Donald Trump's oldest child, Donald Trump Jr., turns 45 on December 31.
He has five children with ex-wife Vanessa Trump and speaks Czech fluently.
Trump Jr. and Kimberly Guilfoyle ran in the same circles before they started dating in 2018.
Donald Trump Jr. has a bachelor's degree in economics from the University of Pennsylvania's Wharton School of Finance.
Trump Jr. graduated in 2000. Donald Trump Sr. also attended Wharton.
He worked as a bartender for a year in Aspen, Colorado, after college, and wrote that his drinking became a "recipe for disaster."
In 2001, Trump Jr. spent 11 hours in jail after he was arrested and charged with public drunkenness.
"Once I got going, it wasn't easy to stop me — which, when you're in college, isn't a huge problem, as long as you're getting your work done," Trump Jr. wrote in his 2019 book, "Triggered: How the Left Thrives on Hate and Wants to Silence Us." "But once I started thinking about a career and a life beyond school, it was. To be honest, I didn't know how to drink in moderation."
He has since given up drinking.
"I have an all-or-nothing personality; just ask anyone who knows me," Trump Jr. wrote in "Triggered." "Being compulsive works for some things — give me a job to do, and I'm going to get it done — but it's not so good for vices."
He continued: "One thing about us Trumps is that we have plenty of willpower. I would come to find that it was easier for me to ignore alcohol than it was to try to control it. Eventually, I would give up drinking for good."
Trump Jr.'s father introduced him to his first wife, Vanessa Haydon, at a fashion show where she was modeling in 2003.
Trump Jr. recalled the awkward moment his father introduced them in a 2006 New York Times profile, saying that Haydon looked at them "like we're taking crazy pills."
"You know, I'm 25 at the time, I did perfectly well with girls. It wasn't really my M.O. to have my father try to pick up girls for me," he said.
Trump and Haydon got engaged in November 2004, and they married at Mar-a-Lago in November 2005.
He and Vanessa had five children together before divorcing in 2018.
The oldest child is daughter Kai Madison, followed by Donald John III, Tristan Milos, Spencer Frederick, and Chloe Sophia.
He speaks Czech fluently.
Trump Jr. spent summers fishing, boating, and hunting with his mother Ivana Trump's Czech parents, Milos and Maria Zelnicek, according to New York magazine. The Zelniceks also lived in Trump Tower half of the year.
Trump Jr. donated to Hillary Clinton's 2008 presidential campaign.
CNN reported that Trump Jr. donated $4,000 to Clinton's first presidential campaign in 2008.
He's an avid hunter.
Trump Jr. and Eric Trump co-own a private hunting range in a rural community in upstate New York.
Trump Jr. also took an eight-day trip to Mongolia in 2019, during which he hunted a rare breed of sheep. The trip cost taxpayers more than $75,000 in Secret Service protection, according to documents obtained by a government watchdog group.
Trump Jr. and his girlfriend, Kimberly Guilfoyle, ran in the same circles before they started dating in 2018.
Guilfoyle and Trump Jr. were introduced by mutual friends and were photographed together at events in New York City in 2007 and 2008. At the time, they were in other relationships.
Guilfoyle remained connected to the Trump family for years and told the San Jose Mercury News in 2017 that she was in talks to become the White House press secretary.
Three months after Trump Jr.'s wife Vanessa filed for divorce in 2018, Page Six reported that he and Guilfoyle were dating.
In 2021, Trump Jr. and Guilfoyle bought a $9.7 million home in a gated neighborhood about 20 minutes from Mar-a-Lago.
Trump Jr. and Guilfoyle sold their house in the Hamptons for $8 million in March 2021. A month later, they purchased an 11,300-square-foot waterfront estate in the Admirals Cove neighborhood of Jupiter, Florida. The home has six bedrooms and 11 bathrooms, People magazine reported.
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