The 39-Year-Old Bernie bro who’s running against Nancy Pelosi next November launched his campaign in SF Wednesday night, with the curious profile of a self-proclaimed Democratic Socialist who’s also made $170 million in tech.

Speaker Emerita Nancy Pelosi will be 86 years old and running for her 21st term (!) in Congress should she run again in November 2026. It’s no secret that Scott Wiener is itching to run for the seat, as is Pelosi’s daughter Christine Pelosi, though neither would dare run unless Pelosi decided to retire.

The same courtesy is not being extended by Pelosi challenger Saikat Chakrabarti, who’s already declared he’s running against Pelosi for the seat. We have previously described Chakrabarti as a “39-Year-Old Bernie bro,” though that may be reductive. He was director of organizing technology for the 2016 Bernie Sanders presidential campaign, helped recruit Alexandria Ocasio-Cortez to run for Congress, served as her campaign manager, and also served as her chief of staff for about eight months after she won.

Mission Local was in the house as Chakrabarti officially kicked off his campaign Wednesday night at Valencia Street’s The Chapel, in front of a reported 600 people. He repeatedly name-checked his fellow Democratic Socialists Ocasio-Cortez and NYC mayoral candidate Zohran Mamdani.

“It is clear as daylight: We are living in the middle of a fascist coup,” Chakrabarti told the crowd. “This is about an overwhelming demand for change right now.”

Pelosi has effectively demolished her opponent in 20 of these consecutive elections, so Chakrabarti is certainly looking at an uphill battle. Though his campaign released an internal poll in September saying that 51% of the district’s voters once supported Pelosi “but now think it’s time for a change.” (Notably, that is not at all the same thing as saying they would vote for Saikat Chakrabarti over Nancy Pelosi.)  

And Chakrabarti has another challenge on his hands in that he calls himself a Democratic Socialist, but is worth at least at least $167 million (a higher net worth than Pelosi) because he was a founding engineer at Stripe. That’s… kind of a difficult needle to thread! But he did his best to do so Wednesday night.

“I did not work harder than my teacher or a nurse or the people cleaning our offices,” Chakrabarti told the audience. “I just won the startup lottery.”

He faces yet another possible political pitfall in that he donated money to defeat his own fellow Democratic Socialist Dean Preston. Chakrabarti gave $500 to opponent Bilal Mahmood’s 2024 campaign for the D5 supervisor seat, and a whopping $10,000 to Mahmood’s 2023 DCCC campaign (DCCC money can be used as something of a slush fund to run for other offices).

You can name all the elected Democratic Socialist officials in the US on about one hand. Chakrabarti spent big to take one of them down, so it’s a very open question whether the DSA crowd would forgive that. (Chakrabarti also spent $500 on Michael Lai’s unsuccessful D11 supervisor campaign against progressive Chyanne Chen.)  

“I actually like both Bilal and Dean in that election,” Chakrabarti told Mission Local. “But Bilal really had done a lot of work and a lot of research on how to make it easier and cheaper to build housing in the city.”

Regardless, the primary for this election is June 2, 2026, and the general election is November 3, 2026. Should Pelosi run, it’s entirely possible that she and Chakrabarti could both finish in the top two in June, and then face off again in November.

Related: Pelosi Has a 2026 Election Challenger, an AOC Guy Who’s Reportedly Worth At Least $100 Million [SFist]

Image: @nadiarahmansf via Twitter