Kimberly Guilfoyle, the U.S. ambassador to Greece until she was effectively fired on live television on Tuesday when the new White House press secretary said that President Trump had asked for her resignation, was at one point engaged to Donald Trump Jr., the president’s eldest son. The couple owned a $9.7 million home in Florida, appeared at Trump rallies together and sent each other adoring posts on Instagram. Guilfoyle posted on Instagram on Valentine’s Day 2022.
Trump is married to a Florida socialite and model. Guilfoyle, who was nominated as ambassador to Greece by the president soon after her engagement to his son was broken off two years ago, is out of a job after a series of damning reports in The Wall Street Journal, including that she asked a Republican donor to pay off $100,000 on her American Express credit card just before her Senate confirmation hearing in July 2025. Guilfoyle, 57, was not a surprise at the White House, where many saw her as a flamboyant party girl with questionable judgment.
Her supporters said she was in fact a substantive person underneath the glitz. Guilfoyle, a former Fox News host and a former prosecutor in San Francisco and Los Angeles, was once married to Gavin Newsom, who would go on to become governor of California and one of the Democratic Party’s most outspoken critics of Mr. Guilfoyle with Gavin Newsom, then her husband, after he won the election for mayor of San Francisco in 2003.
Newsom later became governor of California and one of the Democratic Party’s most outspoken critics of Mr. Trump.Credit...Marcio Jose Sanchez/ Either way, Ms. Guilfoyle was a Trump insider with a prominent role in the family and its political operation.
The president’s swiftness in firing her showed his willingness to cut off anyone who becomes a liability and an embarrassment. But it also left her with little reason to remain loyal to the president and his family at a time when Mr. Trump’s political authority is ebbing.
In announcing her resignation, she decried what she called false accusations and said she would vigorously defend her reputation. Speaking to reporters outside the White House, Mr. Trump did little to suggest he would continue to keep her close.
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