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.
