And then there were three: The race to succeed Nancy Pelosi takes shape

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Will San Franciscans be voting on whether to put cars on the Great Highway again next year?

This seems to be a question akin to: Will Mayor Lurie post internet videos of himself drinking coffee? 

In short: Yes, you can count on another Great Highway ballot measure in 2026.

All of San Francisco has the next several months to practice their bad Al Pacino “Just when I thought I was out, they pulled me back in” impressions.

Will this ballot measure win? No. Not even the people who will be ardently backing it expect it to win. So why do it? 

A drive along the Great Highway was more than just a scenic oceanside trip. It also got you someplace. With this ballot measure, the reverse will be true: It’s not so much about the destination. It’s about the trip. Confused? Don’t be. Here’s what we wrote on Nov. 3:   

Nobody seems to think a ballot measure in 2026 to reopen the highway would pass. But if such a measure were to be put before the electorate, and if a bloc of Chinese voters ran to the polls, and if there were a Chinese candidate running in a high-profile race — well, that would surely be interesting …

All of this happened, more or less. 

With Supervisor Connie Chan’s entry last week into the race to succeed Rep. Nancy Pelosi, all of this is also becoming less and less of a hypothetical. So, expect such a ballot measure. But expect more ballot measures, and not just about the Great Highway.

Expect one in June for the primary and one in November. Surely one will be about putting cars back on the highway and the other will be about … zoning? Or maybe marijuana dispensaries on Taraval? So long as it gets large numbers of motivated Westside Chinese voters out to the polls, does it matter? 

Chan joined State Sen. Scott Wiener, wealthy former tech executive/Rep. Alexandria Ocasio-Cortez lieutenant Saikat Chakrabarti, and several minor candidates who, perhaps, lost a bet, to run for California’s 11th congressional district.

It will be an interesting race, in the “May you live in interesting times” meaning of that word. But also a somewhat maddening one. 

It harks to a scene in the film “L’Armee des Ombres” in which French Resistance fighters realize they have to kill a collaborator. But they’ve never done it before. And they don’t know how.

Nobody still in the business has run a real San Francisco congressional race. Pelosi has held this seat since 1987. There hasn’t been a serious and competitive race for two generations.

The rules in federal races are different from state, which are different from municipal. The candidates and their strategists will have to figure this one out as they go. And we’re all along for the ride. 

At the 2006 White House Correspondents Dinner, Stephen Colbert, in his right-wing blowhard persona, took the piss out of President George W. Bush. 

“The greatest thing about this man is he’s steady. You know where he stands,” said Colbert. “He believes the same thing Wednesday that he believed on Monday, no matter what happened on Tuesday. Events can change; this man’s beliefs never will.” 

This was not meant as a compliment. Bush, who was to critical thinking what he is to portraiture, understood this.   

You could say the same thing about Wiener, though. In this case, however, it is a compliment.

Wiener is not looking for splashy causes to hitch his wagon to. He has held a core set of beliefs on housing policy, streamlining, equality, etc. for decades, and has soldiered on through the hard times and the good. 

We’ve said it before and we’ll say it again: Voters, it seems, value ideological consistency. Until you disagree with them. And then you’re on your own. 

So, Wiener believed what he believed on Monday and again on Wednesday. But, on Tuesday, San Francisco closed down the Great Highway and recalled Supervisor Joel Engardio.

And, for whatever reason, Wiener chose to antagonize the city’s most volatile voters at their moment of triumph, haranguing them on the day of the recall election for “freezing the city in amber” and acting to “deeply harm San Francisco and San Franciscans.” 

The fate of a windswept highway and upzoning in the avenues are now galvanizing political forces. City leaders have taken to selling the upzoning plan not on its merits but by promising that the state of California will give it to this city good and hard if we fail to pass it. 

Wiener was essentially the legislative dentist creating the sharp-toothed mandates that would be used to do this. This one could come back to bite him. 

So, Scott Wiener may have a brewing Westside problem. Some of the voters who most emphatically pushed him to victories vs. Jane Kim and Jackie Fielder may now be smarting over the Great Highway, upzoning and recall issues.

It will be a potential bellwether to see where more conservative groups, like the Chinese American Democratic Club, which supported Wiener in the past, fall this time.    

But, if you were a betting person, he’s still the favorite (if you’re betting on the others: Get odds). Wiener has, by far, the best name recognition and nobody but nobody will work harder.

He has a stronghold in District 8, the neighborhood that consistently has the highest voter turnout, and is also the only significant moderate or LGBTQ candidate in the race. It is hard to conceive of him not finishing first in the primary and nigh-impossible to conceive of him not finishing in the all-important top-two.

Is it his race to lose? Possibly. Could he lose it? Definitely.  

The roadmap to a Connie Chan victory, meanwhile, is an old and familiar one. In fact, in the same year that Pelosi first won her congressional seat, Art Agnos won a mayor’s race with a coalition of progressive voters and the Asian community — and the Asian community is now much larger. 

Chan, in fact, has a potentially larger base to draw from than Wiener: Asian/Chinese voters, the Westside and then an assortment of Great Highway refuseniks, disgruntled neighborhood dwellers and others who are chafing against what used to be referred to as “Downtown.” 

Within that coalition are conservatives, even Republicans. Wiener is a bête noire for voters who never turn off Fox News and go to people like Megyn Kelly for their fair and balanced news.

There is an unintended symbiotic relationship here, in which right-wing loons and provocateurs generate millions of page views by decrying Wiener as a menace because of his advocacy for trans people and participation in gay street festivals; Wiener then reminds San Francisco voters that he is the bête noire of right-wing loons and provocateurs.  

Less red-pilled conservatives, meanwhile, may gravitate to Chan because of Wiener’s YIMBY housing policies. 

There is a precedent for this: When Kevin de León quixotically took on Sen. Dianne Feinstein in 2018, he outperformed the incumbent in red counties, despite being objectively more liberal than Feinstein.

Conservatives voted against the more conservative Feinstein because of either policy disagreements or personal animus, instead siding with the lesser-known liberal. 

This will be something to keep an eye on. But a Chan victory, by and large, requires her to do big numbers in the Chinese community, which would potentially negate Wiener’s LGBT stronghold in District 8. 

Would 60 percent be enough? Maybe not. It may take even better numbers than that. Those totals will be hard to produce. But nobody said running for Nancy Pelosi’s seat would be easy. 

As for Chakrabarti, he is a young, energetic, charismatic — and extraordinarily wealthy — wild card.

He, too, has a lane: San Franciscans have already proven they’ll vote for wealthy non-politicians, even one who isn’t charismatic. Chakrabarti definitely has charisma to spare — and a $167 million smile.

Insofar as the outsider who wants to shake things up is a viable pitch, Chakrabarti is a viable (self-funding) candidate.

But Chakrabarti’s lane is narrow. Voters in search of a progressive candidate with a record can vote for Chan. Voters in search of a tech-savvy urbanist with a record can vote for Wiener. 

Chakrabarti is also in the unusual position of appealing to San Francisco voters who gravitate to national left-wing politics without yet having the backing of San Francisco voters who gravitate to San Francisco left-wing politics.

As we’ve noted before, while any insurgent left-wing candidate (even one without matinee-idol looks and a winning smile) would want to liken himself to New York City mayor-elect Zohran Mamdani, this isn’t yet something Chakrabarti can reasonably do.

He got off on a bad foot with the local Democratic Socialists of America by putting money into unseating the only DSA supervisor, Dean Preston. Chakrabarti also donated to the campaign of District 11 candidate Michael Lai.  

Chakrabarti can certainly win over elements of the city’s left — and, for that matter, YIMBYs. But the years-in-the-making army of DSA precinct-walkers of the sort that undergirded Mamdani’s victory will not materialize. He will have to find a new and different way of winning. 

To an extent, every candidate will. They will also be facing issues that no San Francisco candidate has dealt with in decades, if ever. This is a federal election, so Israel policy is, finally, germane. But not just Israel policy: If you don’t know the candidates’ One China policy, expect to by June. 

The candidates and their strategists will have to figure this one out as they go. And we’re all along for the ride.