Trump Jr.’s increasing prominence also comes at a time of heightened scrutiny by the special counsel investigating Russian interference in the 2016 election, who is examining his role in a Trump Tower meeting with a Kremlin-aligned lawyer. Trump has fretted to confidants about the fate of his eldest son, concerned he may be in legal jeopardy regardless of whether he knowingly conspired with Russian agents to obtain dirt on Democratic nominee Hillary Clinton.
But if Trump Jr. is rattled, he is not showing it. He boarded a propeller plane this past week for his annual vacation in the wilderness of the Canadian Yukon, where he is out of cellular range. Through an aide, he declined an interview request for this article.
In a statement to The Washington Post, the president defended his son’s meeting with Russians.
“Don has received notoriety for a brief meeting, that many politicians would have taken, but most importantly, and to the best of my knowledge, nothing happened after the meeting concluded,” Trump said.
Trump is determined to be the central Republican force in the fall campaign, and Trump Jr. is poised to be a key player in a strategy aimed at galvanizing the president’s most ardent supporters. And for many in Trump’s political base, seeing Trump Jr. in the crosshairs of special counsel Robert S. Mueller III may be more of a benefit than a drawback.
“In a normal Republican universe . . . a guy like Don Jr., with all that baggage, would be very problematical,” said Republican strategist Mike Murphy, a Trump critic. “But in the new Trump universe, with different laws of gravity, every campaign is seen as just a big Republican primary. So it’s all Trump all the time.”
Another plus, according to some Trump allies, is that Trump Jr. serves as a physical reminder to Trump voters that failure in November raises the specter of impeachment.
“He is fundamentally educating the American people that we must have a Republican House in November, because the alternatives are first and foremost the impeachment of his father,” said David Bossie, Trump’s former deputy campaign manager.
Trump Jr. — who, together with brother Eric, took over the family’s real estate and branding company when their father became president — is planning an aggressive fall schedule of appearances from Montana to Texas to New York to help Republicans maintain their Senate and House majorities.
“He can bridge anyplace,” said House Majority Leader Kevin McCarthy (R-Calif.). “It’s genuine. He’s not there because, ‘Oh, I’ve got to go make this trip.’ He wants to be there. . . . He connects with people.”
In many ways, Trump Jr. carries the spirit of his father’s “Make America Great Again” movement. Like the president, he uses social media to fan conspiracy theories, air grievances and troll adversaries. He busts through boundaries of political correctness and relishes public feuds, especially with those he deems liberal elites.
“Don is a chip off the old block,” said Cliff Sims, a former White House and Trump campaign staffer. “He’s a savage on Twitter and a force of nature on the stump.”
Trump Jr. attracts plenty of controversy along the way. He co-hosted a Washington screening this month of “Death of a Nation,” a film by conservative firebrand Dinesh D’Souza (whom the president pardoned) alleging ties between the Democratic Party and Nazis. In an interview there, Trump Jr. compared the Nazi platform in the early 1930s to today’s Democratic National Committee platform.
During the 2016 campaign, Trump Jr. sparked a public outcry when he likened Syrian refugees to a bowl of Skittles that included a few that “would kill you.” A spokeswoman for Wrigley, the company that makes the colorful candy, condemned the analogy: “Skittles are candy. Refugees are people.”
Former White House press secretary Sean Spicer said Trump Jr.’s connection to his father’s political base is authentic. “All you need to do is look at his tweets to realize he speaks to the base and they love him,” Spicer said.
Trump Jr., 40, and his wife, Vanessa, who have five children, are currently in the middle of a divorce. He has been dating former Fox News host Kimberly Guilfoyle.
Of the president’s five children, Trump Jr. has perhaps the most complicated relationship with his father. He was 12 when Trump’s contentious divorce with first wife Ivana burst into public view, and he reportedly did not speak to his father for a year. Later, after college, he lived for a year in Aspen, Colo., another apparent attempt to distance himself from family complications.
Trump and Trump Jr. speak infrequently, according to people close to both men. Trump has long doubted whether his son could live up to his expectations. Ivana Trump recalls in her 2017 memoir that when she suggested naming their son Donald Jr., Trump told her, “You can’t do that! What if he’s a loser?”
Trump said his namesake has turned out to be “a wonderful son” who has taken to the new family business: politics.
“Don has proven to be a very good public speaker and was a very likable presence on the campaign trail,” Trump said in the statement to The Post. “People like when he represents me in front of groups of people. I always get a favorable response. . . . Don likes and enjoys politics, but he likes seeing great results for the American people even better, and that is why he is involved. He truly believes that I am making America great again and loves being a part of it.”
Murphy suggested that deploying Trump Jr. as a campaign surrogate only serves to stroke the president’s ego.
“Somewhere in the White House there’s a ‘yes’ man telling the president how great it is that Don Jr. is going to make 28 stops next week,” Murphy said. “It’s all about pleasing the emperor.”
While both father and son love to rail against the coastal elite, the president is an unabashed credentialist and still privately craves the approval of the establishment institutions he claims to despise. Trump Jr., by contrast, truly does not care about being accepted by high society, people close to him said.
Trump Jr., an avid outdoorsman, typically travels with a slim entourage, sometimes just a lone Secret Service agent. On his Instagram account, he posts photos of his children playing (affectionately dubbed “the monsters”), and memorializes his hunting and fishing expeditions.
“You see Republican activists and donors come up to him wanting to talk about hunting,” said former Trump campaign adviser Jason Miller, who has traveled with Trump Jr. “They want to talk about shooting, they want to talk about specific types of fishing and they want to get into details of outdoors life.”
Campaigning last month in Montana for Senate candidate Matt Rosendale, Trump Jr. told a rollicking crowd in Great Falls that he feels at home because he used to spend a month every summer out west, living in the back of his truck and exploring the land.
“I’m, as many of you probably know, [a] big shooter, big hunter, big fisherman,” Trump Jr. said. “That’s why I also feel ridiculous in this suit, but we’re just going to do it, okay?”
Trump Jr. intends to return in September to stump for Rosendale and also is making plans to campaign next month with Sen. Ted Cruz in Texas as well as with Senate candidates Marsha Blackburn in Tennessee, Kevin Cramer in North Dakota and Josh Hawley in Missouri.
Trump Jr. also is scheduled to headline August fundraisers in New York for Rep. Lee Zeldin (R-N.Y.) and Rep. Mike Braun (R-Ind.), the GOP Senate nominee in his state. The president’s son seems at home with the wealthy donor class, according to Wayne Berman, a Blackstone Group executive who has helped arrange some fundraisers featuring Trump Jr.
“He fits in with the finance crowd because a lot of them are interested in things other than politics and a lot of them are interested in the real estate business, which he talks about with depth and specificity,” Berman said.
Trump Jr. coordinates his campaign travel with the White House and the Republican National Committee largely through his political adviser, Andy Surabian, a former Trump campaign and White House official who previously worked for Stephen K. Bannon, the president’s former chief strategist.
Trump Jr.’s friends described him as charitable and a man of high character, in marked contrast to the caricature of his father as a narcissist.
Zeldin recalled that during his congressional delegation trip last Christmas to the Middle East to visit U.S. troops, Trump Jr. asked him to call him from a base in Jordan. When Zeldin called, Trump Jr. had him put his phone on speaker so he could wish the Special Operations forces a “Merry Christmas.”
This was the kind of political touch that critics say is sometimes missing from the president, who has yet to visit troops in a war zone.
McCarthy tells of riding with Trump down Pennsylvania Avenue to an event where Trump Jr. would be speaking.
“The president said to me, ‘He really likes this and he’s really good at it,’ ” McCarthy recalled. “My comment back was, ‘He is a natural.’ ”