Saikat Chakrabarti, the 40-year-old millionaire who once served as Alexandria Ocasio-Cortez's chief of staff, kicked off his campaign for Nancy Pelosi's San Francisco congressional seat Friday by posting a video endorsement from a drag queen known as "Peaches Christ." The stunt drew swift backlash online, and not just from the right.
Chakrabarti shared the footage on social media shortly after announcing his intention to run, as the New York Post reported. The video also revealed plans for an April 4 "Drag Me To Vote" meet in San Francisco. He will face San Francisco City Supervisor Connie Chan and State Senator Scott Wiener in the June midterm contest.
The race is shaping up as a window into the progressive left's priorities, and its blind spots. A Silicon Valley tech millionaire with thin roots in the district is betting that drag culture and activist credentials will carry more weight with San Francisco voters than experience or local ties.
Chakrabarti made his name in progressive politics, not in San Francisco neighborhoods. He worked in Silicon Valley tech before pivoting to political organizing. He founded two political action committees, Brand New Congress and Justice Democrats, designed to recruit and fund progressive candidates nationwide. That pipeline helped launch Ocasio-Cortez's career, and Chakrabarti became her first chief of staff.
He resigned from her office in 2019. Federal investigators then launched a probe into possible finance misdeeds connected to his work. The inquiry was later reviewed by the FEC, which found no wrongdoing, and no charges were ever filed.
But the cloud lingered. And his opponents are happy to remind voters about his thin connection to the city he now wants to represent in Congress.
State Senator Wiener went after Chakrabarti earlier this month on social media, attacking both his wealth and his lack of local roots. "My opponent is using his vast personal wealth to try to buy a seat in Congress," Wiener posted. He added:
"I'm not worth hundreds of millions like he is, but what I do have is decades of real experience delivering for San Francisco."
Wiener also wrote: "Being hyper-rich can buy you a lot of things, but it shouldn't be able to buy you an election." When a progressive state senator from San Francisco is calling you a rich carpetbagger, the populist lane may be harder to claim than you think.
In the video, Peaches Christ framed the race in sweeping terms. "San Francisco has a rare opportunity right now," the drag performer said. "This congressional race will decide whether we keep accepting business as usual or whether we send someone to Washington willing to actually challenge the systems that created the crises we're living through."
Grand words. But plenty of people watching weren't buying it.
One commenter wrote: "Dude what is this? no one is forcing you to do this? just focus on affordability please." Another took aim at the class dynamics: "Nothing like being dragged to back a billionaire when there is another option who is not a billionaire or a billionaire's bro." A third urged voters toward Connie Chan: "Vote Connie Chan. Also, why aren't y'all supporting the woman of color whose running who is also backed by labor? What is your class analysis here?" And another cut to the core: "The guy has zero track record in San Francisco. Bad choice, Peaches."
That last line captures the problem neatly. Chakrabarti is asking San Franciscans to send him to Washington based on national progressive credentials and a drag queen endorsement, not based on anything he's done for the city.
The seat opened up because Pelosi announced in November that she would step down. At 85, with retirement looming, her departure fits a broader pattern of aging Democratic House leaders finally leaving the stage. Maryland's Steny Hoyer, 86, recently announced his own retirement after decades in Congress, underscoring the generational turnover underway in the Democratic caucus.
Longtime San Francisco consultant Eric Jaye told The New York Times he believes Pelosi's retirement is all but certain. "I think she's going to retire, and it's a moot point," Jaye said, as Newsmax reported. That same report noted that some observers see Pelosi's daughter, Christine Pelosi, as a potential candidate for the seat, adding another layer of Democratic dynasty politics to the mix. Jaye added of Pelosi: "I doubt she has any appetite for that. And she has nothing left to prove."
Pelosi herself has remained active in shaping Democratic succession elsewhere, backing JFK grandson Jack Schlossberg in a Manhattan congressional primary. Whether she'll weigh in on her own seat's future remains an open question.
Chakrabarti's campaign launch tells you everything about how a certain wing of the Democratic Party thinks about politics. The theory: identity signaling and national progressive branding can substitute for local credibility. The drag queen endorsement isn't an accident. It's a strategy. In San Francisco, cultural performance is supposed to be its own qualification.
But even the left-leaning commenters pushing back on the video seem to understand something Chakrabarti doesn't. Voters in a city crushed by homelessness, crime, and unaffordable housing want someone who has actually been in the trenches, not a tech millionaire who parachuted in with AOC connections and a famous drag performer on speed dial.
The "Drag Me To Vote" event planned for April 4 will test whether San Francisco progressives are willing to trade substance for spectacle. Chakrabarti is betting they will. His opponents, and a growing number of skeptics in his own political lane, are betting they won't.
Chakrabarti's candidacy raises a question the left rarely asks itself: When does progressive branding become its own form of elite entitlement? A wealthy outsider with no local track record rolls into town, wraps himself in activist credentials, and expects the seat to follow. The drag endorsement is the cherry on top, a cultural signal meant to short-circuit any scrutiny of whether the candidate has earned the job.
San Francisco voters will decide in June. They'll choose between a city supervisor, a state senator with decades of local work, and a Silicon Valley millionaire whose biggest claim to fame is helping AOC get elected somewhere else.
If you can buy a congressional seat with money and a costume, San Francisco will prove it. If not, Chakrabarti may learn that even in the most progressive city in America, voters still notice when someone hasn't bothered to show up.
