I met Kimberly Guilfoyle at the first Mediaite holiday party in December 2016. She was surprisingly friendly, verging on flirty, which should have surprised me less than it did. On-air talent have often cozied up to Mediaite writers and editors on the theory that it would get them better coverage. It never did. I left the party thinking she was fun, not really a deep thinker, and largely harmless.
Within six months she reached out and wanted to talk to me on the phone. A mutual friend offered a sort of gentle prep or warning I’ve thought about many times since. Kimberly was a nice person and a friend, this person said, but she shouldn’t necessarily be trusted with everything that came out of her mouth. I wasn’t hearing that I hadn’t sensed already, but it was a useful reminder from someone else who knew the person. The cable news talent racket is a small world in which most people know one another, for better and worse.
The phone call was about whether she should take the job of White House press secretary. Sean Spicer was on his way out, or was rumored to be, and she said the job had been offered to her and she wanted my advice. I had read the reports that she was being considered. By then I’d developed a decent sense of what news was real and what was planted, and all of it read to me as intentionally planted, designed to get her name out there for the plum administration gig. The call did nothing to change my mind. She wasn’t asking for advice; she was trying to get me to write the exclusive. She spent thirty minutes on background walking me through her own candidacy, and I entertained it, because she was good company and because that’s the job. At the end I told her not to take it. I never wrote a word.
Yes, that call was on background, and I’ve kept it for eight years. I’m breaking it because nothing she told me stayed private; she said it all herself, on the record, two weeks later. What stayed private was what I thought she was doing, and that part is mine.
That was the spring of 2017. Infowars first reported her name as a Press Secretary candidate in May, then the New York Times reported Trump had floated it to allies, and on May 16 she told the Bay Area press she was “in talks” and that it would be “an honor to serve the country.” Mediaite ran it that afternoon, from the Mercury News, not from me. Fox News answered with a statement that she was under a long-term contract. Two weeks later she told The Five‘s audience the president had called her that morning. On June 29 she signed a new deal with Fox News. Spicer resigned in July and Sarah Huckabee Sanders got the job. Guilfoyle got Donald Trump Jr., to whom she later became engaged. Then not engaged.
After her engagement broke off, she became the United States ambassador to Greece until this week, when Trump asked her to resign after The Wall Street Journal reported that she had asked a Republican donor named Eric Deters for $100,000 after promising to help with his legal and tax problems. They also reported she flew on Greek businessmen’s private jets, and that she promoted a Greek construction company while working closely with its chief lobbyist. She denies all of it.
When administration officials showed Ambassador Guilfoyle the Deters texts, she insisted they were AI-generated per the WSJ report. Deters has since filed a defamation lawsuit against her and announced he’ll play a 16-minute recording by the end of Friday. I have no clue now what’s on the tape, but I do know who she is. She revealed as much to me on a call I’ve kept to myself until now.
Lisa Kennedy Montgomery went to the Daily Mail on Thursday with her own memories of sitting next to Guilfoyle on The Five, most of them about sex, and I’d leave the sex out of it. Jane Mayer reported it in The New Yorker in 2020, two years after Guilfoyle left Fox News amid a harassment investigation she has always said found nothing. What Kennedy’s piece is good for is two words, “insanely charming,” which she uses in the same breath as “unrelenting narcissism,” and I have no reason to doubt either half. Kennedy also neatly summed up the strange pathology of almost every on-air television personality, but I digress.
Almost everybody who dealt with Guilfoyle came away liking her. I get it, I liked her too, but that was 2016 before Donald Trump had moved into the White House. I had a friendly half-hour chat on the phone with a woman I was fairly sure was either exaggerating or lying to me, and I didn’t mind, and that’s her whole trick. The person who thinks she can make a reporter enjoy being used is the person who can ask a donor for a hundred thousand dollars and expect him to say yes.
The Senate confirmed her to her ambassadorship on September 18, 2025, along with a batch of other nominees. It’s hard to believe anyone actually vetted Kimberly Guilfoyle because nobody needed to. Everyone already knew who she was, and qualities I found suspect on that 2017 call never bugged the same people who sent her to Athens. They saw it as a feature. By their standards, the only thing she ever did wrong was put in writing her request for the money from a rich Trump donor. Allegedly.
But she never showed the character quality to be a brand ambassador, let alone an ambassador to Greece.