Donald Trump Jr.’s long path to politics

Donald Trump Jr. talks with reporters during the 139th Easter Egg Roll on the South Lawn of the White House April 17, 2017 in Washington, DC.
Who is Donald Trump Jr.?
02:15 - Source: CNN

Story highlights

Donald Trump Jr. is the President's eldest son

He is facing controversy for a meeting during the 2016 election

Washington CNN  — 

Donald Trump Jr. wasn’t always comfortable being in his father’s shadow.

The father and son have a complicated history that includes a tabloid divorce and a year without speaking, Trump Jr. told New York Magazine in a 2004 profile. But later, the senior Trump found a key role for his son in the family real estate business – and eventually, his political circle.

“I think I probably got a lot of my father’s natural security, or ego, or whatever,” he told New York Magazine. “I can be my own person and not have to live under his shadow.”

Trump Jr. added that he looked up to his father, but noted their differences.

“I’d like to be more like him when it comes to business – but I think I’m such a different person, it’s hard to even compare us. His work persona is kind of what he is. I have a work face, and then there’s my private life,” Trump Jr. has said.

More than a decade later, the hard-charging, no-apologies eldest child of Donald Trump found himself his father’s most visible and outspoken 2016 campaign surrogate. And in June 2016, Trump Jr. was in a position of power in the trusted inner circle of the presidential campaign of the Republican presidential nominee, his father, for whom he would go to great lengths to help elect.

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Attorney on Trump Jr.: Meeting was legal
01:22 - Source: CNN

New scrutiny

Trump Jr. is now embroiled in a new wave of scrutiny in the wake of New York Times reporting that prompted him to release emails he exchanged with Rob Goldstone, a publicist, arranging for a June 9, 2016, meeting with a woman described in the emails as a “Russian government attorney.”

In the email exchange with Goldstone, which he published in full on his Twitter account Tuesday morning, Trump Jr. was promised “official documents and information that would incriminate Hillary and her dealings with Russia” that was “part of Russia and its government’s support for Mr. Trump.”

“If it’s what you say I love it,” Trump Jr. replied to Goldstone, who represents the son of an Azerbaijani-Russian businessman close to the Russian government.

The meeting, he said in a tweet Thursday, turned out to be “nonsense.”

Natalia Veselnitskaya, the Russian lawyer who met with Trump Jr., as well as his brother-in-law Jared Kushner and then-campaign chairman Paul Manafort, denied any connection to the Russian government in an interview with NBC.

Mark Corallo, a spokesman for the President’s legal team, reiterated an earlier statement on Monday evening, saying: “The President was not aware of and did not attend the meeting.”

President Donald Trump was silent on social media on the report and the emails until Wednesday, tweeting several times Tuesday on other topics. White House deputy press secretary Sarah Huckabee Sanders read a statement on his behalf at the daily press briefing.

“My son is a high quality person and I applaud his transparency,” Sanders said, reading the statement from the President and referring questions to Trump Jr.’s lawyers.

Trump tweeted Wednesday morning that his son “did a good job” in his Tuesday evening appearance on Fox News, calling the new scrutiny a “witch hunt.”

“My son Donald did a good job last night. He was open, transparent and innocent. This is the greatest Witch Hunt in political history. Sad!” he wrote.

House and Senate intelligence committee members have indicated they want to talk to Trump Jr. and others who were at the June 2016 meeting. His lawyer, Alan Futerfas, says he has not yet received a request, but his client will work “with any committee or office to convey what he knows.”

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Gorka: Russia meetings didn't need disclosure
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A complicated relationship

Donald Trump Jr. had a complicated childhood relationship with his namesake.

Trump Jr., then 12 years old, was reportedly devastated by his parents’ messy divorce and news of his father’s affair with Marla Maples, which unfolded publicly.

“How can you say you love us? You don’t love us! You don’t even love yourself. You just love your money,” Trump Jr. told his father, according to friends of Ivana’s cited in a 1990 Vanity Fair report.

He didn’t speak to his father for a year, he told New York Magazine.

“Listen, it’s tough to be a 12-year-old,” Trump Jr., then 26, told the magazine in the 2004 profile, which also featured his siblings.

“You’re not quite a man, but you think you are. You think you know everything. Being driven into school every day and you see the front page and it’s divorce! THE BEST SEX I EVER HAD! And you don’t even know what that means,” he told the magazine. “At that age, kids are naturally cruel. Your private life becomes very public, and I didn’t have anything to do with it: My parents did.”

During the presidential campaign, Trump Jr. was more charitable. He told CNN’s Anderson Cooper during an April 2016 town hall that the divorce was “a difficult thing” but said his father has “always been there.”

“I think throughout our lives, he’s always been there. It’s usually been on his terms. It wasn’t a typical ‘let’s go play catch in the backyard’ sort of father/son relationship,” Trump Jr. told Cooper. “But we always went to job sites with him. We’d be in his office playing with trucks as a 6-year-old while he’s negotiating deals with presidents of major companies.”

Trump Jr. and siblings, Ivanka and Eric, were primarily raised in New York City by their mother, Ivana Trump.

All three of the eldest Trump children grew up holding summer jobs at different Trump properties. Trump Jr. spent his summers mooring boats to the dock all day for minimum wage at the Trump Marina in Atlantic City, Ivanka Trump wrote in her 2010 book.

He attended boarding school at Pennsylvania’s prestigious Hill School and later obtained an undergraduate degree from his father’s alma mater, University of Pennsylvania’s Wharton School.

Trump Jr. accrued a hard-partying reputation while at Penn, and spent the year after graduation in Aspen, Colorado, where his habits continued.

“I used to drink a lot and party pretty hard, and it wasn’t something that I was particularly good at,” he told New York. “I mean, I was good at it, but I couldn’t do it in moderation. About two years ago (2002), I quit drinking entirely. I have too much of an opportunity to make something of myself, be successful in my own right. Why blow it?”

He ultimately moved back East to join the family business, working at the Trump Organization in real estate development, and also spending some time in the spotlight as a boardroom adviser on “The Apprentice.”

Trump, now 39, lives in New York City with his wife, Vanessa, a former model, and their five children, ranging from three to 10 years old.

Campaign Trump Jr.

Trump Jr. emerged as one of candidate Donald Trump’s leading surrogates on the campaign trail, crisscrossing the country speaking on his father’s behalf. He styled himself as the Trump family member who best understood his father’s working-class supporters across America, and advised his father alongside Ivanka and Eric.

An outdoorsman, Trump Jr. learned to hunt and fish from his Czech grandparents, Ivanka Trump wrote in 2010. He participated in multiple hunting outings during the campaign, including in Iowa the week before the caucuses.

And at last year’s Republican National Convention in Cleveland, Trump Jr. put his father over the top in the delegate count as he officially secured the nomination. He called his father a “mentor” and “best friend” in his convention speech.

In an interview with The Associated Press, Trump Jr. said he is open to the possibility of running for office himself in the future.

“Maybe someday,” he said. “It’s not something I’m doing now. But you never know, it’s fascinating stuff.”

Social media

Trump Jr. has long been unfiltered and outspoken on social media, echoing the distinctive voice and even the punctuation of his father’s tweets, often sparking backlash before and after the 2016 presidential election.

He came under fire during the campaign for likening Syrian refugees to a bowl of Skittles in a September 2016 tweet.

“This image says it all. Let’s end the politically correct agenda that doesn’t put America first. #trump2016,” he tweeted, with a graphic that said: “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.”

Earlier that month, he made headlines with a controversial Instagram post. The photoshop composition featured his father leading a band of “deplorables,” with political allies and the cartoon “Pepe the Frog” by his side. What Trump Jr. later said he did not know, was that “Pepe” has been appropriated as a mascot and preferred meme of the white supremacist alt-right movement.

As far back as 2011, Trump Jr. tweeted some eyebrow-raising commentary on women.

“Ever notice that if u get a herd of mothers together they aren’t physically capable of talking about anything but birth pregnancy & diapers?” he asked in a July 2011 tweet that has since been deleted.

And he spoke about a Trump Organization employee in another now-deleted June 2012 tweet.

“At dinner w our greenskeeper who missed his sister’s wedding 2 work (luv loyalty 2 us) “No big deal hopefully she’ll have another someday”;)” Trump Jr. tweeted.

Since his father assumed office, Trump Jr. frequently posts in defense of the President, often criticizing the media and occasionally retweeting conspiracy theories.

On Saturday, he retweeted a clip from the movie “Top Gun” that was altered to show the President “taking down” a fighter jet marked with the CNN logo.

“One of the best I’ve seen,” he wrote, alongside the “crying-laughing” emoji.

Trump Jr. seemingly acknowledged his controversial persona in a Saturday tweet after his sister Ivanka faced criticism for holding her father’s seat at the G20 summit.

“If the left is so “outraged” about Ivanka sitting in for a few minutes, maybe they’d be happier if I sub in for a while??? LMK,” he wrote.

Trump Jr., post-inauguration

As Donald Trump prepared to take the oath of office in January, he formally turned over his real estate business to his two eldest sons. Trump Jr. currently serves as the executive vice president of development and acquisitions at the Trump Organization.

But Trump Jr. was bitten by the political bug, and has traveled the country, speaking at Republican party dinners and campaigning for Montana congressional candidate Greg Gianforte.

“I thought I was out of politics after election day,” Trump Jr. said in March, speaking at the Dallas County Republican Party’s Reagan Day Dinner, where he recalled his father’s unpredictable path to the presidency.

“I thought I’d be going back to my regular job. I thought I’d be really excited about it. But once you get a little bit of a taste of that action, it’s hard to leave. You know, listen, deals are still exciting, but when you’re sort of the guy out there 24/7, every day fighting in this thing – it’s like a great fight, the intensity. I don’t miss the politics, I promise. I want nothing to do with the politics, but I miss the intensity of that,” he said, reminiscing about the no-sleep, fast-paced days of the campaign when he paraded around as one of the only surrogates.

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He has traveled to the White House on multiple occasions, including the Easter Egg Roll, the announcement of the Supreme Court nomination of Neil Gorsuch, and a small family celebration for his father’s birthday. He’s also been a frequent guest on Fox News, where he gave his first interview since posting the emails on Tuesday evening with Sean Hannity.

“In retrospect, I probably would have done things a little differently,” Trump Jr. said.

In the interview, he defended his actions by saying he wanted to hear what they had to say.

“Maybe this is something,” Trump Jr. said of his thinking leading up to the meeting. “I should hear them out … This was again just basic information that was going to be possibly there … I wanted to hear them out and play it out.”

Although he doesn’t have a role in the administration like his sister, Ivanka, who serves as a formal White House adviser, he is actively involved in the President’s 2020 reelection campaign.

Trump Jr. and Eric Trump, along with Eric’s wife Lara, held multiple meetings with high-level officials at the Washington office of the Republican National Committee in late May, a Republican source confirmed to CNN at the time. The meetings between the trio of Trumps and the various groups were held to make sure everyone was “on the same page,” according to the source. The group discussed the midterm election and 2020 reelection outlook, as well as assigning roles moving forward.

Trump Jr. has continued to be one of his father’s staunchest and most vocal defenders. He expresses frustration about the Russia controversy that’s overshadowed much of the first months his father’s presidency, often blaming the media and Democrats in tweets for deflecting attention from the administration’s accomplishments.

After the President criticized London Mayor Sadiq Khan in a June 4 tweet following a terrorist attack, his son came to his defense, speaking more broadly about his social media strategy.

“Every time he puts something out there, he gets criticized by the media all day every day and by everyone else and guess what, two weeks later he’s proven to be right. It (terrorism) happened again and we keep appeasing it and we keep saying ‘OK, it’s going to be great, we’ll hold fast and we’re going to keep calm and carry on.’ Maybe we have to keep calm and do something,” he said in an interview with ABC last month.

Trump Jr. also speculated to ABC that there may be White House employees working against his father.

“There’s probably plenty still in the White House, there’s plenty of holdovers that aren’t necessarily working in his best interest,” he said.

CNN’s Greg Krieg and Hunter Schwarz contributed to this report.