Messages reviewed by the Journal show Guilfoyle urging Deters to wire the money directly to American Express so the payment would leave no visible paper trail. She also repeatedly warned him against documenting their financial arrangements, saying he could jeopardize her ambassadorship.
Guilfoyle offered to use her connections to senior Trump administration officials to help Deters with IRS and Justice Department matters, as well as secure an interview with Tucker Carlson, for which Deters had promised up to $1 million.
Messages indicate she contacted the incoming IRS commissioner about Deters' tax dispute and sought assistance from people connected to Carlson. Deters, who previously paid Guilfoyle $300,000 in speaking fees, refused to cover the credit card bill and claimed she had failed to deliver any of the favors he sought.
Guilfoyle's attorney disputed the authenticity of the messages and maintained that she was owed money for earlier speaking engagements.
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🇺🇸🇬🇷⚡️ — U.S. Ambassador to Greece Kimberly Guilfoyle, Donald Trump Jr.’s former fiancée, allegedly pressured Trump donor Eric Deters to pay a $100,000 American Express bill shortly before her Senate confirmation hearing in July 2025, according to WSJ.
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