Illustration by Nigel Buchanan

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The Real Story of Donald

Trump Jr.
BY JULIA IOFFE
June 20, 2018

All he ever wanted was to make his dad proud, but things have
never turned out quite right for Donald Trump Jr. Even now,
despite finding his purpose as a bombastic star of the far right,
Junior’s personal life is in shambles and the specter of Robert
Mueller looms large. As Julia Ioffe discovers in talking to old
friends and Trump World insiders, it’s never been trickier to be
the president’s son.

...................................................

On a recent Thursday afternoon, Donald Trump Jr. buckled himself into a coach seat
on a packed plane—just like any nameless fellow might—and flew west to Utah. There, for
a few blissful spring days at a hunting retreat far from his myriad worries in New York
and Washington, Donald Trump Jr., eldest son and namesake of the president of the
United States, was simply Don.

He rode through the mountains, gabbing with Robert O'Neill, the former Navy SEAL who
has said he was first into bin Laden's bedroom and who, after taking careful aim over the
shoulder of the terrorist's youngest wife, shot him square in the head, killing him
instantly. O'Neill is a big supporter of the president, but he and Don didn't talk politics. “I
was really impressed with his knowledge of ballistics and harvesting animals,” O'Neill
told me. “I was a sniper in the SEALs, and he knew pretty much what I knew about
ballistics.”

More than once during their time together, O'Neill says, Donald Trump Jr. called
attention to the fact that he must come off like a walking contradiction. “You didn't think
the son of a billionaire would be a hunter,” he said again and again, according to O'Neill.

Don is hardly shy about this particular passion. His neighbors in upstate New York
complain that his tract of land there sounds like a military-grade shooting range (perhaps
ironic, given that he's appeared in a promotional video for a manufacturer of gun
silencers).

For much of Don junior's life, EDITOR’S PICK

the hunter's camo he's worn
has helped him not to
Culture
disappear but to stand out, to
Melania Trump on Her Rise,
differentiate himself from his
Her Family Secrets, and Her
father, the real estate tycoon True Political Views: “Nobody
who never understood his son's Will Ever Know”
fascination with the outdoors.
(“I am not a believer in
hunting, and I'm surprised they
like it,” Trump told TMZ of his
two eldest sons.)

Only when he began campaigning for the White House did Donald Trump see some value
in his son's bloody pastime. According to Sam Nunberg, a Trump adviser at the time,
when an invitation arrived from the governor of Iowa to go hunting ahead of the state's
crucial caucuses, Trump joked, “Don, you can finally do something for me—you can go
hunting.”

It's hard being Don. Struggling to make a mark. Living as the junior to Trump senior.
Existing as the shy kid who takes solace in the outdoors. Growing into a man who
desperately wants his father's love and pride yet is always mindful of the distance
between them. His struggles are compounded by the perception that his life of privilege
ought to be effortless. Though to understand the strange gantlet of duty and drama that
has marked that life is to wonder how anything would be simple for Donald Trump Jr.

“I think Don gets it a lot. Everyone talks about Ivanka, but Don also has a lot of pressure
on him,” says a former Trump adviser. “Everyone wants approval from the father,
especially if the father is Trump. He has a special place in his heart for Ivanka. But Don is
the eldest son, he's named after him, he's doing the nitty-gritty on the real estate, he's got
a lot of responsibility, and Trump is tough on everybody. He's the alpha male. He sees his
son as somebody he has to groom.”

When a Brazilian journalist asked Don in 2010 whether there was much pressure being
Donald junior, he replied, “There probably shouldn't be. But there is for me, because you
want to please someone like that, and he's a perfectionist. There's definitely always that
shadow that follows you around, like how is this guy, the son of someone so good at what
he does, going to act?”

...................................................

According to his first wife, Ivana, Donald Trump was never keen on bequeathing his
name to anybody. It was Ivana who wanted to call their newborn Donald junior. “You
can't do that!” Trump is quoted as saying in Ivana's memoir, Raising Trump. “What if
he's a loser?”

Don tells his own story about coming into the world on December 31, 1977. “I like to joke
that my dad wanted to be able to claim me as a dependent on his taxes for 1977,” he once
told Forbes, “so he told my mom she had to have me before midnight and, if she didn't,
he'd make her take a cab home.” (Ivana wrote about her labor being induced by doctors.)

So began the difficult, defining struggle of Donald Trump Jr.'s life—to make himself
useful while carrying a name so beloved by the man who bestowed it that he put it in gold
letters on buildings all over the world. When he was growing up, his dad called him
Donny—a moniker the elder Trump would never go by. “[It's] a name I hate,” he
explained in The Art of the Deal.

Fraught though their relationship has sometimes been—at one point Junior refused to
speak to his father for a year—Don has lately found improbable purpose and renown as a
savage defender of his father. His once private desires to win his father's approval now
come packaged as angry tweets and memes tearing down his dad's opponents as illogical,
histrionic socialists. At age 40, he has become like every other angry white man raging on
the Internet, exorcising his psychic traumas through ghastly rhetoric and febrile
conspiracy theories, like when he retweeted Roseanne Barr's false claim that George
Soros, a Holocaust survivor, was actually a Nazi collaborator.

Ten-year-old Donald Trump Jr. in 1988. Ron Galella, Ltd.

This sort of thing has endeared him not only to pro-Trump Republicans but also to the
populist fringe that propelled Trump to power. “Don junior is royalty,” says Mike
Cernovich, a right-wing activist. “Don junior is loved by the base. He's accessible, he's in
the trenches, he's sharing the memes, pushing out stories that other people aren't. It
shows that he's reading what everybody else is reading. I know it's a really dumb litmus
test for a politician, but he's the one you'd want to have a beer with.”

Don's bona fides as an outdoorsman have helped, too, and have earned him some sway in
his father's administration. It was Don who recommended that former Navy SEAL Ryan
Zinke—a fellow hunting enthusiast who once reportedly referred to Hillary Clinton as
“the Antichrist”—should be tapped as Trump's secretary of the interior.

To the president's most ardent supporters, Don is venerated as a natural incarnation of

everything the MAGA brand stands for: transgressive and defiant white, rural
masculinity. “He's a fighter,” says one Breitbart editor. “The stuff he's focused on is the
stuff the conservative movement is focused on. It's not an act. With him, I think it's
genuine.”

To people who have known Don for decades, this identity is jarring. He had always loved
the outdoors. But the use of the Pepe the Frog meme and tweeting about taking away half
his daughter's Halloween candy “because it's never too early to teach her about
socialism”—that isn't the Don they recognize. “I don't remember him having political
views,” says a friend of Don's from college. “You've been hearing his dad for a long time,”
but as for Don's views, “I didn't see anything emerge until the campaign.”

For years, Don seemed contentedly inattentive to politics. “He probably had the opinion
that most New Yorkers have of politicians—they're full of shit,” says sometime Trump
business partner Felix Sater, who worked with Don on the ill-fated Trump SoHo project
in Manhattan. “He wasn't political. He didn't like politics.”

So old friends were shocked by the demagogic fury he unleashed. “What's surprising is
that the tone and the rhetoric are so”—the college friend grasped for a term—“so Fox
News-ish. The anger is surprising. None of us would've guessed that he would've been so
outspoken in either direction. It hit me strange to see this guy that was a friend in college
all over the news in this way.”

Those who have seen the political transformation from hunting-businessman father to
the most prominent MAGA troll explain it as a simple, sporting calculation. The snarling
political persona, the friend contends, is a show for an audience of one.

“He wasn't a political animal until this started,” says Charlie Kirk, who ran the Trump
campaign's outreach to millennials, of Don's partisan awakening during the 2016
election. “He did it to help his dad. He got dragged into this fight out of loyalty.”

...................................................

Being noticed was always something of a struggle. That evening he was born, little
Don was left by his parents to the care of the hospital's nursery. His father headed home
to celebrate New Year's Eve, while Ivana put a boa and a mink over her hospital gown
and went to visit a girlfriend recovering from back surgery on another floor of the
hospital.

Don had little luck with the first of his nannies, under whose watch he both broke his leg
and nearly drowned. From there, a succession of caregivers followed, though Ivana was
also active in her three children's upbringing. In her telling, she instilled strict Eastern
European discipline in the house. By several accounts, Don came in for the most
punishment. “Don got in trouble with me more often than the other kids, probably
because he was the oldest,” Ivana wrote in her memoir.

Largely absent from childhood tales is the father. “He would love them, but he did not
know how to speak to them in the children's way of thinking,” Ivana said of her ex-
husband on The Wendy Williams Show last year. “He was able to speak to them only
when they came from university, when eventually he was able to speak business to them.
Otherwise, he really did not know how to handle the kids.” The interactions were
apparently alien in both directions. “The children,” Ivana wrote in her book, “didn't know
how to relate to him, either.”

Nowadays, Don puts a happy gloss on his dad's parenting style—which he believes, in
hindsight, was career prep. “He's a business guy first and foremost, so we spent a lot of
time with him, but it was always in a business environment,” Don told Oprah in 2011.

Some paternal lessons have stuck with Don, who tries still to parse the old fatherly
instruction for the faintest wisdom. For instance, a key Trump mantra, according to both
Ivana and Don, neither of whom agreed to be interviewed for this story, was “Don't trust
anyone.” Trump would test his children on this maxim. “He'd say, ‘Do you trust me, your
own father?’ ” Don once recalled. “We'd say, ‘Of course we do!’ And he'd say, ‘What did I
just tell you? You didn't take the lesson!’ It was certainly an interesting Trump moment,”
Don continued, talking at a pressured, sober clip, “because it's not something you'd see
any conventional parent-child conversation go that way, especially not fully
understanding what the concept of trust was.”

If the lessons didn't take, Don had his father's own example to demonstrate
untrustworthiness. On the day before the boy's 12th birthday, Marla Maples—who was
then carrying on an affair with Donald Trump—crossed paths with Ivana at Bonnie's in
Aspen and uttered her nine infamous words: “I'm Marla, and I love your husband. Do
you?” According to Ivana's book, Don witnessed the whole scene.

When divorce proceedings began and the paparazzi set up camp outside Trump Tower
and Don's school, Ivana decided to explain the situation to her children. Ivanka, 8, and
Eric, 6, got the sanitized version. Twelve-year-old Don, Ivana concluded, “could handle
hearing the truth.” After being told about his father's mistress and the fact that his
parents would never live together again, Don stopped speaking to his father.

Soon after that, as Trump engaged Ivana in an epic public feud, he dispatched a
bodyguard to his triplex apartment with instructions to bring his elder boy down to his
office. Don, still not talking to his father, descended with the bodyguard to the 28th floor,
and a few minutes later, Ivana, who described all this in her book, got a phone call. It was
Trump, looking for some leverage by announcing that he was going to keep Don and raise
him alone.

“Okay, keep him,” Ivana said she told him. “I have two other kids to raise.”

A few minutes later—his bluff out-bluffed—Trump ordered his boy to be taken back
upstairs. “Donald never had any intention of keeping his son,” Ivana wrote.

In his telling, Don was caught in that lonely isthmus of awareness where one doesn't
understand everything but knows enough to be deeply wounded by it. “Listen, it's tough
to be a 12-year-old,” he told New York magazine in 2004. “You're not quite a man, but
you think you are. You think you know everything. Being driven to school every day and
you see the front page and it's divorce! “Best Sex I Ever Had”! And you don't even know
what that means. At that age, kids are naturally cruel. Your private life becomes very
public, and I didn't have anything to do with it: My parents did.”

Don, Ivana noted, “expressed his pain with anger, and he was really angry.” Don's
reprieve from the glare of Manhattan had always been the summers spent with his
maternal grandparents in rural Czechoslovakia. But between the separation and divorce,
his grandfather Milos died suddenly of a heart attack. It was yet another blow to Don, for
whom Milos was a sort of father he never had. “Being in Czechoslovakia with my
grandfather was the most memorable time in my life,” Don wrote in an aside in Ivana's
book. “My grandpa would say, ‘There's the woods. See you at dark!’ He taught me how to
fish, rock-climb, camp, shoot with a bow and an air rifle. Czechoslovakian summers were
my introduction to ‘the great outdoors’ and an era that lives in me that I hand down to
my children.… I miss him. I will always miss him.”

People close to Don say Milos is the key to understanding him. The imprint stamped on
Don as a boy by his grandfather is still evident, says Anthony Scaramucci, a Trump ally
who briefly served as White House communications chief: “He's a very down-to-earth,
grounded guy, and I think a lot of that comes from his mom's parents, who he used to
summer with. Spending several months in [Communist] Eastern Europe, seeing the
difference between what was happening in Eastern Europe in the 1980s and his life in
New York—it gives grounding and perspective.”

For a child raised in a gilded triplex, Don seems to have gotten a disproportionate share
of what pain there was to go around. Shortly after his grandfather's death, Don found
Bridget, one of his nannies, passed out from a heart attack in the basement of Ivana's
Greenwich home. He called the ambulance and the adults, but she was pronounced dead
at the hospital. When his mother remarried, her new husband's son roughed up and
choked the then adolescent Don. On top of that, when Junior, at age 15, tried to take a
girl on a date, it immediately made it into the tabloids: Ivana wanted the world to know
that she had armed him with condoms.

“Poor Don. He really got the brunt of everything,” Ivana wrote. “No wonder Don likes to
go in the woods and escape from everything.”

...................................................

When Don headed off to

college at the University of
Pennsylvania, his father's alma
mater, his relationship with his
dad seemingly hadn't fully
recovered. Mad as he was at
Donald Trump, Don was also
Donald Trump, but smaller,
less accomplished, and more
wounded. He assumed a
posture of studied normalcy
and stuck to being Don, rather
than Donald Trump Jr. “He
wasn't quick to volunteer his
name or put it out there who he
was or try to use that to his
advantage,” says the college
friend. “I remember thinking
that if he used his name more,
he probably could've gotten
more girls.”

A freshman-year friend, Dan

Friedman, remembers a
strange conversation on that
theme. Friedman says that one
day, as he and Don sat in a Illustration by Nigel Buchanan

dining hall, Friedman jokingly

warned him to watch out for
girls—gold-digger types—who would try to take advantage of him. “And he said, ‘What do
you mean? I don't know what you're talking about,’ ” Friedman recalls. “I think he was
playing dumb; he knew what I was talking about. He didn't go as far as denying his
identity, but it was very clear that he wanted to downplay it.”

It wasn't just the Trump name that Don avoided; he apparently steered clear of his
father, too. A former classmate recalls how “Don's dad came to campus to give a speech,
and he refused to go because he was mad at his dad over divorcing his mom.” (The
Trump camp disputes this classmate's recollection, claiming Don was seated in the front
row.) Don's anger expressed itself in other ways, too. “He had a reputation as the kind of
guy who would get to drinking and start fights,” says a college acquaintance. “He was a
fall-down drunk.”

In June 1999, the summer before Don's senior year, Fred Trump, Donald's own
overbearing and emotionally abusive father, passed away. Don didn't seem to feel the
same private grief that he'd harbored after the death of Milos. He asked a few of his
friends to go with him to the wake because he didn't seem comfortable being alone at the
event. “A few of us went to the wake with him, and I just remember how peculiar the vibe
was,” recalls Don's college friend. “It was the only time I met his dad. It just had a
cocktail-party vibe. It was just odd.” (The Trump camp disputes this, claiming Don did
not bring friends to his grandfather's wake.) After graduating, Don escaped to Aspen and
spent a year and a half doing what he loves most, hunting and fishing—and avoiding what
he must have felt was inevitable: going to work for his father.

But in 2001, Don did just that. He succumbed to the centripetal force that is the Trump
Organization—“It's very hard to veer from that track,” Don has said—by joining the
family firm. Very quickly his job became doing whatever chore was in the offing—a sui
generis job he's held for years. “Don, like most other people, gets assigned to a project
and winds up overseeing all the various aspects, from construction, marketing, design,”
says Sater. “Sometimes he works in tandem with Ivanka or Eric, and then reports to
Trump. They share or split main responsibilities. He's worked on pretty much everything
over the last ten years. Don has had his hands in just about every Trump project over the
years.”

In those early days back in New York, the assiduously private Don also found that the
tabloids, which had made his parents famous, were waiting for him. Just before his 25th
birthday, Don went to see Chris Rock at Manhattan's Comedy Cellar. He got a little
drunk. Sources later told the New York Post that “people at a neighboring table thought
Trump was reacting too enthusiastically to [Rock's] ethnic humor.” Three couples said
they asked Don to pipe down but that he refused. Finally, two young men his age took
matters into their own hands—the matters being their beer steins, which they lobbed
directly at Don's triangular brown mane. Don was taken to St. Vincent's to have his head
stitched up, and according to the Post, the two barroom vigilantes were released on bail.
(“I'm going to get those motherfuckers, that's for sure,” Trump senior told the New York
Daily News.)

Eventually, Don stopped drinking and started dressing like his father, a cartoon of a
Manhattan capitalist, all pinstripes and wide lapels and pastel satin ties. He mended
things with his father, or at the very least gained some awareness of his dad's view of the
divorce. By 2004, he was telling New York magazine that perhaps it wasn't just his
father's fault: “But when you're living with your mother, it's easy to be manipulated. You
get a one-sided perspective.” In 2006, he referred to himself as “a brat” for having once
hung up on his dad. Somewhere along the line, outsiders could see why the two men had
the same name. “Don also has a big personality,” Nunberg says. “He's got that larger-
than-life persona, like his father; he has his big, nice office on the 25th floor; and you
hear him beating the shit out of someone on the phone, like his father.” (Another source
warned me about Don's “quick temper.”)

In interviews from this time, he is an eager carnival barker, selling his father's brand
while also eagerly trying to demonstrate how much he has learned about business—the
business. Soon, he glimpsed the wisdom of lending his valuable name to other people's
projects. In 2010, he signed on to help hawk Cambridge Who's Who, a self-billed “leading
professional branding and networking organization.” In a promotional video for the firm,
Don says over the soft tones of a keyboard that “Cambridge Who's Who is your exclusive,
by-invitation-only, private PR firm.”

The company, headquartered “in Long Island's premier office building,” turned out to be
less than premier. Its then president, Randy Narod, once owned a nightclub and a bagel
store and had been barred from the securities industry after sending someone to sit for
his exam. By the time Don came on as a spokesman, Cambridge Who's Who had amassed
some 400 complaints filed with the Better Business Bureau, according to The New York
Times.

Despite some successes, like overseeing the construction of the Trump International
Hotel & Tower in Chicago, Don continued to get his famous name caught up in the wrong
deals. In 2006, he helped launch a mortgage brokerage called Trump Mortgage, bragging
that it was the “only company in a $3 trillion industry that anyone has actually heard of.”
Within months it was defunct, an early casualty of the housing crisis. In 2006, he was
kicked off the condo board of the Trump apartment building at 220 Riverside Drive in
Manhattan, amid board members' concerns that $80,000 of the condo's money had
disappeared on account of nebulous “office expenses.” (He was eventually reinstated.)

The setbacks seemed not to trouble Don, who never had the requisite hunger to be the
true titan of commerce, the man he saw in his father. Don was happier hunting or sitting
by the pool at Mar-a-Lago than closing deals. He enjoyed the fruits of his father's labors
more than he liked laboring for more fruit. “He has a more balanced life,” a source close
to Don told me. “It's harder to become a captain of industry if you don't make a lot of
sacrifices.”

“I feel bad for him, honestly,” said a person at the 2016 Trump
Tower meeting.

And so Don has seemed content to take direction from his father—and not merely on
matters professional. One night in 2003, while father and son were attending an event,
Donald Trump spotted a blonde woman and pointed her out to his son. She was Vanessa
Haydon, a young model who had made news dating Leonardo DiCaprio and a Saudi
prince. “Vanessa walked in front of me at this big fashion show,” Donald Trump recalled
on Oprah's show in 2011. “She looked so beautiful, I said, ‘Don, that's the person you
should marry.’ ” According to Vanessa's own recollection, shared with the Times, the
forgetful Trump accidentally introduced her to his son twice. Then, when she ran into
Don several weeks later, she remembered him as “the one with the retarded dad.”

Despite his father's hand in their coupling, Don earned a scolding from his dad over the
way he proposed—a Trumpian publicity stunt in which he scored a free engagement ring
by popping the question in a jewelry store at the Short Hills mall in New Jersey. “You
have a name that is hot as a pistol,” Trump senior told Larry King, lamenting the
situation. “You have to be very careful with things like this.”

By all appearances, the stylish Vanessa fit right in as the newest Trump. But she had her
own complicated adolescence. Her wealthy father, Manhattan attorney Charles Haydon,
was actually her stepfather. As newly minted Haydons, Vanessa and her sister were
catapulted into a life of posh prep schools and a home on the Upper East Side.

Vanessa's rebellion, a friend from that time recalls, was very specific: She dated a young
man named Valentin Rivera, who told people he was a foot soldier for the Latin Kings, a
Hispanic gang. Rivera, who recently went public in an interview with the New York Post,
was raised in an apartment atop the Yorkville branch of the New York Public Library,
where his father was the caretaker. According to the article, Rivera delivered weed
around the city. Vanessa apparently reveled in all this. “She talked with an urban,
gangster accent,” the friend remembers. “She wore big hoop earrings, hair slicked back.
She thought she was a gangster. She had a gangster boyfriend, and she acted like a
gangster herself. She was somebody who went out of her way to intimidate people by
having a scary boyfriend that could hurt people.”

Vanessa seemed very much in love with Rivera, as much as a teenager could be, and
despite her family's disapproval, when Rivera found himself in Rikers Island for assault,
she visited him there. The couple eventually went their separate ways, and in the years
that followed, Rivera, who could not be reached for comment, was jailed several times for
crimes ranging from weapons charges to negligent homicide.

Before Vanessa married his son, though, Donald Trump apparently did his due diligence
and discovered that his future daughter-in-law had dated a Latino gangster—a bad look
for an image-obsessed family. Trump called Vanessa into his office and confronted her
about her relationship with Rivera. Vanessa flatly denied it.

...................................................

Joe Raedle/Getty Images

By the time his father ran for president, Don had cultivated a public image as a kind of
prudent sidekick. He appeared on The Apprentice as an earnest good cop to his dad's
bellicose “You're fired” character. As Don peddled his father's business ventures around
the world, he came into plenty of contact with Russians. “In terms of high-end product
influx into the U.S., Russians make up a pretty disproportionate cross section of a lot of
our assets, say, in Dubai and certainly with our project in SoHo and anywhere in New
York,” he said at an industry conference in 2008. (The Trump SoHo project, which he
developed with Sater, ended up being sued for fraud, resulting in a settlement.) “We see a
lot of money pouring in from Russia.”

Don repeatedly tried to develop Trump properties in Russia, but despite the country's
lucrative oil boom—and the gilded dovetailing of Trump and Russian aesthetics—he
couldn't quite manage Moscow and its corruption. “It is a question of who knows who,
whose brother is paying off who, et cetera,” he said after making half a dozen trips there
in a year and a half. “It really is a scary place.”

The most infamous of his failed Russian deals—the one that backfired monumentally and
now may imperil his father's presidency—had nothing to do with real estate. In June
2016, when a set of Russians with oblique ties to the Kremlin reached out to Don through