Rep. Nancy Pelosi waited months to weigh in on who should replace her in Congress. When the 86-year-old former House speaker finally made her pick, San Francisco Supervisor Connie Chan, the reaction from her own city was swift and hostile.

Pelosi formally backed Chan on Monday, just weeks before the June 2 primary, releasing a short campaign video alongside the endorsement. In it, she offered a familiar appeal: "I know this district, I know the Congress, and I know Connie." She added, "I'm proud to endorse Connie Chan, and I ask you to join me in electing her to Congress."

What followed was not gratitude. It was a public rebuke, not from Republicans, but from San Franciscans across the city's own political spectrum, including investors, tech leaders, pro-housing activists, and even some progressives, all questioning Pelosi's judgment and her connection to the city she has represented for nearly four decades.

A race Pelosi tried to stay out of

Pelosi announced last year that she would retire when her term expires in January 2027. The field to succeed her quickly filled. State Sen. Scott Wiener, who had announced an exploratory committee for the seat back in 2023, emerged as the early frontrunner. Progressive multimillionaire Saikat Chakrabarti, a former staffer to Rep. Alexandria Ocasio-Cortez, also entered.

Polling reported by the New York Post showed Wiener holding roughly 40 percent support, with Chan and Chakrabarti locked in a neck-and-neck tie for second at around 20 percent each. For months, Pelosi stayed neutral. Then, with the primary just two weeks away, she chose Chan, the candidate trailing the frontrunner by a wide margin.

The timing raised immediate questions. So did the choice itself.

Critics unload on X

Investor Sheel Mohnot captured the mood of many San Francisco critics in a post on X dated May 18, 2026. He didn't mince words:

"WTF. Pelosi endorsed Connie Chan, a progressive supervisor in SF who opposed the Chesa Boudin recall, blocked every form of housing, and voted against streamlining permits and cutting red tape. The opposite of an abundance candidate."

The reference to Chesa Boudin, the former San Francisco district attorney ousted by voters over soft-on-crime policies, is telling. That recall was a rare moment when San Francisco's electorate rejected the progressive establishment. Chan, Mohnot argued, stood on the wrong side of it.

Pro-housing activist Daniel Owens went further, accusing Pelosi of being fundamentally disconnected from the city she claims to know so well:

"Pelosi isn't pro-housing. She doesn't even understand local SF issues on a deep level. She's been disconnected from SF culture for decades. She relies on a small inner circle here, while almost entirely focused on national DC politics."

That charge, that Pelosi has spent decades in Washington while losing touch with the people she represents, is not new. But it carries more weight now, as she attempts to hand-pick her successor in a district where residents are pushing back against the old guard.

A theory about family politics

Tech investor Kim-Mai Cutler offered a more personal theory for why Pelosi bypassed Wiener. She posted on X that the speculation in San Francisco circles centered on a family grudge.

"The theory is she's mad that Scott blocked [Pelosi's] daughter out from running."

The background: after Wiener announced his exploratory committee for Pelosi's House seat in 2023, Pelosi's daughter Christine Pelosi decided to seek Wiener's state Senate seat instead. Whether that sequence of events actually drove Pelosi's endorsement decision is unconfirmed, Cutler herself framed it as a "theory." But the fact that it circulated so openly, and so quickly, says something about how San Franciscans view the endorsement. They see it less as a policy judgment and more as insider maneuvering.

Pelosi offered no public explanation for why she chose Chan over Wiener or any other candidate.

Wiener: the frontrunner Pelosi passed over

The candidate Pelosi declined to endorse is, by the numbers, the one best positioned to win. Wiener has built a national reputation championing aggressive pro-housing and LGBTQ+ laws in Sacramento. The Washington Times profiled him as a policy-driven lawmaker unafraid of a fight, noting he was expected to win the California Democratic Party's endorsement for the seat.

Longtime Sacramento lobbyist Chris Micheli told the Washington Times, "Sen. Wiener only does the tough bills. He never shies away from a significant political battle." But Wiener has also generated controversy. He changed his position earlier this year and said Israel had committed genocide in Gaza, after initially declining to use the term. That shift drew backlash from Jewish and pro-Israel groups and led him to step down as co-chair of the state Legislative Jewish Caucus.

Wiener himself acknowledged the sensitivity of the decision. "For a period of time I chose not to use the word 'genocide' because it is so sensitive within the Jewish community," he said. "But ultimately I decided I had been effectively saying 'genocide' for quite some time."

Whether Pelosi's decision to skip over Wiener had anything to do with his Israel stance, his housing record, or something more personal remains an open question. She hasn't said.

Chakrabarti fires back at the establishment

Saikat Chakrabarti, the progressive multimillionaire and former chief of staff to Ocasio-Cortez, wasted no time dismissing Pelosi's endorsement. He cast it as exactly the kind of establishment politics voters should reject.

"That's how we're going to win this thing, not because of corporate PACs or establishment endorsements but through the support of San Franciscans."

Chakrabarti has his own problems. He was reportedly passed over for the endorsement of his old boss, Ocasio-Cortez, despite frequently invoking her name during the race. In a deep-blue district where progressive credentials are currency, that silence from AOC is notable.

Still, Chakrabarti's framing, Pelosi's blessing as a liability, not an asset, captures a real dynamic. In a city where voters recalled their own district attorney and have grown increasingly frustrated with housing costs, homelessness, and bureaucratic paralysis, a nod from the outgoing establishment may not carry the weight it once did.

Y Combinator CEO takes aim at Chan

Garry Tan, CEO of Y Combinator, delivered some of the sharpest criticism, targeting Chan directly on X. He accused her of practicing identity politics at the expense of the community she claims to represent.

"Our community needs to care more about the policies that affect Asians and less about the color of people's skin. SF has produced an unusual kind of grifty Asian American politician that virtue signals by hurting our community like Connie Chan. This must stop."

Tan's language was pointed, and it reflects a growing frustration among parts of San Francisco's tech and business community with progressive officials they view as more interested in ideological signaling than practical governance. Whether one agrees with Tan's characterization or not, his willingness to say it publicly, about a candidate freshly endorsed by one of the most powerful Democrats in American history, illustrates how diminished Pelosi's influence may be on her own home turf.

What the backlash reveals

None of this criticism came from Republicans. There is no meaningful Republican presence in this race. The attacks came from investors, tech founders, housing advocates, and political observers who live in San Francisco and want different leadership than what Pelosi is offering them on the way out the door.

The complaints share a common thread: Pelosi, after four decades in Congress, no longer understands what her own constituents need. She endorsed a candidate who opposed the Boudin recall, resisted housing development, and fought against streamlining permits, positions that put Chan at odds with a growing coalition of San Franciscans tired of progressive governance that delivers ideology instead of results.

Pelosi's endorsement video was short. Her explanation was shorter, she offered none beyond "I know Connie." For a district grappling with housing shortages, public safety failures, and a cost of living that has driven residents out by the thousands, "I know Connie" may not be enough.

The June 2 primary will settle the question. But the reaction to Pelosi's pick already tells us something important: even in one of the most reliably Democratic districts in America, the old guard's word doesn't carry what it used to.

After 40 years in Washington, Pelosi tried to hand-pick her replacement. San Francisco looked at the choice and said no thanks.