Centimillionaire Socialist: Political Experts Weigh Saikat Chakrabarti’s Chances as Pelosi Announces Retirement

With Nancy Pelosi’s announcement Thursday that she will not seek reelection to Congress in 2026, political analysts are reassessing the prospects of Saikat Chakrabarti, the progressive challenger who launched his campaign earlier this year to unseat the 85-year-old speaker emerita.

Pelosi’s departure sets in motion what will likely be one of the most-watched and consequential congressional races of 2026, according to Mission Local. Chakrabarti, who was raised in a Bengali Hindu household in Fort Worth, Texas, was the first to throw his hat into the ring, announcing his candidacy in February—21 months before the election, the publication reported.

The Challenger’s Profile

Chakrabarti, a 39-year-old former Stripe engineer who previously told The Standard that he’s a centimillionaire on paper, served as campaign manager and chief of staff to New York Democratic Rep. Alexandria Ocasio-Cortez. He was a top campaign aide to Ocasio-Cortez when the future progressive star, then a 29-year-old New York bartender, pulled off her stunning defeat of Joe Crowley, a 10-term incumbent and member of the Democratic House leadership.

At Chakrabarti’s official campaign kickoff party in July in the Inner Sunset, a rowdy crowd of 500 gathered to launch the activist’s bid, The Standard reported. Though Chakrabarti could self-fund his campaign with the tens of millions he earned as an early Stripe employee, he faces an uphill battle, the publication noted.

Political experts offer mixed assessments of Chakrabarti’s chances now that Pelosi has cleared the field by announcing her retirement.

“The progressives have always been disappointed in Nancy Pelosi. They’ll continue to be disappointed with Nancy Pelosi, but the progressive left senses an opportunity to push the moment of generational change,” said Sonoma State Political Science Professor David McCuan in an interview with CBS San Francisco.

According to GrowSF, an organization tracking San Francisco politics: “We think Chakrabarti might have a shot at winning—or, at least, a better shot than any challenger in many years.” The organization noted that Pelosi’s last challenger, DSA member Shahid Buttar, lost badly in 2020 with just 22% of the vote.

However, GrowSF also cautioned that while “Chakrabarti is a well-known figure with a national profile, and he has a lot of money to spend on his campaign,” it warned that “younger voters also tend to not vote in the numbers that older voters do.”

Polling Suggests Opening

An internal poll done for Chakrabarti’s campaign, which was conducted by Beacon Research and first shared with The Hill, found 51 percent who said that they had supported Pelosi “in the past but now think it’s time for a change.” The poll found a separate 31 percent who said they supported the former House Speaker in the past and still want her to represent the district, while 14 percent said they had never supported her, The Hill reported.

Chakrabarti offers a stark shift away from the Pelosi political machine that has dominated San Francisco for nearly four decades. “He represents change from what we know, and that’s not necessarily his background, but he’s not coming in as a career politician.”

In a three-way match-up between Pelosi, Chakrabarti and Republican candidate David Ganezer, 46 percent chose or leaned toward the incumbent; 29 percent supported the progressive candidate and 11 percent supported Ganezer, according to The Hill. When it becomes a head-to-head between both Democrats, Pelosi comes out ahead at 47 percent, while Chakrabarti receives 34 percent, and 19 percent say they’re not sure, are undecided or refuse to say, the poll found.

A GrowSF poll from February 2025 showed Pelosi’s support at just 52% among San Francisco voters.

A Crowded Field Expected

With Pelosi’s retirement, the field is expected to expand significantly beyond Chakrabarti.

State Sen. Scott Wiener has launched a 2028 bid for Pelosi’s seat, according to the San Francisco Examiner, while the representative’s daughter, Christine Pelosi, is considered a possible candidate. Another name widely discussed as a potential candidate — possibly with Pelosi’s backing — is San Francisco Supervisor Connie Chan, Mission Local reported.

The race could make history, according to the San Francisco Chronicle. If Wiener wins, he would be the first openly gay person to represent San Francisco in Congress, while either Chan or Chakrabarti would be the first person of Asian descent to do so, the Chronicle noted.

The Generational Divide

“There’s no comparison to the power that Nancy Pelosi has, and what she brings,” said David McCuan, political science professor at Sonoma State University, in an interview with KTVU. “She will outraise him,” McCuan said. “She will out-endorse him, she’ll probably even outwork him in some ways, because that’s Nancy Pelosi.”

However, with Pelosi’s retirement announcement, those dynamics have shifted dramatically. Among a crowd of more than 600 people who attended a recent Chakrabarti campaign event at The Chapel in San Francisco, many in the mostly 20s and 30s crowd erupted in waves of cheers whenever Chakrabarti mentioned Ocasio-Cortez or New York mayoral candidate Zohran Mamdani, Mission Local reported.

Nadia Rahman, former co-president of the San Francisco Women’s Political Committee, told The Standard that Chakrabarti offers a stark shift away from the Pelosi political machine that has dominated San Francisco for nearly four decades. “He represents change from what we know, and that’s not necessarily his background, but he’s not coming in as a career politician,” Rahman said.

Campaign Strategy and Message

Chakrabarti has a vision “to build a whole movement” and rebuild the economy, which he likens to Franklin D. Roosevelt’s post-Great Depression programs under the New Deal, according to SFGATE. He referenced the Reconstruction Finance Corporation, a 1932 government agency that helped restore public faith in the economy, as a guiding light for his own vision, the publication reported.

According to GrowSF: “Early campaign rhetoric indicates that Chakrabarti will run ‘from the left’ (that is, on a more progressive platform than Pelosi), but even in San Francisco most voters are moderate.” The organization advised that “Chakrabarti would do well to focus on the issues that matter most to San Franciscans, like housing affordability, homelessness, and public safety.”

Asked how he plans to build a voter base, Chakrabarti told Mission Local that he began his campaign assuming his base would be young people or progressives, but during doorknocking found that “the voter base is much larger” than expected, with seniors, residents in “more moderate or conservative parts of the city” and even some Republicans expressing support.

The San Francisco Chronicle noted that the contest to replace Speaker Emerita Nancy Pelosi “could turn into a proxy for bigger questions facing the left: What kind of candidates will lead the way, and which messages will resonate with voters?”

Pelosi was first elected to the House in a 1987 special election, according to NBC News, meaning her San Francisco-based seat will be open for the first time in nearly 40 years. While she easily bested junior varsity challengers throughout most of her long tenure, the 2026 race is already crowded with varsity-level candidates, and it may grow more so, Mission Local reported.

This story, conceptualized and edited by American Kahani’s News Desk, was aggregated by AI from several news reports.