Supervisor Sheehy fears his key vote to oust Breed as mayor doomed his re-election campaign

Supervisor Jeff Sheehy is no stranger to breaking barriers. Though he’s now San Francisco’s first openly HIV-positive supervisor, he once was a hardscrabble activist in The City, fighting for representation during the 1990s as his community died around him during the AIDS epidemic.

When he was appointed by the late Mayor Ed Lee to serve as District 8 supervisor in January 2017, he carried that ethos with him into office.

“We weren’t allowed in [before]. LGBT folks, people with HIV, we were outside of decision-making circles,” Sheehy told me. “Activists are always challenging power. We’re change agents.”

That activist ethos was also key in his decisive vote to nominate Supervisor Mark Farrell as “caretaker” mayor, ousting Acting Mayor and Board of Supervisors President London Breed in the process. Though power players behind the moderate supervisors wanted Breed to remain mayor, Sheehy, who had been aligned with the moderates, said he bucked his allies for his principles.

As far back as mid-December — the week after Breed became acting mayor — Sheehy expressed in interviews that San Francisco’s mayor also acting as the board’s president was an untenable position, that it was too much power for one person.

“It’s a big deal for the budget. It’s a big deal for everything we do,” he said. “It’s just not the way government is supposed to run.”

Sheehy was quick to point out that he also voted for Breed to become successor mayor. But she lost, which, by procedure, left Farrell as the only choice to end Breed’s dual role. Had Breed been voted as successor mayor, she would have relinquished her District 5 seat.

The act and optics of ousting a black woman who grew up in San Francisco’s housing projects from the Mayor’s Office — who made strides for her own community as the first black woman to serve as The City’s mayor — for a white venture capitalist from the Marina are not lost on Sheehy; he now fears the vote may have sealed the fate of his already difficult campaign to retain his District 8 seat in the June election.

Sheehy lost his first campaign manager in October, as I previously reported. This month, he lost his second manager, only months from the election. The politically influential Harvey Milk LGBT Democratic Club last week endorsed his main opponent, the progressive-aligned City College of San Francisco Trustee Rafael Mandelman, and a committee of the Alice B. Toklas LGBT Democratic Club voted this week to recommend an endorsement of Mandelman as well, though that decision won’t be finalized until February.

But more than any other political loss, the vote for Farrell may have cost Sheehy the backing of Breed’s most prominent potential donor: tech mogul Ron Conway, who has spent hundreds of thousands of dollars in San Francisco elections to back allies of Lee for nearly a decade.

“I’ve never sat down with Mr. Conway,” Sheehy said, noting that discussion of independent expenditure campaigns with the snowy-haired billionaire would be illegal.

“There is this kind of assumption that, if you’re on one of the [moderate or progressive] teams, certain people are going to do [independent expenditures] for you,” he said. “The spending in the last election was ungodly.”

Supervisor Jeff Sheehy stands in the board’s chambers inside City Hall on June 23, 2017. (Jessica Christian/S.F. Examiner)

Now, Sheehy said that backing has vanished. Though the effect of that loss is yet to be seen, Sheehy is a man alone.

Former District 8 Supervisor Bevan Dufty believes Sheehy may have fallen on his sword for the sake of mayoral candidate Mark Leno, which would be momentous for Dufty, a gay politician, because Leno would be the first openly gay man elected mayor of San Francisco if he wins.

“Jeff jettisoned his near-term political reality,” Dufty said, adding that he believes Sheehy saw a “greater cause here.”

Some speculated that Sheehy will be granted political help in his campaign against Mandelman following his vote as well, though Sheehy said progressives would likely stick with his opponent.

Lou Fischer, who has been politically active in local campaigns and the LGBT community for years, doesn’t believe District 8 voters will see the nuance in Sheehy’s decision.

“If I were a D8 voter, I would not have liked it at all,” she said. “It was two days after the Women’s March.”

Though Fischer acknowledged the paid political insiders, City Hall watchers and politically engaged club members may see merit with Sheehy’s separation of powers argument — and that he initially voted to keep Breed as mayor — she added, “People who aren’t as [politically] active as we are see this and say, ‘Whoa, what’s this? It’s the year of the woman!’”

Sheehy now also finds himself without political establishment backing. The progressives are behind Mandelman, and the moderates may view Sheehy as toxic for voting with the progressives.

“I definitely think the decision was worth it,” he continued. “I think there’s too much in politics these days where people shrug their shoulders and they don’t stand up for good process.”