The Wrong Stuff

Candidate Newsom is “narcissistic,” “thin-skinned,” “disloyal,” and “friendless.” And that’s from his former supporters.

An earlier version of this story incorrectly stated that former California Senate majority leader, John Burton, supports Gavin Newsom's candidacy.

On a gray July morning in City Hall, Mayor Gavin Newsom is fidgeting his way through a self-congratulatory press conference about a potential U.N. global warming center at the Hunters Point Shipyard.

Waiting for his turn to speak, Newsom seems at a loss for what to do with his large hands, which he clasps behind his back, then folds neatly in front of his gray sportcoat. He buries them in his pockets, takes them back out, cracks a knuckle, and traces his upper lip with a finger, appearing to smell it.

Josh Edelson
Eric Jaye disapproved of the mayor’s attempt to downplay his affair with Ruby Rippey-Tourk and later left the campaign.
Luke Thomas
Eric Jaye disapproved of the mayor’s attempt to downplay his affair with Ruby Rippey-Tourk and later left the campaign.
Oz Erickson, president of Emerald Fund, continues to support the mayor.
Jake Poehls
Oz Erickson, president of Emerald Fund, continues to support the mayor.
Ken Cleaveland of BOMA says people should be rallying around Newsom 
instead of tearing him down.
Jake Poehls
Ken Cleaveland of BOMA says people should be rallying around Newsom instead of tearing him down.
Strategist David Latterman isn’t convinced Newsom can effectively lead.
Jake Poehls
Strategist David Latterman isn’t convinced Newsom can effectively lead.
Former Supervisor Aaron Peskin doesn’t trust the word of Gavin Newsom.
Paul Trapani
Former Supervisor Aaron Peskin doesn’t trust the word of Gavin Newsom.
Attorney General Jerry Brown hasn’t declared his candidacy for governor yet, but he has a commanding lead over Newsom in the polls and in fundraising.
Attorney General Jerry Brown hasn’t declared his candidacy for governor yet, but he has a commanding lead over Newsom in the polls and in fundraising.
Gavin Newsom doesn’t enjoy the support he once did in San Francisco.
Josh Edelson
Gavin Newsom doesn’t enjoy the support he once did in San Francisco.

It's understandable that Newsom's mind might be elsewhere. After all, he's at the beginning of an underdog's attempt to become governor of California, lagging behind Attorney General Jerry Brown — who hasn't even formally announced his candidacy — both in the polls and in fundraising. Longtime political strategist and policy guru Eric Jaye has recently quit, as have Newsom's chief fundraiser, Paige Barry Arata, and two longtime City Hall staffers.

When it's his turn to speak, Newsom puts on his distinctive lupine charm and commences bold gesturing. But at the end of the event, when reporters gather at the purple velvet ropes with their cameras and recorders pointed at Newsom like so many loaded guns, he grips a nearby pole.

They ask about the staff turnover and about Newsom's "sinking ship," but most of the questions involve his break-up with his longtime strategist, whom the San Francisco Chronicle has referred to as "Newsom's brain."

"What happened with Eric Jaye?" a reporter asks.

Newsom coolly instructs the reporter to get a copy of the statement. Then he launches into passive aggression. "We're moving forward without a beat. Without a hiccup," he says. "The campaign strategy remains the same. There's just one less person that's involved. ... It's not a negative thing from my perspective. Quite the contrary."

"You can't deny that Eric Jaye has had an influence on your policies here at home," another reporter fires. (Newsom slips in a quick "Yes and no.") "Is he still going to be an adviser to you on new ideas?

Newsom dodges. "The critique of me is that I come up with so many new ideas, people sometimes get a little bit blurry-eyed," he says.

The mayor seems to resent the implication of the reporters' questions. Wasn't Eric Jaye the real brains of your operation? Aren't you just a pretty face? To an extent, that irritation is understandable. For years, his rivals and critics — some of them members of the local press — have refused to give the mayor, a gifted and charismatic politician, credit for anything. But for Newsom to downplay the exit of his Svengali as "one less person" in the campaign would be like George W. Bush saying that Karl Rove played a minor part in his political success. It was Jaye who came up with the name for Care Not Cash, the tough-love homeless program that helped elect Newsom.

Jaye is not the first disenchanted strategist to part ways with the slick-haired sovereign. In fact, as Newsom embarks on the greatest journey of his political career — and potentially the first major disappointment — his circle of supporting San Francisco strategists has shrunk considerably.

Outside consultants with statewide campaign experience have come on board. But a disconcerting number of former local strategists and loyalists have said, on and off the record, that they don't believe he would make a good governor. Dismiss them if you will as bitter castoffs, but this much is clear: Newsom has created enemies among his former supporters.


Seek out the political operatives who once worked closely with Newsom, and you'll find that a number have soured on the mayor. Ask them why, and you'll be bombarded with his alleged character flaws. Among them: "thin-skinned," "disloyal," "friendless," "joyless," "Machiavellian," "craven," and "empty." One will tell you that Eric Jaye was "the best-paid babysitter in California." Several will diagnose Newsom with an acute case of narcissism.

"He's probably the worst mayor in modern history," said Jack Davis, a strategist who has worked on the mayoral campaigns of Newsom, Willie Brown, and Frank Jordan. "I pity this poor state if lightning should strike and this cad becomes governor amidst the problems that the state has. He'd have a nervous breakdown. There's no there there."

Although there are also fervent supporters, dozens of interviews with City Hall staffers, strategists, and fundraisers yielded a surprising amount of disapproval.

Well-known consultants Jim Ross and Bob Brigham — who both worked on Newsom's 2003 campaign — and 2007 campaign staffer David Latterman all have reservations. "I'm concerned that his record and his temperament will not be fully vetted by the press," Ross said.

Brigham was more direct. "I think Gavin would be a pretty awful governor," he said, though he's not too worried about it happening: "I don't see any path to the nomination anymore."

Latterman said that although Newsom is intelligent and seems to understand the issues, he simply isn't good at leading people. As to whether Newsom could be a good governor, "the odds are not in his favor. There's not a lot of leadership there. But I leave it open."

Patti Solomon, a former mayoral campaign receptionist who worked at City Hall for more than five years, says she was a true believer in Newsom who has gradually lost faith. In fact, she's writing a tell-all involving her time in the mayor's office, titled Don't Repeat After Me. She says the book won't be finished until the election is over, and that it's about karma, but that's all she would say.

Former California Senate majority leader John Burton, who was a mentor to Newsom, has two words to describe Newsom's employees-turned-critics: jilted suitors. "These are people that he hired once and didn't rehire," Burton said. "If he offered them a job today, they would take it."

Others have theorized that because detractors are jealous of the good-looking, affluent mayor, they're behaving like crabs in a barrel. (As it happens, if you stick a bunch of crabs in a barrel, they writhe and climb on each other. If one crab starts getting close to the top, the others instinctively pull it back.)

A slightly more viable explanation is ideological uniformity. San Francisco residents are largely left of center and generally agree on big issues, so the city's policymakers tend to distinguish themselves by taking aim at opponents' character flaws. "This is a city that eats its own mayors," said Garry South, Newsom's current strategist.

But in interviewing former staffers, supporters, and campaign strategists (many of whom requested anonymity), one can't help but think there may be aspects of Newsom's character that should be examined if he is to become governor. These people criticize him on all kinds of things — not keeping his word, inflating his accomplishments, taking credit for the successful ideas of others, being detached, and caring more about becoming president than improving the city or the state. But in the background, a highly personal issue still looms large in their minds and in the campaign — the Rippey-Tourk affair.

San Francisco voters forgave the mayor for bedding appointments secretary Ruby Rippey-Tourk, who also happened to be married to Newsom's longtime strategist, Alex Tourk. In fact, Newsom was re-elected with an astounding 73 percent of the vote. But those closest to the situation have not been nearly so forgiving. They're friends with Tourk, and they have as many good things to say about him as they have negative things to say about Newsom.

"Alex Tourk is one of the most popular people in San Francisco," Brigham said.

But apparently that wasn't going to stop Newsom from trying to rewrite his sordid history at the expense of the Tourk family.


Although SF Weekly made dozens of requests to interview the mayor and his campaign staff, they delayed for two months, claiming they were taking the requests under consideration.

Only last week did Newsom's longtime aide and former press secretary, Peter Ragone, call to set up a meeting that felt more like damage control than an interview. Ragone — who in 2007 got caught injecting positive comments about the mayor into the blogosphere under a false name — refused to comment on the record.

To counter the spurned strategists' argument that Newsom has no friends or long-standing allies, Ragone eventually provided Tom Hsieh, who worked with Newsom back in 2002 as a campaign manager for his re-election as supervisor, and then as a political director for both of his mayoral campaigns. He's still around for the gubernatorial race.

"I'm working with him because of his ability and willingness to force change in a system that defends and sustains the status quo," Hsieh wrote in an e-mail.

Furthermore, Newsom's political appointees, including Treasurer Jose Cisneros, Assessor-Recorder Phil Ting, and Supervisors Sean Elsbernd, Carmen Chu, and Michela Alioto-Pier have all endorsed him for governor. Calls to all but Ting and Cisneros went unreturned, but those two spoke glowingly of the mayor and their ability to work with him.

As an openly gay elected official, Cisneros said he was particularly impressed by Newsom's work on same-sex marriage. "We're all human," he said. "I can't think of anything I would say about him that I wouldn't say about the rest of us. We all try. We stumble. We get back up. One thing I see with him — he stays dedicated."

In an e-mail, Ting wrote, "He has proven that he is unafraid to tackle difficult issues, offer bold new ideas, and bring people together to solve problems."

Occasionally, even Newsom's biggest critics will admit that he has done some good for the city of San Francisco. They'll give him credit for ending the pay-to-play atmosphere that proliferated under Willie Brown, and many admire him for (briefly) legalizing same-sex marriage, which pushed the issue to the forefront around the nation even as the movement failed at the ballot box in California. Although Muni still has its problems (and costs a lot more), buses and trains are more often on time these days. And homicides and gun violence have recently dropped significantly. Then there's the public health care plan, Healthy San Francisco, which is said to have been successful in providing care to 32,000 residents, many of whom are poor and elderly, without the negative impact on the city's employment rate critics had warned about.

Of course, Newsom's foes love to point out that he doesn't deserve full credit for Healthy San Francisco, since former Supervisor Tom Ammiano rallied the support for the measure. Still, one can't help but think that even if Newsom came up with some brilliant policy and flawlessly implemented it, in the poisonous atmosphere of San Francisco politics, plenty might refuse to acknowledge his achievement.

When it comes down to it, complaints against Newsom from his former staff seem to originate from the personal more often than the professional. They see him as fundamentally disloyal and unconcerned with the well-being of those around him.

Take the departure of Jaye, for instance. Newsom could have attempted to remain neutral in the press about it, but instead he acted as though the loss meant nothing to him. Newsom "owes the fact that we take him seriously to Eric Jaye," said John Shanley, a city attorney who worked for Newsom's 2003 mayoral campaign as the communications director. "He had talented people like Eric Jaye holding his shit together, and [Jaye] gets no gratitude for it. Newsom dealt with Jaye like a piece of toilet paper."

Other former staffers bring up the mayor's inability to manage and work with others. "I don't think he has the temperament to effectively govern the state of California, or lead," strategist Ross said. "You can just see it in his relationship with the San Francisco Board of Supervisors. ... To push the reform that the state needs, I think we need a leader who can work with the legislature effectively."

Aaron Peskin, former board president and well-publicized foe of Newsom, can talk (and talk and talk) about that relationship. Peskin and Newsom's problems started on the corner of Grant and Columbus in 2000, when Peskin was running for supervisor.

Peskin chased Newsom down to that corner to ask for an endorsement, knowing full well he probably wouldn't get it. Willie Brown had appointed Newsom — then just a guy with a prominent judge for a father, connections to the Getty money, and a wine shop — to the Parking and Traffic Commission and subsequently to the Board of Supervisors. Certainly Newsom was indebted to Brown, who had also appointed Supervisor Alicia Becerril, then an incumbent running against Peskin. Complicating things further, Newsom had grown up with another candidate in the race, Meagan Levitan.

But to Peskin's delight, he remembers, Newsom said he had chosen not to endorse anyone. Not more than a week later, Peskin says, registered voters got recorded phone calls from Newsom. He had endorsed Levitan.

"On the board, and in politics, and in life, your word is your bond," Peskin said. As a supervisor, he often had to ask co-workers for their votes and cosponsorship. There were plenty of times he got a "hell, no" for an answer, he remembers, and that was okay. At least he knew where he stood. With Newsom, that was rarely the case.

Former Supervisor Fiona Ma, now in the California Assembly, had a similar experience. When she was running for supervisor in 2002, Newsom told her he'd endorse her candidacy. After a group of her supporters displayed numerous signs saying as much, Newsom changed his mind and asked Ma to take them down.

"His word was ubiquitously known to be bad," Peskin said. "If Gavin said yes, yes could mean no. Maybe could mean yes. No could mean yes."

Of course, you'd expect Newsom not to get along with a political rival like Peskin. But the doesn't-work-well-with-others criticism is echoed by Bevan Dufty, an ostensible ally on the Board of Supervisors.

Dufty points to Newsom's response to a recent piece of legislation amending the city's Sanctuary City ordinance, cosponsored by Dufty and seven other supervisors.

After the legislation was formally introduced last month, Newsom went on the attack to undermine support for it. He even authorized his staff to leak a confidential memo from the city attorney that outlined legal problems with the proposal.

Dufty criticized the mayor for being a latecomer to the process. He says even though the proposal had been in the works for months, the mayor never contacted him to express his concerns during that time.

Dufty, who could prove to be the deciding vote to override a Newsom veto, says only now has he begun receiving calls and e-mails from the mayor's office. "It's just typical of the mayor's relationship with the Board of Supervisors," he said. "It's not collaborative; it's reactive."


Although there was a time before Newsom's re-election when he told the press he wasn't even sure he wanted to be mayor again, he has also expressed a desire to become president of the United States.

Back in 2003, Newsom and Jack Davis held private meetings where they would sip orange-mango juice, Davis said, and Newsom would "unload his heart."

One day, Davis remembered, Newsom confided that he wanted to be president. Davis considers that a noble aspiration, but something about Newsom's admission put him off. "I felt the guy was ready to do whatever it took to make it a reality," he said.

The two also discussed campaign strategy, and Davis said he will never forget the day they agreed that Newsom wouldn't put his name on anything controversial while running for mayor because it would create enemies. "Do you understand, Gavin?" Davis remembers saying. "So we're clear on that one?"

"I understand," he remembers Newsom saying.

Soon after, Davis says, Senator Dianne Feinstein called from Washington and leaned on Newsom to support bonds for Hetch Hetchy. Within a day of telling Davis he'd remain neutral, Newsom gave his support to Feinstein.

Davis immediately set up another meeting. "You and I had an understanding, and you broke that understanding," he told Newsom. "I'm no longer running your campaign."

Although Davis stayed on to help with Care Not Cash, "it was one of those nail-in-the-coffin days." He didn't want to work for a candidate he couldn't trust.

In the end, Davis believes Jerry Brown will defeat Newsom, based on character. "I don't think you're gonna find Jerry Brown fucking somebody else's wife," he said.

Of course, not everybody thinks the affair or issues of character and loyalty will come into play, or that they should. Corey Cook, a political scientist at USF, says that in many cases, character isn't worth bringing up. He'll agree that while politicians are often flawed beings — perhaps more so than the rest of us — it's not their personalities that matter, but rather their ability to persuade, negotiate, and bargain. Cook said he would rather hear about how Newsom plans to manage a gridlocked legislature in what is said to be an ungovernable state.

But experts in the field of political psychology say that particularly during troubled times like those facing California, the personalities of candidates absolutely matter. "Character is the best predictor of what people will do and whether they will be trustworthy," said Lloyd Etheredge, director of the Policy Sciences Center in New Haven, Conn. He recommends that voters listen to their gut about whom to vote for, rather than choosing the candidate who best reflects their own ideology: "You have to respond to them as human beings."

The way Newsom treated two human beings on his staff is expected to come up again and again during the battle for the Democratic nomination.


In February 2007, Gavin Newsom's former appointments secretary, Ruby Rippey-Tourk, returned from rehab and confessed to her husband, Alex Tourk, Newsom's campaign manager, that she had had an affair with the mayor. Tourk resigned immediately, and the affair became public knowledge. Discussion about how Newsom had "broken the man code" abounded.

But the mayor handled what might have been a career-ending situation about as well as he could have. "I want to make it clear that everything you've read is true, and I'm deeply sorry about that," he told reporters at City Hall. "I hurt someone I care deeply about, Alex Tourk, and his family and friends, and that is something I'm deeply sad about and sorry for."

Newsom then checked himself into rehab for alcohol abuse, and came out the other side ready to run for his second term.

San Francisco voters may have been willing to let the mayor slide, but in this tough governor's race, it's likely that his home-wrecking will continue to be rehashed — if not by the Jerry Brown campaign, then certainly by the media.

In an apparent, ill-fated attempt to pre-empt this, Newsom himself has tried to recast the affair in the minds of statewide voters. In June, he told Fast Company magazine that part of the story had yet to come out. Days later, he repeated that to The New York Times Magazine, and added that the affair was much more "benign" than newspapers suggested.

Although Newsom eventually told a group of reporters that he had made a mistake in giving the mysterious statements, political consultants said it was almost certainly part of a strategy to downplay and repackage the affair. When a candidate for governor talks to the national media, there's no going off-script, they say. Everything is planned. Particularly if something is said twice.

The city's politicos have been puzzling over what Newsom could have been referring to, but one strategist close to the situation has a pretty good idea. When Newsom claims we don't know the whole story, the source said, he's referring to information embarrassingly submitted by his wife and then-girlfriend, Jennifer Siebel, in 2007. "The woman is the culprit," Siebel told the San Francisco Chronicle. Siebel also posted in the comments section of an SFist story, claiming that "unfortunately everyone near to [Rippey-Tourk] has stories and says she is bad news" and that the affair consisted of "a few nothing incidents."

No one has offered any specific information — at least in the press — to the contrary. The fact is, it's an open secret that the affair was far more than a few nothing incidents. It went on for months. While it may have been benign for Newsom, during the course of the affair Rippey-Tourk developed a severe drinking problem, which ended only after she checked into rehab.

Solomon, the former receptionist working on the tell-all, was close to Rippey-Tourk and said she has struggled immensely. "She lost her husband. Her job. Her identity," she said. "She's working on getting that back, and she's a beautiful woman, inside and out. She did get the shaft really bad."

Newsom, on the other hand, is running for governor. Although he has stopped telling the press about how there's more to the story, those close to Tourk and Rippey-Tourk are enraged.

In fact, a source close to Jaye says Newsom's statements regarding his affair played a significant role in Jaye's departure. The not-so-amicable parting, which went down on July 24 in Jaye's Storefront Political Media office at 250 Sutter, was a shock to politicos in San Francisco.

The reason Jaye gave was "a fundamental difference in how to run the campaign." Many assumed he was speaking of differences between the strategy he favored — touting new ideas through grassroots social media — versus bulldog strategist Garry South's slash-and-burn tactics.

A long interview with South involved plenty of Jerry Brown bashing, including reference to the attorney general as "a product of the past" without a credible record of leadership. "The best we can do is dredge somebody up from 40 years ago?" South asked. "That's pretty pathetic. Where's our talent pool?"

But another contributing factor to Jaye's departure, a source close to Jaye says, was Newsom's resurrection of the affair he had with the wife of his former campaign strategist. Jaye "was so personally appalled by the attempt to rewrite the history and to minimize the action that it affected his relationship with Newsom," the source said.

"Of course I was troubled by those comments," Jaye said. "I knew they were going to be very hurtful to the family involved."


Around 6 o'clock on August 5, people began trickling through the heavy wooden doors of the Bambuddha Lounge for "Gavin's Summer Soirée," a hometown fundraiser thrown by "friends of Gavin."

Attendees mostly fell into two categories — young, attractive women, and people working the fundraiser. Absent were any heavy-hitting Democrats who helped Newsom reportedly pull together $4 million in a few months during his first run for mayor.

There was, however, a VIP room, reserved for those who donated $1,000 or more. (That meant there were likely no more than four people in it; on the day of the event, only $4,180 had come in from just 69 donors.)

The low attendance echoed David Binder's recent poll, which revealed that San Francisco voters actually prefer Jerry Brown to Newsom by 51 to 34 percent. Statewide, according to a poll conducted by J. Moore Methods, Brown was leading Newsom by 49 to 20 percent.

Those numbers aren't helping with potential donors. So far, Newsom has raised $1.7 million compared to Brown's $7.3 million, which is sure to jump considerably when Brown formally enters the race.

Wade Randlett, an influential national fundraiser who brought in big bucks for Care Not Cash and Newsom's 2003 campaign, is one of those who has abandoned ship. He is concerned with how little progress has been made in the city, particularly in regard to cleaning up the Tenderloin and getting homeless people off the street.

"Philosophically, it's a hell of a long way from Care Not Cash to having city government enforce food scrap recycling in private homes," Randlett said. "If houseflies had a lobby, I'm sure they'd raise millions for him."

Making a transition from local to statewide office is extremely challenging, Randlett said, and those who make the jump are often surrounded by what he called "lifers," longtime friends of the candidate, "the kind of supporters who will crawl across broken glass to help their guy."

"There is no question that Jerry Brown has that core," he said. "The big question is whether Newsom's 2003 core became casual observers because of his handling of the nuts and bolts of running the city where they're trying to raise families."

Ken Cleaveland, the director of government and public affairs for the Building Owners and Managers Association of San Francisco, has also noticed that Newsom is lacking in loyalists. "People that have been his supporters should rally around him," said Cleaveland, who is supporting Newsom for governor. "But perhaps people turn on people like Gavin when they think there are no repercussions."

One donor who continues to support Newsom but asked to remain anonymous says he admires the mayor's refusal to do favors for those who filled his campaign coffers. "People who supported him really hard are now saying, 'Why would I go out and fight battles for him when he did nothing for me?'" the donor said. "A lot of people think that way."

Oz Erickson, a Newsom donor and president of the real estate development firm Emerald Fund, said he believes the fundraising effort has been thwarted by outside factors. "I truly believe that the economy has affected everybody's ability to give generously to campaigns," he said.

Back at Bambuddha Lounge, people who had donated the suggested $35 entrance fee were discussing the election. One woman said she strongly believed Newsom was a good mayor, and would probably beat out "Villagrossa" (she meant Los Angeles Mayor Antonio Villaraigosa, who dropped out in June) and Dianne Feinstein (who has not entered the race). Another young woman, when asked whether she preferred Newsom or Jerry Brown, admitted she had never heard of Brown.

About an hour into the event, Newsom finally swept into the bar, setting off a frenzy of handshakes and white-toothed smiles. Tonight, he said with characteristic effervescence, he would explain why he wanted to run for governor, and it basically amounted to this: He really loves California.

In talking about California, though, it almost sounded as though Newsom were talking about himself. "People have written off this state on many occasions, but California's best days are not behind us," he said. "They're in front of us."

He championed California's diversity, and "our capacity to live together and advance together." He spoke of "the magic of our state that defines our greatness." All eyes in the room were glued to Newsom — a politician adept at charming strangers, but considerably less skilled with those who know him best.

Newsom promised he would do what was right, regardless of the consequences. He said that California needed a leader who doesn't say one thing privately and do another thing publicly. Then, finally, he acknowledged the truth about his campaign. "We recognize we are underdogs," he said. "But the gift of being an underdog is that you can truly be yourself."

That will certainly be interesting, Newsom's critics say, because as of yet they have no idea who he really is, other than a fundamentally disloyal guy with extremely high ambitions and dwindling support. The kind of guy who sleeps with his campaign strategist's wife. Who will do anything to ascend the political ladder. Whose word means little.

Newsom, for his part, is clearly less than pleased with his dissenters. "He blocked me on Twitter," Brigham said. "I'm thinking of unfriending him on Facebook."

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