Saikat Chakrabarti would, on the surface, appear to be a slam-dunk progressive choice to succeed retiring Rep. Nancy Pelosi as San Francisco’s representative in Congress.

In just more than a decade, the forty-year-old Chakrabarti has built a redoubtable record in left-wing politics: he worked on Bernie Sanders’s first campaign for president, cofounded Justice Democrats, and then wrote the Green New Deal bill when he served as Rep. Alexandria Ocasio-Cortez’s pugnacious first chief of staff. He supports Medicare for All, tuition-free public universities, raising taxes on millionaires, abolishing Immigration and Customs Enforcement (ICE), and terminating all military aid to Israel. He has the backing of Represenatives Ilhan Omar and Rashida Tlaib and has promised to take on entrenched interests in the Democratic Party. Last month, he and influencer Hasan Piker filled a club in SoMa for a rally. Chakrabarti may be a centimillionaire, flush with cash from helping to found the payment processing platform Stripe, but he identifies proudly as a class traitor. “I grew up with this simple idea,” Chakrabarti said. “If you get lucky, it’s your duty to help.”

But while Chakrabarti has received the vocal support of a segment of the city’s young and progressive voters, who have plastered signs around the Mission District touting his opposition to the Gaza genocide, other progressive voters have tilted toward Supervisor Connie Chan — leaving Chakrabarti in a fight just to finish second in Tuesday’s primary and qualify for a November runoff against moderate State Senator Scott Wiener. It’s a race that has raised questions not only about the bona fides of each candidate, but also about what San Francisco has become after decades of skyrocketing housing costs and Silicon Valley encroachment and what its embattled progressive community most values in its torchbearers.