Men's Journal

Nearly ruined by a series of personal scandals, america’s most controversial big-city mayor has reemerged to take aim at the governorship of California.

by Daniel Duane

“I just had an off-the-record phone conversation for 30 minutes with Bill Clinton, right before you walked in here, and if any of that was tape-recorded? My God,” says Gavin Newsom, the 40-year-old mayor of San Francisco, as he sits at his grand City Hall desk. The Democratic primary is still in full swing, and Hillary’s husband has just finished railing against media mistreatment of his wife, but Newsom’s real point seems to be that Bill Clinton himself called this office, on this phone.

Until very recently such a tête-à-tête would’ve been unimaginable — not just because Newsom, by comparison to the supernova ex-president, is a pip-squeak West Coast mayor, but because for a while there, Newsom’s political career looked like roadkill.

It began fabulously: Five years ago, as an earnest, Bobby Kennedy–obsessed 36-year-old with a video collection of great political speeches and money from his booming food-and-wine business empire, Newsom eked out a victory to become San Francisco’s youngest mayor in 100 years. He may have been young, but he came armed with innovative social policies, leading man looks, and heavyweight connections. Then, just 36 days in, Newsom took the political bungee jump of authorizing gay marriages, making himself an overnight liberal superstar but pressing such a hot button that he was promptly disinvited from the 2004 Democratic Convention. The California state supreme court soon halted Newsom’s gay marriages, and conventional wisdom held that he’d torpedoed his political future. Then things got bad for real, as Newsom suffered one of the more painful and protracted public humiliations in recent politics, including but not limited to revelations that he’d had illicit sex with a substance-abusing former employee who also happened to be the wife of his good friend and reelection campaign manager, and that he was seeking counseling for alcohol abuse.

But then a funny thing happened. Instead of just quietly crawling back to life as an entrepreneur, Newsom put his head down, got back to work, and won reelection last November by a landslide. (He is still so popular in this forgiving city that he didn’t face a single serious opponent, although the ballot did include a homeless cabbie by the name of Grasshopper.) Which is where we find him now: determined not to blow his second chance, tackling one issue after another with national implications. In the last 14 months alone Newsom has perfected a genuinely innovative approach to homelessness, implemented his own controversial version of universal healthcare, and turned San Francisco into arguably the greenest major city in the United States. As if on cue the California state supreme court even reversed itself in May, legalizing gay marriages in California and turning Newsom into a strong Democratic contender for governor in 2010.

“All of these things interweave with one another,” Newsom tells me, trying for a moment to stick to the good stuff. “They connect. Poverty eradication in light of workforce training in light of issues of economic development and sustainability as it relates to green-collar jobs relating to issues of environmental justice and…there’s a narrative that we use.”

Suddenly, he just stops talking. Newsom’s face, I realize, has been overtaken by other thoughts. He’s staring at me but not seeing me.

“So, anyway, there’s a narrative in there,” he says again, trying to get back on track.

Come again?

Newsom laughs suddenly, a morbid this-job-is-horrendous-and-I-want-to-go-back-to-sleep kind of laugh. “No one cares,” he moans, mock-tragically. “It’s my narrative…it’s hard to explain.”

“I’m here to…I don’t know.” He starts thumping his pen against the table. “Maybe this is just an abject failure,” he says, chuckling.

Jesus, Gavin.

Newsom shakes his head, thinking about it. Then he reconsiders: “I mean, there’s a reason we got reelected overwhelmingly. That means the voters, they kind of get it, right?”

I nod politely. Sure.

“And hey, there’s a lot of evidence of good, and you know, universal healthcare! I mean, no city in America is doing that, but okay, I’ll be honest with you: It’s been a tough few years. And one thing I’ve realized is nobody really cares about you. There are some people who care about me, but, end of the day, most do but really don’t. And that’s great! I’m not their son or wife or husband or daughter. I’m just a mayor. You need to be reminded of that, because you get so caught up with yourself. People care about themselves and their family, and once you figure that out, you’re going to survive.”

He has a point.

“The fact that the party’s embraced me,” he says, “the fact that these guys are reaching out to me, that I’m involved with every element within the party, well, it suggests we’ve moved on.”

The aging, toothless crack whores of San Francisco have always embraced Newsom. It’s a phenomenon I’ve witnessed more than once, most recently while walking outside the Bill Graham Civic Auditorium with Newsom and hearing him talk about the foot massages he gives to homeless people. (“Very spiritual,” he tells me, wryly raising an eyebrow.) It’s not just that Newsom is tall, slender, broad-shouldered in his designer suits. It also has to do with the fact that this pro-business society boy with the gelled haircut everyone calls his Darth Vader helmet routinely walks the city’s worst streets, seeking out panhandlers and trying to get them into city services.

Newsom is that guy in high school who was good friends with everybody and not exactly best friends with anybody; star of all the sports teams but also eager for the chess club dorks to love him. He has severe dyslexia, so he knows what it means to struggle. He was always ambitious but had to study twice as long as everyone else. So when he wades into the crowd at this once-every-six-weeks Project Homeless Connect event, which offers everything from free long-distance phone calls to bus tickets home to fresh hypodermic needles, he radiates both the humility he learned in those years and the practiced charisma of a guy who has always been good at popularity contests.

Brushing his fingertips over the pink Mohawk of a punk-rocker chick in full dominatrix garb, Newsom asks, “Hey, what kind of gel do you use to get it to stand up like that?”

“No gel,” she replies, grinning widely. “The dye gives it enough hold.”

“They’re photographing me in my underwear, Mayor Newsom!” screams a skinny, middle-aged rattlesnake of a woman. “Down at the Third Street police station, Mr. Mayor! They’re getting high, too, smoking crack! You better be careful, or they’ll photograph you in your underwear too!”

“Well, I wear boxers,” Newsom says, with an easy smile. “How about you guys?” He’s bonding now with a pair of filthy, festering, blind-drunk bums. “Seriously,” Newsom asks, “boxers or briefs?”

This side of Newsom — mixing charm with a young wonk’s optimism that he can reinvent social policy— is by far his most dominant. Yet it got overshadowed by the gay-marriage hullabaloo and the lapses of judgment that followed. There was a Gatsby-esque crassness to his appearance with then-wife Kimberly as “the New Kennedys” in a Harper’s Bazaar fashion spread in 2004, shot sprawled across the Persian-carpeted floor of an opulent mansion. Then there was the time Kimberly subbed for Newsom at the annual dinner of Empire State Pride Agenda, a gay and lesbian organization. A former Victoria’s Secret model, lawyer, and bawdy loose cannon, she told the crowd, “I know that many of you wanted to see my husband, and some of you had questions out there. Is he hot? Yeah. Is he hung? Yeah. Is he…” — here she waved a limp-wristed hand to indicate bisexual. “Not unless you can give a better” — here she reportedly mimicked eating a banana — “than me.” Peter Ragone, the mayor’s communications director at the time, offered only this comment: “You know we believe in open government, and we support full disclosure.’’ Nonetheless, three months later the couple announced they were divorcing.

But Newsom got seriously sidelined only when his more serious personal failings began to surface. Even before they divorced, Kimberly had up and moved away to New York City, taking an on-camera job with Court TV and leaving him alone most nights. That appears to be when his love of (and access to) fine wine got the better of him. Only one member of the mayor’s team was over the age of 36, and with Kimberly off in New York, Newsom and his senior advisers hung out constantly. “We were the young Turks,” Ragone says. “Idealistic, having a great time together, taking over the world.” La Barca, an old-timey Mexican restaurant with a back room, was one of their regular scenes.

In December 2006, Newsom showed up intoxicated at San Francisco General Hospital, where police officers and family members were gathered to mourn a cop who’d just been killed in the line of duty; this came a couple of months after he was photographed out drinking with a model he’d been dating who was only 19 years old. As it happened, the day before the photos of him with the model appeared, Newsom met a knockout blonde named Jennifer Siebel, an ex-girlfriend of George Clooney’s who has had small parts in more than a dozen films, including Something’s Gotta Give and In the Valley of Elah. She and Newsom were just falling in love — they’ve since become engaged — when the real bomb went off.

Her name was Ruby Rippey-Tourk. She was Newsom’s former appointments secretary, another spectacular blonde and a member of that late-night inner circle as the wife of Alex Tourk, one of Newsom’s closest friends and his point man on homelessness. She was in a rehab program for substance abuse when the clearing-emotional-minefields part led her to tell her husband she’d had sex with the mayor. Alex Tourk confronted Newsom about it and promptly resigned.

In what was clearly the low point of his life, Newsom called a press conference. Standing in a City Hall room packed with reporters and camera crews, and looking at once nauseated, crestfallen, and utterly mortified, Newsom announced to the world, “I want to make it clear that everything you’ve heard and read is true, and I am deeply sorry about that.… I hurt someone I care deeply about, Alex Tourk, his friends and family, and that is something I have to live with.”

“And if you saw him on the other side of the door from that press conference,” says Ragone, “you’d know that was true. Gavin cares deeply about doing good. He takes it hard when he lets people down.”

“It was like Jesus — the breath is out, the miracle unmade,” as Newsom later put it to me. A local television station ran a humiliating segment on how Newsom had broken the “man code” against “bedding a buddy’s wife.” Days later Newsom held yet another press conference to announce that he was seeking alcohol counseling, which didn’t so much secure an alibi as complete his humiliation — and kick off a months-long nightmare of media prying.

“We couldn’t put a foot out of Room 200 [the mayor’s City Hall office] without the entire local press corps — print, TV crews, radio — hitting us with this fusillade,” Ragone says. “It was like an Uzi. I mean, this was really personal, painful stuff for Gavin.”

The atmosphere within City Hall became equally nightmarish. The city Board of Supervisors took Newsom’s diminished stature as an opportunity to fight nearly everything he proposed. And supervisor Chris Daly, in a routine hearing about budget cuts, felt at liberty to state that Newsom “artfully dodges every question about allegations of his own cocaine use.” Newsom was attending a conference on solar energy when reporters confronted him about this. He denied the claim of cocaine use, saying it was made “so gratuitously, so erroneously, that it’s just patently false.”

“I remember that,” he tells me. “I was like, I can’t win. It’s just, Oh, have you stopped beating your wife? It was a pile-on. It was unbelievable. That’s when I stopped reading the paper. I live in a big apartment building, so they stack up all the newspapers downstairs, and then a doorman brought them up and there was a stack from the whole week next to my apartment door. I’ll never forget. It was half-page photos every single day.”

Mike Farrah, another member of Newsom’s inner circle, says, “Any other guy — they would just go to the Bahamas for a while, right? But Gavin couldn’t do that. He’s the mayor. He has to just keep showing up at work. I mean, imagine that.”

This doesn’t take a great leap, because the first event I see at Homeless Connect is a press conference, and as the TV cameras roll, Alex Tourk is at the podium. No longer in government, he’s a homelessness policy guy now, which means he still works with the mayor’s office every day. While Tourk talks, Newsom stands next to me at the back of the room, watching. Tourk then moves to one side and Newsom clears his throat as he steps forward. He doesn’t acknowledge the awkwardness of the moment. He doesn’t have to. Every person in the room knows the score.

“Go long!” Newsom yells. “You hear me? Just go long!” It’s a glorious spring day in the Mission District neighborhood, and Newsom has taken the quarterback’s spot at a City Hall–sponsored flag-football game with a bunch of teenagers. He hasn’t bothered to bring sneakers — just hands his suit coat to one of the members of his entourage and rolls up his sleeves — but the truth is that he plays ball the way Clinton eats barbecue, meaning it makes him terrifically happy and he knows he looks good doing it.

He grew up in Larkspur, California, as the athletic son of an athletic mom. Tessa Menzies married William Newsom when she was only 19; they had two kids by the time she was 21 and divorced soon after. William Newsom, a lawyer, moved four hours away to the Olympic ski village at Squaw Valley, California, near Lake Tahoe. Eventually he became a state appellate justice. Newsom’s younger sister, Hilary Newsom Callan, recalls that their mother rented one of their bedrooms to boarders and worked three jobs to support the family: “She was a waitress on Friday and Saturday nights, she was the assistant buyer in the children’s department at I. Magnin, she was getting a real estate license, and she was working one night a week as a secretary.” A terrific tennis player, she also found time to pitch batting practice for Newsom at a neighborhood diamond. “They were both lefties and switch-hitters,” says Callan.

Newsom was a good enough athlete that, in his senior year of high school, the Dodgers and the Rangers both showed interest in him. (“I just found an old box with all those scouting cards,” he told me that day on the football field in the Mission District. “I was clearing out storage to move in with Jen and there it was.”) But he knew he had better opportunities.

William Newsom didn’t make a pile of money — state judges never do — and he nearly bankrupted himself with two unsuccessful runs for political office and a San Francisco restaurant venture that went belly-up. But he was terrifically well-connected. His own father had been a confidant of a two-term California governor, and William himself was an old friend of both Jerry Brown, another former governor, and Gordon Getty, son of oil tycoon J. Paul Getty. He and Gordon had gone to the same Catholic school as kids, and they remained close. Gordon and his wife Ann were the only witnesses at William and Tessa’s wedding, and Gavin and his sister accompanied the Gettys on family vacations. In 1973, when kidnappers grabbed a Getty grandson and mailed his severed ear to his mother, it was Newsom’s father who flew to Italy, delivered the $2.7 million ransom, and brought the boy home.

When Gavin graduated from Santa Clara University, where he played baseball, and decided to open a wine shop with Gordon Getty’s son Billy, Getty money was there to help finance them. Newsom became a regular in the gossip pages, as did his girlfriend, socialite Kelley Phleger, who left Newsom to marry actor Don Johnson. Newsom and Billy Getty even branded their growing business empire — including a restaurant on the exact spot on which Newsom’s father’s restaurant failed — with the name of an opera written by Gordon: PlumpJack. When it came time for Newsom to marry Kimberly Guilfoyle, the Gettys paid for the 500-guest spectacle held at their Pacific Heights mansion. The Gettys also lent the young newlyweds a million dollars to buy a home of their own.

Still, Newsom’s political personality is defined less by socialite glitz and far more by a hunger to succeed in areas where a distant father struggled — and to make a hardworking mother proud. Tessa died of cancer in 2002, right before Newsom’s first mayoral campaign, and by all accounts he was destroyed by the loss. “A lot of people see him in terms of silver spoon,” says his sister, “but he has a work ethic beyond my imagination. He’s much more complex than he seems in photos.”

“My mother had a way of not making us feel privileged,” Newsom told me when I first interviewed him in 2004. “If we had the privilege of going on a summer trip with the Getty family, we would come back and my mother would remind us real quick: ‘That was great, but here’s reality.’ I’ve always understood you can’t take things for granted. You have to fight hard every day. She was a model of that, of sacrifice and hard work. And my father as well, but differently, because he was differently situated, with more freedom than this mother who had to raise two kids and make ends meet.”

Newsom puts in famously long hours and keeps up his boyhood practice of reading political biographies and self-improvement books, underlining them and writing personal Cliffs Notes — like the stack I once saw in his office, with typed-up summaries for Good to Great and the Social Sectors, The 4-Hour Workweek, Life’s a Campaign, by Chris Matthews, and Wisdom for a High School Grad. Because of the dyslexia, “I have a hard time reading,” he says. “Underlining makes it indelible; the book will become ingrained in my mind.”

Playing ball is a different matter. It comes much more naturally to him, which is why he relishes going down to the Mission District event to throw the football around and play Big Man on Campus. Wading through the crowd, Newsom slaps hands with everybody — “Whassup? Whassup?” — and spins a basketball on his index finger. Then he shuffles his thin-soled loafers across the grass and tells the receiver to go long. Way long.

The kid’s big and rangy, and you can tell he’s not sure what this middle-aged white guy means by “go long.”

“I’m serious,” Newsom tells him, smiling. “Go long.”

Newsom calls for the snap and the boy takes off running, looking back over his shoulder as Newsom dodges the rush. Then the ball’s in the air, almost on target, bouncing to the ground just beyond the kid’s reach.

“The Board of Supervisors did this to me, browbeating me so bad.” That’s how Newsom explains how he looks after climbing alone out of his limo, on San Francisco’s quiet Cole Street. He walks with me to a coffee shop called Cafe Reverie in what is best described as a whole-body impersonation of a crab with a broken shell. His spine makes a hard right turn out of his pelvis, putting his entire upper body on a 45-degree sideways angle to his legs.

It’s tempting to think he’s all cramped up because he’s finally agreed to talk to me about the bad stuff (“Scandal! Controversy!” as he puts it, laughing), but Newsom’s spine has been bothering him since last summer, when he played in a celebrity softball game, with Jimmy Kimmel and Bobby Flay. Newsom took too many cuts in the underground batting cage and herniated a disk. The day before we meet it flared up again.
Hobbling into the cafe, Newsom orders a medium half-caf and follows me to a deserted back patio. We chat about Eliot Spitzer, who has just been busted for dallying with a prostitute, and also about Spitzer’s replacement, David A. Paterson, who has just brightened up one of his first press conferences by announcing that he and his wife have both had multiple extramarital affairs and that at least one of his was with a state employee.

“David’s an old friend,” Newsom says, smiling and shaking his head in mock pain. “And now he’s like, ‘I did this, and then I did that, and then I did that!’ But he has a huge heart. He’s a decent person. And what I did was very different. I wasn’t married.”

Then Newsom’s tone changes, as if he’s decided to get down to business. “Look, bottom line, what I did was wrong. For the rest of my life, I will regret it. When you know better, that’s the hardest part to accept within yourself. In a life where I’ve lived appropriately, and always felt like I’m a good person — I’m not perfect, but I’m trying — I don’t go out of my way to hurt people, and the fact that I was involved with something that hurt somebody…”

His voice trails off for a moment, and he’s leaning forward in the wrought-iron chair.

“I should say this candidly,” he offers, unprompted. “This is why I stopped drinking. It wasn’t like I feel like I have this horrible addiction. It’s that I needed clarity. And I needed to change my behavior.

“So I went to my old friend Mimi at Delancey Street,” an old and unorthodox substance-abuse center in San Francisco. “She’s not one of these Up with People, AA, hold-hands types. No. She’s like, ‘Shut the fuck up. Let me tell you.’ It ain’t a therapy session. So I began seeing her — tonight I see her again with Jen — and I am so glad I did that. Because then you are able to confront: Why do you feel you need to have a bottle of wine? Every night? But it was my life. I have seven restaurants, two wineries, and now I can’t even taste my new releases. I have no idea how our sauvignon blanc is. But it had become my narrative of who I was, and my connection to people and to my family and my friends and even to my father. Even to my father’s friends. So to stop all that — that’s me confronting something totally different than politics. It’s been very powerful.”

Newsom says he has learned a lot about the human capacity for forgiveness from the experience, especially from all the people who called to offer support. What did they tell him? “This too will pass,” he recalls. “It was extraordinary, the support — from politicians, from well-known families that had experienced this.”

Did Bill Clinton reach out then, too?

“No! God, no. They’re smarter than that. They knew it would’ve been a national story.”

Another curious part of the experience is that Newsom now feels like a therapist himself. “I get people coming to me,” he says. “Really successful people, spilling everything, and I’m like, ‘I’m not sure that anyone knows this, and I’m not sure that you want me to know this.’ I mean, extraordinarily well-known people who just feel that connection. And even real people out on the street, like when I go down to homeless shelters. So my life is richer now because of it. People have connected to me, where before they didn’t, because I was some gel-haired kid hanging out with the Gettys. But it’s a good thing to stumble and be humbled, because inevitably you will be.”

Most of all, Newsom says he’s learned the importance of carrying on. “For me, it was just powering through it,” he says. “Every day: powering. And days became weeks became a month became two months and people moved on, and then it was, ‘Okay, what are you doing about healthcare?’ People cared less about me than about what I could do for them.”

For Newsom this has been profoundly liberating. He doesn’t have to be a perfect human being, it turns out; he just has to be a good mayor. Something about that revelation has reignited Newsom’s political ambition — and ruled out any return to the cozy millionaire’s lifestyle.

“I’ve got a bug or a passion,” he says. “I’ve got to stay connected in some social-justice or environmental way. Is it manifested precisely in being mayor of this city? No. I don’t think there’s any job in the world that is greater, but it’s also… Just. Incredibly. Hard. I’m not supposed to say that, because people love when it looks easy, but it’s a hard job. That’s why I love it, but also hate it for the same reason.”

Newsom pooh-poohs the idea of a run for Congress or even Senate. He’s not interested in legislative positions, just executive ones. A factor in his favor: His stance on same-sex marriage is not the liability people once thought it was. That’s true even in conservative Southern California, where reaction to the state supreme court’s recent decision was mostly positive.

“Governor of California,” he tells me. “That’s not something that I’m immune from seeing, in sort of the idea of athletes seeing themselves in the future…visualizing.” And in fact, in July, after we talked, he launched an exploratory bid for that office.

But before he gets ahead of himself, he injects the caution he’s learned the hard way. “Doesn’t mean I’ll get elected, of course.”

This article originally appeared in the September issue of Men’s Journal.