“You earn voters, then you become independent. You don’t become independent then earn voters.”


SupervisorJeff Sheehy is on his third political consultant in his quest to retain his District 8 seat, a fact that has been much repeated to portray his campaign as one in disarray — and, none too subtly, claim it’s a campaign he doesn’t even really desire to win.

The San Francisco Chronicle did all of that, endorsing his opponent Rafael Mandelman, a move as inconceivable only a few years ago as the paper hiring a full-time marijuana editor.

Well, they did that.

Our paper of record also offered Sheehy a bit of free psychoanalysis based on his “rambling” answers: “It was almost as if Sheehy were tacitly asking us to do him a favor by endorsing his opponent.

They did that, too.

Sheehy resents the above passage. And, for what it’s worth, he offered us an answer that was anything but rambling when we asked why he’s gone through so many consultants: “Consultants suck.”

He smiles, sheepishly, and walks that statement back. But only a little. “I take the blame for it. I am not a good fit with a consultant. A consultant,” he pauses, “is, like, a weird concept.”

Consultants, like, try to figure out how to get more people to vote for you than your opponent. Consultants try to get Candidate A to tailor Messages B, C and D to Voters E, F and G who live in neighborhoods H, I and J. This does not appeal to Jeff Sheehy. “My view is, ‘What is the right thing to do?’ I want to keep talking about the right thing to do, even if it doesn’t poll well.”

Sheehy has, by and large, undertaken this approach during his year and change in office after Mayor Ed Lee tapped him to replace Scott Wiener. And, lo and behold, it doesn’t poll well.

The fledgling supervisor has, whether he means to or not, made his independence into his defining political trait. On Jan. 23, he voted to retain London Breed as mayor but found himself outvoted. He then went on to provide the deciding vote for Mark Farrell, along with five of his left-leaning colleagues.

Sheehy was, clearly, voting against his self-interest — his move alienated him from much of the city’s right and did little to endear him to much of the city’s left — and for what he claimed was the “right thing to do” — for one person to serve as both mayor and board president for an extended period of time, he says, is untenable.

“One of the things that surprised me about the vote is, why would anybody be surprised?” he reflected months later. “I am notoriously independent. Ask people who knew me from 20 years ago. ‘Sheehy! No one knows what he’s gonna do!'”  

This has left him isolated in the political gang warfare of City Hall; moments after Breed was ousted as mayor and pandemonium ensued, Sheehy turned to me and deadpanned, “I guess Ron Conway won’t run an independent expenditure campaign for me.”

But you’d think voters wouldn’t be affected by these internecine pressures and allegiances. You’d think voters would want their leaders to act independently from pressure brought or dictums laid down by political figures or special-interest groups or big donors. You’d think voters would appreciate a leader unafraid to tell you when something sucks.

Well, you’d probably be wrong.

Sure, voters say we want our representatives to do the right thing. The morally right thing. The people-over-special-interests thing. That’s what we say. But that’s not what we mean. “What we mean,” says San Francisco State University political science professor Jason McDaniel, “is we want them to do what we want them to do because what we want is the right thing.”

Independence, then, needs to be tethered to something. It’s not clear Sheehy — whose district includes Dolores Park, Mission Dolores and the Valencia corridor — is tethered to anything. “I was appointed,” he notes. “So I didn’t have to figure out how to put together a team. A base.”

And that shows. If he’d done that, his base would tolerate and perhaps even celebrate his occasional unpredictable votes. Sheehy’s predecessor, Scott Wiener, did that. He would occasionally carry legislation or make votes that defied expectations. But he also built up that base, and a reputation as a housing guy, a transit guy, the quality-of-life guy, and a supervisor who wrote so many ordinances that he was referred to by a colleague as a “legislative Pez dispenser.”

Independence, then, is something a politician must earn from his or her voters — once he’s earned voters. “You earn voters, then you become independent,” explains Jim Ross, a campaign consultant who ran Gavin Newsom’s successful 2003 mayoral run and now specializes in more left-of-center endeavors. “You don’t become independent, then earn voters.”

Ageneration ago, more voters had deep city roots, and the time — and financial ability — to study up on political issues or even get involved in campaigns. That’s no longer the case. Now more than ever, it would seem, voters are looking for “shorthand” to decide on candidates and the sometimes dozens of measures put before them. And, in this city, you’re either a so-called “progressive,” or a so-called “moderate,” with the backing of the political clubs and unions and captains of industry unique to one or the other. Or, you’re like Sheehy, suddenly a long-shot candidate whose behavior is so baffling to this city’s political handicappers that they believe he’s intentionally self-sabotaging himself (he says he is not).

The plight of Jeff Sheehy is a prime example that the divide between “progressives” and “moderates” is not a construct. “I didn’t realize these teams were so set,” he admits.

And these distinctions are not meaningless. There is a popular narrative that San Francisco’s political offices are held by a battalion of interchangeable political lefties and one candidate for office is really no different than another and, by extension, it doesn’t matter who wins and it doesn’t matter who you vote for.

If someone is telling you this, it means one of two things: 1. They don’t know enough about San Francisco politics to be offering you their opinions, or; 2. They know plenty enough and are trying to mislead you for their own ends.

San Francisco, like most every big American city, is an ideologically left-of-center place led by ideologically left-of-center officials. But cities don’t run on ideology; the issues that divide us are municipal, not ideological. Every leader in San Francisco is progressive enough, until the question arises of how to pay for something. You can argue about the nomenclature “progressive” and “moderate,” but, for sanity’s sake, the most expeditious way to define them relates to how they view regulation and land-use. “Progressives” would tend to favor taxing and regulating businesses and extracting concessions from developers. “Moderates” would tend to favor allowing businesses and developers to flourish. “Moderates” favor market solutions. “Progressives” are wary of the market.  

This is all fodder for a panel discussion, but the point here is, as Sheehy has learned, that politicians here are incentivized to walk a line. “It gives politicians networks to plug into,” he says. “Support. Money.”

Lots of money.

“There were always conversations, like, there will be resources that will come into your race that you won’t be able to talk to people about,” Sheehy says. “There’s just an undercurrent of that on the moderate side. If you’re on one team, things like that are gonna happen. If you’re not a team, nobody is coming for you. This is one of the things that motivates people to be on a team.”

The team dynamic, Sheehy says, is something Tony Winnicker reviewed with him prior to his fateful Jan. 23 vote. While progressive supervisors accused Ron Conway of arm-twisting for votes on Breed’s behalf, Sheehy describes his conversations with Winnicker — a former advisor to Mayor Ed Lee who now serves as a consultant to Conway and other businesses and nonprofits around town — as cordial. “Everybody understands everything,” Sheehy explains. “You support your team or you don’t.” The consequences hardly need be explained.

Winnicker declined to go into specifics regarding his conversations with Sheehy. “I have tried to be helpful and supportive of his chances for re-election.” And, not inconsistently, he did urge him to back Breed. “At the time, I told Jeff that Mark Leno is supporting his opponent, and London Breed was supporting him,” recalls Winnicker, “My point was, you win in politics by having allies. Loyalty matters.”

Not so long after Winnicker imparted this advice to Sheehy, I witnessed a city worker take a call from him and, to avoid the prohibition against doing campaign work on city property, actually climb out the window.

Sheehy, in his own way, climbed out the window as well.

“Jeff Sheehy makes his own decisions,” sums up Winnicker. “He charts his own course.”

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