Donald Trump Jr. Reveals About His Unexpected Ties with Diddy

It has turned out as a surprise to many to learn that Donald Trump Jr. has an unexpected connection to hip-hop mogul Diddy. This link dates back long before his father Donald Trump fell out with Diddy over the 2020 presidential election. As Trump Jr. revealed in an April 2024 interview, he was acquainted with the famous rapper because they traveled in similar elite social circles before Trump entered politics.

"I sorta grew up in that world. Before politics, I used to get invited to the cool person parties," he told DJ Akademiks. However, Trump Jr.'s ties to Diddy ran even deeper through his ex-wife Vanessa Haydon's close friendship with Kim Porter, who was Diddy's long-term partner and mother of three of his children. "She was really good friends with Kim Porter. They'd do photoshoots together," Trump Jr. said of Haydon and Porter's relationship.

In a shocking claim, he alleged that before Porter's death from pneumonia in 2018, she had confided in Haydon that she was "really afraid" of Diddy, as per The Daily Mail. While officials ruled Porter's death a natural cause, Trump Jr. appears to raise doubts in the interview. After getting married in 2005 at Mar-a-Lago, Trump Jr. and Haydon had five kids together before divorcing after a 12-year marriage. He is currently engaged to Kimberly Guilfoyle, a devoted Trump supporter. 

Another layer to Trump Jr.'s Diddy connection involves his reported past affair with singer Aubrey O'Day from Diddy's Making the Band reality show. In 2018, amid his divorce from Haydon, rumors swirled that Trump Jr. had an extramarital relationship with O'Day after meeting on Celebrity Apprentice in 2011.

Sources claimed it was a "very serious" affair that Haydon discovered. Since those reports, the outspoken O'Day has been open about her involvement with both Trump Jr. and her former boss Diddy. Following recent legal issues for Diddy, O'Day tweeted cryptically "You reap what you sow" and suggested she was "in the CENTER of REALLY knowing ALL" about the two men.

While O'Day defended Trump Jr.'s intelligence despite his "ignorant" statements, she was more critical of her time in Diddy's Danity Kane singing group. "We were scared to death with what would happen with Puff each day...I experienced everything from race [remarks] to sexism and a lot of it was scary," she told Variety in 2019.

However, the singer also gushed about her "soulmate" connection with Trump Jr. during that same interview, doubling down on surprising prior comments calling him her soulmate.

Porter passed away from a lung infection while she was sleeping in the year 2018, according to NBC News. The coroner stated, "It was later determined Porter died from lobar pneumonia... The manner of death was certified as natural." The former model complained about a sore throat a few weeks before she passed away.