Shady Rumors That Have Plagued Don Jr. During Trump's Second Term

When your last name is Trump, it's a given that internet gossip will follow you for the rest of your life. This comes with some perks, but it also has its downsides, which Donald Trump Jr. knows all too well. He's been the subject of some seriously unsavory internet scuttlebutt for years. For instance, the brutal nickname Don Jr. reportedly had in his wild college days came back to haunt him during his father's second presidential term. The eldest Trump son was reportedly dubbed "Diaper Don" by his peers, thanks to his penchant for drinking too much and subsequently wetting himself in his sleep. Awkward.

Don Jr.'s embarrassing college nickname isn't the only unflattering rumor that's made the rounds either. President Donald Trump likely embarrassed his son even more when he randomly mentioned him during the divisive politician's 2025 White House Christmas address on December 14, 2025. "When I kick the bucket someday, I figure... I think he'll be here for about two days. He'll go and pay his respects and we'll say, 'Where's Don?' He'd rather be in some jungle," Donald quipped (via YouTube). As such, we can't help but wonder whether there was some semblance of truth behind the joke. 

After all, speculation that the president and his eldest son don't exactly have the best relationship has been rife for years. Unsavory nicknames and strained familial bonds are hardly the most eyebrow-raising rumors that have been swirling about Don Jr. As it turns out, the eldest Trump son has been the subject of much more sinister scuttlebutt too.

No one wants to be the subject of a drug scandal, but Donald Trump Jr. hasn't been able to escape rumors that he regularly uses cocaine. A November 2024 video of the businessman taking his hand out of his pocket and proceeding to rub his gums went viral on social media, with Jon Cooper, who was formerly Barack Obama's Long Island campaign chair, posting the clip to his feed on X, formerly known as Twitter, and captioning it: "Don Jr. nonchalantly rubbing cocaine on his gums while standing next to his daddy in front of TV cameras speaks volumes." Of course, there's no proof that he had cocaine in his pocket, and there's no way to know whether he was indeed spotted taking a hit in front of the cameras or simply trying to dislodge something from his teeth. 

Unsurprisingly, though, these rumors refuse to die. During President Donald Trump's second inauguration, in January 2025, speculation was rife that Don Jr. had been taking cocaine while at the event. A viral clip on TikTok claimed to show the eldest Trump son ducking out of the cameras' view for a brief moment to snort the drug. "Getting a bump of that devil's dandruff," the caption read. Footage of the same moment from another angle captured by ABC News, however, revealed that Don Jr. bent down to talk to Vice President JD Vance's mother, Beverly Atkins. Of course, rumors continue to abound.

In 2019, there were rumors that Donald Trump Jr.'s hunting trips might land him in court. It came after an infamous expedition to Mongolia, where the businessman was hunting the endangered argali sheep. It later came to light that Don Jr. didn't have a permit to do so, and in fact, it was only issued in the aftermath of his hunting expedition, after he met with then-Mongolian president Khaltmaagiin Battulga. The whole ordeal seemed fishy. Additionally, Don Jr. killed a red deer, another animal not allowed to be hunted without a permit. It appears that his father, President Donald Trump, isn't a fan of big game hunting, once calling it a "horror show," per The Guardian. That hasn't stopped Don Jr. from continuing the so-called hobby, though. 

In February 2025, speculation was rife that the eldest Trump son killed a ruddy shelduck during a trip to Italy. He faced complaints from politicians who saw a video of him boasting about his spoils and determined that he'd shot the endangered animal. They asserted that he'd broken the law, both in shooting it and hunting in a country where he's not a resident. Don Jr. denied any wrongdoing, proclaiming that he had all the necessary permits. An Italian journalist who reported about the incident on X updated the thread about a week later, penning, "Law enforcement raided the hunting estate that hosted Trump Jr.'s hunting trip: 1,400 birds and 8,500 allegedly illegal rounds of ammunition seized. Meanwhile, the Veneto region clarified that Trump Jr. had all the necessary permits."

There were plenty of signs that Kimberly Guilfoyle and Donald Trump Jr.'s breakup was messier than it seemed, and the former Fox News host apparently confirmed this when she appeared to take a subtle jab at her former fiancé during a November 2025 interview on Greek television. The newly-appointed U.S. ambassador to Greece praised her two ex-husbands, California Governor Gavin Newsom and Eric Villency, and even noted that she and Newsom spent a "fabulous honeymoon" in Greece, per Radar Online. Then, speaking about Villency in particular, Guilfoyle professed that they are still good friends, even calling the former couple's relationship "wonderful." 

As for Don Jr., Guilfoyle didn't say anything about him at all. Ouch. Rumors are rife that the couple's split was anything but amicable, with sources previously telling the Daily Mail, in September 2024, that the eldest Trump son was seeing Palm Beach socialite Bettina Anderson behind Guilfoyle's back and that she didn't see their split coming. Likewise, Don Jr.'s decision to dump Guilfoyle for Anderson reportedly all came down to pleasing his father. "Don Jr. has always wanted to look good in his father's eyes. Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him," a source dished to People.

Those who find themselves disturbed by the results that President Donald Trump's second term have yielded will be positively alarmed by whispers that his eldest son, Donald Trump Jr., might take a crack at following in his footsteps come 2028. In March 2025, anonymous Trump insiders disclosed to Mediaite that Don Jr. absolutely plans on throwing his hat in the ring. "Don has been the most politically involved of all the Trump kids and has always kept the lanes open for a presidential run. He is a valued voice for his father, and a real possibility to be a contender in 2028," one such insider shared. Another source doubled down, adding, "One hundred percent he will run, but only for president not VP. He is older and more experienced than JD [Vance]. In about a year, real conversations will start about him running." 

Don Jr. vehemently denied these assertions in a rather crude statement to Mediaite, in which he wrote, "Are you f***ing r****ded? I'm actually glad you're printing this bulls**t though because at least now the rest of the press corps will see how sh***y your 'sources' are and how easily you're played by them. Congrats, moron." But then, barely two months later, the businessman was singing a very different tune during his visit to Doha, Qatar. When asked about his rumored presidential aspirations during Bloomberg's Qatar Economic Forum in May 2025, he answered, "I don't know, maybe one day, you know — that calling is there," per CBS News.