The Shady Side Of Gavin Newsom

People love to throw shade at Kimberly Guilfoyle and her relationship with Donald Trump Jr., but they may forget her ex-husband Gavin Newsom has a shady side himself. Back in 2001, Guilfoyle and Newsom were just married and dubbed "the new Kennedys," thanks to their roles as the first lady and mayor of San Francisco. The couple split in 2005 and took radically different paths — Newsom went on to become the governor of California, while Guilfoyle landed a job at Fox News, became an advisor to former President Donald Trump, and got engaged to his son. Referencing their time together, Newsom once told CNN (via Business Insider), "She was a different person [at the time of the marriage]." That seems clear. But this is really a story about Newsom, not Guilfoyle.

While Guilfoyle draws plenty of hate for her political transformation, Newsom has also sparked criticism for his personal and public choices. Remember the time he flouted the COVID-19 rules he imposed by attending a birthday dinner in 2020? Or the time he released a spot on Fox News, seemingly trolling Florida Governor Ron DeSantis and his conservative opponents? According to some reports, Newsom allegedly cheated on Guilfoyle during their marriage with the wife of his then-campaign manager. And while he did apologize, it was too little, too late. When it comes to shadiness, Newsom just might have his ex-wife beat.

In 2005, reports surfaced that Gavin Newsom had an affair with the wife of his then-campaign manager, Ruby Rippey-Tourk. According to the New York Times, this happened when Newsom was in the process of splitting from Kimberly Guilfoyle, who had been living in New York pursuing a career in TV. When Ruby came clean about the affair, her husband, Alex Tourk, immediately resigned from Newsom's re-election campaign. Newsom admitted his wrongdoing, telling reporters, "Everything you've heard and read is true. And I am deeply sorry about that." He added, "I've hurt someone I care deeply about, Alex Tourk. And that is something I have to live with."

Guilfoyle didn't publicly comment about the affair, but she married furniture CEO Eric Villency the same year that she and Newsom divorced. Newsom quietly moved on, too, marrying Jennifer Siebel in 2008. He expressed contrition for the affair as recently as 2018, telling the San Francisco Chronicle, "I apologized for it. I learned an enormous amount from it. And I am every day trying to be a champion and model ... to deal with the issue that we need to focus on, which is the crisis with men and boys in this state and in this country."

Ironically, the affair is something that Newsom has in common with Guilfoyle's current fiancé, Donald Trump Jr. Trump Jr., who cheated on his ex-wife Vanessa Trump with Danity Kane singer Aubrey O'Day.

Gavin Newsom's affair was far from the only time his bad behavior raised eyebrows. California was one of the strictest states in imposing COVID-19 rules, and Newsom was proactive in issuing a stay-at-home order, but apparently, he felt that his own rules didn't apply to him. In November 2020, the politician was spotted attending a birthday party at Napa Valley's French Laundry restaurant. In the photos, Newsom was seated close to other guests, none of whom were wearing masks. The backlash was swift, and — as he did after news of his affair broke — Newsom quickly issued a mea culpa. "I made a bad mistake," he said (via CNN). "I should have stood up and ... drove back to my house. The spirit of what I'm preaching all the time was contradicted. I need to preach and practice, not just preach."

While those are nice words, Californians were still annoyed. Los Angeles Times' Robin Abcarian criticized the governor for his hypocrisy, writing, "[Newsom], who has been among the state's most vocal advocates of playing by the pandemic rules that he created, blew it. He did not, in his own tired phrase, meet the moment. I mean, they do say the food at the French Laundry is to die for. But is it?" In this case, Newsom epitomized the double standard that sees politicians enjoy special privileges that ordinary people don't.

When Gavin Newsom wasn't flouting COVID protocols, he was throwing shade at his ex, Kimberly Guilfoyle. In a 2019 interview on PROFILE by Buzzfeed News, Newsom was asked directly about Guilfoyle's relationship with Donald Trump Jr. "[Donald Trump and I] may have had a private moment on that conversation, which in and of itself, makes life just interesting," he said, reiterating, "Life's interesting." It's a little bit of a shady response, considering that he and Guilfoyle once vowed that they were "very close" and "planned to remain that way," per The San Francisco Chronicle. Additionally, in 2018, Newsom publicly sent his well-wishes to Guilfoyle after learning that she and Trump Jr. were dating. "No, it's fine. I wish her well, and them well," he told KQED.

Therefore, Newsom's snarky response seemingly sparked a war of words between the exes. Upon hearing his remarks, Guilfoyle took jabs at Newsom, even claiming in a 2022 speech that her former husband was never "making it to the White House." In 2023, she appeared on "The Charlie Kirk Show," where she claimed that while he'd once fought for the small businesses of America — he'd now become seduced by the radical left.

In today's political landscape, Gavin Newsom's liberal policies put him at odds with other conservative figures, including Florida Governor Ron DeSantis. For example, DeSantis has been responsible for banning books in schools across Florida, and in 2023, he pushed to help other red states do the same. Democrats in liberal California don't really agree with book bans, and Newsom took to X to let DeSantis know that. The California governor posted a picture of himself reading Toni Morrison's "Beloved" — a banned book — captioning it, "Reading some banned books to figure out what these states are so afraid of." Newsom has been vocal about the need for education reform, saying in his 2022 State of the State address, "And I'm not talking about that version of education 'reform' being promoted in some states, where they're banning books." Taking aim at Florida and DeSantis' then-newly-passed law that prohibited teachers from talking about gender orientation in the classroom, he added, "Where you can sue your history teacher for teaching history and you can't even say the word 'gay.'"

Newsom went on to receive lots of flack for his X post. One user pointed out that his photo featured Harper Lee's "To Kill a Mockingbird," a book "that was banned by the city of Burbank. In California." This user also called Newsom's take "Absolutely beyond parody."

Gavin Newsom's social media stunt wasn't the only time he trolled Ron DeSantis. That same year, Newsom ran an ad on Fox News that pointedly took aim at DeSantis, turning the rhetoric that DeSantis uses on its head. "We're about to celebrate Independence Day — but Freedom is under attack by Republican leaders in states like Florida," Newsom said in the spot, citing the state's decision to ban books and restrict speech. Newsom received his fair share of criticism and praise for the ad. Some felt it was good to see DeSantis humbled, while others opined that the commercial was expensive and wouldn't accomplish much.

However people felt about it, everyone can agree that there's no love lost between Newsom and DeSantis. In late 2023, the two men clashed in a fiery debate called the Great Red vs Blue State Debate. Both politicians seemed more interested in trading insults than actually answering Sean Hannity's questions, prompting the host to plead that they cooperate with him. "I'm not a potted plant here," he added, according to the BBC.

In the debate, Newsom also clarified that he's not running in the 2024 election. Some people might be happy to hear that, given the less-than-exemplary behavior outlined above.