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The conservative host suggested the 57-year-old is now “a problem” for the Trump administration.
Conservative commentator Scott Jennings has thrown Kimberly Guilfoyle under the bus on live TV over claims of her wild cash demand.
Guilfoyle, the U.S. Ambassador to Greece, was previously engaged to Donald Trump Jr., before splitting in 2024. On Wednesday, the 57-year-old became engulfed in a scandal over a payment she allegedly requested from MAGA donor Eric Deters, who asked her for favors with the Trump administration.
The former Fox News host asked Deters, a former congressional candidate from Kentucky, for $100,000 to cover her American Express bill, but without leaving a paper trail, a report in The Wall Street Journal alleges.
Deters has since revealed their damning text correspondence, including Guilfoyle telling him, according to the Journal, “I really wish you would stop papering all these things. What a nightmare. You’ll literally cost me my ambassadorship. Stop writing. Stop papering all these things. It’s really dangerous. And just call me on signal.”
In another message, she allegedly wrote: “Honey please I need you to get this done for me today. You could just send it here.” That was sent on July 3, 2025, days before her confirmation hearing on July 9.
Deters was looking for Guilfoyle’s assistance in “getting the attention of the new Trump administration on some personal tax and legal issues,” according to the Journal.He claimed that Guilfoyle told him if he provided the money for her bill, “I will be your Trump ride or die, forever and ever.” He stated, “She never came through on anything.”
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Guilfoyle’s lawyer, Jesse Binnall, said he disputes the messages’ authenticity but declined to provide specifics to the Journal. The lawyer claimed that Guilfoyle was paid to speak at events ahead of her nomination, and she “was owed a balance for traveling to and supporting these patriotic events.” Deters told the paper he did not owe Guilfoyle anything.
Jennings appeared on CNN’s The Arena With Kasie Hunt on Thursday. Hunt asked Jennings how claims of Guilfoyle’s motivations to seek money for possible access to the administration would “go over in Trump’s world.”
Trump ally Jennings, who has been linked to the vacant White House press secretary role, initially said, “Pass.”
The right-wing commentator then admitted, “It’s extremely unseemly, these text messages. There’s no other way to read it.”
Jennings added, “May not be illegal, has to be investigated. I assume that at the State Department, that is the next thing that will happen.”
Jennings also touched on the awkward fact that Guilfoyle met with Secretary of State Marco Rubio on Thursday, during his trip to Greece.
When asked about the incident by reporters in Greece, Rubio refused to comment. “If someone gives information to a newspaper or a media outlet, the media outlet reports it, you immediately turn to me and say, ‘I need you respond to our reporting.’ That’s not the way this process works,” Rubio said.
Jennings defended Rubio, saying, “I assume what he meant was, there will be a process by which we look into this, gather our own information, and then we will report to you when we have some findings that aren’t just us getting a hit on a tarmac with a newspaper report. I think that’s actually perfectly fair.”
However, Jennings doubled down on his criticism of Guilfoyle, addressing her “principles.”
“If I were in her shoes right now, I would be considering what I wanted to tell the president, the Secretary of State, about my future,” Jennings stated.
“Because when you’re in an appointed position like this, and you hold a position of trust with the government, and then you become a distraction or an embarrassment to your principles, that’s a problem.”
He added, “And if this story continues to spiral or more bad information were to come out, only she would know that, and she needs to be transparent with her principles about that.”
Deters did not pay Guilfoyle’s American Express bill, according to the Journal, and told her making the payment would end his marriage. In June 2025, he sent her a photo of a memo and stated, “I have paid you $300,000 over the years. As of this memo, I have not received one favor. I am not naive or a sucker. I need results.”
The Daily Beast has contacted the White House for comment.
