During a 2018 meal at Delancey Street Restaurant in San Francisco, Nancy Pelosi sat down with Alexandria Ocasio-Cortez and her campaign manager and offered up an unsolicited lesson on the way the world works.
Pelosi likely had little idea that Ocasio-Cortez — then a congressional candidate from New York who had just defeated powerful Democratic incumbent Joe Crowley — would become a star of the party known simply as AOC. Perhaps even more surprising is that her campaign manager, Saikat Chakrabarti, a former software engineer and staffer on Bernie Sanders’ 2016 presidential campaign, is now running to replace Pelosi in Congress.
As Chakrabarti tells it, the scheduled 30-minute chat turned into an hour-and-a-half monologue from Pelosi on politics, including a theory that a far-left talking point to abolish U.S. Immigration and Customs Enforcement was the product of Kremlin influence.
To an observer, it might have looked like Pelosi was trying to intimidate the upstart into submission with an alpha-dog display of strength. But Chakrabarti perceived a different dynamic.
“I think Speaker Pelosi, from the very beginning, felt very threatened,” Chakrabarti told The Standard a week after announcing he will run in 2026 to replace Pelosi in Congress.
His campaign has parallels to AOC’s first race, from challenging an aging — albeit incredibly popular — incumbent to pitching a set of progressive policies in the face of President Donald Trump’s assault on federal institutions and Democratic norms.
“Incumbents tend to put a lot of faith into both their incumbency being overwhelming, and their political power amongst the political gatekeepers,” Chakrabarti said.
Pelosi, whose office declined to comment, is a two-time speaker of the House who ruled the Democratic caucus with an iron fist and led the resistance to Trump’s first term in office. She’s widely seen as the most accomplished woman in the history of U.S. politics and has repeatedly cruised to reelection, often securing more than 80% of the vote.
In her nearly four decades in office, Pelosi played a pivotal role in combating the HIV/AIDS crisis, transforming the Presidio from a military base into a national park, and securing money to clean up the Hunters Point Shipyard. Her work in getting federal funds during the Covid pandemic was pivotal in addressing the health crisis.
But many of these signature achievements are now under threat, and it’s unclear if she will run beyond 2026. In the first month of Trump’s second term, Democrats have appeared adrift in thwarting Republicans’ efforts to dismantle the federal government alongside Elon Musk’s Department of Government Efficiency.
A San Francisco political strategist with more than two decades of experience said it would be surprising if Pelosi runs again in 2026.
“In fairness, her husband just had a kidney transplant, and the donor was her daughter, so they’ve had a lot of family matters,” the source said, alluding also to the 2022 home invasion that nearly killed Pelosi’s husband.
“But if she’s not stepping forward as the voice of the resistance as she did so effectively in 2016, you have to wonder if she really has her heart in running for another term.”
‘Not the time for polite politics’
Chakrabarti, 39, was born in Fort Worth, Texas, to Indian immigrants. He attended Harvard and worked on Wall Street before coming to San Francisco to start a tech company and later work as the second engineer hired by Stripe. Chakrabari acknowledged that he is, on paper, a centimillionaire.
After leaving Stripe, he joined Sanders’ presidential campaign, which might seem an odd fit for a techie but made sense to those who know Chakrabarti.
“A lot of what you’re doing at a startup is figuring out what people need from you, figuring out what you can do to make their life easier — which is not really that much different from talking to voters,” said Ross Boucher, a friend and former colleague at Stripe.
After the Sanders campaign, which recruited a new crop of leaders to run for Congress, Chakrabarti managed AOC’s campaign then served as her first chief of staff. That gig lasted just eight months, and Chakrabarti’s exit came shortly after a scorched-earth series of (since deleted) tweets targeting Pelosi after she diminished legislative efforts by AOC and a group of progressive newcomers known as “The Squad.”
Pelosi, as speaker of the House, prevented the Green New Deal — a sweeping policy framework intended to address climate change and inequality — from advancing to the Senate.
Congressional staffers rarely have the temerity to challenge their bosses behind closed doors, let alone attack the speaker of the House in full public view, and many in and around Congress have speculated that Chakrabarti was fired. He said his departure from AOC’s office was already planned so he could start the think tank New Consensus.
Chakrabarti intends to pitch San Francisco voters on universal guaranteed healthcare, college, and child care while calling for stronger federal intervention to build housing and address the root causes of kitchen-table issues. He said his candidacy is part of a clarion call for a new wave of Democrats to run for office.
Klarissa Reynoso, who was a staffer in AOC’s office when Chakrabarti served as chief of staff, said “he is part of this movement of people who aren’t going to take this shit anymore.”
“This is not the time for polite politics,” Reynoso said. “It’s time to give it everything you’ve got.”
In the last two weeks, Pelosi has amped up her statements on the Trump administration’s executive orders and a Republican budget that would give the wealthiest Americans a $4 trillion tax cut. But her future remains uncertain.
Political insiders have speculated that she wants to pass the baton to her daughter, Christine Pelosi, an attorney who has served in the national Democratic Party. However, sources say there have been no recent rumblings of a campaign.
State Sen. Scott Wiener has been anxious to run for Pelosi’s seat and launched an exploratory committee in 2023. But as a good Democratic soldier, who has been among San Francisco’s most outspoken elected officials on Trump, Wiener insists that he would never launch a challenge to Pelosi.
If Pelosi were to wait until the fall to make a decision on her future, only to then bow out, that could open the door for a candidate like Chakrabarti to make an unencumbered pitch to San Francisco voters. He said he intends to take a direct-to-consumer approach to voter outreach by advertising one-on-one meetings and speaking to any and everyone, including right-leaning podcasts that Democratic candidates often avoid.
“There’s a fundamental culture in the Democratic Party that we shouldn’t be trying to pitch some overarching message or story to the American people,” Chakrabarti said. “On the right is an actual narrative. There’s no story on the left.”