A former federal prosecutor laid out why President Donald Trump has every reason to protect Kimberly Guilfoyle after explosive new reporting on her finances.
Andrew Weissmann, a former federal prosecutor, told host Sarah Longwell on Thursday’s episode of “The Illegal News” that turning on Guilfoyle would be “too risky” for the president. “Keep your friends close and your enemies closer,” he said.
Guilfoyle, the U.S. ambassador to Greece and Donald Trump Jr.’s former fiancée, is facing scrutiny after The Wall Street Journal reported on texts in which she sought $100,000 from a donor to cover her American Express debt.
According to the reporting, the donor complained he wasn’t seeing results, and Guilfoyle pressed him to stop discussing their arrangement and move the conversation to Signal. Longwell noted that the donor, Eric Deters, has since claimed he did not pay. Guilfoyle’s attorney, Jesse Binnall, said she disputes the authenticity of the messages but offered no specifics.
Despite the revelations, the Trump administration has not turned on Guilfoyle. Her boss, Secretary of State Marco Rubio, declined to address the allegations, saying he had no idea whether they were true.
Weissmann said Trump learned from Michael Cohen, his former fixer who turned on him. “One of the reasons that Michael flipped is for very little money he could have stayed in the tent and he didn’t,” Weissmann said. “The lesson for Donald Trump is, you know what, penny-wise, pound-foolish, better to keep people inside the tent and not out.”
He also hinted at what Guilfoyle might be holding. “Who knows, he may very well know and Don Jr. may very well know what else she knows,” Weissmann said.
In a normal administration, Weissmann said, Guilfoyle “would no longer be the ambassador and the Department of Justice would be opening a criminal investigation into the solicitation of a bribe.” He compared the texts to evidence from his days prosecuting the mob, when suspects would ask to be called back from a pay phone down the street. “If you’re not hiding anything, what’s the problem?” he said.
He predicted the current Justice Department would not act, “for the same reason they didn’t look into Signalgate,” referring to the 2025 scandal where Defense Secretary Pete Hegseth discussed military strikes in a group chat that included a reporter. When asked whether Guilfoyle could ultimately land a pardon, Weissmann was blunt. “Absolutely,” he said.
But Weissmann flagged one exposure a pardon may not fix. If she took the money, he said, “she has a tax problem.” He said she’ll need careful advice to avoid committing a tax crime going forward. “That is going to be income to her in my unprofessional tax opinion,” he said.
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