Barbara Walters Nearly Married One Of Donald Trump's Most Notable Allies

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One of Barbara Walters' most famous exes is Donald Trump's former lawyer, Roy Cohn. In Susan Page's 2024 biography "The Rulebreaker," she shared that the famed journalist's father introduced her to his lawyer when she was 25. According to the SF Gate, although Barbara was mostly apolitical at the time, she still disliked Cohn due to his work for the controversial senator Joseph McCarthy. 

So, when Barbara's father, Lou Walters, mentioned to Cohn that she was eager to meet him, she corrected him and truthfully stated that wasn't the case at all. Yet, against all odds, Walters still struck a romantic connection with Cohn, who was a closeted gay man. In Page's book, she claimed that Trump's fixer had asked for Barbara's hand in marriage on numerous occasions. One such instance even occurred on the night before the iconic news anchor walked down the aisle with her second husband, Lee Guber, in 1963. 

Speaking to WCBS-TV in 1982, Cohn admitted that he had a 45-minute chat with Barbara on the eve of her wedding, during which he tried deterring her from the marriage with a long list of reasons. Although he was unsuccessful in his attempts, he still held Walters in the highest regard. He had nothing but positive things to say about her, gushing: "She, to me, is everything a woman should be. She's pretty. She's brilliant. She's fun. We never had a dull second" (via UPI). Cohn similarly praised Barbara in a 1972 interview with the New York Times, labeling her "a standup girl all the way, very independent but very soft." And the once-popular news anchor, who sadly died in 2022, similarly remembered Cohn in a good light.

Speaking to the SF Gate in 2008, Barbara Walters stated that Roy Cohn didn't exactly have a softer side in his personal life, either. However, she believed that her ex made up for it with his humor, intelligence, and connections. In the June 2025 documentary "Tell Me Everything," Cindy Adams, a confidant of the late journalist, claimed that Cohn's connections were at the center of their union. 

"Roy Cohn was famous, so he was worthwhile to Barbara," Adams said, per the NY Post. "Barbara was famous, so it was worthwhile for Roy. They were two people who loved PR." According to her, Cohn and Walters hardly ever got any quality time as a couple. Notably, in her interview with the SF Gate, the late news anchor hinted that Cohn could have also had ulterior motives for their relationship, stating that being with her was a way to maintain his public perception of being a straight man.

However, Walters stressed that Cohn had never opened up about his sexuality or AIDS diagnosis to her. Despite everything, Walters remained loyal to him even when the world turned against him. In 1986, the famed journalist served as a character witness for Cohn during his disbarment trial. While speaking to Vanity Fair in June 2025, the director of "Tell Me Everything," Jackie Jesko, shared that she believed Walters' decision to speak at the hearing served as a testament that their relationship wasn't solely transactional. As for Walters, she told the SF Gate that she had remained in Cohn's corner because he had gotten her father out of a jam.