The Key to Understanding Don Jr.

The president’s eldest son is entitled, oafish, combative—and desperate for his dad’s approval.

Donald Trump Jr. attends the inauguration of his father at the U.S. Capitol on Jan. 20.

Saul Loeb - Pool/Getty Images

Donald Trump Jr. has all the obvious traits of his father: He’s belligerent, dim, and mired in everlasting childhood. But the president’s firstborn is a work of art in the age of mechanical reproduction. He is to Donald J. Trump as a postcard of the Mona Lisa is to the actual Mona Lisa—the image of the thing, absent its original aura. Don Jr. may be as privileged and petty as the president, but his indistinctness prevents him from commanding our gaze the way his dad does.

That hasn’t stopped the 39-year-old executive vice president of the Trump Organization from trying to make a strong impression. Consider:

In addition to tweeting about the libs and exchanging direct messages with Wikileaks, Don Jr. also takes the occasional in-person meeting. In June 2016, he reacted with smirking glee to an email promising dirt on Hillary Clinton, writing to the shady operatives with whom he subsequently confabbed: “If it’s what you say I love it.” Despite the presence of allegedly Kremlin-backed hackers in that Trump Tower tryst, the president’s eldest child testified before the Senate in September that “I did not collude with any foreign government and do not know of anyone who did.” The Washington Post described Don Jr.’s stance vis-à-vis the Russia meeting as “defiant.” Seth Meyers opted for plainer language. “He’s the dumbest member of a family in which there is stiff competition,” the NBC late-night host said. Declaring that the elevator inside Donald Trump Jr.’s skull doesn’t go all the way to the top feels like it lets him off the hook for his odiousness. It also feels true, most of the time. If the Trump administration colluded with the Russians, Don Jr. was clearly not the brains of the operation.

What is going on inside Donald Trump Jr.’s head? To scroll through Don Jr.’s social media feeds is to experience whiplash from the flapping of a lost soul. It’s clear the first son has something to prove; what’s less clear is exactly what that is. The younger Don’s Twitter and Instagram accounts conjure a struggle between all-American domestic contentment and restless, roaming pugnacity (or maybe between a sophisticated PR apparatus and an inveterate boor). He seems eager to project all the carefree trappings of a golden family man, yet he can’t quiet his hyperactive biliousness long enough to sell that curated narrative. Unlike conciliatory Ivanka or invisible Tiffany or robotic, fugue-state Melania, Don Jr. is provocative and confrontational, exuding a mix of toxic masculinity, smug entitlement, and self-owning oafishness.

In addition to the occasional pitch for a Trump Organization product, Don Jr.’s social media feeds feature attacks on his father’s enemies (from Elizabeth Warren to kneeling NFL players to Keith Olbermann to the New York Times). His assaults are typically as clumsy as they are mean-spirited. When the Gray Lady tweeted out an opinion piece warning, “If you let boys be boys, they will murder their fathers and sleep with their mothers,” Trump failed to grasp that the Times was using the Oedipus story hyperbolically to make the point that civilizations have long intuited the dark sides of male desire and felt a concomitant need to regulate it. What resulted was a twirling triple axel of misapprehension, incoherence, and ignorance in which he suggested that he believed Oedipus was a real person:

A Freudian might note that the idea of manhood appears to twist the presidential scion into anxious knots. He takes care to paint himself and his family as “real men,” whether that means documenting his Crossfit workouts, posing majestically in the wilderness, or posing majestically in the wilderness with big weapons. Over Thanksgiving, he uploaded this photo of his two camouflage-clad sons in the branches of a tree:

Like his dad, Don Jr. is obsessed not just with picking fights but with proving in real time that he is winning all of the many battles he’s currently waging. He frequently retweets his own tweets, including one that cast him as a patriot in the American Revolution. He also has a habit of dropping his tweets into Instagram, where he adds captions that lavish his own words with garlands of approval and validation. A typical caption: “Yup! Sounds like a smart guy”—and don’t forget to tag @foxnews.

Presidential children have traditionally been tasked with depoliticizing their parents, as if by purging themselves of opinions they might come to embody the intimate, fireside warmth we long to feel from the first family. Don Jr., who couldn’t humanize a strand of human DNA, invites us to take pity on his own children, like when he used his daughter’s Halloween outing as an opportunity for a lecture on the evils of socialism:

First of all, no kid wants to sit at home while her friends trick-or-treat. Second, the Trump family is a case study in unearned advantages. Third, “sharing is bad” does not seem like the best lesson for a 3-year-old. Fourth, I regret to inform you that this wasn’t the first tweet in which Don Jr. leveraged candy into a political controversy that demonstrated the astonishing scope of his selfishness, callousness, and punchability. In September 2016, he tweeted a picture of some Skittles with the caption: “If I had a bowl of skittles and I told you just three would kill you. Would you take a handful? That’s our Syrian refugee problem.”

When he is not comparing humans fleeing war crimes to chewy fruit-flavored morsels, he’s grinning next to the big game he’s killed (“I’m not going to run and hide because the peta crazies don’t like me,” he retorted) or wading into white nationalist–infested waters and then scratching his head at “haters” who expect him to know whom he’s amplifying.

During his father’s campaign, Don Jr. spread a false story, originating with the alt-right figurehead Vox Day, that a woman giving a Nazi salute at a Trump rally actually supported Bernie Sanders. “It just popped up in my timeline when someone retweeted it,” he demurred. After posting an image of Trump Sr. that included the photoshopped head of Pepe the Frog, a white supremacist icon, the first son told Good Morning America: “I thought it was a frog in a wig. I thought it was funny. I had no idea that there’s any connotation there.” In March 2016, after he participated in an interview with a self-described “white advocate” who once praised slavery as “the greatest thing that ever happened” to black people, Don Jr. informed Bloomberg Politics, “He was brought into the interview without my knowledge,” adding, “Had I known, I would have obviously never done an interview with him.”

These threadbare excuses distill something vital about Donald Trump Jr., the callow son who can’t be held responsible for his actions. He is forever unfledged, climbing the shaky tree he’s not supposed to touch. Profiles of Don often portray him as a forlorn child, materially indulged but denied his father’s love. In one now-famous anecdote posted to Facebook by a classmate of Trump’s at the University of Pennsylvania, the real estate magnate showed up at his kid’s dorm room to take him to a baseball game during his freshman year. “Don Jr. opened the door, wearing a Yankee jersey,” recalled Scott Melker. “Without saying a word, his father slapped him across the face, knocking him to the floor in front of all his classmates. He simply said ‘Put on a suit and meet me outside,’ and closed the door.” (The Trumps have said this didn’t happen.)

Junior’s relationship with his dad can be read as an interlocking series of estrangements and humiliations. According to a New York piece from 2004, father and son didn’t speak for a year following the elder Trump’s divorce from Ivana. Donny was a moody kid, irascible, difficult to reach, and famous for picking “drunken, ‘do-you-have-any-idea-who-I-am’ fights.” Upon earning his college degree, he spent a booze-soaked year as a bartender and ski bum in Aspen, Colorado, before returning to the embrace of the family business. Despite his newfound respectability and commitment, his father’s affection remained elusive. When Don Jr. proposed to his now-wife, Vanessa, Donald went public with a critique of his child. Don Jr. had struck a deal with a jewelry store to get a free ring, worth $100,000, in exchange for re-creating his proposal at a shopping mall. The New York Post’s headline: “Trump Jr. Is the Cheapest Gazillionaire—Heirhead Proposes With Free 100G Ring.” The patriarch’s complaint to Larry King: “You have a name hot as a pistol, you have to be very careful with things like this.”

More recently, Trump brought his winking paternal contempt to bear on a speech in which he anticipated firing Don Jr. and his middle son, Eric, if they bungled the management of his company. A friend of the family told the Washington Post: “Don barely talks to his father, and they barely see each other. … It weighs on him. It does.” (“I feel ridiculous bothering him,” Junior admitted to the Times in March.) Meanwhile, the snubbed firstborn seems more loyal than ever. He tours the nation giving political talks on his dad’s behalf and defends the White House’s every move on Twitter. He suited up as the president for Halloween (presumably before redistributing Chloe’s candy). His office in Trump Tower features a prominently displayed bobblehead of his father alongside photographs of his children, which (with a kind of poetic haplessness) are angled in the wrong direction.

Don Jr., known to friends and family as the “down-to-earth,” “contemplative” Trump, occasionally takes the guise of a sensitive outdoorsman with a melancholy streak. A Twitter meme from March—aptly dubbed “Sad Donald Trump Jr.”— pictures him perched awkwardly on a tree stump, gazing into the distance. Politics, he’s said, “is incredibly enticing. But it’s not human most of the time.” Nature is more comforting. “I wish I got as excited about anything as much as a bird dog going after a pheasant,” he once told reporters.

How should we reconcile Don Jr.’s obnoxiousness with his mournfulness? His chest-thumping tweets, coupled with his family drama, add up to a picture of loneliness warped into aggression. Don Jr. is Trump’s spurned attack dog. He will never catch the pheasant he so desperately wants to crush between his teeth, so he spends his days growling instead. But maybe this redirected self-loathing conceals a more dangerous anger. When Junior claims that Elizabeth Warren is “a fraud … pretending to be something [she’s] not,” or that Hollywood is full of con artists “pretending to be something they’re not,” who is he really attacking? His terror of being exposed as an imposter must exist alongside his knowledge that his dad is the ultimate fake—as a president, and also as a parent.

“In principle, a work of art has always been reproducible,” Walter Benjamin wrote in his treatise about originals and replicas. But in this case, the knockoff doesn’t just degrade the authenticity of the first piece—it exposes its underlying fraud. To earn his father’s love, Trump Jr. will play the lesser version of his dad. He will sneer at the Donald’s haters, regurgitate right-wing talking points, and live the picture of a wealthy scion wafting through the world on his precursor’s achievements. Yet in embodying the president’s traits—his bullying, clumsiness, status-consciousness, and hedonism—Don Jr. isn’t just channeling his familial disappointments into a full-throated defense of his terrible kin. He is also revealing the old man’s fragility. Trump the junior aches for his dad’s approval as Trump the elder craves ours. In pretending they already possess what they so helplessly want, the two men have never looked more alike.