The Shady Side Of Donald Trump Jr.

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It's fair to say that when it comes to throwing shade, the apple doesn't fall far from the Trump family tree. Eric, Ivanka, Tiffany, and Donald Trump Jr. have all proven they've inherited their father Donald Trump's ability to shoot his mouth off over the years, and the latter might well be the most controversial of the 47th's spawn.

Indeed, ever since his dad launched his bid to become President of the United States, Don Jr. appears to have gone out of his way to cause offense in every direction. Whether it's aiming toward his political rivals, the scientific community, or even his own party, the ultimate nepo baby's loose tongue has continually made headlines. But on some occasions, it's his questionable actions that speak louder than his words. From cozying up to white supremacists and slaughtering endangered animals to inciting riots and spreading voter misinformation, here's a look at 14 of the most damaging examples.

Donald Trump Jr.'s first brush with the law came in 2001, a period in which he was working behind the bar of an establishment in Colorado. As well as serving customers with alcohol, the nepo baby also appeared to like a tipple or two himself, judging by the fact he was arrested for being drunk and disorderly.

In an interview with The New York Times 16 years later, Trump Jr. discussed the incident that took place during New Orleans' Mardi Gras, for which he allegedly spent nearly half a day in a prison cell: "We have to be honest with ourselves. I'm not good at it, moderation. You have to have the conversation, be a realist, and say, 'I guess I'm not doing myself any favors.'"

The businessman was also happy to address his arrest in 2019 for the book "Triggered: How the Left Thrives on Hate and Wants to Silence Us." "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," he wrote (via Daily Mail), referring to his old drinking habits. "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." Just like his father, Donald Trump Jr. now claims to be entirely teetotal.

In 2009, Donald Trump Jr. claimed 55 percent of the condos in his father's newly-built $370 million lower Manhattan building, Trump Soho, had been sold. This came just a year after younger sister Ivanka Trump boasted that the number was 60 percent. However, the real figure was somewhere between 15 and 30. And as a result, both nepo babies became the subject of a criminal investigation.

Indeed, Trump Jr. and Ivanka were accused of using inflated sales claims to defraud buyers. According to journalist Andrea Bernstein, the pair even laughed about the situation in one of several damaging emails later leaked. "... The younger generation of Trumps issued the email equivalent of a knowing chuckle, saying that nobody would ever find them out, because only people on the email chain or in the Trump Organization knew about the deception," she wrote in "American Oligarchs: The Kushners, The Trumps And The Marriage Of Money And Power" (via The Guardian). 

Following a 2011 civil case in which those affected — who were refunded a total of nearly $3 million in deposits — vowed not to pursue the matter any further, officials decided to drop any criminal proceedings. Unsurprisingly, the Trumps have continued to claim they didn't do anything wrong.

Best-known for her stint in girlband Danity Kane, Aubrey O'Day certainly got more than she bargained for when she signed up to appear in the 5th season of "The Celebrity Apprentice." As well as finishing third place in the hit reality competition, the singer also claims to have embarked on an affair with one of its married judges.

Yes, although Donald Trump Jr. himself has never admitted to having relations with the vocalist, Kane has proudly boasted about the fact on several occasions. In 2023, she revealed their first sexual experience was in a gay club bathroom while guesting on Michael Cohen's "Mea Culpa" podcast. And then two years later, the star gushed about their relationship to Us Weekly: "He made me feel the smartest and the most beautiful, but he loved my mind more than anything else, and that's what I love about me. The way that we loved was we loved the same." However, she was far less complimentary in 2021 when she let her feelings be known about her alleged ex's views on family values. 

According to the tabloids, the two very different famous faces first got together in late 2011 and carried on seeing each other for several months before Trump Jr.'s wife Vanessa Trump discovered e-mail correspondence between the pair.

In early 2016, presidential nominee Donald Trump came under fire for failing to reject the endorsement of David Duke, aka the leader of the Ku Klux Klan. And his son didn't exactly do his father any favors when he guested on a right-wing radio show alongside a white supremacist.

Yes, while appearing on "Liberty Roundtable," Donald Trump Jr. was asked multiple questions by James Edwards, a man who'd penned a book titled "Racism Schmasism," conceived far right chat show "The Political Cesspool," and essentially once argued African Americans should be grateful for slavery. 

Initially, the Trump circle tried to deny the unfortunate gathering had ever occurred, but when the talk was re-aired, Trump Jr. was forced to explain himself. "Had I known I would have obviously never done an interview with him," he claimed to Bloomberg, insisting Edwards had joined the chat without any prior warning. "This is clearly the mainstream media trying to turn a story into something, much like they did with my father, who I witnessed denouncing David Duke and any KKK endorsement on multiple occasions."

In 2016, Donald Trump Jr. and several other members of his father's POTUS campaign team agreed to meet up with Natalia Veselnitskaya, a Russian lawyer, and three other associates at Manhattan's Trump Tower. The timing of the gathering inevitably drew suspicion, but the nepo baby later insisted the topic of conversation was an adoption program.

"If there was something that came from this that was shady, if it was a danger to national security, I would obviously bring it right to someone," he told Fox News (via Salon) a year later while protesting his innocence. "But I didn't know what anything was, and it turns out it was nothing." Of course, it didn't turn out to be nothing.

In 2018, Donald Trump revealed his eldest child had connected with Veselnitskaya in order to obtain information on his political rival Hillary Clinton but that it was all above board. "... Totally legal and done all the time in politics — and it went nowhere," he tweeted (via BBC News). The 45th's admission came amid an investigation into the meeting by Robert Mueller, the Special Counsel who'd headed up the inquiry into how Russia may have influenced the presidential election.

In 2017, Donald Trump Jr. got tongues wagging when he made the curious decision to drop his Secret Service protection. According to reports, the wish to enjoy more privacy was the root cause. But this just got everyone wondering exactly what he wanted privacy from.

Trump Jr.'s activities had often come under scrutiny from the press, his political opponents, and various watchdogs. And GQ journalist Jack Moore noted how this unusual move coincided with an inquiry into whether his father colluded with Russia during his ascent to the White House, writing, "It's not the best look for a major advisor to and son of the president who is the subject of a serious investigation into possible international espionage to get rid of the government agents who are around him all the time, for a couple of weeks during that investigation."

But having followed the businessman on one of his first unaccompanied excursions — a hunting trip to Canada's Yukon Territory — New York Times Magazine writer Luke Dittrich also questioned whether his attempt to swerve attention would put him in serious danger. "Whatever your politics, whatever you think of Trump, the last thing you would want is for his son to fall into the wrong hands." The plot thickened when just a few weeks later, Trump Jr. chose to recall his protection.

Donald Trump Jr. added to his list of misdemeanors in 2019 when he took to Twitter to publicly out the whistleblower who'd complained about his father coercing Ukraine into smearing his enemies.

According to the Inspector General Act of 1978, agency watchdogs "shall not, after receipt of a complaint or information from an employee, disclose the identity of the employee without the consent of the employee, unless the inspector general determines such disclosure is unavoidable." But that didn't stop the nepo baby from sharing a conservative news report which specifically named the CIA officer who'd sparked an impeachment trial.

Unsurprisingly, Trump Jr. didn't back down when he received pushback for amplifying the rumor. "The entire media is #Triggered that I (a private citizen) tweeted out a story naming the alleged whistleblower," came his defiant response on X. "Are they going to pretend that his name hasn't been in the public domain for weeks now? Numerous people and news outlets including Real Clear Politics already ID'd him." A whole host of more authoritative news sources, however, weren't able to independently verify the whistleblower's true identity.

So it turns out even endangered species aren't safe from Donald Trump Jr. In 2019, news emerged the Mongolian government had retroactively given the nepo baby permission to hunt for the national treasure known as the Argali mountain sheep.

According to ProPublica, the secret service protection required for the trip cost American taxpayers nearly $77,000. But it was the needless slaughtering of a defenseless animal that caused the most anger on social media. 

This wasn't the first time Trump Jr., whose messy love life is already invading Tiger Woods and Vanessa Trump's romance, incurred the wrath of animal lovers, either. Several years earlier, the businessman was heavily criticized for various hunting snaps, including one in which he proudly placed his arms around a leopard he'd murdered and another where he held up the bloodied tail of an elephant while also brandishing a knife. "I'm not going to run and hide because the PETA crazies don't like me," came his defiant response on X. 

Just like his own father — who let's not forget once recommended injecting bleach to combat the disease — Donald Trump Jr. was the science world's worst nightmare during the height of the COVID-19 pandemic. In 2020, he flouted official guidelines by staging an unmasked indoor rally, was briefly banned by Twitter after sharing the dangerous theory that hydroxychloroquine could work as a cure, and in a typical act of tactlessness, tried to downplay the number of fatalities caused by the condition while simultaneously bigging up his father's presidential response.

"Why aren't they talking about deaths?" he asked Laura Ingraham of Fox News (via CNN) about how the media had apparently gone quiet on the subject. "Oh, oh, because the number is almost nothing. Because we've gotten control of this, and we understand how it works." On that particular day, more than 1,000 American people had lost their lives due to COVID-19. Ironically, despite claiming the Trump administration had practically eradicated the virus, he then tested positive himself. 

Trump Jr. then pretty much accused Pfizer of stalling its vaccine to prevent his father from getting re-elected as president. "The timing of this is pretty amazing," Trump Jr. tweeted following the news that the pharmaceutical firm had created a vaccine with 90 percent effectiveness.

Having repeatedly taken aim at Hunter Biden, Donald Trump Jr. then switched his attention to the man's father in 2020. And the accusations toward the future 46th were some of the most heinous you could possibly hurtle: he accused Joe Biden of being a pedophile.

Yes, taking to Instagram, Trump Jr. posted an image of the man who'd soon defeat his dad in the presidential elections in which he remarked (via The New York Times), "See you later, alligator." Bizarrely, it was uploaded alongside a picture of the aforementioned reptile responding, "In a while, pedophile."

Despite quickly claiming the post had been made in jest, Trump Jr. then doubled down on his allegations. He shared a photo collage of Biden being affectionate with children at various Capitol swearing-in ceremonies and interpreted this as an example of "unwanted touching." A spokesman for the soon-to-be POTUS, Andrew Bates, fired back in a statement (via The Guardian), "No repulsive, manipulative tactic will change the subject from how almost 90,000 Americans have paid for Donald Trump's coronavirus negligence with their lives and how the booming economy he inherited from the Obama-Biden administration is now suffering from depression-level job losses."

Despite the fact his father has been sworn in as President of the United States on two occasions, Donald Trump Jr. has repeatedly pushed the narrative that America's voting system is flawed. Of course, most of his theories, funnily enough, only emerged during the one election Donald Trump lost.

In August 2020, the nepo baby amplified a report from Breitbart News which claimed 800 Michigan votes had been declared fraudulently due to the fact they came from dead people. However, these votes had been struck from the ballot by officials, and they'd been submitted by very much living people who sadly lost their lives shortly after.

A month later, Trump Jr. was at it again, this time insisting the radical part of the left-wing were aiming to take over the White House by any means necessary. "Their plan is to add millions of fraudulent ballots that can cancel your vote and overturn the election," he argued (via NPR) before imploring Trump supporters to form a security army. And then in November, he shared the soon-debunked theory that empty ballots were being filled in by poll employees in Pennsylvania.

Donald Trump Jr. seemed even more high spirited than usual when he essentially declared a civil war between his own party on January 6, 2021. "They need to fight for Trump, because if not, I'm gonna be in your backyard in a couple of months," he told attendees (via The Independent) at a rally protesting the results of the recent presidential election. "If you're gonna be the zero and not the hero, we're coming for you."

Of course, Trump Jr.'s words were interpreted as even more inflammatory later that same day when many of his so-called "heroes" marched along to the U.S. Capitol to cause an unprecedented amount of havoc and chaos, resulting in vandalism, multiple injuries, and several deaths.

Joe Scarborough, a one-time congressman and MSNBC host, was just one of several figures who called for Trump Jr. — along with his similarly incendiary dad and Rudolph Giuliani — to be arrested for insurrection. While alongside Mo Brooks, the same trio were also sued by Eric Swalwell, formerly a House impeachment manager, for their involvement in the riots.

Donald Trump Jr. didn't appear to learn anything from his condo fraud close call. In 2024, he and sibling Eric Trump found themselves in court on charges of misrepresenting their dad's assets and bank balance in an attempt to gain better financing deals for their father's real estate portfolio. And they were fined over $8 million as a result.

The nepo babies were also banned for two years from working within any New York firm's executive offices, a ruling which also applied to Donald Trump who was ordered to pay back an astonishing $355 million for the same deception, too. As you would expect, the family didn't take the verdict in good grace.

"We've reached the point where your political beliefs, combined with what venue your case is heard, are the primary determinants of the outcome, not the facts of the case," Trump Jr. fired back after the verdict (via BBC News). "It's truly sad what's happened to our country, and I hope others see it before it's too late to correct course."

In 2025, Donald Trump Jr. got himself embroiled in another scandal when he was accused of taking advantage of Greenland's homeless and financially deprived. According to DR, a broadcaster in nearby Denmark, the nepo baby's team offered them free gourmet meals and swanky hotel rooms if they publicly supported Donald Trump at various events.

The controversy came amid the news that the 47th was looking to take control of the autonomous territory. "These people were clearly in need, and they were used as props," one insider remarked (via Arctic Today). And such claims were backed up by Aaja Chemnitz, a Danish MP from Greenland, who stated she saw many faces she'd encountered on the streets in the Trump visit photos.

"These are people who were invited through social media or brought in for this purpose," Chemnitz said. "I don't think it's acceptable. From what I can see, people were given a free meal in exchange for wearing a hat and acting as extras in social media videos and podcasts." The politician went on to declare that her homeland is thriving and will continue to thrive without the interference of the United States president.