and combine it with her
resources. “My strong concern in the spring of 2007 was that Hillary would get onto a populist message,” Axelrod
said. “But the only message she had in Iowa was experience. It didn’t work.”

He didn’t have to worry. Experience was Hillary’s message, and she was sticking to it no matter what. And
inevitability was its twin: Hillary was so strong, her name recognition so great, her fundraising so daunting and her
campaign so well-organized that nobody else could possibly win. That was the inevitability message. It was not
stupid. Inevitability can get you early money and early endorsements. But it had a big downside.
“Inevitability was wrong for Iowa,” said Michael Whouley, the engineer of John Kerry’s victory there in 2004 who
also advised Hillary. “You cannot tell the people in Iowa that it’s wrapped up. They decide if it’s wrapped up. The
Obama people loved our inevitability argument.”

The Obama staff also loved Hillary’s emphasis on experience, even though something like a mild panic set in
among some Obama supporters and big fundraisers early in the campaign because of it. Some felt that unless
Obama took Hillary on directly over the question of experience, he was going to lose. “We had field people in
Iowa saying, ‘All we’re being asked about is experience, and we’ve got to answer it,’” said Joel Benenson, one of
Obama’s pollsters. “Some wanted to address it, use his bio and everything in his record, and others said, ‘That’s
her turf, we can’t match it.’” But Benenson found they didn’t need to match it. Polling in the late summer of 2007,
he found people cared less about experience than some thought. “A much clearer path to victory was that Obama
was the answer to the change people wanted,” Benenson said. And the campaign told its money people to relax
and not to worry, that the campaign did have a winning strategy besides just Obama going out and making a
bunch of inspiring speeches.

The Obama strategy, Benenson said, was based on three pillars that the campaign would use in Iowa and
afterwards: First, define change as standing up to lobbyists and special interests who were drowning out the voice
of ordinary people. Second, end divisive politics and bring the country together. Third, don’t tell people just what
you think they want to hear, but tell them what they need to know. (In 2008, for example, Obama would oppose a
gas tax holiday.) “These matched up well with qualities that Clinton was viewed as weaker on,” Benenson said.
Several people in the Clinton campaign raised flags about the experience message, and her Iowa people warned
her about depending too much on any message. “In Iowa,” Tom Vilsack said, “it is not the message; it is the
relationship.” Vilsack, a former governor of Iowa, had launched his own presidential campaign in late 2006 but
dropped out and was now backing Hillary. He thought she was a terrific person and would make a terrific
president, but he saw something happening whenever Obama came into the state.

“People felt an attachment to him,” Vilsack said. “And I kick myself for not being more curious about their
canvassing. His volunteers went out into the neighborhoods in the summer of ’07 and asked people: ‘Can we
spend a few minutes of your time?’ Two weeks later, the people got a phone call, four weeks later they got an
invitation to a speech, and six weeks later they got invited to meet Obama at the airport. We didn’t do that until
fall. It’s a reflection of what he did as an activist. He knocked on doors.”

His campaign was relentless and the Clinton campaign was not, but the Clinton campaign felt an Iowa victory
would do everything it wanted: It would validate her message of experience and prove her inevitability. “Basically,
the entire campaign was geared to Iowa,” Guy Cecil, Clinton’s national political and field director, said. “A lot of
other business was getting ignored.”

Harold Ickes, one of Clinton’s top advisers, said: “The decision was made by one and all to make Iowa primo di

“We were all-in in Iowa,” a high-ranking Clinton staffer said. “But we were never higher than second in our own
polling, and our chances of winning Iowa were slim.”

On April 4, 2007, top Clinton aides and Michael Whouley went to the Clinton home in Chappaqua, N.Y., to talk to
Hillary and Bill about Iowa. The meeting took place in Bill’s study. Whouley gave a 20-minute talk about Iowa,
stressing that the state “requires a tremendous commitment of resources and time.”

“I thought she would do well if people saw a softer side of her and got to know her as a person,” Whouley said.
Which was, however, exactly the strategy Hillary and her campaign had rejected. She wanted to keep her “softer”
side to herself. Besides, weren’t people really more interested in universal Pre-K and alternative energy?

Whouley instantly noticed what everybody noticed when talking about Iowa to Hillary: She was uncomfortable with
Iowa, and Bill was of little help. (He had never built an Iowa caucus organization because when he ran for
president in 1992 Iowa favorite son Tom Harkin froze out any serious contenders, and in 1996 Bill was already
president.) Further, Hillary did not like what she saw as Iowa’s “woman” problem. “I was shocked when I learned
Iowa and Mississippi have never elected a woman governor, senator or member of Congress,” Hillary told Des
Moines Register columnist David Yepsen in October 2007. “There has got to be something at work here.”

Perhaps. Or perhaps it is just an historical anomaly. In any case, throwing it in the face of Iowa voters a few
weeks before the caucuses was probably not her most diplomatic of moves. Maybe Hillary believed she could
guilt-trip Iowans into voting for her, or maybe she was already looking for excuses for losing. “The caucuses are a
strange breed of critter,” said Bonnie Campbell, a former Iowa attorney general and gubernatorial contender who
was backing Hillary. “Hillary understood the mechanics, but I did sense an unease in her.”
But Hillary’s comfort level with Iowa was not as important as Iowa’s comfort level with Hillary. And Campbell was
seeing a problem, especially among women. “When I was calling feminists, women activists, they were keenly
fixated on the Iraq war vote, and it trumped their feminism,” Campbell said. She also said that Hillary’s gender
affected how she could respond to attacks by the Obama campaign. “You don’t want to whine because you are a
woman,” Campbell said, “but if you hit back, Iowans say you are not ladylike.”

If women were going to be a problem for the Clinton campaign, that was going to be a big problem. What young
people were to Obama, women, especially older women, were to Hillary: a cornerstone of her campaign. The
Clinton campaign was making elaborate outreach efforts for the votes of older women -- efforts that were
expensive but necessary. “Obama had people willing to lay on railroad tracks for him, and we had old ladies on
oxygen tanks,” one top Clinton staffer in Iowa said. “We had to work twice as hard to get over the enthusiasm

Another Clinton staffer said: “There was an order never to say, ‘Stand up for Hillary,’ because we didn’t want
people worrying that they would have to stand up.”

At the Jefferson-Jackson dinner held in Des Moines on a Saturday night in November 2007, there was a
noticeable difference in the age of the Obama supporters and the age of the Clinton supporters. It became even
more noticeable as the event dragged on for hours. “Obama did the J-J dinner, and you saw nicely dressed
people, young and healthy, for him,” a top Clinton Iowa aide said. “And we were hemorrhaging old ladies. The
lines to the bathroom looked like we were running a senior citizens home or a morgue! They wanted to go home. I
was standing there saying: ‘You can’t go home, lady!’”

Tommy Vietor, Obama’s Iowa spokesman, came into the press room at the event and told reporters that the event
was not just about Obama’s speech, which was very well-received, but about showing organizational muscle. “It
shows you can get people to show up at the same place at the same time,” Vietor said. In other words, if Obama
could get all these young people to show up for a dinner, maybe he could also get them to show up at a caucus.
And maybe the experts were wrong about the youth vote never turning out.

Two of Hillary’s top advisers, Mandy Grunwald, her top media consultant, and Mark Penn, her chief pollster and
strategist, also came into the press room to spin reporters. They had their patter down.

“Our people look like caucus-goers,” Grunwald said, “and his people look like they are 18. Penn said they look like

Penn added, “Only a few of their people look like they could vote in any state.”

Yuk yuk. Except why make fun of the fact that Obama voters looked 18? In the Iowa caucus, not only could 18-
year-olds vote, but most 17-year-olds could vote, too. (You just had to be 18 by Election Day in November 2008.)
Which is why Obama was spending so much time organizing high school students. Duh. Grunwald’s and Penn’s
remarks also symbolized in a small way the difference between the two campaigns: One campaign made fun of
Facebook, while the other was using Facebook and other social networking websites to help win the nomination.

The Obama campaign was doing other things: It was gaming the system. While it was true that caucus voters had
to “reside” in the precinct in which they voted, there was no criterion for residency. If you were willing to swear that
you lived in the precinct, you could vote in the precinct. College voters were, not surprisingly, clumped in college
towns. But the Obama campaign told many of the in-state students to vote at home instead. “We knew college
precincts were going to be easy to win, so we wanted to disperse our horsepower,” Tewes said. “The students
understood it, too. We took them seriously, as seriously as we took 55-year-old activists.”
Tewes had set up in Iowa on Jan. 23, 2007, working out of the Embassy Suites in Des Moines. Teresa Vilmain, a
native Iowan and an expert on politics there, had an apartment in Des Moines and a house outside the city but did
not go on the Clinton payroll until May 2007 and did not become the campaign’s state director until early June,
moving aside the former state director. Vilmain was aghast at how unprepared the Clinton campaign was to
compete in Iowa. “Obama had done two mailings, and Edwards had done three mailings to caucus-goers by
May,” a member of the Clinton Iowa staff said. “It was five months after the Clinton announcement, and we had
had no direct mail yet and no calls.”

Communication with national headquarters -- the lifeline for any state operation -- was dismal, with no functioning
“Iowa desk” in place. “I said: ‘I will take anybody [at headquarters] with a pulse!” an Iowa staffer said. “Anybody!
But how about somebody with a map of Iowa?” As a number of people in the Clinton campaign would note, the
campaign was dominated by people with media and communications experience, not political and field
experience. And even when it came to messaging, there was an extra problem for Clinton. “Barack Obama had
only to do one message: ‘Here is who I am,’” the Iowa staffer said. “We had to do two messages: One, ‘Hi, I am
not the mean, cold-hearted bitch who screwed up health care’ and, two, ‘Here is who I am.’”

Bonnie Campbell also noticed an emotional antipathy to Clinton among some voters. “There were Hillary haters,”
Campbell said. “Nothing Hillary could say or do would ever warm their hearts to her. She had an image that those
people created for her of being manipulative, cold, evil. When she met them one-on-one, those fears evaporated.
But even in Iowa you can’t meet everybody one-on-one.”

At Obama headquarters, in a very old-school, low-tech move, the campaign had put an 800 number on its
literature and in some of its commercials so people could call headquarters to find out where their caucus location
was. In mid-December, three phone lines were handling the calls just fine. By Christmas, the number of lines had
grown to eight because the phone traffic was so heavy. “Two days later,” Paul Tewes said, “it exploded. We had
to put 20 lines in a back room, and they rang constantly.” Not everybody calling was an Obama supporter. In fact,
one out of every four callers had not committed to voting for Obama, which indicated to Tewes that a lot of people
were going to make up their minds at the very end.

The end came on caucus night, Jan. 3, 2008. Jerry Crawford, who was Clinton’s Midwest coordinator, got to his
caucus site and did not like what he saw. “There were 90 people in line to change their registration to Democratic
so they could participate in the caucus, and they went overwhelmingly for Obama,” Crawford said. “These were
people who were angry and frustrated with their government, and Obama did the best job at being the vessel they
poured their frustration into. That was the story of Iowa. Had she won in Iowa, she would have been the

David Plouffe and Barack Obama went to visit a caucus site in Ankeny, north of Des Moines. It was wild and even
a little weird. “We got there and there was no place to park, and clearly the turnout was high,” Plouffe said. “There
was a guy dressed as Gandalf [from “The Lord of the Rings”] with an Obama video playing on his staff. There
were Republicans and high school kids and college kids and Democrats who had never caucused and
independents and die-hard caucus-goers.”

Plouffe thought he had died and gone to heaven. “It was the manifestation of what we were trying to build,” he
said. “I said to myself: ‘Even if we only win here, it was worth it.’ We felt everything we did was justified. Our
strategy was based on them, and Barack got to see it.”

The voting universe had expanded dramatically. Young people came out in record numbers, representing 22
percent of the total vote and 30 percent of Obama’s vote.
(Afterward, a Clinton number cruncher told me that the youth vote’s having gone from 17 percent in 2004 to 22
percent in 2008 was “statistically relevant” but “marginal.” An Obama number cruncher called it “massive,”
pointing out that it represented a increase of nearly 30 percent.)

Obama got 57 percent of the youth vote, compared with 11 percent for Hillary. Hillary also lost women ages 30 to
55. But she clobbered Obama among older women, those women who were on oxygen and had waited in line for
the restrooms at the J-J dinner. “Women over 65 appreciated the barriers Hillary had overcome and trusted her,”
a Hillary staffer in Iowa said. “Middle-aged women viewed her much more cynically. They questioned her
sincerity, and they were enthusiastic for Obama. They had Clinton fatigue and Monica fatigue. She couldn’t break
through with that baggage.”

When it was all over, it was Obama with 37.6 percent, Edwards with 29.8 percent and Hillary with 29.5 percent.
Some in her campaign were mortified by the third-place finish. It had cost them, one of her top national staffers
told me, an incredible $28 million to $29 million.

Tom Vilsack would continue working hard for Hillary, going to state after state with the campaign, but he saw the
implications of the Iowa loss immediately. “For Obama, it was not just a victory,” he said, “but an affirmation that a
predominantly white state would support an African-American man in shockingly large numbers.”

One other thing was clear: Hillary Clinton was not inevitable anymore. Bonnie Campbell spent caucus night with
Hillary and Bill at their suite in the Hotel Fort Des Moines. “I was devastated,” Campbell said. “But Hillary was
wonderful. ‘Well,’ she said, ‘we will just go on to New Hampshire.’ And they left that night.” The Clinton campaign
plane to New Hampshire left about 1 a.m. But those on board immediately noticed that Patti Solis Doyle, the
campaign manager, and Mike Henry, the deputy campaign manager, were missing. Both had decided to return
home to Washington. Some on board the flight would never forgive them. This was the time to rally around the
candidate, to pull together, to be a campaign family. And even if the campaign was not really a family, it was at
least important to maintain the illusion on this of all nights. Both Solis Doyle and Henry would be gone from the
campaign by mid-February.

© 2008 Capitol News Company, LLC

Part Five: 100 percent delusional

By: Roger Simon
August 24, 2008 10:13 AM EST

The question for Hillary Clinton was not whether South Carolina was going to be bad — South Carolina was going
to be bad — the question was whether it was going to be a loss or a disaster. The Democratic National
Committee had moved South Carolina up in the voting calendar to Jan. 26 to give African-Americans a more
prominent role in choosing the nominee, and it was estimated that nearly half the Democratic primary vote there
would be black.

Early on, Hillary was leading in the polls among blacks both in South Carolina and nationally, but Barack Obama
had stated that once black people saw that white people would vote for him, blacks would feel empowered and
vote for him also. He had won virtually all-white Iowa, and South Carolina would be a testing ground for his

Hillary had beaten him in New Hampshire and Nevada (though Obama had gotten one more delegate there than
she did), and now the Clinton campaign faced a crucial decision: Should it make a real play in South Carolina or
downplay South Carolina to concentrate time, energy and staff on the 22 Super Tuesday states that would follow
South Carolina on Feb. 5?

It should have been an easy call. “South Carolina is a graveyard for American politics and for politicians going in
and having the race card played,” said Doug Sosnik, who had been Bill Clinton’s White House political director in
his second term and was now advising Hillary. “South Carolina is a highly racially charged state.”

A very high-ranking Clinton staff member put it more bluntly. “I never thought we could win South Carolina,” she

So why did the campaign decide to compete there?

“Those strategic decisions were based on research and targeting, and, yes, I was part of the group that signed
on,” she said, “but it was a group grope. We fought over targeting and the nuances and demographics of

Fighting is one thing. But when critical campaign decisions are a “group grope,” it may be a sign that your
campaign is in trouble. It was not, in the end, the fault of the staff, however. It was the fault of the Clintons
The campaign competed in South Carolina because the Clintons, chiefly Bill, insisted on competing there. The
staff plan was that after Nevada, Hillary would campaign in the West, especially among Hispanic constituencies,
and Bill would raise money in New York and campaign in Georgia and Alabama.

But Bill Clinton didn’t like that plan. “He thought it was crazy not to spend every day in South Carolina,” a top aide
said. “He thought he could make it close.” Bill thought he could do well not just with black voters in South
Carolina, but also with white voters. Before Bill Clinton became the first black president, he was the “Bubba”
president, the kid from Arkansas with AstroTurf in the back of his pickup truck, and he believed he still had the old

There was every reason to believe, however, that the magic was fading. Joe Erwin could see it. Erwin, a popular
former Democratic Party chairman in South Carolina, had decided to join the Obama campaign after several
personal phone calls from Obama. Hillary had called him, too, and her calls were nice, polite and correct. She
thanked him for all he had done for the party in South Carolina. “She was respectful,” Erwin said. And how about
Obama’s calls? “He took time to get to know my family,” said Erwin. “He would call my house on Friday night and
talk to my daughter and wife and say, ‘What are you doing? Oh, you’re cooking dinner? You like to cook?’ And
then he is talking to my 17-year-old daughter on the phone, and she is jumping up and down.”

Erwin decided to go with Obama in early September (with Steve Hildebrand, Obama’s deputy campaign manager,
carefully orchestrating or “rolling out” out the endorsements, it was not announced until mid-December), when
some polls were showing Obama down by as much as 14 points in South Carolina. But Erwin was not especially
worried. “When it was early on, I could tell traveling around the state and being at fish fries and festivals, black
voters just did not know Obama,” Erwin said. “He didn’t have a personal connection yet with voters, black or
white. It took black voters awhile to believe it. The biggest thing was his victory in Iowa. So many black voters told
me that to see him win in state that was so white was a signal that this candidate can win.”

And Bill Clinton was not helping. On Jan. 7, at a speech in Dartmouth, N.H., an angry, finger-wagging Bill had
called Obama’s campaign a “fairy tale.” Even though Bill later would say he was merely talking about Obama’s
claim that he had always opposed the Iraq war, many African-Americans, including Jim Clyburn, a highly
influential congressman from South Carolina, were insulted. (Clyburn publicly told Bill to “chill a little bit” and “tone
it down.” It was good advice, which Bill followed. For five days.)

“I thought President Clinton would be a significant asset to them, and I was just as surprised as anybody with
some of the things he said,” Erwin said. “You just kind of shook your head. I can’t believe he meant to be hurtful,
but it was hurtful to people of color who I know in this state. I think it backfired. President Clinton is -- has been --
so popular with African-American voters in South Carolina, but he ended up not working so well here.”

Obama pollsters could see the effect of Bill Clinton’s comments in the polling. “It pushed people to Obama,” one
said. “People saw it as crossing the line.” The Clinton campaign staff had, for once, been correct. South Carolina
was ground the Clintons should not have contested.

“We could have skipped South Carolina,” a Clinton adviser said, “and there would have been a one-day press
story and then, after we lost, the press would have said what Bill said: ‘Jesse Jackson had won that race, too.’
The press would have said it! Not Bill!” (On primary day in a rally in Columbia, S.C., Bill had pooh-poohed
Obama’s impending win by saying: “Jesse Jackson won South Carolina twice, in ’84 and ’88,” meaning that
Obama’s South Carolina victory would be as insignificant for him as it was for Jackson. It was widely viewed as
racially insensitive.)

The Clinton staff made effort after effort to divert the Clintons from South Carolina. Staffers told Bill that Super
Tuesday was the prize. South Carolina would not be ignored -- there was a debate there that Hillary could not
skip -- just downplayed for strategic reasons. Bill didn’t go for it. “He was caught up with the energy of the
campaign,” an aide who was close to him said. “He said: ‘We can win anywhere!’”

But they couldn’t win anywhere. Hillary couldn’t win in South Carolina, and one staffer summoned up the courage
to put it to Bill flatly. “Mr. President,” he said, “I think you are wrong.”


“And it didn’t matter,” a staffer said. “I love Bill, but he was 100 percent delusional. It was a classic case of his
overestimating his own strength.” So the Clinton campaign started pouring resources into South Carolina.
Things did not go well. “It was horrid, horrid,” a staffer said. “We sent Iowa [staff] people to South Carolina and
they quit! I was begging people on the phone to stay, and they said, ‘We have nothing to do! There is no
organization here!’ But we had decided to double down in South Carolina. It was obnoxious.”

Don Fowler, a gentlemanly, highly respected former chairman of the Democratic National Committee, was
working hard for Hillary in his home state of South Carolina. He was also spending time with Bill, who was putting
his own spin on things. “Bill Clinton told me there were people in the campaign who thought they should skip
South Carolina, not because they could not win here but because they felt South Carolina was not significant,”
Fowler said, “He told me he was hellbent for leather that she would compete in South Carolina.”

Fowler knew his state and knew Hillary would lose, but he felt the Clinton campaign might keep the loss to 10
points or less. But he also saw something that had been seen in Iowa: People who normally didn’t care about
politics cared about Obama. “Obama ignited a flame within people who I and many others didn’t see as real
players [in a primary election],” Fowler said. “They were predominantly younger people or even mild
conservatives. They had long thought the Democratic Party was kind of dirty and not for nice people. But they
thought Obama was different.”

On the day of the primary, the signs were not good. “I ran into a man, a white man, from one of the finest families
of Charleston,” Fowler said, “and he said: ‘I voted for Obama!’”

Fowler was shocked. “I don’t think he had ever voted for a Democrat for president in his life,” Fowler said.

And then the man said, “What’s more, Mama voted for Obama, too. And she’s 85!”

Barack Obama would crush Hillary Clinton in South Carolina by 28.9 percentage points, the first blowout of the
primary campaign. African-Americans made up 55 percent of the voters, and 80 percent of them voted for
Obama. It was the first concrete evidence that what Obama had predicted was true: Black voters, having seen
that white voters would back him, now would back him, too. He was not a symbolic candidate or a movement
candidate, he was a real candidate. He was a black man who actually had a chance to get the nomination.

Black voters were more than just one of the interest groups that made up the Democratic Party. They were
essential to victory. No Democratic presidential candidate since Lyndon Johnson had won the white vote in a
general election in America. Jimmy Carter won once and Bill Clinton won twice by getting enough of the white
vote and an overwhelming black vote. And now South Carolina showed that Obama could get an overwhelming
black vote.

And it had an added significance: The South Carolina blowout froze superdelegates. How could superdelegates
now publicly back Hillary and risk overturning the judgment of pledged delegates without gravely insulting -- even
disenfranchising -- black voters? “We lost the superdelegate race after South Carolina,” a top Clinton staffer said.
“It became racial. Members of Congress are about taking care of No. 1. A wisdom took root: If you were against
Obama, you would get primaried and picketed.”
Getting “primaried” was the scary part. Because congressional districts in this country have become so
gerrymandered, incumbents rarely lose in general elections. So what incumbents fear most is primaries, which
they can lose. And now, members of the Clinton campaign believed, Obama operatives were calling members of
Congress, all of whom were superdelegates, and threatening to find, fund and run primary opponents against
them if they committed to Hillary.

David Plouffe, Obama’s campaign manager, told me his campaign did not do this, though Steve Hildebrand did
say that superdelegates were reminded that some would see a racial dimension to overturning the decision of
pledged delegates. “We definitely made that argument,” Hildebrand said. “But superdelegates were always
treated with respect.”

By the end of the campaign, South Carolina would be viewed by both campaigns as a turning point.

“South Carolina gave us the velocity not only to survive Feb. 5, but be dominant in those races,” Plouffe said. “It
was a much larger margin than expected, and there was recoil of people to Clinton tactics. That worked to our
core campaign message of turning the page.”
A Clinton aide said: “Competing in South Carolina was bigger than any Mark Penn blunder and bigger than the
experience versus her softer-side blunder. It was the central decision that lost the election.”

A top Clinton staffer said: “It was so dramatic a loss for us and so dramatic a win for him that it gave permission
for Ted Kennedy and Caroline Kennedy and [Arizona Gov.] Janet Napolitano to say with a clear conscience, ‘We
are going for him.’”

After South Carolina, Bill Clinton’s role changed. “Bill went from being Hillary’s entree to the black community to
being her entree to the white, rural community,” a Clinton aide said. Which was not entirely a bad thing for the
Clinton campaign. After the Rev. Jeremiah Wright’s inflammatory remarks and Obama’s comments about how
some small-town voters had grown “bitter” and “cling to guns or religion,” it was clear that Obama was going to
have some problems in rural, white America, and for the Clinton campaign to have Bubba back was a plus in
certain parts of the country.

“Clearly in South Carolina, Bill Clinton was a negative,” Plouffe said. “But Bill could be very effective. I didn’t like to
get his schedule of small towns and read it. While he said some things that were troublesome and they didn’t help
their campaign, he was toiling away, doing a lot, seeing a lot of people. It was a very smart use of him, and I was
troubled by the sheer volume.”

Plouffe went on: “He had a brutal schedule mid-February through June 3 and was doing six to eight events a day.
Michelle is good, but she has a family. If they had used Bill more in Iowa, in 20 to 25 smaller counties of Iowa, it
might have helped them there. And in Indiana and Texas [both of which Hillary won], his visits had an outsize

But the campaign had not used Bill more in Iowa, and Hillary’s victories in Indiana and Texas would not make a
difference in the outcome of the race. South Carolina made a difference.

“It was so horrible a loss for us that it brought back ‘Clinton fatigue,’” a very senior staff member said. “It brought
back the ‘ick’ factor.”

© 2008 Capitol News Company, LLC

Part Six: Why believe the superdelegates?

By: Roger Simon
August 24, 2008 09:26 AM EST

At the beginning of the 2008 campaign, very few people even knew what a superdelegate was. It was like the
Electoral College before the 2000 election. Who cared? Whoever won the popular vote became president, right?
And whoever got the most pledged delegates in the primaries and caucuses became the nominee, right?

Well, maybe. And maybe not. Superdelegates had been invented to protect front-runners and make sure dark-
horse candidates didn’t catch fire and run away with things. The superdelegates were the party bosses, the fat
cats, the power brokers, the insiders. They included all Democratic members of Congress, members of the
Democratic National Committee, Democratic governors, former Democratic presidents, former Democratic vice
presidents, former Democratic leaders of the U.S. Senate, former Democratic speakers of the U.S. House of
Representatives, former Democratic minority leaders and all former chairmen of the DNC.

One out of every five delegates on the floor of the convention would be a superdelegate, and fully 56 percent of
them would be members of the DNC. All of which was fine with the Hillary Clinton campaign. In the beginning.
First, she wasn’t going to need superdelegates, and second, if she needed them, they would be there for her.
Heck, an awful lot of them owed their positions to her husband.

All of which bothered the Obama campaign. Superdelegates existed to prevent outsiders from winning, and
Obama was the outsider. “We entered Iowa with an incredible superdelegate deficit,” said David Plouffe, Obama’s
campaign manager. Congressional members from New York state and several members of the DNC were
publicly committed to Hillary, and Obama had, well, just about nobody. “Our theory was that we wouldn’t get
superdelegates until we started winning,” Plouffe said.
Which was always the risk for the Clinton campaign: Obama actually could start winning, and that might cause a
stampede among the supers. The solution was obvious: Lock up the supers early. Call them and get their public
support. Get them to hold a news conference, issue a press release, go on cable, whatever. Just as long as it was
public and they felt locked in. Bill Daley, who had been a member of Bill Clinton’s Cabinet but was now backing
Obama, came from a long line of politicians (his father had been mayor of Chicago, and his brother was the
current mayor), and he knew how pols acted. “Superdelegates were going to put their fingers up and go with the
wind,” Daley said. “I assume Clinton actually believed it when a lot of supers said privately they would be with her.
But why would you believe them? They are politicians!”
McAuliffe, who was Hillary’s campaign chairman, felt he was often marginalized by the campaign. He was not a
member of Hillaryland but instead was categorized as one of “The White Boys” (which gives some idea of how
well people got along on the Clinton campaign). McAuliffe said that, except for raising money, which he was
prodigious at, he was kept so far out of the inner circle that he was given only two hours’ notice that Hillary was
going to make her formal announcement for president. McAuliffe was mistrusted by the members of Hillaryland
because he was so close to Bill, but underutilizing him would have at least one serious impact: He was not being
used to line up the party insiders, even though as a former DNC chairman, he was the ultimate party insider.
“Why not have me call the superdelegates?” he said. “I knew them all. I had been with the DNC for 30 years! I
had appointed many of the superdelegates.” Yet McAuliffe was not authorized to call superdelegates until
February 2008.

Barack Obama and his wife, Michelle, had been calling superdelegates since March 2007. They were not making
spectacular inroads, but they knew these were first calls, they were laying a groundwork and when Obama
actually started winning contests, superdelegate support would follow. By its count, the Obama campaign went
into the Iowa caucuses 100 superdelegates behind Hillary Clinton. But Iowa changed everything. Winds were now
blowing, and politicians were sticking their fingers up and taking measurements.

After Hillary’s Iowa loss, Harold Ickes, a top Hillary adviser who was an expert on the party’s delegate rules
(having helped write some of them), urged both Hillary and Bill to start calling superdelegates. Hillary had always
been reluctant to call superdelegates (as well as donors), and when she did, she was often eager to show that
she was different than her public image. “She was so engaging and human, but that is not what we showed on
the campaign,” one of her top-ranking staffers said. “So when Hillary made a call, she would talk 30 to 45
minutes! We needed two-minute calls. We needed her to say: ‘Hey, I need you. Thanks.’” Bill would also call
superdelegates, especially DNC members, but many told him they saw no reason to announce their intentions in
public so early in the game. Why should they stick their necks out? What if Obama won? He would be running the
party, and he would remember who had opposed him.

Bill was not pleased. “Many of these people owed their political lives to the Clintons!” the source said bitterly. “The
Clintons raised money for them and lent their coattails to them!” And now they were stiffing the Clintons. Such is
politics. Bill made more calls than Hillary and made a big effort to lock up Ted Kennedy, who would end up
endorsing Obama after his huge victory in South Carolina. “There were people who should have been with the
Clintons, and the president started getting very frustrated,” the source said.

Bill Clinton’s comments about Obama’s campaign being a “fairy tale” and about Jesse Jackson’s having won
South Carolina in 1984 and 1988 were seen as provocative and racial, which is the last thing the Clinton
campaign needed. It now realized -- very late -- that the superdelegates might be needed to win the nomination.
Which meant that superdelegates might be asked to take the nomination away from the first potential black
nominee, which was going to be tough under the best of circumstances, but impossible if the campaign was going
to become racially supercharged.

“The president’s behavior did not play well with a lot of superdelegates,” the source said, “and we started fighting
for their neutrality instead of their endorsement.”

Which was yet another death knell. You can’t gain ground by asking people to stand on the sidelines. Jeff
Berman, who was Obama’s national director of delegate operations, saw what was happening as soon as the
primaries and caucuses actually began. “The DNC members were waiting in 2007 to see if Barack would actually
win the election,” he said. “After Iowa, they began moving to Barack. By then [Clinton] had won all the supers who
could easily be won, but the remainder were sympathetic to Barack. There was a flow of support to him.”
It was more than just everybody liking a winner. The Obama campaign began hitting hard on the notion -- first
privately in calls to the supers and then publicly -- that superdelegates should not overturn the choice of the
pledged delegates. The Obama campaign was always based on winning a majority of pledged delegates and
having the superdelegates validate that win. “The concept of letting the voters pick the nominee had a lot of
weight to it,” Berman said. “David Plouffe really developed that inside and outside the campaign.”

Plouffe said: “She got the low-hanging fruit [among superdelegates]. But the rest didn’t commit to her early when
she was the ‘incumbent’ candidate. In April and May [after she had lost the pledged delegate race] she made the
electability argument, but that wasn’t working.” Near the end, the only argument Hillary had left was that, first, she
was winning in the popular vote, a metric that was not only in dispute but also irrelevant, since the popular vote
had nothing to do with the way delegates were apportioned, and, second, that she was the most electable in the
fall against John McCain. The superdelegates were not impressed.

And not by accident. For months, the Obama campaign had been selling the same message over and over. “One,
we believe we are the most electable and, two, we are going to win pledged delegates and the winner of the
pledged delegates should be nominee,” Plouffe said. “We tried to get that as a prism through which the election
was viewed. It wasn’t that hard because most supers felt it was fair.”
Philippe Reines, who was Hillary’s Senate spokesman and then a campaign adviser, said:
“We didn’t think we’d need the supers. We succeeded with 40 to 50 congressional supers by working them in
2007, but when the environment changed, we lost them.”

On Feb. 13, following a 9-0 string of victories by Obama in primaries and caucuses, Plouffe did something very
unusual for him. Though running the campaign, he did not have a high public presence. He was soft-spoken
(even more so than David Axelrod, Obama’s chief strategist, who was famously soft-spoken for someone so
constantly on TV), and he often seemed reserved and a little bit shy. But the campaign was worried that the press
was missing a big story: For all intents and purposes, Obama had just wrapped up the Democratic nomination for

“We didn’t think the press corps was getting it,” Plouffe said. “We now had an insurmountable lead in pledged
delegates, and we wanted to say so. It was a decision not made lightly. We got out of character and said it
forcefully, and we did it to secure superdelegate support. The race was being covered as a dead heat, and it
wasn’t a dead heat.” Though Clinton was ahead in superdelegates, the Obama campaign was more than 150
ahead in pledged delegates. Plouffe now wanted to put his marker down: The only way Clinton was going to win
was if the supers handed it to her. And they were going to have to take responsibility for the firestorm that would
follow any such move.

“We believe it’s next to impossible for Sen. Clinton to close that pledged delegate count,” Plouffe said on a Feb.
13 conference call with reporters. True, there were several states to go and Clinton could be expected to win
some of them, but she would have to win by huge margins to overcome Obama’s pledged delegate lead. Plouffe
said that Clinton would have to win Ohio and Texas by “blowout” proportions and that he didn’t expect that to

(Actually, the Obama campaign expected to do better in both states than it ended up doing. It lost both of them
and after the primary campaign was over and I asked Axelrod to list the major mistakes of the Obama campaign,
he put the Texas loss near the top of his list. “We probably misplayed the Ohio-Texas week pretty badly,” he said.
“We had a better shot at winning Texas than Ohio, but we treated them as equal. We split our resources. We only
lost by three points in Texas, and, if we had won there, we might have ended the primaries and won the race right
there and saved ourselves a lot of time and money.”)

On the conference call, Plouffe was asked if the superdelegates could still decide the party’s nominee. “I think
there’s a growing chorus of concern out there that people do not think that superdelegates should overturn the
result of the contests,” he said. “You know, at the end of the day, I think it’s much more likely than not that the
superdelegates ratify that outcome.”

After the primaries, Plouffe told me: “Our argument was not that you can’t do this to an African-American, but
winning pledged delegates and not getting the nomination would be catastrophic [to the party]. We always
believed if we secured the pledged delegates, we would be the nominee. We were never that worried about the
It was typical of the Obama campaign, however, that even though it was never that worried about the
superdelegates, it had an aggressive superdelegate operation, with the staff, the candidate and his wife making
call after call to the superdelegates, month after month. “People like to be courted,” Plouffe said.

Harold Ickes, who was in charge of Clinton’s superdelegate operation, said: “The Obama campaign beat us very
early on to the punch about how to talk about pledged delegates. It was the voice of the people vs. party insiders
and Washington special interests. It was a neat dovetail with his characterization of Hillary as a Washington
insider and him as taking on Washington and lobbyists. We never were able to overcome it. I thought it was
unlikely that superdelegates would overturn pledged delegates.”
Philippe Reines, a Hillary adviser, said, “The minute our path to victory involved the votes of the superdelegates,
we lost. The apparatchiks of the party were not going to hand it to her.”

Had Hillary Clinton won among pledged delegates, however, the results would have been very different. She
would have become the nominee. So why didn’t she do it? There were several reasons, including the fact she
was up against a powerful campaigner with a powerful message. But there was another reason: Once again, her
campaign just didn’t get it.

The rules of delegate selection in the Democratic Party, while complicated, are not rocket science. They are
simple enough even for a few journalists to understand. Nor are the rules new. The only thing novel about them in
2008 was how critical a role understanding them would play in the outcome of the race. The original game plans
of both the Obama and Clinton campaigns -- win the first four contests and force the other person out -- had
collapsed, and after that it was going to be a long march. What made the difference is that the Obama campaign
had plans and provisions for the march and that the Clinton campaign did not.

Berman, and Plouffe been making very specific plans since April 2007 about winning delegates. They both knew
the media would concentrate on states won: Who would win Iowa? Who would win New Hampshire? That often
determined the outcome right there. “One candidate wins and knocks out the others, who run out of money,”
Berman said. “But you don’t know in advance if there will be a knockout.” By the end of January 2008, there was
going to be no early knockout. The candidates were splitting victories and defeats (though some were more
dramatic than others), and the status of Michigan and Florida was going to remain in limbo. (Both states had
violated party rules by moving up their primaries too early in the calendar and had been stripped of their
delegates. Even though the punishment was approved by Ickes, it would end up being a serious blow to Clinton,
costing her delegates she desperately needed.)

So Feb. 5, Super Tuesday -- which the media alternatively called Mega Tuesday, Giga Tuesday, Tsunami
Tuesday or Super-Duper Tuesday -- with its 22 states and more than 1,650 delegates at stake out of 2,026
needed to win, was going to be a very big deal. By the summer of 2007 -- a time when the Clinton campaign’s
field and political operations were still in a state of confusion -- the Obama campaign had completed its strategic
planning for Super Tuesday, even thought it was hoping the race would not get that far. “There was also a budget
for it,” Berman said. Which is very important in presidential campaigning.

The Obama campaign decided it would not contest every state at stake on Super Tuesday. It saw no point in
making an effort in Bill Clinton’s home state of Arkansas, for example. But in one of the most crucial decisions of
the campaign, the Obama forces decided winning wasn’t everything. “We determined how to contest the states
we expected to lose,” Berman said.

In the Republican Party, winning states and winning delegates are closely related. Because Republicans want to
pick their nominee early to avoid a drawn-out and divisive contest, the Republicans have winner-take-all rules:
You win a state, and you get all the delegates. The Democratic Party, wanting to be “fair” to underdog and
maverick candidates, bans winner-take-all contests: You win delegates on a proportional basis and by
congressional district. The percentage by which you win a state and whether the districts have an even or odd
number of delegates at stake are important. Again, it is complicated, but it’s not rocket science. And not secret.

“We took a look at the congressional districts, projected winning margins and competed where we thought we
could limit her margins to what we could live with,” Berman said.
“We wanted to hold Hillary’s margin to the smallest number of delegates possible. She would win a state, but not
achieve a large delegate advantage.”
Illinois and New York, the two home states of the candidates, were a good test of this strategy. Both candidates
would, of course, win their home states. New York had 232 delegates at stake and Illinois had 153 delegates at
stake, which meant that Hillary had what seemed to be a 79-delegate advantage going into Feb. 5. But that’s not
how it came out. “We got 197 delegates out of the two states, and she got 188,” Berman said. “This was quite an

Now take two other Feb. 5 states, Idaho and New Jersey. Idaho? Did the Clinton campaign care from Idaho? It
did not. To the Clinton campaign, Idaho was an odd place that had more potatoes than people, and it was also a
caucus state, which the Clintons hated. New Jersey was a different matter. It bordered New York, it was a primary
state and it was Clinton Country. But the Obama campaign targeted key congressional districts in New Jersey to
keep Hillary’s victory margin there as small as possible. “In Idaho, we had a 15-3 win in terms of delegates, and in
New Jersey, she had a 59-48 win,” Berman said. Do the math. Obama gets a 12-delegate net win out of Idaho --
tiny, weird, potato-infested Idaho -- and Hillary gets only an 11-delegate net win out of New Jersey. “So we got a
greater net gain out of Idaho than she got in New Jersey,” Berman said.

There were those on the Clinton campaign who understood rules and strategies, too, but felt stymied by a top
echelon that did not. “Why didn’t we have delegate discussions earlier?” a senior Clinton staffer in the political
operation said. “That should have happened at the beginning of 2007! You know the number of delegates per
state, and there should have been a plan to get delegates that was revised as time went on. I arrived on Oct. 3,
three months before the Iowa caucus, and there was no plan.”

Harold Ickes also knew the rules, having written some of them over his long career in the Democratic Party. He
says he wrote memos that were ignored. “I should have yelled and screamed more,” Ickes said. Another Clinton
adviser said: “Harold ultimately adheres to structure and protocol and the rules of the road. He was not on the
morning calls, and he wasn’t treated as essential to the endeavor. He can be quite passive.”

Another high-ranking staffer said that even when the Clinton campaign did try to plan ahead, it sometimes didn’t
matter. “We did budgets and overviews, and went to Patti [Solis Doyle, the campaign manager] and Mike [Henry,
the deputy campaign manager] and we were told it is not going to happen. They didn’t understand the framework
and how to win in this framework. Or they cared and the money wasn’t there,” the staffer said.

Guy Cecil, the national political and field director, said: “A budget was put forward to redeploy every Iowa and
New Hampshire staffer to every Feb. 5 state and the caucus states and hire new people. And it came back:
‘There is no money to do that.’”

Ickes said: “There was a lack of experience, knowledge and appreciation of the role of delegates. The delegate
operation was viewed as completely separate from the political operation. This, coupled with a very weak --
extraordinarily weak -- staff was the real fault of the campaign.”

Even so, the Clinton campaign had projected winning Super Tuesday by enough to put Hillary ahead in the
delegate count. “When we saw Guy Cecil’s proposal for Feb. 5, it said we would come out 40 to 50 pledged
delegates ahead on Feb. 5 by winning big states like California, New York, New Jersey, 12 battleground states
and leaning states,” a top Clinton staffer said. “According to his plan, we would have been ahead after Feb. 5. The
projections were just off. Did they have better targeting? I guess.” (Cecil told me he could never get full funding for
his victory plan.)

Obama won Super Tuesday by 15 net delegates, winning 13 out of 22 states. There was no wild cheering in the
Obama campaign, however. (There was hardly ever wild cheering in the Obama campaign. “I can’t remember a
low or high point in morale,” Berman said, which pretty much typifies the Obama campaign.) The campaign felt it
had now missed two opportunities to wrap up the campaign: The first was not winning New Hampshire after its
Iowa victory, and now it lacked a decisive victory on Super Tuesday. Furthermore, the press was not helping.
“The press bought into the argument by Hillary that her winning New York, California and New Jersey were
important because they would matter in the general election,” Plouffe said. “I was astounded.” Plouffe was
astounded because it was such a silly argument. No matter who won the primaries there, the Democratic
nominee was going to win New York, California and New Jersey in the general election.

“We considered Super Tuesday a solid day but not a winning day,” Berman said. “It essentially was a draw
because it did not provide either candidate with political momentum.” The Clinton campaign, however, had not
anticipated the race ever going past Feb. 5. Typically, the Obama campaign had anticipated it, had planned for it
and, perhaps most important, had the money for it. “David Plouffe had kept money in the budget to compete when
the Clintons were tapped out,” Berman said. “We had offices open and staffing where Hillary was apparently dark.
She never quite got to some states or maybe they threw in something that was terribly too little, too late.”

Not that Hillary Clinton was going to drop out. Some on her campaign knew that it was going to be impossible for
her to get ahead of Obama in pledged delegates and that the superdelegates would swing over to him. But
Clinton was a fighter, not a quitter. And her campaign took on a momentum of its own, a momentum divorced
from political reality. The long march would continue.

The Obama campaign would not wait for it, however. Immediately after the Pennsylvania primary on April 22
(which Obama lost), Obama secretly began his general election campaign. “After Pennsylvania, we started to
move some staff to general election states,” Hildebrand said. “We directed start-up teams to go in and be very
quiet.” General election staffing would begin in 17 states, including Georgia, Ohio, Virginia, New Mexico,
Minnesota and Wisconsin. “We had them go in and start doing some very quiet activities like looking for potential
office space and supporters,” he said. A dozen experienced organizers who had been working in primary states
were also dispatched to Chicago to help put together Obama’s field plans for November.

True, Hillary Clinton would not withdraw for another six weeks. But the march had already passed her by. “We
had to plan for the general election,” Hildebrand said. “We had the resources to do it, and we didn’t have time to

The last weeks were terrible ones for the Clinton people. They knew they could not get ahead in pledged
delegates and hoped against hope that the superdelegates would come to their rescue. They hoped for an
Obama scandal to surface. Something new about Tony Rezko, something new about the Rev. Jeremiah Wright.
Anything. “We hoped that that the superdelegates would see that she was the better and more electable
candidate,” Wolfson said.

And did you believe they really would?

“It’s all we had,” he said.

David Plouffe had thought the Obama campaign was going to have to be nearly perfect, because Hillary’s
campaign was going to be so strong. So was he surprised when her campaign didn’t turn out to be as strong as
he thought?

“Yes,” Plouffe said. “And grateful every day.”

© 2008 Capitol News Company, LLC