Saikat Chakrabarti's $10 million bid for Pelosi's seat collapses without winning a single precinct

 June 3, 2026

Saikat Chakrabarti, the former chief of staff to Rep. Alexandria Ocasio-Cortez, poured $10 million of his own money into the race to succeed Nancy Pelosi in California's 11th Congressional District, and came away with nothing. Not a single precinct. With half the votes counted as of Wednesday morning, Chakrabarti sat at just 15%, far behind Democratic state Sen. Scott Wiener at 41% and San Francisco Supervisor Connie Chan at roughly 29%, the New York Post reported.

The Associated Press projected that Wiener and Chan would advance to face each other in November. Chakrabarti, the former Stripe executive who built his political brand around his connection to Ocasio-Cortez, was shut out entirely.

That makes this one of the more expensive primary-season failures in recent memory: a self-funded millionaire who ran hard on progressive celebrity, enlisted a controversial leftist streamer, and still couldn't beat the San Francisco establishment on its own turf.

The Pelosi factor

Before Pelosi endorsed Chan, polls showed the San Francisco supervisor running slightly behind Chakrabarti, with both competing for the second-place slot behind Wiener. Pelosi's endorsement appears to have changed the math dramatically. Chan surged past Chakrabarti and into the general election.

Pelosi had previously gone after Chakrabarti publicly, challenging claims about his ties to San Francisco. The former speaker, who held the seat for some 40 years, was not about to hand her district to an outsider with deep pockets and a résumé rooted in national progressive media rather than local politics.

Ian Krager, a spokesperson for Pelosi, offered a terse post-election comment that landed like a verdict:

"You best not miss."

He didn't need to say more. The numbers said it for him.

AOC's conspicuous silence

Perhaps the most telling detail of Chakrabarti's campaign was the endorsement he didn't get. Ocasio-Cortez, the woman whose political career Chakrabarti helped build, refused to endorse her own former chief of staff in this race. That silence spoke volumes about the limits of the progressive brand when real votes are on the line.

Former Newsom campaign strategist Addisu Demissie cheered the result publicly on X, singling out Ocasio-Cortez's decision to stay out of it:

"Can I just say, AOC earned some real respect from me not endorsing this charlatan."

Chakrabarti was best known for his tenure as Ocasio-Cortez's chief of staff, a stint that ended after he clashed with congressional Democratic leadership. He campaigned heavily on that connection, but it turns out San Francisco voters were not especially moved by it.

Ocasio-Cortez herself has faced an uneven stretch politically. She was talked over by a crowd at an Eid celebration where she tried to preach solidarity, and her influence on the national stage has drawn increasing scrutiny.

Zero precincts, $10 million spent

The precinct-level results are where the loss goes from bad to comprehensive. As of Wednesday morning, Chakrabarti had not won a single precinct in the entire 11th Congressional District. Not one neighborhood. Not one corner of San Francisco looked at a $10 million campaign and said yes.

At his election watch party Tuesday night, Chakrabarti struck an optimistic tone with volunteers, telling them not to worry.

"I know that the numbers don't necessarily look great right now, but I don't want anybody to fret. This was expected."

Fifteen percent of the vote and zero precincts won was expected? That is a remarkable definition of going according to plan. As of Wednesday morning, Chakrabarti had not publicly conceded.

Meanwhile, some observers have noted that Ocasio-Cortez's own media-avoidance strategy raises questions about her 2028 ambitions, and her decision to skip this endorsement may have been part of a careful calculation about where to spend political capital.

What the race exposed

Chakrabarti's campaign tested a theory that progressive celebrity, national media attention, and personal wealth could substitute for local roots and institutional support. San Francisco, one of the most left-leaning districts in the country, answered clearly: no.

Wiener, a sitting state senator, ran as the frontrunner and held that position throughout. Chan, backed by Pelosi's endorsement, consolidated the establishment lane. Chakrabarti occupied a space that apparently didn't exist, the outsider progressive in a city that already has plenty of progressives, none of whom needed a former tech executive from out of town to tell them how to vote.

The appearance alongside Hasan Piker, the controversial leftist streamer, may have generated online attention. But online attention and precinct-level votes are two very different currencies, and Chakrabarti came up empty on the one that counts.

Some have speculated that Ocasio-Cortez could pursue even higher office. An AtlasIntel poll placed her atop the 2028 Democratic presidential field, a data point that says less about her viability than about the state of the party's bench. If her former chief of staff can't win a precinct in San Francisco with $10 million, the progressive movement's electoral ceiling deserves serious questions.

The bottom line

Wiener and Chan will face off in November for the seat Pelosi held for four decades. Chakrabarti will not be on the ballot. His campaign spent roughly $667,000 per percentage point earned, and still couldn't crack a single precinct.

Pelosi's political machine, even after her retirement from the seat, proved more durable than a millionaire's checkbook and a celebrity endorsement strategy. The San Francisco establishment showed it can still close ranks when it wants to, and progressive outsiders with national profiles learned, expensively, that name recognition on cable news does not translate to votes in the neighborhoods.

Ten million dollars buys a lot of yard signs. It doesn't buy a congressional seat when the voters can see right through you.


About Tim Harrison

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