When people think of American politics, President Donald Trump and his family are among the first names that come to mind.
While Donald, Melania and Barron have had their fair share of internet scrutiny, it is Trump’s eldest child whose controversial reputation, outspoken political views, and personal life have drawn the most public attention.
From his public relationship with former Fox News anchor Kimberly Guilfoyle to his current engagement to Bettina Anderson, Donald Trump Jr. has made considerable headlines for his personal life.
His split with Guilfoyle was reportedly quite abrupt, with rumors of Trump Jr. seeing Palm Beach socialite Bettina Anderson before the breakup making the rounds in public circles.
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Back in 2024, a source even told PEOPLE that Don Jr. took Anderson “on a trip to Alaska and introduced her around as his girlfriend while he was still very much with Kim.”
Donald Trump Jr. was married to Venessa Haydon from 2005 until 2018. They officially split in February 2022. The couple also shares five children.
Rumors surrounding the President’s eldest son goes beyond his love life and relationships.
According to The List, one such long-circulating speculation stemmed from his college years, when classmates allegedly nicknamed him “Diaper Don,” a reference to excessive drinking and embarrassing behavior.
The claim about the nickname ever died down. It, in fact, resurfaced during Donald Trump’s second term, which began in January 2025, much to Trump Jr’s discomfort.
In February 2025, a video of Trump Jr. displaying hunted birds during a trip to Mongolia went viral online. The footage had critics convinced that he allegedly shot an endangered ruddy shelduck.
Trump Jr. denied any wrongdoing and Italian authorities confirmed he had all the required permits, though several birds and ammunition were reportedly seized from the hunting estate that hosted him.
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In late 2024, a video showing Trump Jr. rubbing his gums went viral online, prompting critics to speculate that he was using cocaine, though no evidence supports these claims.
Similar speculation occurred during Donald Trump‘s inaugural ceremony in January 2025. A TikTok video falsely claimed Don Jr. briefly stepped out of view to snort cocaine.
Footage from another angle later showed he had simply bent down to speak with Vice President JD Vance’s mother. Despite repeated clarifications, this gossip does not seem to end.
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More recently, the President himself added to his son’s troubles. During the White House Christmas address on December 14, 2025, Trump made a statement, suggesting that his eldest son might not be around when he passes away.
“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,” POTUS said.
Previously, there have been reports of tension between the father-duo. However, Trump Jr. has continued to publicly support his father’s political agenda and defend him against critics, suggesting that earlier reports of conflict were exaggerated and unfounded.
Earlier this year, an anonymous insider told media outlets that Trump Jr. was seriously considering a presidential run in 2028, but he strongly denied those claims.
But a few months later, while speaking at the Qatar Economic Forum, he left open the possibility of a future bid, saying “maybe one day” and that “that calling is there,” although he did not commit to a campaign.
Meanwhile, in several interviews during his second term, Donald Trump has given mixed reactions about running for a third term. Presently, the 22nd Amendment of the American Constitution states that “No person shall be elected to the office of the President more than twice.”
However, MAGA supporters believe that a possible modification might allow Donald Trump to run for a fourth term, which would make it 12 years at a stretch for him.
Thus, in the interview with NBC News from March 2025, Trump clarified, “I don’t want to talk about a third term now because, no matter how you look at it, we have a long time to go.”
