Ivanka and Jared left the White House behind for a life in Miami. Eric is running the family business. Tiffany got married. Barron is a budding strategist at NYU.
Of all the Trump children, no one has stuck closer to their father’s side than Donald Jr., the president-elect’s eldest son.
The 46-year-old Mr. Trump has found political power and personal fortune in stoking the flame of the Make America Great Again movement his father started. He has an array of conservative-focused businesses, from a publishing company to a seven-figure annual podcasting deal. Forbes recently estimated Mr. Trump’s worth — largely built in the wake of his father’s political career after Jan. 6, 2021 — to be around $50 million.
For that reason, his associates say, he has no plans to join the administration. But he also understands what his siblings and several first-term administration officials learned the hard way: Trying to serve as a gatekeeper for his father is a politically perilous exercise.
In recent weeks, as the president-elect builds out his administration, his son has served as something of a loyalty scanner. As they review candidates at Mar-a-Lago in Florida, the president-elect is concerned with who looks good and who can deliver a message, people around them say. His son is focused on whether they mean what they are saying, and if they present a threat to the MAGA order.
Donald Trump Jr. has championed appointees and nominees who not only share the president elect’s views on policy but have also passed the most important purity test: They support the falsehood that he won the 2020 election, and downplay his decision to encourage a mob to storm the U.S. Capitol two months later.
In recent appearances, Donald Trump Jr. has made it clear that he believes that everything that has happened since early 2021 happened because true loyalists dug in and kept on believing, watching in the wings as Democrats made a series of strategically fatal decisions on economic and social policy.
“Now you got four years where we know what we’re doing, where we have a chance to start from scratch with people who we know are absolute warriors for the movement,” he said on the conservative activist Charlie Kirk’s podcast last week. “Now you’re stuck with that for four years.”
It was Donald Trump Jr. who saw the early threat that Robert F. Kennedy Jr.’s candidacy posed to his father’s campaign, and who, allies say, tried to brainstorm ways to bring him into the fold.
Since Mr. Kennedy was chosen as the nominee for Health and Human Services secretary, Donald Trump Jr. has kept him close, even feeding the notoriously health-conscious Mr. Kennedy a McDonald’s burger aboard his father’s plane and then taking a picture of it.
This is a tactic Mr. Kirk suggested was akin to a mob strategy: “If you think someone is an informant, you make them take a little drugs,” he suggested during the podcast interview.
“Bobby did have some McDonald’s,” Donald Trump Jr. said. “We definitely had some fun with that one.”
Loyalty First
This loyalty-first approach explains how and why Matt Gaetz, a fierce Trump defender, was selected as the nominee for attorney general. (The subject of an investigation involving sex trafficking, Mr. Gaetz pulled himself out of consideration last Thursday.)
It explains how Sergio Gor, Donald Trump Jr.’s business partner at Winning Team, their conservative publishing company, was selected to lead the White House Personnel Office. And it explains how JD Vance, the vice president-elect, was chosen, as well.
Each choice amounted to a set-it-and-forget-it guarantee, not only for a president who demands fealty but also for a son prepared to enforce his father’s demands.
Donald Trump Jr. declined a request for an interview through a spokesman, but others who are close to him were cleared to speak on his behalf, including Mr. Kirk. “He only weighs in when something is particularly important to him,” Mr. Kirk said, “or where he feels as if there might be something that would not be in his father’s best interest.”
Topics that are most important to him include issues around the 2nd Amendment, the border, privacy and foreign policy, several allies said, with one prominent example: Donald Trump Jr. was an early champion of Mr. Vance because the two men shared the belief that the United States should stop the flow of aid to Ukraine.
He is also a crusader in the so-called anti-woke movement, and seems to revel in being hated and feared by liberal Americans who accuse him of harmful and divisive beliefs. Week after week, he publishes a torrent of posts on social media, targeting an array of topics and people that are red meat to the MAGA base, from transgender Americans to members of the news media.
A prime example of Donald Trump Jr.’s typical fare appeared on his Instagram account last week, when he asserted that “biological & objectively attractive women are allowed to win beauty pageants again. WE ARE SO BACK!!!” The post drew a fire emoji from Elon Musk, the world’s-richest-man-turned-MAGA-surrogate. On Mr. Kirk’s podcast, Donald Trump Jr. said that he and Mr. Musk recently spent three hours aboard the president-elect’s plane “talking about space.”
“He has a real commitment to developing both the policies and the personnel,” said Newt Gingrich, the former House speaker, who was recently a guest on Donald Trump Jr.’s podcast. “He’s a sentinel trying to defend the president and Trumpism from people who would like a job but don’t necessarily have the right credentials to do it.”
This means that other threats, like former Gov. Nikki Haley of South Carolina, a first-term appointee who later fell out of favor for, among other things, criticizing Mr. Trump’s response to the riot at the Capitol, have not fared as well. She is now a figure of mockery for the president-elect’s son. When Ms. Haley criticized Mr. Trump’s cabinet picks this week, Donald Trump Jr., as he often does, used social media to fire back.
“If Nikki Haley really wants a cabinet filled with neocon warmongers to satisfy the billionaire donors that control her, she should try running for President and winning herself,” he wrote. “Oh wait, I forgot she already tried that and lost in a landslide.”
An Evolving Relationship
For a son who at times has taken pains to differentiate himself from his father, on style if not substance, he has remarked to associates that, as it turns out, he might be more like his father than he initially realized.
He has long embraced his father’s grievance-based brand of politics. He is ubiquitous at Trump rallies, on social media and on conservative podcasts, serving as a megaphone for Mr. Trump’s base, rather than trying to lead from inside.
“He’s on the outside. He has his businesses,” Mr. Gor said. “Sometimes people on the outside like Don have more influence than people on the inside.”
It is a striking evolution for a father-son relationship that has at times been distant and tense.
He did not speak to his father for a year after Mr. Trump divorced his mother, Ivana, during an affair with Marla Maples, who would become his second wife. While his father enjoyed the perks of life in towers and seaside mansions, Donald Trump Jr., who was taught to hunt and fish by his maternal grandfather, preferred life outdoors. (A father of five, he will leave his father’s side to go on a Thanksgiving-week hunting trip with one of his children.)
And, in 2017, he earned Mr. Trump’s ire for becoming a central figure in the investigation into the Trump campaigns’s ties to Russia — earning him a reputation with the first-term White House as being reckless. His nickname among some first-term aides was Fredo — as in the hapless eldest son of the fictional Corleone family, according to one of those aides.
He is still careful not to ever try to eclipse his father, a half-dozen associates said, but he has since proved himself and his value to Mr. Trump. He has turned his efforts to identifying and cultivating a new generation of MAGA-loyal politicians, including Mr. Vance and several new Republican senators in the next Congress, like Bernie Moreno of Ohio, Tim Sheehy of Montana, and Jim Banks of Indiana.
“If you have a son who is smart, hardworking and wants to help you,” Mr. Gingrich said, “you sort of have to think, why wouldn’t you listen to him on occasion?”
Embracing a movement fueled by grievances has also been personally enriching. Helping his father crystallize a political movement led to lucrative projects like a podcast deal with the conservative site Rumble, which an adviser said was worth a yearly salary of seven figures before advertising.
He founded a hunting magazine — “a lifestyle brand for nonconformists” — called Field Ethos. He is building a conservative media platform, called MxM. He hobnobs with donors, and announced at a recent summit that he was joining the venture capital firm 1789 Capital. The firm is run by Omeed Malik, a financier who has long promoted the idea of a “parallel economy” fueled by American conservative consumers.
Mr. Gor said in an interview that Winning Team, their publishing company, had about 15 authors and had published three books by the president-elect. He said the endeavor was lucrative.
So Donald Trump Jr. has no plans to leave that behind for a life inside the White House gates, where aides who veer too close to the inner workings of the Oval often find themselves on the outs.
“The midterms will be here before you know it, and he’s looking ahead on how to build these majorities in the House and Senate,” Mr. Gor said. “He can explain some policy positions better than some elected individuals, and that’s why people trust him.”
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