'Jealous' Kimberly Guilfoyle tried to sabotage Trump Jr.'s new romance, report says

Contrary to any of the polite things Kimberly Guilfoyle has said about Donald Trump Jr. leaving her for Palm Beach socialite Bettina Anderson, America’s ambassador to Greece was privately “seething,” according to a new report, and reached out to Anderson’s billionaire ex-fiancé to work together to break up the new couple.

That’s according to a new report in the Daily Mail, which also said that Guilfoyle, the 57-year-old former Fox News host who is fervently loyal to President Donald Trump, plotted with William ‘Beau’ Wrigley, the heir to the Wrigley chewing gum fortune, to leak negative stories about Anderson to the media.

The stories focused on portraying her as a calculating social climber who only pursued the president’s oldest son to gain access to his wealth, power and celebrity, the Daily Mail also said.

“Kimberley is determined not to be seen as a loser,” a source close to Guilfoyle, Trump Jr., Anderson and Wrigley told the Daily Mail. “She is wild with jealously about Bettina.”

The Daily Mail said it reached out to Guilfoyle, Wrigley, Trump Jr. and Anderson for comment, while a source close to Anderson said: “All this story really shows is just how jealous and petty Guilfoyle really is.”

Whatever alleged plot was hatched up by Guilfoyle and Wrigley, it didn’t work.

Trump Jr., 48, and Anderson, 39, were married in two separate ceremonies last month. The first was a small, private ceremony in West Palm Beach on May 21, followed by a destination wedding, reminiscent of John F. Kennedy Jr.’s iconic 1996 wedding to Carolyn Bessette, at a luxurious private island in the Bahamas. Over the Memorial Day Weekend, the couple exchanged their vows in a small island chapel, in front of close friends and family, including three of Trump Jr.’s four siblings — Ivanka, Erica and Tiffany — and several of Trump Jr.’s five children.

President Trump, first lady Melania Trump and Trump Jr.’s youngest half-brother, Barron, didn’t make the trip, and Guilfoyle probably wasn’t invited, even though she was once considered part of the Trump family’s inner circle.

But from the Daily Mail report, it sounds like the ambassador has had trouble getting over the fact that she wasn’t the bride walking down the aisle to marry the president’s oldest son.

Guilfoyle, the San Francisco-born ex-wife of California Gov. Gavin Newsom, had been expecting to tie the knot with Trump Jr., at least since they became engaged in 2020. They began dating in 2018, during Trump’s first term, and the two quickly became known as the “prom king and queen of MAGA land.” They became popular campaign surrogates for Trump, though they reportedly had a tendency to allude to their love life at fundraisers. Trump Jr. also always showed delight in having Guilfoyle do a sexy dance at public events, including before both took the stage at Trump’s Jan. 6, 2021 rally before his MAGA supporters stormed the U.S. Capitol.

But the love story of Guilfoyle and Trump Jr. secretly ended in 2024, several months before Trump was re-elected president, according to the Daily Mail. The U.K. tabloid reported that Trump Jr., 48, had blindsided Guilfoyle by starting a romance with Anderson, 39.

People magazine reported that Trump Jr. came to feel that Anderson, with her honey-blonde hair and “Waspy” model looks, would “impress” his father and perhaps make her a more ideal, long-term partner, both romantically and politically. Guilfoyle’s tendency to wear tight dresses and excessive makeup had supposedly become less alluring to Trump Jr., according to the report.

It was officially revealed in December 2024 that Trump Jr. and Guilfoyle had split and that he had begun dating Anderson. This news coincided with Trump announcing that he had nominated Guilfoyle to be his ambassador to Greece. Unfortunately for Guilfoyle, she came to be seen as the woman jilted by the president’s son, while there were reports that Trump hoped to send his son’s ex-fiancée to Greece so that she would be out of his way. But it’s also likely that the appointment was for her political loyalty.

In an interview earlier this year with the New York Times, Guilfoyle insisted that she was “happy for Don.” The interview took place in Athens, where Guilfoyle began serving as U.S. ambassador in Greece in November.

But privately, Guilfoyle was “nursing humiliation” over Trump Jr. leaving her for Anderson, according to the Daily Mail. In the months after he went public with his relationship with Anderson, Guilfoyle became determined to end his new relationship, so she teamed up with Wrigley to do so, a source close to the situation told the Daily Mail.

“It was the most unholy of alliances, let’s just put it that way,” the source told the Daily Mail. Another source told the Daily Mail that Wrigley had reached out to Guilfoyle, not the other way around. He reportedly wanted to share concerns he had from his engagement to Anderson, which ended in 2017. He wanted to explain “serious issues he felt Don ‘should be aware of,'” the source said.

Insiders offered a couple of different takes on Anderson’s relationship with Wrigley. The first is that she, then 30, was a “hot, young girl,” who was seen as a rebound girlfriend, following Wrigley’s divorce from his second wife.

“I think she was genuinely into him and the relationship, and he wasn’t,” a member of Wrigley’s household staff told the Daily Mail. Another insider described the Wrigley/Anderson relationship as “fast and furious” and said she was “pushed to get engaged very quickly.” Wrigley and Anderson planned a lavish destination wedding in Ireland and had already sent out invitations, but the wedding was called off because Anderson wouldn’t sign a prenup, a former staffer said.

When they broke up, Wrigley asked Anderson to leave his $98 million estate in North Palm Beach. “She was heartbroken,” the former staffer told the Daily Mail.

This time around, with Trump Jr., Anderson did sign a prenup, the Daily Mail reported.

And the wedding went forward, in spite of any alleged efforts by Guilfoyle and Wrigley to prevent it from happening. According to the Daily Mail, the best the two could do was to help facilitate some negative media coverage about the new couple. A Palm Beach socialite who has known Anderson since childhood told the Daily Mail: “Kim got in contact with all of us.”

Meanwhile, people in Palm Beach were happy to spread the word about Anderson’s family scandals and her reputation as “a social climber,” the Daily Mail reported. However Anderson is seen in Palm Beach, she did manage to marry the son of one of the most powerful people on the planet. And, it’s possible that she will enjoy another rare honor. Reports say that she and Trump Jr. would love to hold another wedding ceremony — their third — in the White House, with his father and the first lady present.

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