As Gavin Newsom prepares to announce his presidential bid, likely sometime at the beginning of next year, and is set to release his memoir next week, he is attracting increased press scrutiny into his early political career. That invites all sorts of risks for Newsom, as his early history is filled with colorful scandals and controversies. Of course, that’s likely why Newsom is putting his book out now: It will get the media scrutiny out of the way, thereby preventing things from blowing up in his face during his official presidential campaign. (RELATED: Newsom Confesses His Disturbing Role in the Euthanization of His Mother) One topic that Newsom really wants to get out of the way is his checkered past with womanizing. On the one hand, some of his relationships exhibited enormous and inappropriate power imbalances. On the other hand, some of his relationships with celebrities and the elite showcase the extent to which Newsom has lived a charmed life of privilege among the upper class. (RELATED: Jennifer Siebel Newsom’s Feminist Meltdown) On Friday, the London Times published an explainer on seven of the women who have engaged in romantic relationships with Newsom. But the paper missed much about how these seven relationships all showcase negative characteristics of the future presidential candidate. I’ll give you the real lowdown on all of these love affairs. But really, if you want to know the full extent of how bad Newsom’s womanizing makes him look, you’ll have to check out my book, Newsom Unleashed: The Progressive Lust for Unbridled Power. Kelley Phleger Kelley Phleger is the woman who tore Newsom’s heart into a million pieces and left him with an inferiority complex that could only be satisfied by seeking the presidency. If Newsom was Gordon Getty’s pseudo-son, Phleger was Gordon Getty’s pseudo-daughter. Getty employed her in his mansion as a private nursery school teacher for his grandchildren, but she could more accurately be described as a San Francisco socialite. In Gordon Getty’s eyes, Newsom and Phleger were the match made in heaven who were destined to be together. It certainly seemed as though everything would work out. Newsom and Phleger were engaged, lived together, and even shared a dog. They were the darlings of San Francisco’s elite, the joint heirs of Gordon Getty. Yet that all came crumbling down at the place where it all started, Gordon Getty’s mansion. At a birthday party for Willie Brown that Phleger attended as Newsom’s date, she met the actor Don Johnson, who was starring at the time in Miami Vice. Johnson had been married four times previously and was nearly 20 years older than Phleger. Yet he publicly flirted with Newsom’s date, which understandably upset Newsom. In rather quick fashion, Phleger — ever the San Francisco socialite — left Newsom for the famous actor and married him instead. Perhaps she calculated that Johnson’s fame would be greater than Newsom’s. Of course, in this, she ended up being wrong. Newsom — again understandably — entered into a depressive period after losing his socialite fiancée to the first celebrity to seek her affections. Years later, he even called the breakup of their relationship a “divorce.” Jewel The singer Jewel in 1997 at President Bill Clinton’s inauguration gala (John Mathew Smith/Wikimedia Commons/CC BY-SA 2.0) After Phleger dumped him, Newsom returned to his role as playboy of San Francisco’s high society. He spent nights out drinking at the favored locales of the elites and spent many an hour alongside his beloved pseudo-father, Gordon Getty. At this time, Newsom and his best friend, Billy Getty, Gordon Getty’s other son, were buying up bars and restaurants frequented by San Francisco’s elite, leveraging their roles as the darlings of the city’s high society. In 1997, Stanlee Gatti, a San Francisco party designer, explained the appeal of one of their establishments, the Balboa Café, to the New York Times: “There’s an association with the Gettys — with Billy Getty and Gavin Newsom,” he said. “People do go because it’s kind of cool to go to their joint.” Note that among San Francisco’s upper class, Newsom was considered a Getty in all but blood. Amidst all this socializing as the prince of San Francisco high society, Newsom was introduced to and briefly dated the pop star Jewel, whose music was surging in fame at the time. This relationship was only natural for Newsom, a member of the upper crust of society. And yet Newsom wants to use his new memoir to make us believe that he, a person who casually dated a famous pop star in his 20s, grew up poor and struggling. Sure, he faced great difficulties from his parents’ divorce when he was young. It is extremely difficult for anyone to face the breakdown of their family. But the reality is that Newsom grew up so privileged that he was handed elite status, plentiful investments that created him a business empire, and political connections that handed him a position on San Francisco’s Board of Supervisors without even a single vote being cast. From there, Gordon Getty’s political allies, including Willie Brown, worked in lockstep to get Newsom elected as San Francisco’s mayor. Jewel dated Newsom not because he was your average San Franciscan who grew up on baloney sandwiches, but because he was the personification of San Francisco’s elite. Kimberly Guilfoyle Kimberly Guilfoyle appears in 2019 with Donald Trump Jr., whom she was engaged to for a time (Gage Skidmore/CC BY-SA 2.0) Newsom and his best friend and pseudo-brother, Billy Getty, shared a taste in women: the debutantes of high society. Before Newsom dated Phleger, Billy Getty dated her. And before Newsom dated Kimberly Guilfoyle, Billy Getty dated her. As things stand today, with Guilfoyle having made herself into a sort of MAGA darling, people often wonder what on earth drew Gavin Newsom to her. But the answer is easy: Guilfoyle was a prominent member of society. She was an ex-Victoria’s Secret lingerie model, accomplished lawyer, and regular TV commentator. If Newsom was looking for his political wife — and he was — she seemed to check all the boxes. She was beautiful, famous, smart, a lawyer, and she appeared to be on the cusp of even greater fame. However, people I spoke to for my book told me that they perceived her to be a snobbish jerk at the time she was in a relationship with Newsom. She had a reputation for not caring to lend her efforts to helping Newsom’s career, as she was more focused on her own TV fame. Newsom and Guilfoyle married in December 2001 before 500 members of San Francisco’s elite. The wedding was paid for and hosted by — who else? — Gordon Getty. The reception was, of course, held at his Pacific Heights mansion. Later, Newsom disclosed that the cost of the reception was $233,416, in 2001 money. Guilfoyle wore Vera Wang for the occasion, which Jennifer Siebel awkwardly copied during her 2008 nuptials with Newsom. The marriage did not go particularly well. In Newsom’s defense, it appears that this was largely because Guilfoyle was much more interested in her TV career than playing political wife. Fairly soon after their marriage, Guilfoyle up and left and set up an apartment in New York City so that she could make frequent television appearances. She pretended for a while that this long-distance marriage would work even while her husband was mayor. Yet, at the same time, Newsom was publicly yearning for his wife to come home. Guilfoyle came home briefly to pose for a provocative spread with Newsom for Harper’s Bazaar in which the two of them lie out together — but where else? — on an oriental rug in the Getty mansion. The article called them “one of the most glamorous political unions since Jack and Jackie,” thereby reinforcing the perception of Newsom as a member of the high-society elite. In January 2005, the pair announced that they were getting divorced. Ruby Rippey-Tourk Oh dear, this is a bad one. Really, the press needs to be demanding questions of Newsom about this relationship because it is truly not okay. How Newsom treated Ruby Rippey-Tourk is extremely, extremely concerning. It should be disqualifying for political office. Ruby Rippey-Tourk was married to Newsom’s dear friend and campaign manager, Alex Tourk. The Tourks had a baby boy together. Ruby was Newsom’s appointments secretary when he was mayor — a major power imbalance. Ruby confessed to suffering from difficulties with alcohol and cocaine during this period. And yet Newsom carried out an affair with her. After she confessed the affair to her husband as part of her rehab, the pair got divorced, and their son was forced to spend his life between his parents’ homes. Yes, Newsom — who so bemoans the fact that his childhood was troubled by his own family’s breakdown — chose to foist that life on a little boy. Ruby was very beautiful, but she was very troubled. Years later, she told a media outlet that she was shopping around a book that would tell her story of “hitting rock bottom with Newsom after 20 years of alcoholism and coke use.” These two factors — the fact that she was Newsom’s secretary and struggled with substance abuse — made her all the more vulnerable to Newsom, who was a nationally famous mayor of a major city. Yet Newsom has comfortably escaped scrutiny for this relationship, including from the #MeToo movement. During the time of the movement’s ascendence, some people did raise a few questions about Newsom’s past dalliance with his secretary, but Ruby herself stepped in to stifle the complaints. On Facebook, she wrote of #MeToo: “I am doubtful that it applies. Yes, I was a subordinate, but I was also a free-thinking, 33-[year]-old adult married woman & mother.” But we really should not be letting this go, especially because of extremely concerning comments that Jennifer Siebel, Newsom’s future wife, made about Newsom’s relationship with Ruby. On the blog SFist, Siebel wrote of the affair, “[H]e’s been so hurt by this all — personally and professionally — and it was a few nothing incidents when she showed up passed out outside of his door.” I’m sorry, what? The “incidents” that constituted Newsom’s extramarital affair began when Newsom’s secretary showed up “passed out outside of his door”? Newsom — and Siebel — really need to explain this, because this does not sound okay. Especially when put in the context that Rippey-Tourk struggled with substance abuse. What kind of boss has an affair with his secretary with substance abuse problems who shows up passed out outside his door? I sincerely hope Siebel was just confused when she said this, because this is extremely wrong. But whatever the reality of her comments, I think we can all agree that a mayor shouldn’t be having an extramarital affair with his drug-abusing appointments secretary, and that, if he does, there is something deeply wrong with his moral compass. Sofia Milos The actress Sofia Milos in 2010 (Glenn Francis/CC BY-SA 3.0) Newsom’s conception of himself as a celebrity member of the elite has never ceased. This is true to the extent that he devoted his attention when mayor to dating a TV star, Sofia Milos. Milos was perhaps Newsom’s answer to Kelley Phleger’s Don Johnson. After all, the two both starred in crime dramas set in Miami. Johnson starred in Miami Vice, while Milos starred in CSI: Miami. Newsom’s dating a celebrity was lovingly followed by the city’s gossip outlets. Locals saw the mayor–actress pair kissing outside of a bar favored by the city’s elites at 2 a.m. Even the New York Times got in on the action, tracking down the bar’s owner to ask her what she thought of the mayor’s new woman. ABC News reported around this time that Newsom was increasingly going by the nickname “Mayor McHottie.” While San Francisco seemed enchanted by their high-society mayor’s celebrity relationship — which was even featured in a spread in People magazine — it remains to be seen whether mainstream America will look so fondly on Newsom’s centering of his celebrity romantic relationships during the course of his mayoralty. Newsom acted as a Hollywood celebrity in the way he dated Milos. To visit her in Los Angeles, he stayed at the celebrity-favored Chateau Marmont hotel. He also joined her in attending a benefit dinner for the Church of Scientology, the religion she belonged to. Milos likewise utilized her relationship with Newsom to prop up her own celebrity credentials. Newsom was, after all, nationally famous for his decision to give marriage licenses to same-sex couples. She told People in an exuberant interview: “Gavin is not just a handsome, charming mayor; he’s also passionate.” Brittanie Mountz Here we come to another problematic relationship: Newsom’s relationship with teenager Brittanie Mountz. Hot take: A 39-year-old mayor of a major city should not date a 19-year-old. Yet that’s exactly what Newsom did with Brittanie Mountz. Apparently, the pair met when Brittanie was Newsom’s waitress at a restaurant favored by San Francisco’s elite, Aqua. The restaurant described itself at the time as “a bastion of San Francisco power dining where execs make big decisions while eating small portions of fantastically prepared, sparklingly fresh seafood.” Brittanie and Newsom attended the opening gala of the San Francisco Symphony together, a major event for him to announce his relationship with a teenager. In 2006, tickets for the event, which was known as one of the most elite events of the San Francisco social calendar, began at $1,600. The press did not realize until later that she was a teenager because she had claimed to be 26 on her MySpace profile. But that was not to be the end of Newsom’s relationship with Mountz. He attended a black-tie dinner-dance at the M.H. de Young Museum with her during the week that she turned 20 years old. The two were photographed leaning in close together. Newsom and Brittanie also attended the opening of the upscale Westfield San Francisco Centre mall — which in 2023 shut down because of San Francisco’s homelessness and crime disasters. This appearance generated controversy because Brittanie was spotted drinking a glass of wine, and it was not legal for her to consume alcohol. Here, of course, the press’s attention was misplaced. The mayor was dating a waitress just out of her teenage years, and they were worried about her underage alcohol consumption, not the power imbalance in the relationship. In fact, San Francisco Chronicle columnist Leah Garchik said of Mountz, “I haven’t heard anyone say anything negative about the young woman he’s seeing.” Garchik continued, “It’s a live-and-let-live city, and we have a young handsome mayor. More power to them.” Newsom pointedly refuses to mention Mountz in his new book. Jennifer Siebel Newsom Then-Lieutenant Governor of California Gavin Newsom and his wife, Jennifer Siebel Newsom, in 2013 (John Medina/WireImage/GLAAD/CC BY-ND 2.0) Oh dear again. I don’t have space to go over Jennifer Siebel Newsom’s many scandals here — you’ll have to go to my book for that. But Jennifer Siebel came from an incredibly wealthy family and had every imaginable privilege thrown at her. Ultrawealthy private schools paved her way to Stanford University for both undergraduate and business school. Upon graduation, she pivoted to becoming an actress. Her performances weren’t exactly high-brow, however. One film in which she appeared, The Trouble With Romance, focuses on the sex lives of four couples and was described by the New York Times as “thoroughly disgusting.” In the trailer, she appears in her underwear on nine separate occasions. While her career as a C-list actress wasn’t exactly a raging success, it did give her major connections. One of those was with George Clooney, whom she dated. Another was with Harvey Weinstein, with whom she struck up a friendship that was close enough that she would reach out to him for advice when Newsom was caught having an affair with Ruby Rippey-Tourk. (Siebel later accused Weinstein of raping her, but he was not found guilty of the charges related to Siebel.) Siebel’s connections also allowed her to be set up on a blind date with the mayor of San Francisco and future governor of California. Apparently, Newsom and Siebel, an ultrafeminist, immediately hit it off. But she melted down a few months after they began dating when his affair with Rippey-Tourk was exposed. She went on a long rant on the blog SFist about how she thought the secretary was at fault for the affair she had with her boss. “I am producing a documentary on strong iconoclastic women who inspire us and can serve as role models to girls around the world, but i am not going to blindly support a woman who has cheated on her husband multiple times and watch while my boyfriend is the only one who gets punished,” she said. “I have tried to see Ruby’s side of the story but unfortunately everyone near to her has stories and says she is bad news.” Ruby, she claimed, had thrown herself at her boss. “I am a girls’ girl and I’ll always be one,” Siebel claimed, before adding, “i just wish as women that some of us had more respect for ourselves and didn’t always throw ourselves at the men.” Soon, Siebel and Newsom got engaged in Maui, where they were spotted at the Four Seasons Resort Maui at Wailea. Their wedding, at her family’s Montana ranch, was officiated by a woman obsessed with New Age practices who worships “Quran Yin, the Goddess of Compassion.” For the pair’s wedding, numerous guests flew in on private jets, again illustrating Newsom’s role among the elite. The financial scandals surrounding Siebel should be something that dogs Newsom on the presidential campaign trail. By 2021, hundreds of thousands of dollars had been given to Siebel’s California Partners Project at the governor’s request, including $100,000 from Silicon Valley Bank, creating the impression of insider influence via financial benefit. Similarly, it was reported in 2021 that companies with business interests in California had donated $800,000 to Siebel Newsom’s charity, the Representation Project. Several of the companies that donated to Siebel Newsom’s charity, from which she collected a salary, went on to receive no-bid contracts with the state of California under Newsom’s governorship. Also drawing financial scrutiny was the fact that Siebel Newsom profited handsomely from the showing of her gender justice films in California public schools. At one point, the director of the California Association of School Counselors said that the increased state investment in school counselors — which Siebel Newsom had a major role in — would lead to greater licensing of Siebel Newsom’s films in California schools. ***** The women from Gavin Newsom’s life will haunt his presidential campaign. His relationships with Ruby Rippey-Tourk and Brittanie Mountz make him look like a creep who took advantage of vulnerable women — his subordinate and a teenager. Meanwhile, his relationships with Kelley Phleger, Jewel, Kimberly Guilfoyle, Sofia Milos, and Siebel Newsom speak to the privileged life he has led among the elite and, in some cases, to his questionable associations. Perhaps the woman in Newsom’s life who should raise the most questions, however, is Newsom’s mother, who was murdered in front of him in an act of illegal euthanasia that he did nothing to stop. Ellie Gardey Holmes is the author of Newsom Unleashed: The Progressive Lust for Unbridled Power. READ MORE: Newsom Confesses His Disturbing Role in the Euthanization of His Mother Jennifer Siebel Newsom’s Feminist Meltdown The Growing Liberal Backlash Against Newsom Image licensed under CC BY-SA 3.0.