Ex-AOC chief of staff going after the most powerful woman in Congress

Saikat Chakrabarti hopes his tech experience and work with iconic progressives can vault him over Pelosi and into Washington, D.C




Saikat Chakrabarti hosts a Zoom call with potential voters and supporters from his campaign office in San Francisco on April 21, 2025.Douglas Zimmerman/SFGATE

By Anabel Sosa, Senior California politics reporter

May 1, 2025


All at once, Saikat Chakrabarti is a nobody, a Silicon Valley millionaire and a humble job applicant.

“I’m not choosing to challenge the most powerful woman in Congress. I am just choosing to challenge my congressional representative in San Francisco,” he said last month at Manny’s, the famous political venue in San Francisco’s Mission District. He was speaking to roughly 120 people during his first public event since announcing he would challenge Rep. Nancy Pelosi, the speaker emerita who has represented San Francisco in Congress since 1987, in a primary election next year.

This is the first time the 39-year-old, who spent the last decade helping recruit and elect progressives to Congress, is running on his own.

“I think we can’t just have this anti-Trump movement,” he said at the panel. “Right now, the Democrats are going to have a choice: They continue standing for slow, iterative change and the status quo … or are we going to present an actual vision for rebuilding society?”

During an hourlong panel hosted at the iconic community cafe, Chakrabarti argued that a change is needed. He said repeatedly, with conviction, that there is a “real coup going on in D.C.” and that Democrats aren’t doing enough to stop it. He believes established Democrats like Pelosi are ignoring the bigger problems facing Americans, which have led to the “authoritarian” rise of President Donald Trump.

Saikat Chakrabarti responds to a question during an interview in San Francisco on April 21, 2025.Douglas Zimmerman/SFGATE


That’s the bulk of Chakrabarti’s pitch to voters as he works to establish himself as a viable challenger to Pelosi, over a year before Californians will cast their ballots. Pelosi has filed paperwork to run in 2026 but has not publicly shared her plans. Regardless, Chakrabarti is positioning himself as a fresh-faced candidate who is in a rush for change.

Andrew Dupree, a 35-year-old San Francisco resident, came away from the Manny’s event with a sense that Chakrabarti understands the grievances of San Franciscans.

“He made a great point that people are feeling economic pain. The cost of living is going up. Even in San Francisco, people are struggling,” he said. “My question is, how are you going to build a coalition of liberals?”

"A progressive, I guess"

Chakrabarti’s story is one of humble beginnings: He was raised in Fort Worth, Texas, by immigrants from India. His father came to the U.S. with “20 bucks in his pocket,” Chakrabarti often says, yet he was able to build a middle class life off a single income. That principle is the centerpiece of his campaign: that a hard worker should be able to make a good life. But stories like his father’s have been replaced by a modern world where “a few people” make “an ungodly amount of money” while “most people can barely make rent,” he told the crowd at Manny’s.

Chakrabarti admits he was one of those “ungodly amount of money” people. He attended Harvard University, worked briefly on Wall Street, then moved to San Francisco in 2009. A few years later, as a precocious computer programmer, he struck gold as the second engineer ever to join Stripe Inc., the multibillion dollar payment services platform.

“I really hate the inequality of it,” he said. “I’m proud of what I built, but I didn’t work harder than a teacher or a nurse.”

FILE: Rep. Alexandria Ocasio-Cortez, left, speaks on a phone as Saikat Chakrabarti, her senior campaign adviser, stands by in New York on June 27, 2018. Bebeto Matthews/AP


Eventually, he left Stripe to work under two of the biggest progressive names in politics: Sen. Bernie Sanders and Rep. Alexandria Ocasio-Cortez. But Charkabarti doesn’t want to fit into a box.

“I mean, I identify as a progressive, I guess,” Chakrabarti told SFGATE a few days later during a lunchtime interview at his home/campaign headquarters in Duboce Triangle, the quaint and colorful San Francisco neighborhood where he lives with his wife and kids. “But it’s really hard to know what that word means these days.”

He is wearing a flannel and jeans, and his campaign manager and longtime colleague, Zack Exley, is sitting next to him. Chakrabarti is slightly hunched forward, finishing a salad from a nearby cafe.

“I really do sort of dislike having all the labels,” Chakrabarti continued. “Just because I want to campaign on the actual stuff I want to do, the actual solutions.”

Those ideas, he says, include universal health care and child care, as well as scrapping dirty money in politics — all standard progressive ambitions upheld by his former bosses.“I guess wanting to get rid of money in politics makes me a progressive,” he laughed.

He adds, “There’s some new stuff I’m also trying to run on,” which he says involves focusing on how “the government actually executes, and makes stuff happen, and builds stuff.” “I am not sure what bucket that really falls in. I think it’s just kind of practical.”




Saikat Chakrabarti poses for a portrait in San Francisco on April 21, 2025. Chakrabarti is a Democrat seeking to unseat incumbent Rep. Nancy Pelosi, who represents California’s 11th congressional district. Douglas Zimmerman/SFGATE


He 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. At Manny’s, 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 way I imagine this going is, I’m trying to pitch these big ideas as the way the Democratic Party should be operating,” he says between bites. “The Democratic Party is so underwater right now ... the only way voters are going to trust it again is ... if a whole new movement takes over.”

He has said he will largely self-fund his campaign and will not accept money from corporate political action committees. He said he is prepared to match Pelosi, who is a fundraising juggernaut, to make it “a fair race.”

As Exley tells it, Chakrabarti got his foot in the progressive politics door almost accidentally when he joined Bernie Sanders’ 2016 presidential campaign as “a lowly programmer.”

“No one knew he was some Silicon Valley big shot,” said Exley, who at the time was a senior Sanders adviser. He recruited Chakrabarti to work on software tools to help boost Sanders’ campaign. That was, he said, before Stripe “totally took over the world.”

After his stint on the Sanders campaign, Chakrabarti co-founded a political organization called Brand New Congress (later renamed Justice Democrats) with Exley. Their ambition was to recruit progressive candidates to Congress.

FILE: Rep Alexandria Ocasio-Cortez, D-N.Y., center, leaves a news conference in the Capitol Visitor Center after responding to negative comments by President Trump on July 15, 2019. Saikat Chakrabarti appears at left. Tom Williams/CQ Roll Call


Ocasio-Cortez, a Democrat from New York, emerged as one of the only successful recruits. After Ocasio-Cortez’s shock victory in 2018, in which she won a primary against Rep. Joe Crowley, who was the No. 4 Democrat in the caucus at the time and a possible successor to Pelosi as speaker, Chakrabarti went to work as Ocasio-Cortez’s chief of staff. He started to make a splash on Capitol Hill, including butting heads with Pelosi.

In July 2019, Chakrabarti criticized moderate Democrats for supporting border funding with harsh words on Twitter, saying they were “hell bent to do to black and brown people today what the old Southern Democrats did in the 40s,” Vox reported at the time. Pelosi later scolded Democrats and their staffers about keeping their opinions off Twitter.

“A whole bunch of the caucus was upset, and I was really mad about it,” Chakrabarti told SFGATE about why he spoke up about the funding.

Some thought the dustup with the caucus leader prompted Chakrabarti’s departure from Ocasio-Cortez’s staff the next month, but Chakrabarti told




FILE: Saikat Chakrabarti, the chief of Staff for Rep. Alexandria Ocasio-Cortez, D-NY, works with staff in his office in the Cannon House Office Building in Washington, D.C., on June 26, 2019. Mary F. Calvert for the Washington Post via Getty Images


SFGATE that “the plan was always for me to leave” after he helped the freshman congresswoman launch the Green New Deal. He added that his family was expecting a child, noting, “It so happened, Pelosi got mad at me about some tweets at the same time.” He moved back to San Francisco in 2019 and has been working since for New Consensus, a think tank that has promoted the Green New Deal and other economic renewal projects.

Still, he says: “Trying to make things change in Congress requires pushing a little bit, ruffling some feathers.”

An uphill climb

To get his name out there, Chakrabarti has hosted small events around San Francisco, including the April panel at Manny’s and the weekly town hall meetings he holds with potential voters over Zoom from his Duboce Triangle home. He knows he has ground to make up against not only Pelosi, who has a nearly 40-year head start, but also any other challengers who may emerge if she chooses not to run.

That could include California state Sen. Scott Wiener, a Democrat from San Francisco and a former city supervisor who is known widely in California but not far beyond state borders. He has said he won’t run against Pelosi, but if the 85-year-old decides to retire, he’ll likely to join the race. Others question if Pelosi will tap her daughter Christine for the post.

Saikat Chakrabarti responds to a question during an interview in San Francisco on April 21, 2025.Douglas Zimmerman/SFGATE

Becoming a household name will prove difficult for Chakrabarti, said Eric Kingsbury, a political consultant in the Bay Area. He notes she is “uniquely qualified” and has deep ties to her city.

“I struggle to see an appetite for someone to run against her,” he told SFGATE. “San Francisco is a small town masquerading as a big city… I have heard great things, but I have not seen him around at all. I’m not sure that he has the familiarity with these communities that other candidates might bring.”

His appearance at Manny’s helped at least a few potential voters see his potential. Phillip Dupree, the twin brother of Andrew Dupree, said, “It’s less crazy for Saikat to run than Wiener,” arguing that an incumbent Democrat running against Pelosi would cause a bigger political rift within the party. With Chakrabarti, at least voters can hear an alternate message without it splintering the existing caucus, Philip Dupree said.

Back at Chakrabarti’s makeshift campaign office — which is a one-bedroom apartment on the bottom floor of his multifamily home — the candidate is preparing to do more outreach. It’s a stripped-down space with a couch, TV, bed, desk and computer monitor with a large LED light panel that is set up for Zoom calls with voters. (The second floor of the home is owned and inhabited by Chakrabarti’s childhood best friend; he and his family live on the third floor.)

Chakrabarti was running late for this particular session. He swiftly answered the rest of SFGATE’s questions before hopping on his swivel chair and greeting potential voters on his screen.

One participant, a man who introduced himself as David, spoke bluntly.

“You’re not just running against any congressperson, you may be running against the congressperson,” he said. “How will you defeat Madam Speaker?”

Chakrabarti smiled.

“You’re right. There are obviously a lot of people who voted for her for years. ... I’m not trying to run to be the next career politician and sit there for 40 years,” he said, talking to the computer screen. “I really want change.”

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