Guilfoyle texts ‘extremely unseemly’: Jennings

CNN contributor Scott Jennings on Thursday criticized the newly reported text exchanges between U.S. Ambassador to Greece Kimberly Guilfoyle and a Republican donor, which have raised concerns about the Trump administration official’s conduct.

“It’s extremely unseemly, these messages. There’s no other way to read them,” Jennings said on CNN’s “The Arena” show.

Jennings, who has been floated as a potential successor to former White House press secretary Karoline Leavitt, told host Kasie Hunt the messages warrant an investigation into Guilfoyle.

In exchanges over text and Signal ahead of her 2025 Senate confirmation, the then-nominee of President Trump requested $100,000 from attorney Eric Deters to pay off her credit card bill.

Deters told NewsNation , The Hill’s broadcast partner, on Thursday evening he had given Guilfoyle $300,000 prior to the request.

Jennings pointed to Secretary of State Marco Rubio’s comments to reporters in Greece on Thursday, in which the secretary said he was uncertain whether the story about Guilfoyle was “true or not true.”

Rubio criticized journalists asking him about The Wall Street Journal ’s reporting before he had a chance to review the facts, saying, “That’s not the way the process is going to work.”

“When he talks about a process, 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 hit on a tarmac with a newspaper report,” Jennings said.

Guilfoyle, a former Fox News host and ex-fiancee of Donald Trump Jr., was confirmed by the Senate to serve as the U.S. ambassador to Greece in September 2025.

“If I were in her shoes right now, I would be considering what I wanted to tell the president and the secretary of state about my future because when you’re at 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,” Jennings said.

“If this story continues to spiral or more bad information were to come out, only she would know that,” he continued. “And she needs to be transparent with her principles about that.”