The life of Donald Trump Jr., who once lived out of a truck, didn't speak to his father for a year, and is making waves on a book tour with his girlfriend

Madeleine Sheehan Perkins
Donald Trump Jr. speaks at the Western Conservative Summit at the Colorado Convention Center July 12, 2019. (

Andy Cross/MediaNews Group/The Denver Post / Getty

  • Donald Trump Jr., son of President Donald Trump, is an executive vice president of the Trump Organization.
  • The 41-year-old, who has five children, has lived the majority of his life in the shadow of his father and sister Ivanka, but since his dad became president, his outspoken, anti-political-correct stance has come into its own.
  • While Ivanka and his father are seen as city-dwellers, Donald Jr's love of guns and the outdoors has made him a vital tool to connect with American voters.
  • And while his relationship with his father has been far from smooth — he refused to speak to him for a year when he was 12 — he's now one of his dad's most effective political tools.
  • Visit Business Insider's homepage for more stories.

Donald Trump Jr. has become his father's son.

He hasn't always seen eye-to-eye with his famous dad, but since Donald Trump Sr. become president, Jr. has come back into the fold. In November he told The Wall Street Journal, "It took me probably 41 years to realize I was a lot more like my dad than either of us had ever thought. Our default mode is, I guess, attack."

He used to be the detail-oriented and business-focused child, content to leave the spotlight to his father and his sister Ivanka, but he's now a fundraising regular, often traveling the country to speak on his father's behalf. For the 2018 midterms, he made more than 70 campaign appearances, according to the Washington Post.

It's been a busy few years for the eldest son who was also put in charge of leading The Trump Organization with his brother Eric. He was embroiled in the Russia investigation and weathered a messy divorce.

Most recently, his book tour for "Triggered: How the Left Thrives on Hate and Wants to Silence Us," is making waves.

Here's his life so far.

Donald Trump Jr. was born in Manhattan on December 31, 1977, to Donald Trump and his first wife, Ivana. As the first-born, he was named after his father. But according to the Los Angeles Times, he was not always the adoring son.

AP Images/Richard Drew

Sources:, Los Angeles Times

As a child, he spent six to eight weeks during the summers in Czechoslovakia with his grandparents. Trump learned his outdoor skills from his maternal grandfather Zelnicek, who he was particularly close with, and who acted a role model for him growing up. His grandfather let him loose, telling him, "there is the woods. See you at dark."

REUTERS/Lucas Jackson

Source: The New York Times


It was a stark contrast to life as a Trump in America, where he was accompanied by bodyguards. At 12, he was whisked off to boarding school with his brother Eric after his parents' divorce. He went to The Hill School in Pottstown, Pennsylvania, for high school.

Chip Somodevilla/Getty Images

Sources: Vanity Fair, The Guardian

In 2004, he told New York Magazine it had been tough being 12. "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. At that age, kids are naturally cruel."

Ron Galella/Ron Galella Collection / Getty

Source: New York Magazine

His father made the divorce a public affair, which wasn't easy on Trump Jr., who was more aware of what was going on than his younger siblings. According to Vanity Fair, he yelled at his father, “You don't love us! You don't even love yourself. You just love your money!" He then spent a year refusing to speak to his father, hanging up on him whenever called.

Ron Galella/Ron Galella Collection / Getty

Sources: The New York Times, Vanity Fair

After high school, Trump went to the University of Pennsylvania's Wharton School of Finance, where his father and sister also went. He studied finance and real estate. He also rowed crew, joined a fraternity, and garnered a reputation as a big partier.

Wikimedia Commons

Sources: The Trump Organization, The New York Times

At university, he didn't try and live up to his father's reputation. Jennifer Ireland Kubis, who knew him there, said, "He wasn't into the gold. He was trying to escape it." Scott Melker, another classmate, wrote a viral Facebook post where he said every memory he had of Trump was of him stumbling around campus falling over or passing out while drinking. He also said Trump "absolutely despised his father, and hated the attention that his last name afforded him.”

Matthew Peyton / Getty

Sources: The New York Times, Los Angeles Times

After graduation, Jr. took a year off from studies and work. He lived in the back of a truck in Aspen, Colorado, where he hunted, fished, and occasionally worked as a bartender. He's said he was the first graduate of Wharton to do such a thing. It was during this time he developed his patience and need for silence, according to the Washington Post.


Sources: Vanity FairThe New York Times, The Washington Post

In 2001, he was arrested for public drunkenness in New Orleans during Mardi Gras, and spent half a day in jail.


Sources: The New York Times, Los Angeles Times, The Guardian

His love of nature was a key factor in him later giving up drinking. He spoke about it in 2016 at a fundraising speech in Salt Lake City. "I know that the benefits I got from being in the woods, from being in a duck blind, from being in a tree stand at 5 o'clock in the morning, kept me out of so much other trouble I would have gotten into in my life," he said. In 2003 he officially quit drinking.

Lucas Jackson / Reuters

Source: The New York Times

In September 2001, he returned from "the wilderness," and went to work for his father. His mother once said, "When they turned 21, I handed them over to him and said, 'Here's the finished product.'"

Mike Blake/Reuters

Sources: Vanity Fair, The Guardian

In 2003, Trump's father introduced him to Vanessa Kay Haydon, a model who once dated Leonardo DiCaprio. They soon started dating.

Jean-Paul Aussenard / WireImage / Getty

Sources: The New York TimesThe New York TimesVanity Fair

It was a public affair and made even more so when Trump accepted a free $100,000 ring in exchange for recreating his proposal in a New Jersey mall. Along with a critical New York Post headline, which called him "the cheapest Gaillionaire," his father took a shot on at him "Larry King Live," where he said, "You have a name that is hot as a pistol, you have to be very careful with things like this.”

Mychal Watts / WireImage / Getty

Source: The New York Times

The couple married on November 12, 2005, at the Trump family's Mar-a-Lago resort in Florida.

Joe Raedle/Getty Images

The couple had five children: Kai (born in 2007), Donald III (2009), Tristan (2011), Spencer (2012), and Chloe (2014). Their New York apartment was described to the Los Angeles Times as "controlled chaos."

REUTERS/Mike Theiler

Sources: People, Los Angeles Times

It didn't take long before Trump rose to be executive vice president of the Trump Organization. After his first completed project, he told his dad the building should say Trump Jr. His father disagreed. Still, Trump Jr. was put in charge of various building projects, hotels, condos, and golf courses. Notably, he took the lead on constructing the Trump International Hotel and Tower in Chicago.

REUTERS/Russell Cheyne

Sources: Vanity Fair, The Trump Organization, The Guardian

In a 2006 cover story on the two eldest children, Forbes called Ivanka "the spotlight-loving Ms. Outside" and Donald "the detail-obsessed Mr. Inside."

Richard Drew/AP

Source: Forbes

One of his focuses was working with Russian businesses. In 2008, he told Eturbonews he'd visited the country half a dozen times trying to find business. He also said it was a "really scary place," in regards to corruption.

J. Kempin/FilmMagic / Getty

Source: Los Angeles Times

Trump was a dutiful son. He appeared as a boardroom adviser with Ivanka on their father's reality-TV show "The Apprentice," as well as a judge for some of his father's Miss USA pageants. But he told AP there was constant pressure to perform. "In my father’s own words, he would fire us like dogs," he said in 2006.


Sources: New York Times, Los Angeles Times, The Guardian

In 2010, Trump started his own building-materials company, Titan Atlas Manufacturing, with two business partners. But by 2012, the company ceased operations after tax liens were filed for unpaid sales and withholding taxes.

Alex Wong/Getty Images

Sources: Vanity Fair, The Post and Courier

Titan Atlas continued with legal troubles through 2016. A lawsuit involving the company brought by Saint-Gobain Adfors, an international construction company, has been pending since April 2016. The actual warehouse has also caused issues as it's environmentally contaminated.

REUTERS/Joshua Roberts

Sources: Vanity Fair, Mother Jones

On June 16, 2015, Donald Trump announced he was running for president. When his father asked him what he knew about politics, Jr. told him he'd watched the news the previous night, which was enough to put him to work. And Trump Jr. worked hard for his father, rising at 4.30 a.m. and working late every night. He introduced him at rallies, gave interviews, and ramped up his Twitter presence.

Saul Loeb-Pool/Getty Images

Sources: CNN, Los Angeles Times, The Guardian, The Washington Post

Trump's hunting background, in stark contrast to the more refined personas of his sister and father, was harnessed by the campaign as a way to connect with many Americans.

John Minchillo/AP Images

Source: The Washington Post

But his love of hunting also caused some issues during the campaign when a picture surfaced of him and Eric posing with a dead leopard from 2010. Possibly the worst photo for Trump Jr. was one where he was holding a knife in one hand and a severed elephant tail in the other. He didn't appear too fazed by the online vitriol and said to one critic, "I'm not going to run and hide because the PETA crazies don't like me."

Lucas Jackson / Reuters

Source: The Washington Post, The New York Times

As his father ran for the presidency, Jr. continued to stir the political pot. In one tweet he compared Syrian refugees to Skittles. "If I had a bowl of skittles and I told you just three would kill you, would you take a handful?" the tweet said. "That's our Syrian refugee problem."

Donald Trump Jr.

Sources: AP, Business Insider

Another time when complaining about the media, he said the media would be "warming up the gas chamber" if Republicans acted like 2016 rival Hillary Clinton. The Trump campaign later said clarified his comments were about capital punishment and not the Holocaust.

Andy Cross/MediaNews Group/The Denver Post / Getty

Sources: Business Insider, Los Angeles Times

As Roger Stone, one of Trump senior's former confidants, put it to the Washington Post, "Basically, Trump Jr. is the voice of undiluted Trumpism."

Joe Raedle/Getty Images

Source: The Washington Post

After his father won the presidency, Trump joined the transition team's executive committee. In early 2017, Trump spoke at a fundraising dinner, and said he thought that would be it, that he would be out of politics after Election Day. But he didn't stop. He said he couldn't.

REUTERS/Shannon Stapleton

Sources: Vanity Fair, The New York Times

Donald and Eric became trustees of the Trump Organization and took control of the company together when their father became president.

REUTERS/Gary Cameron

Sources: Business Insider, The Washington Post

But since his dad's ascension to president, Trump Jr. has been one of his father's most vocal defenders. The Los Angeles Times described him as a "virtual attack dog." In June 2017, he blasted former FBI Director James Comey, posting over 80 tweets during Comey's live testimony before a congressional committee.

AP Photo/Jae C. Hong

Sources: Business InsiderThe Associated Press, Los Angeles Times

Trump Jr. became his father's No. 1 man.

Joe Raedle/Getty

Source: Los Angeles Times

In March 2017, Trump fell into political hot water when he tweeted a quote from London Mayor Sadiq Khan that made it look as if he were relaxed about terrorism in London. Trump's tweet came after a terrorist attack in Westminster, but Khan's quote was 6 months old.

Donald Trump, Jr./Twitter

Source: The Guardian

In July 2017, Trump became one of the key figures in the Russia election meddling controversy, after The New York Times reported that he'd taken a meeting with a Russian lawyer who told him she had damaging information about Hillary Clinton. Instead of calling the FBI in response to the information, he said, "I love it."


Sources: Business Insider, The Guardian

The news led some to raise new questions about whether the Trump campaign colluded with the Kremlin to meddle in the election. And it briefly made Donald the most Googled child of Donald Trump. In the end, the former special counsel Robert Mueller found there was no coordination with Russia and the Trump campaign.


Sources: TwitterBusiness Insider, The Wall Street Journal

In November 2017, The Atlantic reported that during the 2016 election, Trump was in touch with WikiLeaks, the anti-secrecy website that published wave after wave of damning information on Hillary Clinton's campaign from hacked emails.

Donald Trump Jr./Twitter

Sources: Business Insider, The Atlantic

In March 2018, Trump's home life took a hit when Vanessa filed for divorce. The two battled it out in court to decide the terms of their split.

REUTERS/Carlos Barria

Source: Business Insider

After news of the divorce broke, rumors swirled that his Twitter use was a determining factor, and that he cheated on her with Aubrey O'Day in 2011 when the singer was a contestant on "The Apprentice."

Neilson Barnard/Getty Images

Source: Business Insider

In May 2018, Trump started dating former Fox News host Kimberly Guilfoyle. She's since become a senior adviser for the Trump campaign. According to the Washington Post, Trump was quickly using his love life for material on the campaign trail.

AP; Invision; Business Insider/Rebecca Harrington

Sources: Page Six, The Washington Post, The Washington Post

And despite his comments about pulling away from politics, Trump instead stopped trying to expanding the Trump Organization, which he told friends was difficult to do while his father was president, according to the Washington Post.

Kathy Willens / AP

Source: The Washington Post

He's become sought after for his versatility at rallies and fundraisers. For the 2018 midterms, Trump made about 70 campaign stops to help boost morale for Republican candidates. Yet despite his appearances, a White House official told the Washington Post he probably had less influence at the White House compared to Ivanka and Eric.

John Bazemore / AP

Source: Washington Post

In 2018, he continued to be prolific on Twitter. He retweeted conspiracy theories about businessman George Soros being a Nazi, he liked a tweet that said migrant children separated from their parents by Trump's administration had been coached by liberals, and he attacked CNN several times, including anchor Anderson Cooper, based on a 10-year-old photo.

Associated Press/Matt Rourke

Sources: The Hill, Newsweek, Vox

In 2019, Trump went after Hunter Biden, Sen. Joe Biden's son, for his role as a board member on a Ukrainian energy company. Although there was no evidence of wrongdoing by the Bidens, he said, without any apparent irony, that he wished his name was Hunter Biden so he could make millions off his father.

Paul Morigi/Getty Images for World Food Program USA

Sources: The Wall Street Journal, The Daily Beast

In November 2019, he published "Triggered: How the Left Thrives on Hate and Wants to Silence Us," which criticizes "PC culture," as well as the special counsel Robert Mueller. It's been touted as the "book the leftist elites don't want you to read."

Angela Weiss / AFP / Getty

Sources: The Wall Street Journal, The Washington Post, The Guardian

In November, Trump and Guilfoyle appeared on the 5000th episode of "The View," to promote his book, but it quickly became a heated back and forth, in particular with Megan McCain, late Sen. John McCain's daughter, who asked how he felt about the pain his family had caused. Trump said he didn't feel good, but he and his family were doing what they had to for America.

Lou Rocco / ABC / Getty

On his book tour, loud conservative supporters heckled him offstage at UCLA when he refused to answer questions. He said he was trying to avoid giving the media soundbites that could be distorted by the left wing social media. But the crowd wasn't buying it.

Mark Ralston / AFP / Getty

Sources: The Wall Street Journal, The Guardian

As for Trump's future, he's skirted around questions about his own political ambitions, and said he's focused on his father's reelection in 2020. But who knows what comes after that. He's no longer living in his father's shadow.

John Moore/Getty Images

Sources: The Wall Street Journal, GQ