Trump Reportedly Knew About Don Jr.'s Affair With Aubrey O'Day (& Wasn't Happy About It)

Donald Trump has had quite a few relationship scandals and cheating allegations surface over the years (there's a lot more than his drama with Stormy Daniels), but he apparently holds his son, Donald Trump Jr., to a higher standard. Donald reportedly knew about Donald Jr.'s alleged affair with singer Aubrey O'Day, which happened while he was still married to ex-wife Vanessa Trump (who is rumored to have had an affair of her own).

In his book "Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass," published in June 2024, author Ramin Setoodeh writes (via OK!) that he asked Donald about the reports of alleged infidelity and he admitted, "I had heard that, actually." Setoodeh also wrote that Donald knew that O'Day had recorded a song that was reportedly about her affair with Donald Jr., but Donald said that he "hadn't heard the song."

Donald's remarks corroborated comments made by his former lawyer, Michael Cohen, during an episode of his "Mea Culpa" podcast back in July 2023, when he had O'Day as a guest on the episode. Cohn recalled telling Donald Jr. at the time that his father was "really f***ing pissed" at the embarrassing affair, which allegedly was conducted between 2011 and 2012. He recounted: "I said, 'Your dad called me in to talk about you and Aubrey... What are you going to do? Your dad is f***ing serious. You won't even have the ability to get into the building and pack your s**t up. You better start thinking twice."

Donald Trump Jr. tied the knot with Vanessa Trump in a ceremony at Mar-a-Lago in November 2005. In March 2018, just over a year into his father's presidency, they announced their separation and finalized their divorce later that year. During their time together, they welcomed five children — daughters Kai and Chloe, and sons Donald, Tristan and Spencer.

Danity Kane singer Aubrey O'Day opened up about her alleged relationship with Donald Jr. in 2023. She claimed that Donald Jr. was trying his hardest to figure out how to make their relationship work and leave Vanessa in a way that wouldn't cause controversy. "He was fighting to stay with me, he was having us meet with media trainers, he created a five-year plan," Aubrey told Michael Cohen during her appearance on his podcast. The singer said Donald Jr.'s biggest fear was that a tabloid cheating scandal could ruin his kids' chances at getting into private schools. She claimed that Donald Jr. planned to separate from Vanessa and then frame his romance with Aubrey to look like it began after his split.

However, Aubrey said that things wound up getting "tricky," and that she didn't feel she could keep up the ruse. Looking back, she said she lacked "the maturity or self-love" to end the relationship sooner, so they ultimately called it quits. Aubrey went on to release a song titled "DJT" on her 2013 album "Between Two Evils," which was allegedly inspired by their affair. Shortly after his separation from Vanessa, Donald Jr. went public with his relationship with Fox News commentator Kimberly Guilfoyle, and the pair went on to get engaged in December 2020.