The two men had for years had a difficult relationship. Trump’s ex-wife Ivana recounts in her 2017 book, “Raising Trump,” that when she suggested naming their newly born first child Donald Jr., Trump protested: “You can’t do that! What if he’s a loser?” After his parents divorced, a 12-year-old Trump Jr. refused to speak to his father for a year. Later, he seemed intent on escaping the celebrity businessman’s shadow and reputation. At the Fiji fraternity at the University of Pennsylvania, Trump Jr.’s nickname was Ron Rump, and his fraternity brothers called him Ron. “He loved it, perhaps because it gave him an extra level of anonymity,” one of them recalls. Rather than working for the Trump Organization immediately after college, Trump Jr. spent a year and half in Aspen, Colo., skiing, hunting, fishing and tending bar at night.
In 2001, he moved back to New York City and took his place at the company. But his greatest contribution to the family business came on the set of “The Apprentice,” which he joined as an occasional boardroom judge in the show’s 2006 season. He was valued by the producers as a stabilizing presence, running interference between the cast and crew and the volatile star, his father. When Trump would berate crew members for a mistake, one “Apprentice” producer recalls, Trump Jr., speaking from a well of personal experience, would console them: “It’s not your fault; it’s your turn.”
People who worked on the show remember him often trying to lighten the mood. “He provided the comic relief, because his dad doesn’t have a sense of humor and Ivanka wasn’t someone who made jokes,” says Clay Aiken, the “American Idol” winner who appeared on “The Celebrity Apprentice” in 2012. “He was perfectly fine to take the piss out of himself, but sometimes he’d make a joke about his dad — and then you could tell he was really nervous his dad wouldn’t like it. His self-esteem was in the gutter.”
Much of the popular image of Trump Jr., especially among liberals, seems to stem from those years: “uselessly trying to impress a man who can only be impressed by himself” (GQ); “a recurring liability and a chronic headache” (The Daily Beast); the “Fredo” of the Trump family (Twitter). In the first days of Trump’s presidency, he seemed poised for more of the same. After the election, while Ivanka and Kushner headed to Washington, Trump Jr. stayed behind in New York, ostensibly to run the Trump Organization with Eric. But he had little to do. He was in charge of the company’s international portfolio, and while he could continue working on overseas projects that predated his father’s election, he couldn’t embark on new ones.
For a time, he tried to play a role in shaping the administration’s public-lands policy and other issues related to his outdoor activities, which had earned him the Secret Service code name Mountaineer. Senator Steve Daines, a Republican from Montana, used an elk-hunting trip with Trump Jr. in November 2016 to lobby the incoming administration to pick an interior secretary from the Mountain West. “I wanted a Westerner,” Daines says, “and Westerner doesn’t mean West Virginia. It doesn’t mean Oklahoma.” Trump Jr. recommended Ryan Zinke, then a Montana congressman and a friend of Daines’s, for the Department of Interior job. Zinke got the nod but resigned in December 2018 after a scandal-plagued tenure.
Trump Jr.’s relatively low public profile ended on July 8, 2017, when The New York Times revealed his role in arranging the Trump Tower meeting the previous summer between Trump campaign officials and the Russian lawyer and her associates. Though little seems to have come out of the meeting, a bipartisan Senate Intelligence Committee report released this month found that the Russians had “significant connections to the Russian government, including the Russian intelligence services.”
A few days after the Times article ran, Trump Jr. went on Sean Hannity’s Fox News show to defend himself in a softball interview. “There was nothing to tell,” he said of the meeting. “I wouldn’t have even remembered it until you started scouring through this stuff.” His stock among conservatives rose as he proceeded to wage a sustained campaign against the news media, Mueller and congressional investigators pursuing their own Russia inquiry. (It was reported this month that in 2019, the Senate Intelligence Committee’s Republican and Democratic leaders made a criminal referral of Trump Jr. and several other Trump associates to the Justice Department for lying or providing contradictory testimony to the panel.) He became a frequent guest on Fox News and an enthusiastic participant in the political fights of the moment. “Don’s favorite part of politics is getting punched in the face with a jab and responding with a haymaker,” one person close to him says.