The Real Story of Donald Trump Jr.

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.
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Illustration by Nigel Buchanan

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, the hunter's camo he's worn has helped him not to disappear but to stand out, to differentiate himself from his father, the real estate tycoon who never understood his son's 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.”


Illustration by Nigel Buchanan

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 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.”

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 an intermediary promising damaging information on Hillary Clinton that “would be very useful to your father,” Junior couldn't have been more curious. “If it's what you say,” Don infamously wrote back to them, “I love it.”

According to evidence and testimony released by the Senate Judiciary Committee, Don next made a few calls, a couple to Russia and a couple to a blocked number. (Investigators pointed out that Donald Trump Sr. uses a blocked number.) Don then set up a meeting at Trump Tower with the Russians, one of whom—lawyer Natalia Veselnitskaya—was said to be connected to the Russian prosecutor general, an old ally of Vladimir Putin.

And so on June 9, 2016, Don—along with his brother-in-law, Jared Kushner, and Trump campaign manager Paul Manafort—began a fateful confab in a conference room in Trump Tower. According to a person who was there, after some pleasantries about the view of Central Park, Don got straight to it.

“So I believe you have some information for us?” he asked. Veselnitskaya began reading from prepared remarks about DNC donors the Ziff brothers, their alleged tax evasion, and the connection she saw between them and Putin critic Bill Browder. According to testimony, Don tried to get the conversation back on track. “ ‘So can you show us how does this money go to Hillary?’ ” two of the participants recall him asking. Veselnitskaya shot back, “Why don't you do your own research on her? We gave you the idea.”

According to one of the participants in the meeting, Don began to realize he wasn't going to be handed what he was hoping for. “The light just went out in his eyes,” the participant told me recently. “He was totally disinterested.”

Veselnitskaya then went into a long, tangled exposition about the Magnitsky Act and the adoption of Russian children, but it seemed like the two sides were now talking past each other, says the participant. Manafort seemed to fall asleep. Kushner grew agitated, asked why they were talking about adoptions, and left. According to the meeting participant, Don recognized that things had turned futile—but offered to stay in touch. The participant said Don had a parting message for the Russians: “ ‘When we win’—he said when, not if—‘when we win, come back and see us again.’ ”

That meeting, which Don had hoped would prove useful, has since become as useful as a hole in the head. It is now a prime focus of the investigation led by special counsel Robert Mueller into potential collusion between Russia and the Trump campaign.

“I think he regrets taking the meeting,” a source close to Don told me. “Does he regret it because he thinks he did something wrong? No. He regrets it because it ended up causing a situation that wasted a lot of time and money.”

The New York Times recently reported that Don also met with an Israeli and an emissary from two Arab princes seeking to help his father win the election.

“Maybe he's not an intellectual, but he tried to be useful for his family,” the participant from the Russia meeting told me. “I feel bad for him, honestly.”

Last fall, when Don was called before the Senate Judiciary Committee, which was investigating potential links between his father's campaign and the Russian government, he seemed oblivious to the gravity of the mess he'd created. “In the breaks between the questions, he was making dumb jokes about how absurd it was that he was even there,” says a source familiar with the investigation. “He had this sense of impunity at a time when it was dangerous, when it seemed like it was the Hill that would get them.”

Instead of being wary of his questioners, Don wanted to be helpful and calmly acknowledged that he had corresponded with WikiLeaks during the election. He then happily turned the correspondence over to congressional investigators, helpful as ever. “He wasn't embarrassed to be revealing that he had exchanged DMs with WikiLeaks,” says the source, even though it was by this point abundantly clear to the American officials that WikiLeaks had links to Russian intelligence. “He's too stupid to be malicious.”

The source's impression of Don was that he, like seemingly everyone else in Trump's orbit, was uselessly trying to impress a man who can only be impressed by himself. “He's hustling and trying to do what he can to contribute but without knowing where the lines are,” the source said of Don, adding ruefully, “He's a sad and tragic figure.”


John Moore/Getty Images

Useful as Don has tried to be to his father, his blunt re-invention as a political warrior has perhaps been costly in surprisingly personal ways. In March, as Mueller's investigation gathered steam, Vanessa filed for divorce. The New York tabloids, descending on the carrion of yet another Trump marriage, speculated that Don's political transformation and volatile social-media presence were to blame. Rumors began to circulate in Trump World that Don had taken to drinking again.

When news of the divorce broke, the papers dug into Vanessa's past and reported on the marinara fortune she suddenly inherited—a windfall that seemed to free her from Don, who, the tabloids wrote, had kept her on a tight financial leash. (A rep for Vanessa denied the allegations of money problems between her and Don.) “Page Six” also unearthed an old affair Don allegedly had with flash-in-the-pan pop star Aubrey O'Day, whom he'd met on the set of Celebrity Apprentice. It had been Don's father, “Page Six” claimed, who'd ordered that illicit relationship to end in 2011. According to another report, Trump's fixer, Michael Cohen, had been called in to keep the story quiet. In Don's marriage and in its breach, it seems it was his father who called the shots.

For her part, O'Day has declined interview requests but continues to fuel conversation. It was revealed that after the illicit romance supposedly ended, O'Day recorded a hardly veiled ballad called “DJT.” And days after news broke this past spring that Don had moved on to date Fox News host Kimberly Guilfoyle, O'Day wrote on Instagram, “He's still searching for me in every other woman.”

The perennial tabloid fascination with Trump-family drama might not surprise Don, but it apparently now stings him. After a childhood seared by the trauma of divorce, he's keenly aware that his five children are today in the same position he once was. His eldest, Donald Trump III, is now 9—old enough to wonder why his family's struggles are in the papers, much like Don junior once had. “The way he looks at everything [written about him in the press] is ‘What will the kids think?’ ” says Don's friend, “and the answer here ain't a good one.”

And yet for all the tumult—and for all the lingering legal woe the Mueller probe portends—there's perhaps another way to glimpse these prismatic days of Donald Trump Jr.'s.

His father, by virtue of being in the Oval Office, is no longer in the one directly above him, which, by some accounts, has freed Don up to thrive—to court attention or to settle scores on his own terms.

There's little doubt that as a political creature, Don has grown more sure-footed. Once reportedly derided by Trump campaign staffers as “Fredo,” the Corleone child who can't seem to do anything right except endanger his family legacy, Don has now become one of Trump's most useful spokesmen.

“It's not that he doesn't want the Trump Organization to succeed, but I think he's enjoying the challenge of his political efforts,” says the source close to Don. “And it's more exciting than what he's been doing for the last 20 years. This is something new in his life that he happens to be good at.”

Scaramucci told me about a night in Pittsburgh, just before the election, when he took notice of the effect Junior was starting to have. Don was scheduled to talk to a crowd that the local officials figured would be about 400. “Over 3,000 showed up to hear him speak,” Scaramucci said, noting that Don has clearly found a voice and tuned it to a frequency that resonates. And in the coming months, he'll be making a big push to campaign for Republicans ahead of this year's midterms—firing up his father's base. “He's not really even a surrogate; he's a substitute,” Scaramucci told me. “You see the difference?”

Like Republican populists of the past decade, Don speaks of “real Americans,” people he defines as “the forgotten people between New York City and Malibu.” It's an improbable notion: that the billionaire's kid from 66 stories above Fifth Avenue is the one who speaks for the disaffected and the overlooked. But it's no less surprising than the faint rumors suggesting that he might someday run for office—a way to finally, perhaps, make a name for himself.

Julia Ioffe is a GQ correspondent. She wrote about the rise of Melania Trump in the June 2016 issue.

This story originally appeared in the July 2018 issue with the title "Junior! The Real Story of Donald Trump Jr."