Weird Things About Kellyanne Conway's Relationship With Donald & Melania Trump

Kellyanne Conway has had longstanding ties with both Donald Trump and Melania Trump for many years. During Donald's presidency, Conway not only worked at the White House, but she was a staunch defender of the then-first lady. "The woman is beautiful inside and out," she said on Fox News in February 2017 when speaking about Melania, the New York Post noted. It was surprising when Conway left Donald's administration in 2020, but it was far from the end of her relationship with the Trumps.

As Donald prepared for the 2024 election, a report from Puck came out that Melania wanted Conway back on Team Trump. "She is unhappy; that's why she didn't go out on Super Tuesday. Kellyanne is the only person Melania trusts," the outlet wrote in March 2024. By August, Puck reported that, in addition to Melania, Eric Trump and Lara Trump were vocal about their desire to see Conway become Donald's campaign manager. On the heels of that report, the former president spoke to The New York Times and denied that he was shaking up his campaign team. The relationship between Donald and his former aide had been a complicated one.

In her 2020 memoir "Here's the Deal," Conway expressed how she really felt about Donald. "I had two men in my life. One was my husband. One was my boss," Conway wrote. "One of those men was defending me. And it wasn't George Conway," she added. The friction between Conway's husband and Donald further complicated her standing with the Trumps.

Kellyanne Conway's ex-husband, George Conway, had a very public fraught relationship with Donald Trump while he was in office. George was openly bashing Donald online, and that caused tension between the then-POTUS and his aide. This caused Melania Trump to come to Kellyanne's defense. "Donald, this is not her fault," the former first lady said, as Kellyanne recounted in her memoir "Here's the Deal," adding, "We don't control our husbands—and you don't control us!" Kellyanne felt torn between her husband and her boss, believing George's fixation on trashing Donald on social media had become a problem. "Clearly he was cheating by tweeting," she wrote in her memoir. According to Kellyanne, her husband's anti-Trump tweetstorms "violated [their] marriage vows." 

Not long after that book was published, Kellyanne and George were set to divorce after 22 years of marriage in March 2023. As outlined in her book, Kellyanne put the blame of their split solely on her ex-husband.

When news of the Conways split went public, the former "The Apprentice" host wasted no time kicking George while he was down. "Congratulations to Kellyanne Conway on her DIVORCE from her wacko husband, Mr. Kellyanne Conway," Donald wrote on Truth Social in March 2023. "Free at last, she has finally gotten rid of the disgusting albatross around her neck," he added in the lengthy post trolling Kellyanne's ex. Donald enjoyed throwing barbs at George, almost as much as he enjoyed publicly gushing over Kellyanne.

When Kellyanne Conway published her 2022 memoir "Here's the Deal," she openly sided with Donald Trump over her husband, but she also made claims that rubbed the one-time president the wrong way. According to Conway, Trump had confided to her that he lost the 2020 presidential election. "I may have been the first person Donald Trump trusted in his inner circle who told him that he had come up short this time," Conway wrote. Trump, of course, had claimed that the election had been rigged in Joe Biden's favor. "Writing books can make people say some very strange things," he fired back on Truth Social in May 2022 while taking aim at Conway.

The friction between Trump and Conway was short-lived, and the former White House aide was back in his good graces just two months later. It appeared the relationship between the former boss and employee ran deeper than a business relationship. "Kellyanne occupies unique and prime real estate in Donald Trump's legacy and heart, and that's why they're in regular touch," a source told the Daily Beast in July 2022. "I have a very good relationship with Kellyanne," Donald told the outlet only two months after bashing her online.

That same month, Donald fawned over Conway while speaking at a rally in Washington, D.C. "I love Kellyanne!" he told the crowd, as noted by Business Insider. "I see my Kellyanne. I love Kellyanne," Donald added while addressing Conway, who was seated in the audience.