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The Express Gazette
Wednesday, October 14, 2026

Kimberly Guilfoyle Resigned After Allegedly Breaking Key 'Trump World' Rule, Strategist Says

Democratic strategist Julie Roginsky suggested Guilfoyle's departure as ambassador to Greece stemmed from violating an unwritten rule about financial dealings.

US Politics • 3 hours ago
Kimberly Guilfoyle Resigned After Allegedly Breaking Key 'Trump World' Rule, Strategist Says

Kimberly Guilfoyle, former U.S. ambassador to Greece and an ally of former President Donald Trump, resigned after allegations that she solicited a $100,000 donation to cover her American Express bill. Democratic strategist Julie Roginsky suggested that Guilfoyle's resignation was prompted by her violation of a cardinal rule within "Trump World": engaging in financial "grifting" without Trump's direct involvement or knowledge.

On MSNBC's "MS NOW," Roginsky elaborated on the unwritten rules of the Trump administration, adding her own to those previously stated by Eugene Daniels, who cited loyalty, being less famous, and avoiding embarrassment. Roginsky's proposed fourth rule stated, "if you’re going to grift, you can’t grift without Trump being in on it." Roginsky believes Guilfoyle's actions in Greece fell afoul of this principle, as Trump was apparently unaware of or not a participant in her financial dealings.

Guilfoyle announced her ambassadorship was "coming to an end" shortly after a Wall Street Journal report detailed the allegations. She has since called the claims "false" and stated her intention to "vigorously defend" her name. Trump himself commented on the situation Monday, stating, "We’re not happy" and that he was "looking at" firing her.

Roginsky speculated that Guilfoyle would likely be allowed to maintain a certain level of financial comfort in exchange for her silence regarding the Trump family. "She’s gonna be allowed to make a living, and that’s going to be the deal," Roginsky said. "And I don’t expect that we’re gonna hear anything from her that’s going to embarrass her. She’s not going to leak against this family, because she’s going to know that if she does, she’s out."

Roginsky further suggested that Guilfoyle, who was previously engaged to Donald Trump Jr., benefited more from her proximity to the family during the Trump administration than she might now. "Once you’re out of the circle, you’re an ex, which means you’re disposable. And she did not get that memo," Roginsky stated, implying Guilfoyle did not understand her diminished standing after leaving her influential position.


Sources