Kimberly Guilfoyle’s Ugly Texts About Younger Love Rival Leaked
Donald Trump’s Greek ambassador wasn’t so glowing about Don Jr.’s new flame.

Getty Images
Ugly text messages that appear to show Kimberly Guilfoyle slamming her ex’s new girlfriend have been exposed.
Guilfoyle, now 57, began dating Donald Trump Jr., now 48, halfway through his father’s first term. They got engaged in 2020 but split four years later, around the same time Trump was busted getting cozy with Palm Beach model and socialite Bettina Anderson, whom he is now married to.
Guilfoyle, who was previously married to California Gov. Gavin Newsom, remained a friend of the Trump family, however. A source told People in December 2024 that they were “still enamored with her.”
Indeed, she was named President Donald Trump’s ambassador to Greece around the same time as the People article was published.
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But Guilfoyle now finds herself in the public eye once more, for an entirely different reason. On Wednesday, The Wall Street Journal reported that the former Fox News personality asked a MAGA donor to pay her $100,000 American Express bill without leaving a paper trail.

Deters appeared in a series of photographs with Guilfoyle when they met.
Eric Deters
“It won’t show up anywhere if you wire money to American Express,” she wrote on Signal, according to messages the Journal reviewed. “Please.”
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That donor, Eric Deters, a former lawyer and congressional candidate in Kentucky, wanted access to the Trump administration, and, when Guilfoyle failed to deliver, the relationship went south.
Now he has gone scorched earth, releasing a 150-page media-ready document full of explosive claims, including ones about Guilfoyle.
Among the screenshots, correspondence, social media posts, and press coverage, Deters included text messages he confirmed that Guilfoyle sent about Anderson, 39.
Her lawyer, however, disputes the authenticity of the messages.

Guilfoyle, whose messages feature a light background, raged about Anderson, according to Deters, whose message is in blue.
Eric Deters
In one undated exchange, the sender, allegedly Guilfoyle, complains about Anderson, while appearing to dismiss an unidentified story in the Daily Mail.
“I was having a f---ing great time Saturday and we had a f---ing amazing time when we got home Saturday night that’s a nonsense. That’s his ex-wife’s friend. It’s all lies, but she’s a cloud chasing horror that plays the story in the Daily Mail to get attention,” the message reads.
It is possible the sender was supposed to say “clout chasing” and “placed the story,” rather than “cloud chasing” and “plays the story.”
Donald Trump Jr. and Bettina Anderson.
Kevin Lamarque/REUTERS
The comment about “his ex-wife’s friend” might refer to Vanessa Trump, who was married to Don Jr. and had five children with him before they divorced and he got together with Guilfoyle. Vanessa Trump and Anderson were friends until the latter hooked up with the Trump scion, according to Page Six.
The response, which Deters confirmed to the Daily Beast was his, was equally foul-mouthed.
“What a c--t,” he writes.
The sender agrees, writing, “Yeah, she literally sent the Daily Mail bikini photographs of her to try to include in the article.”
Explaining his coarse language, Deters told the Daily Beast, “I was just being her support animal lol.”
It is unclear which article the pair are referring to, but the publication ran an article in September 2024, headlined, ‘Donald Trump Jr. is ‘caught kissing’ glamorous Palm Beach socialite Bettina Anderson during brunch date without fiancée Kimberly Guilfoyle.’
The Daily Beast has contacted Guilfoyle, her lawyer, and Bettina Anderson, now known as Bettina Trump, for comment.

Don Trump Jr. and Kimberly Guilfoyle stand on stage at CPAC in 2021.
Joe Raedle/Getty Images
The story comes as more text messages between Guilfoyle and Deters show the ambassador begging him to clear her credit card debt, according to the Journal.
Her apparent panic came just days before she was confirmed by the Senate in July 2025.
“Honey please I need you to get this done for me today,” she messages Deters, adding a prayer hands emoji.
She also linked a PDF with bill payment instructions from American Express, according to Deters. “You could just send it here,” she wrote.

Eric Deters with Donald Trump Jr. at Freedom Fest 2025.
Eric Deters for Kentucky and America
In return, Guilfoyle reportedly promised to use her connections to relieve tax and legal issues Deters had run into, he claimed. According to documents seen by the Journal, she even sent proof that she was trying. She reportedly showed Deters that she had contacted the then-Internal Revenue Service chief and kept Deters abreast of efforts to lobby the Justice Department about his legal troubles.
Deters ultimately did not make the payment. He says he told Guilfoyle, then still freshly split from Donald Trump Jr., that doing so would end his marriage. However, the Journal reports that in one message, Deters wrote that he had paid Guilfoyle $300,000 over the years and had “not received one favor.”

Kimberly Guilfoyle, seen with Archbishop Elpidophoros of America, has opted for a series of low-cut tops while meeting with Greek Orthodox clergy as U.S. ambassador.
Kimberly Guilfoyle/Instagram
He allegedly added, “I am not naive or a sucker. I need results.”
Guilfoyle, seemingly panicked, responded that Deters needed to stop creating a paper trail.
“Stop papering all these things,” she wrote, according to the Journal. “It’s really dangerous... Just call me on Signal.”
In another, she reportedly said, “What a nightmare you’ll literally cost me my ambassadorship stop writing.”
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