WICHITA FALLS, Tex. — Donald Trump Jr. was onstage, telling 1,500 Texans what impresses him about Ted Cruz.
During the 2016 presidential primaries, his father — President Trump — called Cruz “Lyin’ Ted,” implied Cruz’s wife was ugly and falsely suggested that Cruz’s father helped assassinate President John F. Kennedy. Cruz quickly fired back, calling the elder Trump “utterly amoral.”
The impressive part came after that, Trump Jr. said. After Cruz lost, he returned to the Trumps and made peace. He even asked for their help with his reelection.
“That. Wasn’t. Easy,” Trump Jr. said, emphasizing each word. Cruz nodded as Trump Jr. cast the senator’s pivot as proof of his character. “I don’t know if the shoes were reversed that I could have done that.”
For Trump Jr., this was a lesson to live by: If you rebel against Donald Trump, the smart move is always to come back into the fold.
Trump Jr. himself has learned this the hard way. As a young man, he fled to Colorado, far from his father’s empire. More recently, he sought to carve out his own identities, separate from his father’s flame-throwing politics. Trump Jr. said he’d be a voice for conservationists. He said he’d be an independent businessman, withdrawn from politics.
None of those separations — physical or political — lasted very long.
Today, the conservationists still want Trump Jr.’s help, but he has stopped texting them back. The Trump Organization is struggling to hang on to its hotels, but Trump Jr. — one of its top executives — spent much of the fall on the campaign trail, in Texas, Montana, Florida, always on the move.
Trump Jr. has become his father’s top surrogate for a Republican Party that is making the same journey he did: from rejection and rebellion to acceptance and, ultimately, to remaking itself in Trump’s image.
Donald Trump Jr. addresses a standing-room-only crowd at a July rally for Republican Ron DeSantis’s Florida gubernatorial campaign in Orlando. He has made about 70 campaign stops for Republican candidates this year. (Willie J. Allen Jr./for The Washington Post)
At rallies and on social media, the president’s oldest child adopted his father’s approach to campaigning — a mixture of bragging, grievance, flirtation with far-right figures and gleeful trolling of liberals and the media.
It’s not clear where he’s headed, but he’s not going to stop.
“Basically, Trump Jr. is the voice of undiluted Trumpism,” said longtime Trump confidant Roger Stone, meaning that the son is a fighter, striking back at any and all enemies.
During the campaign for the midterms, Trump Jr., who declined to comment for this story, made about 70 campaign stops for Republican candidates.
Onstage, he’d start by sketching his life history, beginning with a story about breaking away.
“I’m the first graduate of the Wharton School of Finance — where my dad went to school — to move out to Colorado, actually, to be a bartender and a fly-fishing guide on the side,” he told a Montana radio station this year.
Up to that point, Trump Jr. had a sometimes distant relationship with his famous father, friends say. The son spent summers in Czechoslovakia, with his mother’s parents. His parents’ marriage broke up — bitterly, publicly — when he was 12. He didn’t speak to his father for some time after that.
In Colorado, the son added physical distance to the emotional divide. He partied and tended bar, but he also spent time hunting and fishing. He developed two qualities his father never had time for: patience and an appreciation for silence.
He still savors those unTrumpian attributes — at least, when he’s hunting.
“We were in a snowbank,” recalled Doug Hurley, Trump Jr.’s guide during a 2014 deer hunt in Iowa. “He was next to a fence post, and I was next to an evergreen tree. It was extremely cold; the wind was blowing directly on us.” After four hours, Hurley said, darkness fell and they had to head home.
“I fist-bumped him,” said Hurley, who is also a narcotics investigator for the state of Iowa. “I’m like, ‘New York City? I didn’t think you could handle it.’ ”
But while his youthful sojourn in Colorado left a lasting imprint on Trump Jr., he stayed only a year, coming home to Manhattan and taking a job at the Trump Organization, as his brother Eric and sister Ivanka eventually would, too.
Trump Jr. had delayed the life his father chose for him. He hadn’t derailed it.
“Did you ever consider any other career?” a lawyer once asked Trump Jr. during a deposition.
“Probably not [since] when I was very young,” Trump Jr. said.
At the Trump Organization, Trump Jr. and his siblings played an advisory role to their father — both in real life and on NBC’s “The Apprentice.” At the same time, Trump Jr. and Ivanka Trump began to create public personas, becoming celebrities in their own right.
Ivanka played the high end: She modeled, designed women’s wear and projected a reserved glamour. Her brother did the opposite. He took up his dad’s old role as a talk-radio guest, pushing boundaries and mocking the politically correct crowd. “You can’t even make fat jokes now!” he said on the raunchy “Opie and Anthony Show” in 2012, according to a clip unearthed by CNN.
Trump Jr. made his love life into a public performance, just as his father had, even if the audiences were smaller.
His father, for instance, once announced his engagement on national TV. Trump Jr. got engaged at a mall in Short Hills, N.J., as part of a publicity stunt for a jewelry store.
After he was married, Trump Jr. also had a habit of tweeting out public messages to attractive women.
“@Hopedworaczyk towel in bubble bath u just ruined every pervs night including me,” Trump Jr. wrote at 10 p.m. one evening in 2011, eschewing punctuation in a public Twitter message to model Hope Dworaczyk. He seemed to be referring to a photo or video of Dworaczyk. “Yes wife will B beating me again when she reads this! 3 2 1.”
When his father reinvented himself as a politician, the son got a chance to reinvent himself, too.
“‘Don, what do you know about politics?’” he recalled his father asking at the start of the 2016 campaign.
“I dunno,” he replied, “I watched the news last night.”
In his father’s threadbare campaign, that was enough.
Trump Jr. said his father’s campaign staff directed him to “get out there and get started!”
On the trail, Trump Jr. found that his love for hunting and familiarity with rural America — traits that made him distinct from his father — were valuable currency.
For a time, Trump Jr. offered a vision of a different role for himself, beyond being his father’s attack dog.
He told conservation groups — often skeptical of his real estate developer father — that he’d be their ally in the White House, fighting to protect wildlife habitat and hunters’ access to federal lands.
“For me, hunting and fishing is my lifestyle. It’s how I choose to live my life,” Trump Jr. told the Theodore Roosevelt Conservation Partnership, a conservative-leaning environmental group, in 2016. He said he would be “the voice in my father’s ear on all of these issues, preserving this.”
Trump Jr. speaks at a campaign rally in Bozeman, Mont., in September in support of Senate candidate Matt Rosendale, who is challenging incumbent Sen. Jon Tester (D). (William Campbell/Corbis/Getty Images)
‘His role is just very different’
At the Republican convention in Cleveland that summer, amid a program of speeches heavy on doom and worry, Trump Jr. used his prime-time slot to offer something different: an upbeat, optimistic speech aimed at undecided voters, not the GOP base, casting his father as a unifier.
“We’ve lost the confidence in our leaders and the faith in our institutions,” Trump Jr. said. “But remember one thing: We’re still Americans, we’re still one country, and we’re going to get it all back.”
The speech seemed like an organic extension of the family man persona — Trump Jr. and his five children celebrating birthday parties, practicing golf swings and goofing around together — that he had touted in social media posts, even if those images were mixed in among others that trolled liberals and peddled conspiracy theories.
When his father won, and Ivanka followed him to Washington, Trump Jr. and Eric were given control of the Trump Organization. They vowed to step back from politics — “It’s not human most of the time,” Trump Jr. told the New York Times — and focus on the business.
Their plan: build dozens of new hotels, mostly in smaller cities, which would turn Trump voters into Trump Organization customers.
Then-candidate Donald Trump, center, accompanied by, from left, Donald Trump Jr., Eric Trump, Melania Trump, Tiffany Trump and Ivanka Trump, prepares to cut a ribbon in October 2016 during the opening ceremony of the Trump International Hotel in Washington. (Jabin Botsford/The Washington Post)
“If we add that American context that we experienced in each one of these little towns, the personality that we got from each one of these people and each one of these stories, there’s something amazing that we can do here,” Trump Jr. said five months after his father entered office.
Trump Jr. had laid out three possible roles for himself: conservationist, uniter, businessman.
None lasted.
On conservation, Trump Jr. did have some impact early on: He helped choose Rep. Ryan Zinke (R-Mont.) as interior secretary. Conservation groups approved, believing the other candidates would give too much leeway to oil and mining interests.
But after that, Trump Jr. seemed to cut off contact with environmentalists.
“Hey, I need to talk to you,” Whit Fosburgh, head of the Theodore Roosevelt Conservation Partnership, texted to Trump Jr. last year, hoping to ask for his help again. Fosburgh felt that, despite Zinke’s appointment, the Trump administration was still giving oil and mining companies the upper hand.
“He wrote back, ‘Sorry, I can’t help you,’ ” Fosburgh said. He said Trump Jr. explained that media scrutiny of his role had caused him to give up his policy influence.
In recent weeks, the Trump administration hired a lawyer who had long criticized federal policy protecting public lands to take charge of crafting legal opinions about those policies — exactly the kind of move conservation groups had hoped Trump Jr. might prevent.
“Don could have been very helpful,” Fosburgh said. Instead, “he’s off the radar.”
Trump Jr. appears not to have had any significant impact on administration policy decisions — a sign that he may have stuck to his vow to steer clear of his father’s government, though not his politics.
“I’ve never been in a meeting where somebody said, ‘Let’s check with Trump Jr. before we make a move,’ ” said one White House official, who spoke on the condition of anonymity to comment on internal discussions. The official said Trump Jr. may have the least influence at the White House among the president’s three eldest children: Ivanka is a White House staff adviser, and Eric’s wife, Lara, is a senior adviser at the Trump reelection campaign.
“His role is just very different,” the official said. “He’s helping to run the family business. Carry on the name. And he’s on the campaign trail.”
At the Trump Organization, the planned hotel expansion hasn’t happened. Instead, the company has fought to hang on to its existing hotels, as President Trump’s rise curdled the brand in some quarters.
“I personally don’t think the Trumps are in great shape, and in terms of the name, it’s probably going to get worse, not better,” said Douglas Russell, chairman of the board of managers at Trump’s hotel in Manhattan. Earlier this year, meeting minutes show, Trump Jr. had to personally argue against a proposal to remove the Trump name from that hotel.
Beyond that, Trump Jr. has mainly stepped back and let Eric wrestle with the Trump Organization’s problems.
Trump Jr. still goes to the office regularly, but friends say he has told them there isn’t much opportunity to expand the business while his dad is president: It’s an “asset management” business now, which doesn’t need his full attention.
Instead, his attention shifted to politics. His father’s shadow had moved, and Trump Jr. ran to catch up with it.
“He’s the No. 1 requested speaker, hands down,” said his friend Charlie Kirk, who, along with Trump Jr. and Dallas businessman Gentry Beach, careened through swing states together in the months leading up to last week’s elections.
This year, Trump Jr., working with a few former GOP campaign officials, spoke at rallies and fundraisers for Republican candidates across the country. Campaign operatives say they value him for his versatility: He’s good with wealthy donors at high-dollar fundraisers. He’s good on stage, with a crowd.
Trump Jr. addresses the Republican National Convention in Cleveland in July 2016. (Toni L. Sandys/The Washington Post)
After Trump Jr.’s marriage ended in divorce, he began dating former Fox News host Kimberly Guilfoyle — who has become a co-star to Trump Jr. on the campaign trail, allowing him again to mine his love life for material.
“I’m the worst boyfriend ever!” he told a crowd in Orlando during an appearance for Florida gubernatorial candidate Ron DeSantis. Trump Jr. gestured toward Guilfoyle, standing offstage, and said he’d turned their planned vacation into a political trip.
In such appearances, Trump Jr. mimics some of his father’s mannerisms — chopping the air with a thumb and forefinger together in an “okay” gesture — veering from I’m-not-tired-of-winning triumphalism into angry resentment that his father doesn’t get the credit he deserves.
“Kill after kill,” he said on a radio show in Montana, bemoaning criticism from Democrats and the media. “Is he not winning? Is it not a track record of success? Is it not an incredible conservative accomplishment?”
Talking about his father on a conservative station in North Dakota, where he was campaigning for Senate candidate Kevin Cramer (R), who handily beat Sen. Heidi Heitkamp (D), Trump Jr. spoke of his father as being very much on the ballot. “All of his policies,” he said. “All of the winning. All of the jobs. The incredible, record, unemployment numbers, all of those things — that’s on the ticket. If Donald Trump came out for oxygen today, the Democrats would be against it.”
On social media, he goes further, recently tweeting that Maine Sen. Angus King “wants to repopulate Maine with Syrian and Somalian refugees.”
The candidates Trump Jr. backed in the midterms won some and lost some. Cruz and Cramer prevailed. Others, like King’s opponent, Eric Brakey, did not.
People around Trump Jr. have speculated about what he will do with the platform he has created for himself.
“Politically active people look at him and say, ‘He’s the president’s son. Who knows?’ ” Cramer said. “Maybe he could be a senator or a governor, or who knows what, really. I do think people look at him and see a political future there, as opposed to just a first son.”
Donald Trump and Donald Trump Jr. speak with entertainment reporters A.J. Calloway, left, and A.J. Hammer during “An Evening with ‘The Celebrity Apprentice’ ” at Florence Gould Hall on April 26, 2011, in New York. (Joe Corrigan/Getty Images)
Last year, Trump Jr. seemed to entertain that idea himself: At a speech to a gun club on Long Island, somebody asked whether he’d run for New York governor.
“His eyes lit up, he got wide-eyed, got a big smile on his face” and said he’d consider it, said Brad Gerstman, a New York lawyer and lobbyist who was there. “It looked like somebody hit something” that he’d already been thinking about.
Today, friends say they don’t believe Trump Jr. has any near-term ambition to step out on his own as a candidate. He and his five children live in New York, a heavily Democratic state where a Trump candidacy would start out as far-fetched. People float ideas to him about moving to Florida or Montana to run for governor or senator.
“There’s been no discussion about him running,” said fundraiser Mica Mosbacher, who worked at President Trump-aligned PAC America First before joining the Trump 2020 campaign as an adviser earlier this year. “I don’t believe he went into this even considering running.”
Instead, friend and political ally Tommy Hicks Jr. and others say they see him remaining in the real estate industry but keeping a hand in politics, much as he does now — raising money, speaking his mind and rallying voters in places where his father is popular.
In closing his Texas remarks, Trump Jr. said Democrats had become radically liberal and “motivated by nothing but hate.” He compared Cruz’s opponent, Rep. Beto O’Rourke (D-Tex.), to New York City Mayor Bill de Blasio. He spoke from the cuff, smiling, looking for all the world like he was running for something.
“He’s not going to stop being involved in politics,” Kirk said. “I can say that with great confidence.”
Trump Jr. listens as his father speaks at the Lincoln Memorial in Washington during a Make America Great Again thank-you concert on Jan. 19, 2017. (Jabin Botsford/The Washington Post)
Illustration by Mitch Gee, Design and development by Joe Moore
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