Controversies That Damaged Donald Trump Jr.'s Reputation Beyond Repair

Ever since former "The Apprentice" host Donald Trump rode a golden escalator down into the 2015 press conference where he announced that he was running for president, American political life has been dominated by the billionaire. Careening from scandal to scandal, crisis to crisis, and back again, Trumpism has become the defining political movement of the post-Barack Obama age. Between his response to COVID-19, his encouragement of the rioters who stormed the United States Capitol on January 6, 2021, his association with Jeffrey Epstein, his war in Iran, and beyond, Donald Trump is one of the most controversial presidents in American history.

Much controversy, too, has focused on his children. In addition to Barron Trump, Eric Trump, Tiffany Trump, and those rumors about Ivanka Trump we couldn't ignore, the president's other son, Donald Trump Jr., has frequently found himself at the center of firestorms of his own making. Yes, his connection to his father means his reputation might have always been in need of some repair, but ever since Don Jr. hit the national stage in his own right, he's imprinted his own personality on both pop culture and politics. From his affair with a pop star to his involvement in his father's finances and beyond, these are just some of the controversies that damaged Donald Trump Jr.'s reputation beyond repair.

Before Donald Trump ran for president, he was best known as a New York billionaire who went on to host his own reality show. NBC's hit series "The Apprentice" sought employees for the real estate baron, putting them through twisted trials meant to prove their business acumen to the man with the brutal catchphrase: "You're fired."

The show also spun off into "The Celebrity Apprentice," which put famous people through the same challenges that the regular contestants got on the flagship show. Donald Trump Jr. served as a judge on "The Celebrity Apprentice," and years later, former Danity Kane singer Aubrey O'Day alleged that she and Donald Trump Jr. had an affair in 2011. Don Jr. had five kids with Vanessa Trump, but they divorced in 2018, at which point the news of the affair broke wide.

Speaking with People in 2019, the "Damaged" singer admitted that it had happened. "We both thought we were each other's soulmates," she confessed, before clarifying that she did not support his current lifestyle. "He's chosen to be in the life that he's in now and be the person that he is now," she said, "and that's not the person that I fell in love with." The president's son has not addressed the situation.

Donald Trump Jr. is an unapologetic outdoorsman, frequently posting photos from hunting and fishing trips on social media. While this hobby certainly resonates with many Americans, many more are upset with just how Don Jr. conducts himself on said hunting trips. He faces regular criticism for the types of animals he chooses to hunt, which have included endangered animals and other so-called "big game" usually considered off-limits.

In 2012, the future "Triggered: How the Left Thrives on Hate and Wants to Silence Us" author and his brother Eric Trump went on safari, posing for photos with dead big cats. The photos went viral online, leading to a controversy where Don Jr. was forced to defend himself against allegations that he and his brother were poachers. "Not a pr move I didn't give the pics but I have no shame about them either," he wrote on X (via The Hollywood Reporter). "I HUNT & EAT game." He also tweeted, "I'm not going to run and hide because the peta crazies don't like me."

That trip reportedly cost "The Celebrity Apprentice" some advertisers, including outdoor supply company Camping World. Still, Don Jr. has continued to hunt over the years, and anger flares up occasionally. In 2025, the Italian government accused Don Jr. and friends of having killed a rare duck.

Plenty of children of U.S. presidents have made big mistakes, and Donald Trump Jr. is no exception. Before his father gave him a gig on "The Celebrity Apprentice," the future author of "Liberal Privilege: Joe Biden and the Democrats' Defense of the Indefensible" had a run-in with the law in New Orleans. The exact details weren't public for many years, but back in 2001, he was arrested for public intoxication. Americablog posted the documents in 2020, revealing that he'd been nabbed at 6:30 a.m. during Mardi Gras, held for 11 hours, and charged a $300 bond to be released.

In 2004, the real estate scion confessed in a New York Magazine interview, "I used to drink a lot and party pretty hard." Though he claimed to have cut back, Don Jr. has been followed ever since by rumors that he is a frequent cocaine user, even reportedly in public, live on television. In 2024, he stood next to his father at a SpaceX launch, and cameras captured Don Jr. rubbing his gums.

He has frequently denied the allegations, including on a 2023 episode of his podcast "Triggered." Don Jr. complained that the media treated him worse than Joe Biden's son Hunter, who has been open about his drug use. Don Jr. claimed, "I give an impassioned speech, and it's 'Don Jr. is on coke.'"

President Donald Trump made his fortune in real estate long before entering politics, ostensibly racking up billions thanks to his willingness to license his famous name to anything from casinos to an ill-fated line of steaks — the aptly-named Trump Steaks lasted only two months! It seems to have worked out for the man who put his name on a book called "The Art of the Deal," somehow turning six bankruptcy declarations into enough money to run for president multiple times.

When Trump entered politics, he handed the reins of the family business to his son, Donald Trump Jr. Don Jr. went to the Wharton School of Finance at the University of Pennsylvania, as his father had, but by the time Don Jr. was called before the court to address numerous allegations of financial fraud, he claimed to no longer remember much about accounting ... even though he's the trustee of the family's company.

In court papers filed in 2022 and reported on by Business Insider, the court alleged that during a deposition, Don Jr. claimed ignorance of the so-called "Generally-Accepted Accounting Principles" that businesses must follow. "[He] testified that his only familiarity with GAAP was 'probably [because of] Accounting 101 in Wharton,' and that apart from knowing that they 'are generally accepted,' he could not identify any other knowledge he has about GAAP," the filing said.

When Donald Trump ran for president in 2016, there were numerous stories about supposed collusion between his campaign and agents of the Russian government. The allegation was that the Trump campaign sought damaging information about his opponent, Hillary Clinton, from Russian operatives who would have had ulterior motives in getting Donald Trump elected.

The president denied what he called the "Russia! Russia! Russia!" hoax for years, but in 2017, the country got proof that the president's son, Donald Trump Jr., had indeed met with Russians at Trump Tower to receive intel. Shockingly, said proof came in the form of emails that were posted to X by none other than Don Jr. himself. He shared screenshots to social media showing that he'd sent a Russian asset an email crowing, "If it's what you say I love it especially later in the summer."

The admission sent shockwaves through the political sphere. Campaign strategist Norm Eisen tweeted, "I have worked on campaigns and as an election lawyer for decades; NEVER seen anything like this, &EVERY other campaign would have called FBI." He wasn't the only member of the Trump family to have worked with Russians, either; here's what we know about Jared Kushner's meeting with a controversial Russian lawyer.

Donald Trump's time in the political sphere has been characterized by his anti-immigrant stance, from the offensive remarks he made when he first launched his campaign to the ongoing ICE raids. In 2016, Trump's son, Donald Trump Jr., joined in the fray, posting a provocative image to X. "This image says it all. Let's end the politically correct agenda that doesn't put America first," he wrote. The image has since been pulled from the platform, but it was widely reported at the time, including by WUNC, to have depicted a bowl of Skittles. The text on top of the colorful candies said, "If I had a bowl of Skittles and I told you three would kill you, would you take a handful? That's our Syrian refugee problem."

Wrigley, the parent company that makes Skittles, was unhappy with the comparison. After all, no candy company wants their customers associating their product with this kind of rhetoric around refugees, and they released a statement criticizing Don Jr.'s post. "Skittles are candy. Refugees are people," they wrote. "We don't feel it's an appropriate analogy."

Many of Donald Trump Jr.'s biggest headline-grabbing moments have been social media-based, and one particular 2019 controversy is no different. That November, Don Jr. took to X to repost an article from the LGBTQ+-focused outlet Queerty. The article was headlined "What you stand to lose by not having sex with people with HIV," and Don Jr. retweeted it with the comment, "Well I can think of one thing."

The joke doesn't even really work; he presumably means that HIV can be deadly, but that's not how the sentence is constructed grammatically, and besides, that's not even really true anymore thanks to advances in medicine.

Princess Diana became an LGBTQ+ icon in part by working to destigmatize AIDS, but that's how Don Jr. made himself an LGBTQ+ villain. Patient advocate Peter Morley wrote on X, "I lived through a time when people with HIV were shunned, ostracized and persecuted. Some people thought they had a death sentence when diagnosed and took their own lives. And your comment, @DonaldJTrumpJr, Is embarrassing, juvenile & DESPICABLE. We will not go backwards."

The year 2020 was rough for the entire world. It was especially chaotic in America, which saw not only the rampant spread of the COVID-19 pandemic, but a contentious presidential election between Donald Trump and Joe Biden. Trump was running for re-election, whereas Biden sought to return to the Oval Office after having served as Barack Obama's Vice President. The election was unusually acrimonious, and things reached new heights when Biden won, and Trump refused to concede.

Those post-election months were characterized by rampant conspiracy theories about the election having been stolen. Everything climaxed in thousands of Trump supporters breaking into the United States Capitol, resulting in several deaths. Months before January 6, 2021, however — just after the election — Donald Trump Jr. posted on X, "The best thing for America's future is for @realDonaldTrump to go to total war over this election,."

A hyperbolic tweet would be one thing, but in the wake of the January 6th attack on the Capitol, text messages were made public that showed Don Jr. actively attempting to orchestrate the results of the election being overturned. CNN reported that he'd encouraged Chief of Staff Mark Meadows to explore efforts to subvert the results, insisting, "We control them all."

Though Joe Biden ultimately did assume the presidency after beating Donald Trump, the Trump family remained in the news throughout the Biden administration. Donald Trump Jr. became a frequent critic of Biden's cabinet, appearing regularly on right-wing cable news. In 2023, he caused controversy when he went after Secretary of Transportation Pete Buttigieg, whose love story will melt your heart, but it seemed to have hardened Don Jr.'s.

"He's the guy who had no business running for president but they let him do that cause he's gay and they check off a box and then he didn't win," Don Jr. insisted in a 2023 appearance on Newsmax (via New York Daily News), "So [they said] 'He's the gay guy, so we gotta give him something, let's make him Transportation Secretary." Buttigieg announced that he and his husband had welcomed twins early in the Biden administration, and the idea of a gay couple having children rubbed Don Jr. the wrong way. "Plus [there's] the time he spent chest-feeding while we were in the midst of a supply chain crisis," Don Jr. said, still upset about the fact that Buttigieg took paternity leave.

Commentators weren't happy with the remarks, hitting out at Don Jr. on social media for the way he'd spoken about a gay administration official. Journalist Aaron Rupar put it simply on X, writing, "Unvarnished homophobia."

Donald Trump Jr. didn't only cause immigrant-related controversy when he tweeted an offensive meme comparing refugees to poisoned Skittles. He also waded into the debate during the 2024 election, which was characterized by racist rumors that Haitian immigrants in Ohio were consuming people's pets. President Donald Trump, for example, infamously claimed without evidence at a debate, "They're eating the dogs ... they're eating the cats" (via Atlanta News First).

Don Jr. appeared on Charlie Kirk's podcast and backed his father up, justifying the family's racism against people from Haiti. "You look at Haiti, you look at the demographic makeup, you look at the average I.Q.," he reasoned. "If you import the third world into your country, you're going to become the third world. That's just basic. It's not racist. It's just fact."

Several things have changed in the years since the controversial moment. Trump won the presidency anyway, and Don Jr. hasn't been quite as public since the campaign. Listening to the son of a president defend his racism isn't yet, as of press time, a job Erika Kirk has taken over from her late husband.

In 2017, People reported on Donald Trump Jr.'s college days at the Wharton School of Finance, diving deep into the allegations of partying and wild-child behavior. They quoted a former classmate's Facebook post, which claimed, "Donald Jr. was a drunk in college. Every memory I have of him is of him stumbling around on campus falling over or passing out in public, with his arm in a sling from injuring himself while drinking."

College is reportedly where Don Jr. met a man named Gentry Beach, who became his best friend for many years. Beach served as a groomsman in Don Jr.'s wedding, and the two were reportedly confidants for a long time. The relationship has since soured, it seems. In 2023, The Wall Street Journal reported that Beach was in possession of emails involving Don Jr., dating back decades, that included racist remarks. The release of the emails was prevented in court.

In 2025, the evident feud reared its head again. The Daily Beast reported that lawyers had sent a letter to Beach on behalf of Don Jr., demanding that he stop name-dropping the political scion in business meetings. Beach, after all, had told The Wall Street Journal plainly, "Everyone views Trump as a transactional president."

While Donald Trump Jr. has mostly kept his head down since his father resumed the presidency, he hasn't been able to entirely escape attention from the tabloids. In 2025, he opened an exclusive members-only club called Executive Branch — a nod to his father's job, of course — and charged members $500,000 to join. Politico reported that other founders included the Winklevoss twins, who famously claimed to have invented Facebook; they were college classmates with Mark Zuckerberg before his complete transformation.

While most details about Executive Branch have been kept under wraps, the Daily Mail published a story in late 2025 sourcing conversations with former staffers. One told the British outlet that he'd seen a famous person insist his staffer fly home to his house in Florida to bring back a specific type of wine. "There was wild stuff that went on there," the source said.

Don Jr. is reportedly collecting these membership fees so that politicians and businessmen can meet away from the prying eyes and ears of the public. "They want a place where they can go and have meetings without reporters or Democrats overhearing them," another source said. The former staffer added, "There is a whole world of rich folk that people don't even know exists."