Donald Trump Jr.'s Little-Known Connection To Diddy Explained

Donald Trump Jr.'s connection to Diddy goes back further than many might realize. His father, Donald Trump, had a longstanding friendship with Diddy that ended when the producer publicly backed Joe Biden for president in 2020. Besides his father knowing Diddy, Donald Jr. was acquainted with the "It's All About the Benjamins" rapper because the pair ran in the same social circles. "I sorta grew up in that world. Before politics, I used to get invited to the cool person parties," Donald Jr. said during an interview with DJ Akademiks on April 17, 2024, when the subject of Diddy was brought up. In fact, Donald Jr. had a close connection to the musician through his ex-wife.

When Vanessa Trump was married to Donald Jr., she was close to a long-time partner of Diddy. "She was really good friends with Kim Porter," he told DJ Akademiks. "They'd do photoshoots together," Donald Jr. added. While discussing Diddy, Donald Jr. raised suspicions about Porter's death and claimed that she told Vanessa that "she was really afraid" of the rapper. Porter died in 2018 from lobar pneumonia. It should be noted that officials "certified [the death ] as natural." Diddy — who had three children with Porter — often spoke about his former partner following her death and remained in mourning long after she passed. "[I]t broke my heart forever," he told ET in September 2023.

Besides the connection through his ex-wife, Donald Jr. was also linked to Diddy through his alleged mistress, Aubrey O'Day.

When Donald Trump Jr. and Vanessa Trump were getting divorced in 2018, reports surfaced alleging he had an affair with singer Aubrey O'Day, who made a name for herself on Diddy's "Making the Band" in 2005, which earned her a spot on the producer's Danity Kane group. The affair between Trump and O'Day reportedly began when she appeared on Season 5 of "Celebrity Apprentice" 2011. "Things started up with Aubrey and Don Jr. toward the end of the taping," a source told Us Weekly in March 2018. "When it started, they were very serious all of a sudden," the insider added. Reportedly, Trump put a halt to the tryst when Vanessa discovered the affair by reading some of his personal emails.

Since news of their reported affair broke, O'Day has not been shy about discussing her time with the eldest son of the former president. O'Day also did not bite her tongue following the raids on Diddy's homes in March. "You reap what you sow," the former Danity Kane singer wrote on X, formerly Twitter at the time. O'Day took to X once again to chime-in on Diddy news after she heard Trump's interview with DJ Akademiks. "[M]y long term EX @DonaldJTrumpJr went on @Akademiks to discuss my EX boss diddy & the conspiracies behind Kim Porter's death," she wrote on April 19, 2024. "I am in the CENTER of REALLY knowing ALL."

In the following days, O'Day posted follow-up tweets about both Diddy and Trump.

On the heels of Aubrey O'Day's tweet about Donald Trump Jr. discussing Diddy and Kim Porter's death, fans asked her to spill the insider info she hinted at. "Everyone with an experience is following all legal protocol and being responsible with their knowledge," she wrote on X on April 20, 2024 — the day after her initial tweet. The "Damaged" singer also came to the defense of Trump when one fan questioned his intelligence. "Don is actually incredibly smart. [All] the ignorant s**t he says is him falling in line with the lane he chose to go down," O'Day wrote on April 22.

This was not the first time O'Day spoke about both Trump and Diddy. She discussed both men during an interview in July 2019. At the time, O'Day gushed over Trump, whom she called her "soulmate" while appearing on MTV's "Ex on the Beach" reality show. Her comments made headlines, and O'Day doubled down on the statement. "It's funny because everyone was like, 'Wow, you're just saying that,' and I was like, 'Yeah, because it's true,'" she told Variety in July 2019.

In that same interview with Variety, O'Day detailed the difficulties of working with Diddy when she was a member of Danity Kane. "We were scared to death with what would happen with Puff each day," she told the outlet. "I experienced everything from race [remarks] to sexism and a lot of it was scary," O'Day added.