There are many reasons that singer Aubrey O’Day says she doesn’t recognize the man that her ex-lover, Donald Trump Jr., has become, from his bellicose support for his father’s conservative positions to his “belittling” social media statements about the LGBTQ community.
What’s really convinced O’Day that something is not “authentic” about Trump Jr.’s current public persona is his relationship with former Fox News host Kimberly Guilfoyle, as she explained in a podcast interview with Michael Cohen, the former attorney and “fixer” for Donald Trump who has become one of Trump’s fiercest critics. O’Day said she can’t believe he’d want to wake up “next to (her) face every morning” or would enjoy her dressing up as a sexy cheerleader, as she reportedly claimed to Trump campaign donors.
When O’Day said she and Trump Jr. were in the throes of their intense love affair in 2011 and 2012, she knew the oldest Trump sibling to be a “brilliant,” thoughtful man, she told Cohen on his “Mea Culpa” podcast. Trump Jr. wanted to extricate himself from his father’s shadow, while, as the vice president of Trump’s real estate development company, he wanted to “help low-income people and build projects that were good for the environment,” she said.
O’Day, a self-described “bleeding-heart liberal,” also said her New York City-reared boyfriend was comfortable hanging out at a gay night club in the city — where, she said, they had sex for the first time in a bathroom.
After O’Day and Trump Jr. met when she was a contestant on his father’s reality TV show, “The Apprentice,” they became friends and lovers who regarded each other as “soul mates,” O’Day said. He also crafted a carefully considered plan to leave his then-wife Vanessa to be with her. O’Day said he’d had affairs with other women but had never been in love with them. Moreover, O’Day said, “I definitely believe I was the best sex that man ever had. We were on a whole other level of sex. It was beyond physical.”
For this reason, O’Day said, she can’t believe that he would be attracted to Guilfoyle or that he would end up with her after finally divorcing Vanessa, the mother of his five children. O’Day expressed particular doubt that Trump Jr. would be happy about Guilfoyle’s reported habit of boasting about their sex life.
O’Day apparently is referring to multiple reports about Guilfoyle’s questionable interactions with donors during the 2020 presidential campaign. According to the book, “Frankly, We Did Win This Election: The Inside Story of How Trump Lost,” by Wall Street Journal reporter Michael C. Bender, Guilfoyle, a senior advisor for Trump’s campaign, enjoyed giving donors “an unwanted glimpse” into her sex life with his son, saying that he liked her to dress up as a sexy cheerleader.
“I don’t buy it for a second,” O’Day told Cohen.
Guilfyole also shared how she called Trump Jr. her “naughty boy” when she “let him out of his cage,” according to an excerpt of Bender’s book.
The relationship between Trump Jr. and Guilfoyle likewise mystified political observers after it was revealed in the spring of 2018, in part because she was once the first lady of San Francisco and formerly married to Democratic California Gov. Gavin Newsom. But after divorcing Newsom in 2006, Guilfoyle became outspoken about her longstanding conservative views as a Fox News host.
As a couple, Guilfoyle and Trump Jr. became known as an in-demand duo at Trump campaign events — “the prom king and queen of MAGA land,” a senior Trump advisor once told Business Insider. Reports also said that the couple sometimes engaged in teasing banter about their relationship at political events, which would please some in the pro-Trump crowd. But Guilfoyle also made people uncomfortable with the sexually suggestive way she talked or acted at events, reports said.
In O’Day’s conversation with Cohen for his “Mea Culpa” podcast, she referred to a damning 2020 report by the New Yorker that said that Guilfoyle’s job as a Fox News host ended because of sexual harassment allegations made against her by a former assistant. According to the New Yorker, Guilfoyle showed lewd photos of male genitalia to colleagues, regularly discussed sexual matters at work, urged the assistant “to submit to a Fox employee’s demands for sexual favors,” and exposed herself to the assistant while asking for a critique of her naked body.
O’Day clearly has a low opinion of Guilfoyle and regards Trump’s relationship with her as a sign that he’s “living outside” his “most authentic self.” O’Day said she “really loved that man.” She also said she still loves him but “who he is now, I love in a sorrowful way.”
Cohen agreed that whatever is going on with Trump Jr. and Guilfoyle – whom he derisively called “Gargoyle” – “is not good.”
During the interview, Cohen also expressed fondness for the Trump Jr. he used to know when he loyally served the family. He agreed that Trump Jr. was “innately” the brightest of Trump’s three oldest children. Cohen became one of the Trump family’s fiercest critics after he served time in prison for tax evasion, campaign finance violations and other crimes which he said were done at the former president’s direction.Cohen confirmed O’Day’s view that her affair with Trump Jr. was serious. He said he knew Trump Jr. was in love with her and heard him call her his “soul mate.”
Initially, no one in the Trump family cared about the affair, and Vanessa Trump probably was aware of it, both Cohen and O’Day said. But at some point, Ivanka Trump raised concerns about the potential for scandal or was concerned about the impact on Vanessa, Cohen said. Trump ordered Cohen to tell his son to end the relationship. Both O’Day and Cohen said that Trump threatened to fire his son from the Trump Organization and cut him out of his will if he didn’t end the relationship.
O’Day expressed sadness that Trump Jr. was never able to fulfill his dreams, including the chance to “marry a woman who was (his) soul mate and to be (his) own man.” She said that he had “all this ability to create positive change and be an inspiration in the world. … He wanted to be something else, instead of what he ended up becoming.”
