San Francisco Is Deciding What Comes After Pelosi

SAN FRANCISCO — The last time there was not a Pelosi or a Burton on the ballot for Congress here, John F. Kennedy was still president.

Yet when San Franciscans go to the polls Tuesday, they will be presented with a very different set of Democratic candidates — and who voters select will offer keen insights on the party and this city, perhaps the capital of American liberalism.

The trio of leading contenders reflects three distinct paths forward for Democrats, fitting for a place which, as the old joke goes, has a three-party system: liberal, very liberal and radical.

In that order — although it’s complicated by issue set, itself a sign of changing times — are roughly: state Sen. Scott Wiener, Supervisor Connie Chan and Saikat Chakrabarti, a former chief of staff to Rep. Alexandra Ocasio-Cortez and onetime tech executive.

The all-party primary will winnow the trio to a duo that will face off in November’s general election.

They are all culturally progressive. This is a city that’s home to the Counterculture Museum, on the corner of Haight and Ashbury. But the three have revealing differences across the party’s new economic and foreign policy fault lines.

This is no ordinary open House seat.

It has been represented since 1987 by Nancy Pelosi, the most enduring and influential congressional leader in modern times. Twice House speaker, Pelosi was, until last year, also the face of the Democratic opposition, dating back to before the start of the Iraq War. Which is to say this city’s congresswoman has doubled as her national party’s leading non-presidential voice for the majority of her nearly 40 years in office.

Those same years have seen Republicans portray Pelosi as the archetypal “San Francisco Democrat” — both far-left and elitist — in the same way they attempted to paint Democratic presidential hopefuls in the same period. Yet Pelosi’s politics have always been more complicated than the conservative caricature, in Washington and at home.

In the capital, she was more pragmatic — accommodating and even prioritizing moderate and red-state lawmakers. She could also be cautious in her opposition to George W. Bush and Donald Trump, frustrating left-wing critics from Cindy Sheehan to, well, Chakrabarti, who jumped in to challenge Pelosi months before the “speaker emerita” announced her retirement last November.

In San Francisco, Pelosi’s politics were center-left from the beginning, rooted in the city’s once-potent neighborhood Catholic parishes, and always institutional. She may have lived with, and prolifically raised money from, the Pacific Heights swells. But the “elitist” tag was always a misnomer locally, as so much of her power here flowed from her deep alliances with labor.

Which is partly why Pelosi has endorsed Chan, who has considerable union backing, but more on that later.

It’s not just who represented the district for so many years that makes this race so significant — it’s the seat itself. Few districts in America incorporate close to the entirety of one large city, but that’s what this is, comprising all but a few precincts of the 7x7 square miles that are the beating heart of the American left.

“San Francisco sets the tone for what it means for our country to act in a more inclusive, more equitable way,” Phil Kim, the city’s school board chair, told me. “That has always been San Francisco’s story.”

Kim is originally from somewhere else, Michigan, but found his way here like so many of the city’s migrants. Over the decades, these newcomers infused San Francisco with its energy and activism, putting it at the forefront of progressivism. This is where birthright citizenship was affirmed in the 19th century, where a general strike cemented 20th century trade unionism, and from whence the Beats flourished, and incubations of the anti-war, environmental and gay rights movements.

While these efforts were largely led by activists pushing the political establishment, the Bay Area eventually produced elected leaders who matched their dynamism.

There were the Burtons — Phil who first won this seat in 1964, and his widow Sala, who succeeded him, and his brother, John, who had a neighboring seat and was also a state political powerhouse. And the names you surely know: Harvey Milk, Jerry Brown, Willie Brown, Dianne Feinstein, Barbara Boxer and Pelosi. It was an array of local talent, perhaps only outmatched by the other Willie, the one at Candlestick, and a band beyond description that first formed further south, in Palo Alto.

Well, Pelosi is the last one still in office of this cohort. And if you count the subsequent generation, the city’s former district attorney lost her bid to be president and the mayor who became governor is on his way out of Sacramento after two terms.

San Francisco is now facing a power outage: a first-term representative to go with a pair of Southern California-based senators, up against a hostile president.

“We don’t have any stars left,” as Brown, the two-time San Francisco mayor, put it to me.

Less urgently, but just as significantly, is the tectonic cultural and financial shift underway here. It isn’t just the 49ers that have moved south since Pelosi first came to office. Much of the energy has moved to Silicon Valley.

There are tech outposts in the city, but Cupertino, Menlo Park and Mountain View are the new capitals of the age.

While much of the innovation has taken place down the peninsula, the new tech money has transformed San Francisco. This is a far wealthier city than the one that elected Pelosi in 1987 and a dramatically wealthier one that sent Burton to Congress in 1964. The Irish and Italian neighborhoods have priced out many of the old cops and firefighters who once lived there, and Black and Latino enclaves have been heavily gentrified.

As for the Counterculture types, well, who can afford it? That museum in the Haight is at risk of becoming a bit too on-the-nose, a collection of what was here. Now, all those ‘San Francisco Is Back’ national stories are about the return of higher rents and multi-million dollar homes snapped up in minutes, not promising new bands or edgy movements.

This has all created an unmistakable sense of resentment and built a new political hothouse in which the race to succeed Pelosi is playing out.

Wiener won’t put it this way, but his bet is that San Francisco is well past “peak Woke” and into its backlash phase. Or what passes for backlash here.

The former supervisor-turned-state-lawmaker is equally renowned locally for his unapologetic YIMBYism and his height — at 6’7 he’s known as The Giraffe. The 56-year-old would also be the first openly LGBTQ+ member of Congress in this gay mecca.

That may lift him with some members of the community. But he’s better defined here by being, no not a moderate, but closer to “left” than “lefter,” as he puts it.

“We have the lefter segment of San Francisco politics, when you can never be left enough and it just gets further and further out there,” Wiener told me after a few hours of canvassing around lower Pacific Heights.

Practically, that means he boasts about being the first elected official to demand the 2022 recall of San Francisco school board members who delayed reopening schools post-Covid and even tried to cancel Abraham Lincoln (which Wiener may have taken personally because he’s colloquially known as Gaybraham Lincoln, for his resemblance to the lanky president).

He said “I believe in free enterprise” with regulations when I asked if he was a capitalist.

And he doesn’t offer any caveats to his support for San Francisco Mayor Daniel Lurie, the Levi Strauss heir who has embraced Bloombergian competence (but with a better Instagram game) and zoomed to approval ratings north of 70 percent.

“He is an extremely capable mayor with a vision for the city,” said Wiener. When I noted that Lurie was no progressive, he shot back: “That doesn’t matter to me, he is deeply committed to the city. And he is moving this city in a positive direction, and I support the mayor.”

Lurie and Wiener both oppose a labor-backed ballot measure that would impose a wealth surtax on large corporations in the city in which the top executives earn 100 times more than the company’s median employee.

The debate over the referendum, Proposition D, has become a major dividing line in the campaign.

Walking around the city, it’s easy to find “Yes on D!” signs paired with Chan posters at lefty bookshops and corner stores.

And Chan has closed her campaign by rallying support for her candidacy and the wealth tax.

“As goes San Francisco, so goes the nation,” she said at a rally with purple-clad SEIU workers late last month near Golden Gate Park, urging her supporters to make sure “billionaires pay their fair share.”

Between greeting farmers market patrons the next day, Chan called herself “part of the labor movement” and made the case for “progressive taxation.”

Born in Hong Kong and reared in Taiwan, Chan came to San Francisco’s Chinatown at 13 and worked her way up in local politics as an aide before being elected to the Board of Supervisors in 2020.

She’s close to labor and part of the NIMBY faction in San Francisco, although she’d call it the "tenant protection" bloc.

Chan, 47, has struggled to raise money, however, and only had $70,000 in the bank according to final, preelection filing.

That meant she was not able, for example, to immediately turn Pelosi’s endorsement into a commercial on local broadcast TV.

Chan cited Chakrabarti’s ability to self-fund and said Wiener had stockpiled commitments for years ahead of the campaign that most insiders here knew he’d launch when Pelosi retired. “We're literally building a plane while flying it,” Chan told me.

However, she has not been as aggressive raising cash as some San Francisco Democrats expected. One local with a history of giving told me he was surprised Chan never called asking for money.

She’s betting on her union allies, though, to carry the day and at least get her a ticket into the final round of voting, when she’d likely face Wiener in what Chan predicted would be a definitional race about class politics.

“Is the corporate Democrat going to win the day from San Francisco, of all places, or is this going to be truly the working people’s candidate?” she asked.

To face Wiener, though, Chan has to first outpoll Chakrabarti, who has already spent nearly $10 million of his own fortune from being an early employee at Stripe, the payment-processing company.

Chakrabarti, 40, is running as the most progressive of the three. He’s already in touch with other left-wing candidates and is vowing to use the San Francisco seat to recruit more insurgents to knock off incumbents the way he seeks to do against Pelosi — and his former boss, Ocasio-Cortez, did successfully in 2018.

“What I'm seeing now dwarfs what I saw in 2018,” Chakrabarti told me. “People are so upset at the Democratic Party.” (Notably, Ocasio-Cortez has not endorsed him, her own former staffer, even as she’s taken sides in other open races.)

Democrats need to offer “a real agenda,” he said, citing Medicare-for-All, free childcare and higher taxes on the ultra-rich. The party, he said, also must be clear-eyed about calling Israel’s actions in Gaza “a genocide,” something Wiener initially was reluctant to do.

Chakrabarti is a San Francisco transplant, like his two rivals and Pelosi herself, but has less of a history of civic involvement here.

If he seems like a British politician who just happened to pick a local constituency to carry a national message, though, he said San Francisco is suited for such a role. “This city has a special role to play, to push against the establishment, to shape the progressive conversations around the country,” Chakrabarti told me.

As for Pelosi, he said he has “a lot of respect for her” but quickly added: “We need something different right now because the existing institutions and establishment have led us to this point.”

Such comments are part of the reason why, last month, Pelosi came off the sidelines and endorsed Chan. The former speaker tends to avoid engaging in local primaries but the polling made clear that it was uncertain Chan would make the November election and that Chakrabarti could slip in with Wiener — both candidates who entered the race before Pelosi announced her retirement. Their ascendance would indicate not only that Pelosi can't control her own succession but that the traditional political forces here matter less than money — and that the city is either more pragmatic or more progressive than the former speaker would have it.

Pelosi appeared in the city with Chan this past weekend and has been feeding her advice and asking questions in the lead-up to the election.

“It’s like she’s troubleshooting your campaign,” Chan told me with evident gratitude. “She’ll say, ‘Have you done this, did you earn an endorsement from this group or that group’ — it’s amazing.”

For years, the betting here was that Pelosi would be playing de facto strategist for her daughter, Christine. But Wiener’s years-long planning made clear that Christine Pelosi would have faced a difficult election, and she avoided the showdown by announcing she’d seek his State Senate seat.

I asked Brown if he thought the former speaker was disappointed she couldn’t pass her seat to her daughter. “Sure,” he said, “She would have loved to have a Pelosi just like the D’Alesandros loved to have a D’Alesandro run Baltimore.”

Word, though, is getting around that Chan has Pelosi’s support.

As Chan was shaking hands and passing out voter guides from the only-in-San-Francisco “League of Pissed Off Voters” in the Outer Sunset neighborhood, a local resident stopped long enough to mention Pelosi’s endorsement.

“She’s good people,” said the voter, Melissa Moore, explaining why Pelosi’s support mattered to her.

At the labor rally, a longtime activist who called Pelosi his “hero,” Tai Mamoe, showed up wearing a t-shirt featuring a picture of him with the former speaker and a warning when I approached him.

“I always go off on people who talk shit about her,” Mamoe said about Pelosi.

He said he had sent Pelosi a letter urging her to endorse Chan and stop what he called the “silent auction” of a race between Wiener and Chakrabarti.

The question now is if Pelosi’s late support will be enough to lift Chan, and at least give her a chance in the fall.

Yet even as she’s finally stepping down at the age of 86, Pelosi is making clear she’s not leaving the San Francisco scene.

On Memorial Day, addressing a large audience assembled at the military cemetery atop the Presidio, she recalled having just visited the nearby graves of Phil and Sala Burton that morning.

As Christine Pelosi sat in the front row, and Chan and Wiener sat in the second, the former speaker said that while this would be her final Memorial Day speech, she “certainly will be with you in the audience in the future.”