According to Kimberly Guilfoyle’s Republican National Convention speech, the state of California is a cautionary tale for what the rest of the United States could become under Democratic leadership—“a land of discarded heroin needles in parks, riots in streets, and blackouts in homes.” In other words, pretty much a post-apocalyptic nightmare. Funny that California just so happens to be the same state her ex-husband now oversees as governor.
Yes, Guilfoyle, who radiated such gung-ho MAGA energy at the GOP convention that she’s since become a meme, who is so down for the cause that she’s dating one of the president’s sons, used to be married to Gavin Newsom, big-time Democrat and California’s current governor. Looking at pictures and videos from 15 years ago, it’s pretty uncanny to see how much her vibe has changed.
When Guilfoyle and Newsom got married in 2001, the San Francisco Chronicle hailed them as the next liberal power couple. At the time, she worked in the city district attorney’s office (where she also crossed paths with the current Democratic candidate for vice president, Sen. Kamala Harris), and he was on the city’s board of supervisors. People who worked with Guilfoyle as a prosecutor spoke highly of her, according to an extensive Washington Post profile from 2018, but she left the job in 2003 to help her husband’s mayoral campaign, which he won. Around the time he was sworn in, she was starting a new job herself, across the country as an on-camera legal analyst.
The best artifact of Guilfoyle’s early media-darling period? Take your pick; it’s either the husband-and-wife Charlie Rose appearance or the Harper’s Bazaar spread from 2004 that’s currently circulating on Twitter, in which the magazine dubbed the couple the “New Kennedys.” Back then, Guilfoyle’s manner was indeed less cable news than Jackie O. In that Charlie Rose clip, she politely laughs at both men’s jokes, dressed in a subtle black long-sleeved jacket. “I stand 100 percent by his side on this,” she says of then–San Francisco Mayor Newsom’s decision to issue marriage licenses for same-sex couples. Even as Newsom describes her politics as “modestly more conservative” than his, her appeals for “hope” and “togetherness” sound a very far cry from Monday’s warnings of riots and drug trafficking. And in the Harper’s Bazaar spread, Guilfoyle and Newsom lounge together in well-appointed interiors—some of which belonged to heiress Ann Getty, who lent her home out for the shoot and whose son Guilfoyle had dated before Newsom, further cementing the pair’s place among the San Francisco elite. Or so it seemed.
When Newsom and Guilfoyle announced their split a few years later, they chalked it up to their bicoastal marriage. Guilfoyle got married again in 2006, to Eric Villency, who now runs an interior design firm. The two had a child together, a son, but that marriage also ended in divorce. (Newsom has also remarried and has children.) Also in 2006, she took a job as the host of a show called The Lineup at Fox News. Guilfoyle told the Post that she was always a Republican, and the Mercury News reported that she indeed registered as a Republican during college. So the move did make a kind of sense. And it was when she started that gig that she began to socialize in the conservative circles that eventually brought her into the Trump family’s orbit. For most of her time at Fox, she had a good relationship with Roger Ailes, the network’s chairman, but one former Trump campaign official told the Post he thought her standing might have suffered after his 2016 ouster. She was one of the women Ailes’ wife called on to publicly defend him amid allegations of sexual harassment, as depicted in the movie Bombshell, and she did so vociferously in an interview with Breitbart News. In a tweet announcing her departure from Fox News in 2018, Guilfoyle wrote that she had made the “bitter-sweet” decision to leave so she could dedicate herself full time to the Trump campaign, though HuffPost reported that she was given the boot due to a human resources investigation and allegations of misconduct.
The Trump campaign has seemed all too happy to deploy her on the campaign trail since, and she certainly fits right in. For instance: The Post reported that Trump-friendly audiences ate up her speeches, including the one where she reportedly bragged about her relationship with Don Jr., telling a crowd of conservative high school students: “What can I tell you? Mama’s a closer.”
As of 2018, Guilfoyle told the Washington Post that she was still friendly with her first husband. During his run for governor, she told the Post she joked to him that she would get Don Jr. to campaign against him and also drew comparisons between the men’s twin slicked-backed hairdos. In 2019, when the then–editor in chief of BuzzFeed News asked Newsom whether Guilfoyle ever came up in his conversations with the president, Newsom would only say, “We may have had a private moment on that conversation, which in and of itself, makes life just interesting.” So you really have to wonder how it went over with him when his ex-wife went on TV and called his state a socialist wasteland.
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