39-year-old former Stripe engineer Saikat Chakrabarti is forming a far-left challenge to take Nancy Pelosi’s seat in 2026, after burnishing his credentials with the 2016 Bernie campaign and as AOC’s chief of staff, and he has quite the personal fortune to run with.

It’s a San Francisco ritual that every two years, some hard-left challenger launches a longshot bid to unseat Nancy Pelosi, generally loses to a Republican in the primary, thus allowing Pelosi yet another landslide victory in November. Though in recent years, Pelosi-watchers have been more focused on when she would retire, and what seems like the inevitable ensuing race between state Senator Scott Wiener and Pelosi’s daughter Christine Pelosi when the elder Pelosi ever does step down.

The far-left challenger for next year’s 2026 election has different ideas. 39-year-old software engineer and one-time Alexandria Ocasio-Cortez chief of staff Saikat Chakrabarti launched a campaign to primary Nancy Pelosi from the left last month. KPIX just gave Chakrabarti an interview, and they describe Chakrabarti as a “tech millionaire” and a “self-made tech centi-millionaire,” so that would distinguish him from some of Pelosi’s ultra-liberal primary challengers in the past.

If you want to know how to pronounce “Saikat Chakrabarti,” you can learn this in his CNN interview above. He’s been hitting the interview circuit pretty hard in the last month, calling the current Democratic Congress "paralyzed and unprepared" for the onslaught of Trump’s second term.

"I've got a lot of respect for a lot of what Nancy Pelosi has accomplished in her time in Congress, but I just think we're in a different era now," Chakrabarti told KPIX. “To really rebuild this party, we need a whole new generation of leaders who are committed to this kind of a vision of really going out there and first admitting that there's a problem, which I think the party often doesn't admit at all."    

The Texas-born son of Indian immigrants made it to Harvard and was one of the founding engineers at the payment processing startup Stripe. He made his fortune, and switched gears to politics to become the Director of Organizing Technology in Bernie Sanders’s 2016 presidential campaign. He then helped recruit Ocasio-Cortez to run for Congress, managed her campaign to its unexpected 2018 primary win, and served as her chief of staff for about a year after.

Now Chakrabarti runs some sort of Green New Deal think tank called New Consensus. And yes, per KPIX, he would self-fund his own campaign to some degree.

As for Pelosi, she’s filed papers to run again in 2026, but has not formally declared she’s running. Her stumble and fall in Luxembourg in December may have raised some whispers about whether she would be up for a 21st (!) term, which would begin in 2027., at which point she would be nearly 87 years old.

Saikat Chakrabarti is not really a rhetorical barn-burner, and is more of a policy wonk. But his message that the Democrats are being too timid could certainly resonate. And if he really has $100 million to his name, we can’t dismiss him outright, regardless of whether he’s up against the legendary Nancy Pelosi, the younger Christine Pelosi, or the seasoned Scott Wiener.

Related: Pelosi, the Biden Whisperer? Former Speaker Reportedly Tells Biden He Won't Win [SFist]

Image: Saikat Chakrabarti via Facebook