I never thought I’d pity Kimberly Guilfoyle, who may still technically be the fiancée of Donald Trump, Jr. In what is publicly promoted as a career advancement for Miss Guilfoyle, she was announced as President-elect Donald Trump’s pick as the U.S. Ambassador to Greece.
Historically, Ambassadorships have often been given to political allies and large donors instead of qualified career foreign services members. Trump, the elder, already broke the mold by appointing convicted felon and family member Charles Kushner (Jared’s dad) as Ambassador to France. Kushner hired a prostitute to sleep with his brother-in-law to blackmail him with a video of the encounter. Trump previously issued Kushner a pardon, which was only controversial by the old standards.
Guilfoyle’s appointment wasn’t a reward for crimes committed but seemingly the means to get her out of the way to make room for Don Jr.’s new girlfriend, model Bettina Anderson. Don Jr probably saved himself a lot of money and lawyer’s fees by not marrying Guilfoyle, trading up without putting a ring on it. Junior broke family tradition by moving to the next woman without a messy divorce. However, like Daddy, he publicly displayed the new woman before ridding himself of the old one. Junior was seen with Anderson at the RNC and more recently photographed holding hands on a nighttime stroll in Palm Beach.
As for poor Kimberly Guilfoyle, many may think she’s getting what she deserves. Kanye may have said it best in his 2009 song Gold Digger (with an assist from Jamie Foxx).
Guilfoyle began her career as a prosecutor in San Francisco; she was often seen at political fundraisers organized by oil billionaire Gordon Getty, whose son William she dated. She later met and married future San Francisco Mayor and current California Governor Gavin Newsome. Guilfoyle often worked in New York on Court TV and the Anderson Cooper show. During her marriage with Newsome, he became involved with his campaign manager's wife. Messy!
Guilfoyle’s divorce from Newsome was final on February 28, 2006. On May 27, 2006, Guilfoyle married furniture heir Eric Villency. They stayed married for three and a half years.
Guilfoyle was quite visible at Fox and met Donald Trump, Jr. In June 2018, Vanessa Trump named Guilfoyle as one of the reasons for her divorce from Don Jr. Around the same time, Guilfoyle was being fired by Fox News for sexual harassment on her part. A female assistant alleged that Guilfoyle frequently displayed herself naked, showed photographs of the genitalia of men she had sex with, and required her to sleep over at Guilfoyle’s apartment. Fox News reached a $4 million settlement with her accuser.
The accusations about Guilfoyle were well known long before she and Don Jr. entered into a secret engagement in 2020 (it became public in 2022). Don knew who and what she was when he began their affair; perhaps that was part of her appeal. Kimberly knew Don was a cheater when she met him, as she was the cheatee. It was inevitable that as she aged, and her plastic surgeries became topics of criticism rather than praise. Don would look to replace her with literally a new model.
So when a Trump is through with a woman, how do you dispose of them? Guilfoyle had taken on a significant role in the RNC and the Trump campaign, which was part of the problem. Don tried to discourage her from wearing tight dresses and was turned off by the negative publicity she generated with her screaming fits into microphones and rumors of suggestions of sexual rewards like lap dances and hot tub encounters to top donors. Guilfoyle had committed the unforgivable sin of being bad for the brand, so she had to go.
There was no reason to believe Guilfoyle would go gentle into that good night. Best to put as much distance between her and the American media as possible. The Greek Ambassador was as close to a win as they could offer. In her official role, she could host parties with Greek billionaires until she found her next wealthy friend with benefits. She and Gavin Newsome were once compared to John F. Kennedy and Jackie. Kimberly may end up like Jackie, marrying a Greek billionaire and living that life.
I guess I don’t feel so sorry for Guilfoyle after all. She’s sure to land on her back, I mean feet. Don Jr allegedly moved to his new woman because she’d be more acceptable to Daddy. I’d say who does that, but it seems the norm in Trump's world. Everyone involved managed to keep the new relationship quiet until after the election. Did they really think Donald Trump’s voters would care about how slimy father and son were? They had to have already known.
This article originally appeared on Medium and is edited and republished with author's permission. Read more of William Spivey's work on Medium.