Rumors About Don Jr. He Just Couldn't Shake Off

Few examples of "like father, like son" are as accurate as that of Donald Trump and his eldest child (and namesake), Donald Trump Jr. With Donald Sr. as a father, it's no surprise that Don Jr. has followed a sometimes controversial life path, building on the family's wealth while finding himself embroiled in multiple public debacles along the way. Naturally, being such a well-known (and sometimes notorious) public figure inspires plenty of rumors, many of which are so widespread that Don Jr. just can't shake them off. 

The businessman has been accused of everything from colluding with U.S. enemies to altering his appearance, and much of this sensational gossip seems too outlandish to be real. However, some of the most widely-circulated gossip about Don Jr. has withstood the test of time because it's based in fact. While not all the most prevalent rumors surrounding Donald Sr.'s firstborn have been proven to be true, many have.

Donald Trump Jr. has shown that he'll go to great lengths to help his father's political career, but one move he made during Donald Trump Sr.'s first presidential campaign sparked both gossip and a dangerous level of controversy. In 2016, Don Jr. joined some of his father's campaign staffers at a Trump Tower meeting with a lawyer named Natalia Veselnitskaya. Meeting with a lawyer is nothing new for the Trump family, but Veselnitskaya reportedly had ties to the Kremlin, which ignited rumors that Don Jr. may have committed treason by meeting with her. 

Although Don Jr. or his father could have easily put the rumors to rest by simply being honest about the nature of the meeting, the two told conflicting stories that spurred further speculation. In a July 2017 statement (via NBC News), Don Jr. claimed that the meeting had a very innocent purpose: "We primarily discussed a program about the adoption of Russian children that was active and popular with American families years ago and was since ended by the Russian government..." However, Donald Sr. offered a totally different take on X, formerly Twitter, a year later: "This was a meeting to get information on an opponent, totally legal and done all the time in politics — and it went nowhere." No Trump family member faced charges over the meeting, but their conflicting statements made it difficult for Don Jr. to quickly put treason gossip to rest. 

Donald Trump Jr. was married to Vanessa Trump for over a decade, but their 2018 divorce gave rise to infidelity rumors that just couldn't be silenced. One of the biggest reasons that Don Jr. couldn't shut down this gossip is that it was all true; sources confirmed to Us Weekly that the businessman did indeed have a short-lived affair in 2011, which ended in early 2012 when Vanessa uncovered his misdeeds. 

Don Jr. and "Celebrity Apprentice" cast member Aubrey O'Day grew close as production on Season 5 drew to a close, and, as one source shared, he made a serious relationship seem like a real possibility. "He told her it was over with his wife, that they were separated and he didn't love her — all of that stuff ... Aubrey fell for him hard. She thought they were going to be together for real," the insider claimed.

Of course, Don Jr.'s promises turned out to be false; he stayed with Vanessa another six years before their marriage finally came to an end. As for O'Day, she told People in 2023 that although she and Don Jr. were once very close, their connection is likely gone forever: "He's chosen to be in the life that he's in now and be the person that he is now, and that's not the person that I fell in love with."

Unfortunately, Vanessa Trump isn't the only one rumored to have been on the receiving end of Donald Trump Jr.'s infidelity. Although Kimberly Guilfoyle's reaction to Don Jr. cheating rumors appeared steeped in maintaining positive optics for Donald Trump Sr.'s 2024 campaign, her deflections weren't fooling anyone. In September 2024, anonymous witnesses confirmed that the gossip about Don Jr. being unfaithful was absolutely true, telling The Daily Mail that the businessman clearly went on a date with Palm Beach, Florida resident Bettina Anderson. 

An isolated incident of cheating is bad enough, but sources suggested there were some real feelings behind Don Jr. and Anderson's rendezvous, explaining: "She seemed totally smitten with Don — and he with her." Guilfoyle didn't publicly address the incident, but a friend told The Daily Mail soon after the story broke that the former prosecutor likely felt she couldn't act due to her heavy involvement in Donald Sr.'s campaign. Whether Don Jr. purposely took advantage of the awkward timing or simply struggles to remain faithful to his partners, infidelity appears to be an ongoing pattern of behavior for the businessman.

Donald Trump Jr. can get pretty riled up during public speeches, and that behavior sparked rumors about the source of his seemingly endless energy. In a 2023 episode of his podcast, "Triggered," Don Jr. revealed a common accusation he hears while complaining about Hunter Biden, saying (via Independent), "I give an impassioned speech, and [people say] 'Don Jr. is on coke.'"

Rumors about Don Jr.'s cocaine use have been very persistent over the years, and new incidents keep adding fuel to the fire. For example, in November 2024, he was spotted mysteriously rubbing his gums while attending the launch of SpaceX's Starship rocket. One netizen posted a video of Don Jr.'s questionable behavior on X, asking, "What happened here with Don Jr. at the SpaceX launch today?" Unsurprisingly, many users took the opportunity to joke about cocaine in the comments section. 

Although there doesn't appear to be any definitive truth to the cocaine use tale, Don Jr. did once have a brush with the law for public intoxication. Arrest records from New Orleans, Louisiana (via America Blog) show the incident occurred in 2001, when the eldest Trump son was just twenty-three. Three years later, Don Jr. admitted to New York Magazine that he had turned over a new leaf: "I used to drink a lot and party pretty hard, and it wasn't something that I was particularly good at... About two years ago, I quit drinking entirely." He doesn't specifically reference the arrest, but the timing of his newfound sobriety suggests he didn't want to repeat his mistake. 

Many celebrities see cosmetic surgery as par for the course in their line of work, and the Trump family certainly has the means to afford such procedures if they wanted to maintain or approve their looks. Several rumors have swirled about Don Jr. getting plastic surgery, and it's hard to argue that he looks very different from throwback photos of him in his youth. However, there are many other reasons a person's appearance changes as they age, and one medical professional believes that Don Jr. has had only minimal work done over the years.

 Plastic surgeon Dr. Gary Motykie has weighed in on the situation, telling The Daily Mail that, in his professional opinion, Don Jr. may have spent as much as $80,000 on veneers, resulting in the straighter, whiter teeth he now sports. Other than these improvements to his smile, Dr. Motykie notes that Don Jr. shows no evidence of having undergone cosmetic procedures. Of course, only Don Jr. himself could truly put this rumor to rest, but the businessman has largely remained mum about his appearance. Unless he says otherwise, this rumor will live firmly in the world of conjecture.