THE

INHERITANCE

T he World
Obama C onf r onts
and the Challenges
to A mer ican Power

DAVID E. SANGER

Harmony Books
New York

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For Sherill
and
Andrew and Ned

Copyright © 2009 by David E. Sanger

All rights reserved.
Published in the United States by Three Rivers Press,
an imprint of the Crown Publishing Group,
a division of Random House, Inc., New York.
www.crownpublishing.com

Three Rivers Press and the Tugboat design are registered
trademarks of Random House, Inc.

Originally published in hardcover in the United States
by Harmony Books, an imprint of the Crown Publishing Group,
a division of Random House, Inc., New York, in 2009.

Library of Congress Cataloging-in-Publication Data is available.

ISBN 978-0-307-40793-1

Printed in the United States of America

Design by Nancy Beth Field

1 3 5 7 9 10 8 6 4 2

First Paperback Edition

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To purchase a copy of 

The Inheritance 
 

visit one of these online retailers:

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Contents

Preface
Introduction: The Briefing
PART I: IRAN
THE MULLAHS’ MANHATTAN PROJECT
Chapter
Chapter
Chapter
Chapter

1:
2:
3:
4:

Decoding Project 111
Regime-Change Fantasies
Ahmadinejad’s Monologue
The Israel Option

PART II: AFGHANISTAN
HOW THE GOOD WAR WENT BAD
Chapter 5: The Marshall Plan That Wasn’t
Chapter 6: The Other “Mission Accomplished”
PART III: PAKISTAN
“HOW DO YOU INVADE AN ALLY?”
Chapter 7: Secrets of Chaklala Cantonment
Chapter 8: Crossing the Line
PART IV: NORTH KOREA
THE NUCLEAR RENEGADE THAT GOT AWAY
Chapter 9: Kim Jong-Il 8, Bush 0
Chapter 10: Cheney’s Lost War
Chapter 11: “Everything Is Appomattox”

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xv

1
3
27
56
86

109
111
145

173
175
232

267
269
285
315

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CONTENTS

PART V: CHINA
NEW TORCH, OLD DRAGONS
Chapter 12: Generation Lenovo
Chapter 13: The Puncture Strategy
PART VI:
THE THREE VULNERABILITIES

345
347
375

397

Chapter 14: Deterrence 2.0
Chapter 15: The Invisible Attack
Chapter 16: Dark Angel

399

Epilogue: Obama’s Challenge
Acknowledgments
Note on Sources
Suggested Reading
Endnotes
Index

445

419
430

475
479
481
485
503

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Pre fa c e

Let us learn our lessons. Never, never, never believe any war will
be smooth and easy, or that anyone who embarks on that strange
voyage can measure the tides and hurricanes he will encounter.
The Statesman who yields to war fever must realise that once the
signal is given, he is no longer the master of policy but the slave
of unforeseeable and uncontrollable events. Antiquated War
Offices, weak, incompetent or arrogant Commanders,
untrustworthy allies, hostile neutrals, malignant Fortune, ugly
surprises, awful miscalculations—all take their seats at the
Council Board on the morrow of a declaration of war.
—Winston Churchill, My Early Life, 1930

T H I S I S A B O O K A B O U T the world that Barack Obama inherited
on that bitterly cold Inauguration Day on the steps of the Capitol in
January, 2009, and the complex, often agonizing choices he now
faces. It looks backward at the seismic events that led America to
lose so much standing and leverage in the world. But it also looks
forward to reimagine ways in which we can rebuild our influence
and power and learn to live in a world in which the United States
acknowledges its limitations while continuing to advance its ideals.
From the steps of the Capitol on that Inauguration Day, you
could almost hear much of the nation—and the world—exhale in relief. But in the ensuing months, you could also hear millions inhale
with apprehension as they recognized that it was one thing to call
for change, and another to bring it about. The global euphoria that
greeted Barack Obama’s ascension has begun to fade. Americans,

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and the world, have come to realize that while installing a new occupant of the Oval Office can dramatically change the tone and image
of the United States, it does not make the knot of Afghanistan easier
to untangle, the mullahs of Iran more pliant, the political problems
of global warming or energy use, or the rise of new global competitors less urgent. In the first few months of the new administration,
all seemed possible. Now, as Obama himself often says to his advisers, the biggest challenge is coping with impatience.
No American president since Franklin Delano Roosevelt, the
commentators reminded us too many times during those inaugural
ceremonies, had inherited a range of problems so seemingly intractable and complex, or a country less certain of its future. Two
wars, an economic crisis that seemed at risk of tipping the country
into a second Great Depression, and a range of new threats that had
festered while the country’s attention and resources were focused
on Iraq seemed to prove Churchill’s famous caution.
In the years before Barack Obama’s election, America knew that
it had taken its eye off the ball. Iraq had proven to be the great distraction—the war so all-consuming for the top leadership of the
country that more potent threats went unaddressed, many huge
opportunities unexploited.
In an American presidential election like none before, Obama
had promised to refocus America’s attention—to withdraw from
Iraq so that America could focus anew on a war in Afghanistan that
he argued was at the center of America’s security concerns; to stop
Iran’s steady march toward acquiring the capability to build a nuclear weapon; and to deal with North Korea and other failing states
with nuclear ambitions. He vowed to redefine our relationships
with China and hit the Reset button with Russia. Obama promised
to reverse America’s detention and interrogation policies, which
had tragically diminished the country’s standing in the eyes of the
world. He vowed to reverse an economic crisis that threatened not
only jobs but also America’s power and influence. Most important,
Obama promised to end an era of huge opportunity costs—and to

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regain the credibility to confront more imminent threats to our security than Saddam Hussein’s Iraq ever posed.
Yet campaigning is one thing; governing is entirely another. It is
a lesson that Obama’s friend and political adviser, former Representative Lee Hamilton, noted at the end of 2009 that Obama has
learned “with a vengeance.” In racing to quell an economic disaster,
manage two wars, and enact a broad social agenda, the new president stretched the system to the breaking point—much as FDR did
in 1933. “The central question that emerges after these months,”
Hamilton said, “is can he make it all work?”
In his first year, Obama shifted the way the world viewed us and
the way we conduct ourselves around the globe. Rather than making
American demands about how other nations must change, he
talked of the “rights and responsibilities” of all nations. That was
one way of saying that no nation—including the United States—can
expect to operate by its own rules, a rejection of the American exceptionalism of the Bush years. Such talk instilled a sense of hope that
America was changing course, that it was finding itself again. This
sense was reinforced by Obama’s decision to reach out to the Muslim world in a way that no American president ever has before—even
though few Islamic nations reached back.
In Europe there was jubilation that America had turned over a
new leaf. So much jubilation, in fact, that the Nobel Committee
awarded the young president a peace prize for his aspirations and for
changing the tone of America’s dealings with the world, rather than
for any concrete accomplishments. As Obama himself said that
morning, he would accept the award “as a call to action, a call for all
nations to confront the challenges of the twenty-first century.”
But it was telling how in America the reaction was quite different. Here the Nobel was something of a political liability—awarded
at the outset of a contest rather than at its finish line. There was an
irony in the fact that the new peace laureate was receiving his
medal just as he was deciding whether to accelerate America’s involvement in an increasingly unpopular war in Afghanistan—one

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he had called a “war of necessity”—and to take far more forceful action to prevent Iran and nations like it from obtaining the world’s
worst weapons.
The Inheritance is an exploration of the tests Obama faces as he
heads into the heart of his presidency, with the sober recognition
that the glow surrounding his election has begun to wear off. America is still grasping the complexities of the tasks it has handed him.
The grand ambition of the Bush presidency after 9/11 was to create “a rip in time,” to reorder the Middle East and the wider world.
Bush’s theory was that the combined effect of America’s military
power and our newly declared intolerance for accepting risks to our security or our interests around the world—particularly nuclear
threats—would convince other nations to surrender their weapons of
mass destruction. The preemption doctrine would put nations on
warning. Our successes in Afghanistan and then Iraq, Bush argued,
would sow the seeds for democratic revolutions. Repressed people
would find the confidence to rise up against self-interested mullahs
and oil-soaked dictators. Some of these events would happen right
away. Others, like democracy’s rise, would become what Condoleezza
Rice called “a generational project.”
But just as Bush dismissed the Powell Doctrine calling for overwhelming force, he repeatedly ignored Churchill’s warning about
the need to prepare for “unforeseeable and uncontrollable events.”
Seven years of covering the Bush administration day by day, traveling with him around the world and around the country, and circling back to talk with the leaders who had dealt with him, left me
less surprised by the administration’s combination of arrogance
and ideological fervor than by the president’s inexplicable resistance, until the final quarter of his time in office, to changing course
as events and outcomes turned against him. Adjustments to strategy
and negotiations with enemies were seen as signs of weakness. For
Bush to acknowledge that the country was paying a heavy, unforeseen price for his decision to invade Iraq, to turn away from
Afghanistan, to coddle a Pakistani dictator in the hope he would

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fulfill his promises, and to scorn big diplomatic initiatives would be
to acknowledge that he and his aides had not fully thought
through the consequences of their policies. We were not only slow to
adjust to the war we were fighting. We were too slow and too
unimaginative to confront the far more potent threats, many of
them nuclear, that were emerging while we were otherwise engaged.
The “decider” became the ditherer, and the nation was set adrift.
America’s challengers were quicker to adapt. They understood
the futility of directly taking on the American military. They probed
instead for our other vulnerabilities and found plenty. Terrorists in
Iraq and Afghanistan designed roadside bombs that hit the soft underside of our armored personnel carriers. The Iranians designed a
nuclear strategy based on the wager that the Iraq experience so damaged our credibility and so overstretched our military that we would
be unable to rally the world to stop Tehran from acquiring the
knowledge and material to build a bomb—especially if Iranian leaders
stopped just short of actually fabricating one. Al Qaeda saw its
chance to regroup; the Taliban saw its chance to retake old territory;
and other militants saw their chance to destabilize a nuclear Pakistan. The North Koreans—those starving, savvy hermits—set off two
nuclear blasts. The Chinese realized that a distracted America could
not react effectively to their rapid rise as the dominant power in Asia,
the world’s fastest-growing consumer of energy, and the banker of
last resort for America’s soaring deficits.
Bush’s second term was a significant improvement. Even while
denying that he was changing course, he experimented. His defense
secretary, Robert Gates, whom Obama retained, publicly questioned why America has more members of military marching bands
than foreign service officers and why we spend vastly more to prepare to fight wars than to prevent them. But the holes dug during
the beginning of Bush’s first term proved too deep to crawl out of by
January 20, 2009. Bush could not find it in himself to make the dramatic, Nixon-to-China reversals of strategy that the moment in history required.

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At the moment when we most needed to act like a truly enlightened superpower, we let fear trump judgment, we depleted our political capital and moral authority, and we sullied our reputation as
the world’s safest, best-regulated place to invest. The scorecard at
the end of eight years was unforgiving: Barack Obama inherited a
country in far more peril—strategically and economically—than
Bush did when he took office.
While Obama’s opportunity remains great, he has discovered
that his options are limited. The symbolism of electing a biracial
president with the middle name “Hussein” proved a powerful antidote to the stereotyped image of America as an intolerant, hegemonic
power. Yet symbolism goes only so far in restoring our leverage and redeploying our portfolio of influence around the world. Eight years
after 9/11, we are still struggling to understand how to balance building schools by day and blowing up terrorist safe-havens by night—
sometimes in the same village—and how to talk to our enemies
without also empowering them.
As described in a new epilogue for this paperback edition, rebuilding American credibility and authority became the greatest
challenge of Obama’s first year. Even as he works to reestablish our
economic influence, he needs to restore the leverage that comes
from backing up diplomacy with the explicit or implicit threat of
military action. He has made clear that withdrawing from the
world—the path America has periodically taken, with disastrous results—is no longer an option. Nor is it realistic to expect that the
United States will retain the huge lead over rising powers that it enjoyed for the first sixty years after World War II. Yet the world still
seems to crave leadership from Washington, and one of the unanswered questions of the Obama era is whether his style—inquisitive,
measured, deliberate—appears decisive enough to blaze the path.
To shape the world we now confront will require more than
restoring the moral power of our example, more than talking to our
enemies, more than freeing up our military, more than once again
making America the most alluring place to invest, to study, and to

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pursue dreams. It will require a mixture of ingenuity, sacrifice, and
risk-taking that Americans have summoned at more trying moments in our history and that we can find in ourselves again.
David E. Sanger
Washington, D.C.
December, 2009

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INTRODUCTION

THE BRIEFING

T H E M O T O R C A D E pulled up to the side of the gleaming new FBI
building on Chicago’s west side at midmorning on the first Tuesday
in September, just as the 2008 presidential campaign was shifting
into its final, most brutal phase. There was a brief pause as Secret
Service agents made one last check of the surroundings and radioed
back to their headquarters that the man they had codenamed “Renegade” had arrived. Barack Obama emerged silently, a few foreign
policy advisers in tow, and quickly took a waiting elevator to the
tenth floor. The candidate strode past the long corridor lined with
identically framed portraits of the special agents-in-charge who have
run the FBI’s operations there since the era when bank robbers such
as John Dillinger were still considered Public Enemy Number 1.
Obama and his team were headed for the FBI’s secure conference
room—a “bubble” that deflects any electronic intercepts—for one of
the quietest rituals of the quadrennial presidential campaign season: a ninety-minute, classified briefing about the world that the
winner of the 2008 presidential election would confront.
Waiting for him in the windowless room was a man who, unlike
Obama, had been able to walk into the FBI building almost completely unnoticed. At sixty-five, J. Michael McConnell, the director of
national intelligence, was pale, a bit stooped because of a bad back,
and wearing wire-rim glasses that made him look like a well-heeled
consultant—the job he had held until President Bush convinced

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him to return to government at the lowest point of Bush’s presidency, as Iraq was dissolving into chaos in the fall of 2006.
The two men who shook hands in the bubble could not have
come from more different worlds. When Obama was a six-year-old
living in Jakarta, McConnell was patrolling the Mekong Delta on a
small Navy boat, seeking out the Vietcong. In 1991, the same year
Obama graduated from Harvard Law School, McConnell was already a veteran of the Cold War, directing the National Security
Agency, the biggest and most technologically complex of the intelligence agencies. By the time Obama was heading into government
service in the Illinois state legislature, McConnell had already retired from the covert world and had started a second career earning
millions from corporations desperate to protect their computer
systems.
Bush had enticed McConnell back to take over a demoralized,
disorganized “intelligence community” that was anything but communal. It employed 100,000 people spread over sixteen agencies
and had become more famous for its internal rivalries than for the
quality of its analysis. McConnell’s first job was to bind those agencies together. But early in 2008, McConnell and his top aides had
identified the first twelve months after the presidential election as a
period of critical vulnerability. It would mark the first transfer of
power since the 9/11 attacks, and McConnell and other top intelligence officials believed America’s rivals and enemies would seek to
exploit the inevitable disruptions of a government transition—even
a smooth one—to test a new president.1 In 2009 there would be little
time to get up to speed. The plan for dealing with al Qaeda had
been sitting on Condoleezza Rice’s desk at the White House on the
morning of September 11, waiting for discussion. The administration’s slowness to understand the threat was sharply criticized by
the 9/11 Commission; after that searing experience, a similar mistake by a new administration would be unforgivable. But McConnell had a second motive: After the intelligence disasters
leading up to the Iraq War, the new president would come to office

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deeply suspicious of anything that landed on his desk in a red “classified” jacket. McConnell needed to demonstrate that the agencies
he oversaw had learned and evolved.
The spy chief commissioned a stack of digestible reports for
Obama and his rival, Senator John McCain, as a sort of field guide to
American vulnerabilities at the end of the Bush era. “We came up
with thirteen topics,” McConnell said. “If you made a list, you’d
probably get eleven or twelve of the thirteen.”2
Among the reports was a grim assessment that al Qaeda—the
terror group whose middle ranks Bush used to claim were being
decimated—had not only reconstituted but had more allies and associates than ever along the forbidding border between Pakistan and
Afghanistan.3 There was a description of how the Taliban were making huge inroads into Afghanistan and how other militants saw an
opportunity over the next two years to attempt the first violent overthrow of a nuclear-armed state: Pakistan. The country was ripe for
the picking: Its weak, corrupt government faced national bankruptcy, an insurgency raged on the doorstep of the capital, and the
Pakistani government had no comprehensive strategy to confront
either threat. Nor did it seem to want one. McConnell himself had
come to the conclusion months before that Pakistan’s aid to the Taliban was no act of rogue intelligence agents but instead was government policy. Nonetheless, Washington kept paying billions in
“reimbursements” for counterterrorism operations to the Pakistani
military.*
Another report summarized the huge strides Iran had made in its
nuclear program while America was focused elsewhere: By Inauguration Day, Iran was estimated to have amassed enough partially enriched uranium to manufacture a single bomb—if the Iranians could
find a covert way to finish the enrichment process. The report’s timeline made it clear that in his first term, the new president will have to

* The encounters with Pakistani officials that led McConnell to this conclusion
are described in chapter 8, “Crossing the Line.”

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decide whether to live with a nuclear Iran or attempt—by diplomacy,
stealth, or force—to disarm it.
There was a study of the economic and military implications of
China’s rise, and another detailed Russia’s angry mix of nationalism
and its perpetual sense of victimization—a dangerous brew on display
just weeks before, during Russia’s invasion of parts of Georgia. Yet another report focused on a recent analysis of North Korea’s nuclear arsenal, which had expanded dramatically on Bush’s watch. There was
even a report on the national security implications of global climate
change—not the usual fare for the intelligence community.
For ninety minutes Obama listened, sometimes tipping back
his chair at the long, beechwood-toned conference table. His aides
were largely quiet as they looked around the room that was decorated in government-issue flags at one end and screens for secure
video links at the other.
Obama wanted to know more—much more—about Iran’s race
for the bomb, the subject of a confusing, internally contradictory
“National Intelligence Estimate” that he had read in its full, classified version in late 2007. How much time would the next president
have to conduct talks with Iran—negotiations Obama promised
during the campaign—before the Iranians got the bomb?
Obama also had questions about Afghanistan, to which he had
committed to send more troops while accelerating the American exit
from Iraq. He had already publicly argued that the Afghanistan–
Pakistan border was the real “central front” in the war on terrorism
and rejected Bush’s insistence that the true battle was in Iraq. Everything in the reports McConnell provided backed up Obama’s assertion. As Michael V. Hayden, the director of the CIA, put it a few
months later, “Today, virtually every major terrorist threat my agency
is aware of has threads back to the tribal areas.”4
Over the course of their discussion the two men wandered onto
McConnell’s favorite subject: America’s huge, unaddressed exposure
to cyber threats that could paralyze the country’s banks, its power
stations, and its financial markets. “They spent a fair bit of time on

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that,” one of the participants said. “More than you might expect.” (It
was a subject that struck close to home: Both the Obama and McCain campaigns’ computer systems were hacked during the race, the
kinds of attacks the federal government and American businesses
face each day. The intrusions appeared to have come from abroad.) 5
It was a daunting set of conflicts as broad and complex as those
that Britain faced a century ago or that Franklin Roosevelt faced in
1933. It was a lot to digest. Obama and McConnell vaguely agreed to
try to meet again before the election for another “deep dive”—
McConnell’s phrase for a plunge into specific subjects, something
he did frequently with Bush.
The follow-up session did not happen before Election Day. Two
weeks after the briefing came the second September shock of the
Bush era: the collapse of Lehman Brothers, followed by the terrifying
plunge of America’s financial markets—and then the world’s. The last
eight weeks of the campaign were dominated by questions of how to
right the economy: bailout plans were announced, discarded, reformulated, and announced again by Bush and his treasury secretary,
Henry Paulson. There were emergency meetings at the White House
that in one case put both Obama and McCain at the same table in the
Roosevelt Room, with Bush in the middle; and a $700 billion authorization by Congress, reluctantly supported by both Obama and McCain, to save some of America’s biggest institutions and try to
stabilize a crumbling market. It was rocky territory for McCain, who
had regularly praised deregulation and declared on the day of the
Lehman collapse that “the fundamentals of the economy are strong,”
a sentence that seemed so out of touch with reality that it cost him immeasurably.
Then, at a little past eleven p.m. Eastern time on Tuesday, November 4, exactly nine weeks after that meeting at the FBI, McConnell’s
world of problems became Obama’s future. In a night that shimmered with history, Americans decisively—but not overwhelmingly—
repudiated George W. Bush and his approach to the world. They
embraced a candidate with less experience than Jack Kennedy had in

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1960 and elected the first black president since George Washington, a
slave-holder, took the oath of office.
His victory secure, Obama appeared at a huge rally in Chicago’s
Grant Park. He had canceled the campaign’s plans for fireworks
and strode to the oversized wooden podium with a relaxed air of
command, but little sign of jubilance.
“If there is anyone out there who still doubts that America is a
place where all things are possible, who still wonders if the dream of
our founders is still alive in our time, who still questions the power
of our democracy, tonight is your answer,” Obama said as he peered
out over a crowd of more than 100,000, a pastiche of a new America:
white and black and Hispanic and Asian. It was a crowd whose
many dreams had been poured into the man just elected the fortyfourth president of the United States.
But Obama knew that while parts of the world would welcome
him as the anti-Bush, it would not be long before he would be
tested. Something in McConnell’s thirteen briefing papers—or
something that the intelligence apparatus did not anticipate—
would soon erupt. Then would come the moment to show that he,
like another young senator propelled into the presidency on soaring
oratory and a nation’s hope for a fresh start, had a spine of steel. In
a speech that Obama crafted to sound less like a victory celebration
and more like an inaugural address, he added some Kennedy-esque
lines that suggested that while an Obama administration would be
about diplomacy and dialogue—with enemies as well as friends—it
would not be about weakness.
“To those who would tear the world down: We will defeat you,”
he told the throng. “To those who seek peace and security: We will
support you.”
It was an inspiring declaration, aimed at an audience far beyond
America’s shores. But Obama’s neat separation of the world into
builders and destroyers had echoes of the man leaving the White
House, the president who had famously declared early in his first
term to all the nations of the world that “you’re either with us or

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against us in the fight against terror.”* Bush quickly discovered that
the nations of the world refused to choose sides quite that clearly and
that some of the nations he needed most, starting with Pakistan,
would be with him on Tuesdays and Thursdays, but against him on
Mondays and Fridays. Many things might change with the arrival of
a new president. This fact of geopolitics would not.
Thirty-six hours after Obama’s victory, McConnell slipped back
into Chicago and the two men met in the same FBI conference
room. This time the director came with the day’s “PDB,” the President’s Daily Brief, the summary of intelligence that occupies the
first hour of the president’s day. This briefing, Obama’s first as
president-elect, was unlike the one before. At Bush’s orders, the candidates’ previous briefings had been restricted to the problems
America faced around the world. This time, McConnell came armed
with the PDB’s descriptions of covert actions, classified “special action programs,” and other steps that the nation’s intelligence agencies, sometimes in concert with the Pentagon, were taking at a
moment when most Americans were understandably focused on the
crumbling of the American economy. It would be weeks—maybe
months—before Obama would be able to get a full sense of the secret
efforts that Bush had launched, the legal authorities that justified
them, and the political land mines he was about to inherit.
“Bush wrote a lot of checks,” one senior intelligence official
told me in the early summer of 2008, “that the next president is
going to have to cash.”

U N T I L 1952 , incoming American presidents rarely had a clue of
what they were getting into.
With the Korean War raging, Harry Truman declared that none

* Bush uttered the famous phrase several times, but most clearly at a joint news
conference in the Rose Garden with Jacques Chirac, then the president of France,
on November 6, 2001.

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of his successors should enter office as ignorant as he had been
about the world he was about to face. It was twelve days after
Franklin Roosevelt’s death in April 1945, that Truman was fully
briefed on a project he had heard only vague rumors about: the
huge undertaking in the deserts of New Mexico to build a nuclear
weapon. Within weeks, he would have to decide whether to drop the
first atomic bomb on Japan, the momentous decision that cost
hundreds of thousands of Japanese lives and likely saved untold
numbers of Americans slated to invade Honshu, my father, Kenneth Sanger, among them.
At Truman’s instigation, a quadrennial tradition began: The
newly created CIA briefed both the Republican nominee, Dwight D.
Eisenhower, and the Democratic nominee, Adlai Stevenson. (In one of
those odd accidents of historical geography, Stevenson received briefings at the Illinois governor’s mansion in Springfield, two blocks
from where Obama began his political rise a half century later.) Unlike
Obama and McCain in 2008, Eisenhower and Stevenson did not get
the same briefing. The agency trusted only Eisenhower, the hero of
World War II, with the fruits of its communications intercepts.6
By the time John F. Kennedy ran for president in 1960, the
briefings centered on the most contentious issue of the campaign:
the bitter argument over the alleged “missile gap” between the Soviets and the United States. Kennedy charged that Eisenhower and
Nixon had allowed the United States to become dangerously vulnerable. There was also the question of who would be tougher in
the defense of Taiwan against Communist China: Nixon alleged
Kennedy didn’t have the steel to face down Mao’s forces. Then there
was Cuba. Kennedy’s campaign accused the sitting administration
of doing too little to help Cuban exiles oust Castro. Nixon later
wrote he “assumed” that Kennedy’s CIA briefings included news of
the covert program already under way to send exiles onto the island
to lead an overthrow of Castro. That program, of course, launched
the biggest disaster of Kennedy’s first year, the abortive Bay of Pigs
invasion. The fiasco unfolded less than three months after Kennedy

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took office, before the young, inexperienced president had learned
the strengths and weaknesses of his advisers and before he understood that even the most confident-sounding intelligence officers
and military officials blow smoke—and underestimate what can go
wrong. It was a bitter lesson for Kennedy in 1961 and an even more
bitter one for Bush in 2003.7
Obama was born four months after the debacle on the coast of
Cuba. But forty-eight years later, as he prepared to take office, several of his top national security aides were asking the same question
Kennedy’s young aides had asked then: What weren’t they hearing?
“The Bay of Pigs is the right analog here,” one of Obama’s national
security advisers told me the week of the presidential election. “We
can guess what we are walking into. But until you turn over the
rocks, you really don’t know what’s there.”
It turned out there were a lot of rocks.
In the last year of his presidency, Bush secretly opened several
new fronts in what he called the war on terrorism—the defiantly illdefined, ever-evolving conflict that became the raison d’être of his
presidency.
In January 2008, and then more dramatically in July, Bush
rewrote the rules of war against the militants who had built a seemingly impervious sanctuary inside the tribal areas of Pakistan,
where they could strike in two directions: against the Western coalition in Afghanistan and against Pakistan itself. Publicly, Bush insisted that he was respecting Pakistan’s sovereignty, that its inept
government was a “partner” in rooting out terrorists. In reality, he
had faced up to the fact that the Pakistani government was aiding
both sides of the conflict, and he ordered regular strikes inside the
Pakistani border—both by Predator drones and, when necessary, by
his favorite branch of the military, the Special Forces. It was an act
of desperation, driven in part by the fact that more than seven years
after the defining, awful morning of his presidency, Osama bin
Laden and his chief lieutenant, Ayman al-Zawahiri, had reconstituted al Qaeda. “The idea that he would go home to the ranch in

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Crawford with these two guys still walking around ate at the president,” one of Bush’s aides told me. “He didn’t say it, but you could see
it in the new strategy.” During the campaign, Obama voiced support
for going into Pakistan to hunt al Qaeda. But what Bush had ordered
was something far more extensive: a search for extremists of many
stripes—a very different kind of undeclared war, and one that, as
Bush left office, was already prompting a ferocious backlash among
Pakistanis.
Obama would soon learn of another major covert operation,
also born of desperation. This time the target was Iran.
Sanctions had taken their toll on the Iranian economy but had
not changed the regime’s behavior. Secretary of Defense Robert
Gates had made clear that a military strike, while possible, would
have awful repercussions. Whatever his inner thoughts, Bush professed to agree. “I think it’s absolutely absurd,” Bush insisted to a
group of White House reporters in early 2007, “that people suspect
I am trying to find a pretext to attack Iran.” He was talking as if his
first term, and the preemption doctrine, had never happened.
Early in 2008, Bush authorized something just short of an attack: a series of new covert actions, some that the United States
would conduct alone, others designed in consultation with the Israelis and the Europeans. Most were centered on a last-ditch effort
to undermine the industrial infrastructure around Natanz, the site
of Iran’s largest known nuclear enrichment plant. Such attempts
had been made before, even during the Clinton administration, but
now the clock was ticking faster. Few believed the effort would
amount to much. “We may be past the point of stopping the Iranians,” one senior intelligence official acknowledged to me months
after Bush signed the orders. But the hope was that the covert actions would at least slow down Iran’s effort to produce enough nuclear fuel for several weapons.
Obama had vowed never to allow Iran to get a nuclear weapon.
During the post-election transition, however, several of his top ad-

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visers acknowledged that the harder question, never discussed on
the campaign trail, would be how close to that goal Obama would
allow the Iranians to get. Should he take the risk of letting the CIA’s
covert efforts move forward before he understood their scope and
what could go wrong—the mistake that Kennedy made? “I wouldn’t
want to bet my country on any of these,” one skeptic of the covert
programs told me, being careful not to reveal more than what was
already circulating about the highly classified projects. Similar efforts had been tried before, he said, and while they worked briefly,
the Iranians had soon discovered them. “I hope,” he confided,
“someone’s ready to tell the next president there’s not much chance
any of this crap is going to work.”
The Israelis had apparently arrived at the same conclusion. In
Bush’s last months in office, they feared that Obama, if elected,
would enter endless, ultimately fruitless negotiations with the Iranians. So they came to the White House in 2008 asking for help with a
plan of their own—a military option to try to neutralize Iran’s known
nuclear facilities. The secret approach triggered a panic in the Bush
White House that the Middle East would again be in flames as Bush
left office, with the United States quickly sucked into the attacks and
counterattacks that would almost certainly follow. The Israelis were
deliberately vague about their intentions, and Bush deflected the request. His aides were hoping that with Israel’s leadership engaged in
a power struggle to succeed Prime Minister Ehud Olmert, the question of military action against Iran would be put on hold for a while.
But the Israeli threat—and the crisis it could provoke—was bound to
be among the most pressing of the issues on Obama’s desk when he
walked into the Oval Office.*

* The secret Israeli approach to the Bush White House is discussed at greater
length in chapter 4, “The Israel Option.”

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E X A C T L Y A W E E K after the huge stock-market plunge in September
2008, Robert Gates, the former CIA chief who had been appointed to
the Pentagon to undo the damage done by Donald Rumsfeld, offered America the words it had been waiting five years to hear. Understandably, given the din of collapsing banks, few heard it.
“I have cautioned that, no matter what you think about the origins of the war in Iraq, we must get the endgame there right,’’ he told
a Senate committee. “I believe we have now entered that endgame.”
When Gates took the job in 2006, he told colleagues that he had
one overarching goal: to guide Bush to that “endgame” as quickly as
possible. From his post as president of Texas A&M, he had been
mystified by Bush’s constant talk of “victory” and appalled by
Bush’s brief sojourn into describing America’s struggle as one
against “Islamofascism,” a misguided effort to cast the war in
World War II terms, a step that even Bush’s own aides believed inflated the enemy’s perception of itself. As a member of the Iraq
Study Group—the bipartisan panel that made the case for an accelerated move toward the exits by early 2008—Gates had visited Iraq
and was sobered by the strategic disarray.8
But Gates’s “endgame” comment wasn’t intended to be taken
simply as a progress report on Iraq. Instead, seizing on the success of
the “surge,” he was testifying about the need to turn more attention
toward Afghanistan and Pakistan. It was there, he said, “the greatest
threat to the homeland lies.” This was the unclassified, watereddown version of what McConnell was telling the candidates—and it
appeared to give the imprimatur of a Republican former chief of
the CIA to one of Obama’s campaign themes.
Just a year earlier, such a comment would have been heresy in
the Bush administration. But Gates was bulletproof. He hadn’t
sought this job. And while he was a skilled bureaucratic player who
made sure he didn’t openly contradict Bush, he was blistering in his
descriptions of how the United States had gotten into this mess.
“We are at war in Afghanistan today,” he told an audience at West
Point in April 2008, “in no small measure because we mistakenly

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turned our backs on Afghanistan after the Soviet troops left in the
late 1980s.” (At that time George H. W. Bush was in office, and
Gates himself was at the CIA.) He pulled no punches about the
NATO allies in Afghanistan, asking the question of what to do
when “some of your allies don’t want to fight.” By his own account,
he had learned during his years in the intelligence world to frame
the question in this way: “If we do this, what will they do? Then
what? And then what?” He would never say so, but he was trying to
force an administration and a president who had spent the first
term imagining how a quick victory in Iraq would beget a resurgence of American power to adjust themselves to a world in which
some investments go bad.
“We are overinvested in Iraq; it’s fixing us in place,” one of Gates’s
closest high-ranking allies told me in the Pentagon one day in the
summer of 2007. The war was about to become America’s longest
military commitment, save for the American Revolution, and he
compared his and Gates’s problem to one of managing a portfolio
with some money-losing stocks—the familiar trap of sunken costs.
“It’s like you invested in a bad mutual fund. You know, then you get
your emotions tied up in the investment. You had an objective in
mind—maybe sending the kids to college. But you become so enamored of the fund that over time you lost track of the objective. And
suddenly you find that you are getting negative returns, but you just
can’t get yourself out.”
Gates’s hope was to get down to ten combat brigades in Iraq by
the time Bush left office—which was about half the fighting force at
the time we spoke. (He didn’t make it, but came close; as Bush was
preparing to leave office, the force was down to fourteen combat
brigades.)
Once America got on the path out of Iraq, Gates said to me in
his office a few months before his Senate testimony, a new president could begin to prepare the American public for the fact that
we would need a far, far longer commitment to Afghanistan. That
was clearly a message Obama’s faithful did not want to hear.

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Yet Afghanistan was not Iraq. Overwhelming military force
wouldn’t work, Gates argued, because it would be impossible to maintain “a much larger Western footprint in a country that has never been
hospitable to foreigners, regardless of why they are there.” But the
American people, the Congress, and the European allies had not yet
learned this lesson, he worried. They were not yet prepared for the
kind of world in which we were forced to pour many kinds of talent
and resources—not just troops—into the failing states that now rank
among our gravest national security threats.
For the next president, Gates said, the deeper lesson of Afghanistan, Pakistan, and problems like them is that America’s challenge is
much more far-reaching. “The structures of national security are
outdated,” he told me. “They are sixty years old; they were products
of lessons learned from World War II and what we needed to fight the
Cold War, and they were great for that. They worked. But we live in a
different and much more complex world.”
Obama was about to discover how much more complex. In the
weeks after his election, it became increasingly obvious that the architecture of the world’s financial institutions, also created in the
1940s, was as outdated as the national security infrastructure. It
had been designed for a world in which economic crises could be
contained in individual countries or regions; the assumption was
that the United States and other large economies would be healthy
enough to pull the world through. But this crisis was different from
the one that struck Mexico in 1994 or Asia in 1997. The crash that
began with falling property prices in Florida and California and
everywhere in between was radiating out around the world. At
home, Obama was confronted by the prospect of the collapse of
General Motors and other automakers. Abroad, fragile nations, unable to attract loans or capital, were being pushed to the brink. At a
meeting of his foreign policy advisers, Obama was told that Pakistan was in about the same shape as GM: It would run out of cash
in months. What looked like a domestic economic crisis was, simultaneously, a global crisis.

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Obama’s advisers agreed his first priority had to be the deepening recession at home. An America wracked by credit freezes, foreclosures, bankruptcies, deflation, and unemployment would have little
leverage in the world. But the reports coming in to Obama once he
began to regularly receive the President’s Daily Brief made it clear
that America’s rivals around the world were not waiting for his economic initiatives. Seizing on the moment of transition, the Russians
were threatening to base missiles near Poland, in hopes of forcing
Obama to back away from Bush’s missile defense plan for Eastern
Europe. The North Koreans were reneging on the deal they had
struck with Bush on nuclear inspections. The Taliban and their associates were fracturing Afghanistan, tribe by tribe, village by village,
compound by compound. An attack on Mumbai, the commercial
capital of India once known as Bombay, threatened a resurgence of
the six-decade-long conflict with Pakistan and once again put the
volatile subcontinent on a hair trigger. And in Iran, perhaps the
problem Obama had the least time to solve, the mullahs were getting closer to the day when they could claim they had everything
they needed for a nuclear arsenal.

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