Skip to main content
Politics

Tech millionaire challenger to Nancy Pelosi draws huge crowd at SF campaign kickoff

“He represents change from what we know,” one attendee said, comparing Saikat Chakrabarti to the longtime congresswoman.

A man in a dark blue shirt speaks into a microphone with one hand, gesturing with the other, standing in front of blurred campaign signs.
Saikat Chakrabarti at the opening of his campaign headquarters Tuesday in San Francisco. | Source: Thomas Sawano/The Standard

With one progressive firebrand of Indian descent taking New York by storm, and another launching a campaign to become San Francisco's next Congressmember, could this officially be “Brown Boy Summer?” 

That's what one attendee joked at Saikat Chakrabarti’s official campaign kickoff party Tuesday evening in the Inner Sunset, where a rowdy crowd of 500 gathered to launch the activist's long-shot bid to unseat Speaker Emerita Nancy Pelosi from Congress in next year’s election. 

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 may lack Pelosi’s name recognition, but he could independently fund a campaign and has amassed a young, passionate, vibes-based following — an essential part of winning in this political era.

Hundreds of supporters and curious voters lined up to get into the progressive candidate’s Irving Street campaign office to hear his plans for Congress. The large crowds required two speeches by Chakrabarti so that everyone had the chance to ask him questions. 

The office was set up to accommodate kids. Attendees posted sticky notes that listed key issues such as healthcare, immigration, and Gaza to the window of another office by a sign asking “What matters most to you?” 

People wait in a long line along a sidewalk that leads to a doorway where a woman seated at a table with a laptop assists those arriving.
People lined up on Irving Street to take part in the kickoff event for Chakrabarti's campaign. | Source: Thomas Sawano/The Standard

Chakrabarti’s populist message, which focused on the cost of living and promoted the “abundance” housing movement, drew cheers and excited responses. He slammed what he described as the Israeli government’s “genocide” in Gaza, called for wholesale structural changes to U.S. foreign policy and denounced President Donald Trump’s climate and immigration policies.

And while Chakrabarti’s prepared remarks came off at times stilted, he responded to questions with a comfort and ease that prompted rounds of applause. 

“We’re not going to be able to turn this decline around with some small reforms. We have to do the big structural changes that we all know are long overdue,” he said. “And if we don't do it, if we don't turn this decline around and deliver real prosperity for a vast majority of Americans, then authoritarians are going to keep winning.”

Though Chakrabarti could self-fund his campaign with the tens of millions he earned as an early Stripe employee, he faces an uphill battle to replace Pelosi, 85, who was first elected in 1987 to represent San Francisco in Congress and served as the first female speaker.

Still, his ambitions coincide with increasing frustration among Democratic voters who are desperate for fresh leadership willing to disrupt the status quo and more aggressively take on Trump and Republicans in Congress. 

Ocasio-Cortez and Vermont Sen. Bernie Sanders have in recent months drawn massive crowds around the country with their “Fighting Oligarchy” rallies, while Chakrabarti has drawn comparisons to Zohran Mamdani, who last month upset his party’s establishment when he won New York’s Democratic primary for mayor. 

A woman in a white top holds a political sign for Saikat Chakrabarti’s 2026 San Francisco Democratic Congress campaign, surrounded by a diverse crowd.
Chakrabarti’s populist message has gained him supporters.​ | Source: Thomas Sawano/The Standard

Nadia Rahman, former co-president of the San Francisco Women's Political Committee, said 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.

Bright yellow sun rays extend from the right, set against a solid light blue background, creating a simple, bold graphic design.

Today’s stories straight to your inbox

Everything you need to know to start your day.

Kudrat D. Kontilis, who serves on the city’s Immigrant Rights Commission but attended the event in an unofficial capacity, said she was drawn to Chakrabarti’s opposition to recent raids and deportations by Immigration and Customs Enforcement.

“We've had the same person for the past 20 terms,” she said, “so it's great to have someone who is bringing fresh ideas and is very clear on his stances on many issues that matter to San Francisco.”

Tuan Hoang, who moved to the city from Houston three months ago, said he came out to learn more about Chakrabarti and agreed with about 90% of his comments.

“The prevailing thought, I think, is that Democrats aren't doing anything, so that was good to hear,” Hoang said, adding that he appreciated Chakrabarti’s strong message on Gaza.

A large group of diverse people gathers closely indoors, attentively listening to a man in a blue shirt who has his back to the camera.
Chakrabarti holds court with supporters and curious voters after the second of two Q&As. | Source: Thomas Sawano/The Standard

Pelosi has not announced whether she will run in next year’s election, but with Trump’s return to power, it’s highly possible she’ll decide to stay put in Congress. Chakrabarti is hardly the only one with ambitions to replace her. State Sen. Scott Wiener has launched a 2028 bid for Pelosi’s seat, while the representative’s daughter, Christine Pelosi, is considered a possible candidate.

Sofia Jesani, a grad student at UC Berkeley who attended the campaign event, said she was initially doubtful that Chakrabarti could win but grew more optimistic after hearing him speak.

“I think with this showing [of people], I'm feeling a little different,” Jesani said. “And with Zohran doing what he just did in New York, I think if we can keep that momentum going … maybe?”

Since last year’s election, Democratic Party officials have acknowledged the need for a compelling vision to lure back voters. While many expect Democrats to win back the House in next year’s midterm elections, as they did during Trump’s first term as president, Chakrabarti said it is imperative for Democrats to challenge incumbents, whom many blame for paving the way for Trump and Republicans to regain control of the White House and Congress.

“When I look at the moment right now, it's similar to the moment we had in 2018, in some ways,” Chakrabarti said. “People were really mad at the Democratic Party. People were looking for some vision of a different future. But I actually think this moment dwarfs what I saw back then.”