Congressional candidate Saikat Chakrabarti is rich beyond most people’s dreams.

He may not be on par with San Francisco’s plentiful billionaires, a class unto itself, but as a centimillionaire, Chakrabarti has more capital at his disposal than most local candidates will amass in their lifetimes. The former Stripe engineer has AirDropped $4.8 million into his campaign coffers.

So how much is he willing to spend to succeed Rep. Nancy Pelosi, a seat he could hold for decades? 

In a wide-ranging interview with The Standard on Tuesday, Chakrabarti told us there’s no limit to how deeply he’ll plumb his wallet to finance his run in the June 2 primary, or beyond it, in the November general.

“That’s going to depend on how much is getting spent against me,” Chakrabarti said. “For me? I’m in this to win it.” 

Chakrabarti claims corporate dollars supporting rival candidates will attempt to drown out his campaign in part because he has pledged to hold the AI industry accountable (opens in new tab). He wants the government to own artificial intelligence models on behalf of citizens and to create a national lab for AI development. Government should swoop in and purchase AI companies for “pennies on the dollar” should the industry bubble burst, he said, instead of offering bailouts. 

Chakrabarti also wants to tax AI companies to create a federal jobs program to retrain displaced workers, who should, in turn, have a place on AI corporate boards.

Of AI’s future, he said, “I ultimately don’t believe that kind of society-wide decision should be in the hands of a few CEOs and corporations.”

But Chakrabarti said his positions come with political risk. “If you talk to any Democratic Party general consultant right now, they’ll tell you, ‘Don’t talk about AI,’ because you might get a million dollars dropped against you (opens in new tab) in your race.”

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Wiener’s own campaign has raised $3.4 million, keeping a jogger’s pace alongside Chakrabarti’s personal spending.

While Wiener hasn’t been knocked out of his top spot in the polls, Chakrabarti’s money may be enough to edge out other candidates. Supervisor Connie Chan and ConnectSF founder Marie Hurabiell have each raised more than $400,000.  

Chan had hoped her years-long tenure on the Board of Supervisors would give her a boost over Chakrabarti, who hasn’t held office but spent years in East Coast politics. But some polls show (opens in new tab) Chakrabarti leapfrogging her by double digits, though insiders say she remains in contention.  

“If I’m someone on Connie Chan’s team, I’m upset [Chakrabarti] entered the race and spent all this money,” said San Francisco State University politics professor Jason McDaniel. “But all that money spent cannot win an election by itself.” 

Chakrabarti has also raised about $360,000 from small donors, many from out of state.

Drawing an accurate account of his personal wealth is difficult.

He listed a wide range of investments in his financial disclosure form (opens in new tab), which is required by law for congressional candidates. A notable share is in the financial payment company Stripe, where he worked as a founding engineer, and his investments are valued at more than $50 million. He also has substantial holdings in Fidelity investment accounts. 

Because financial disclosures report assets in ranges rather than exact figures, his total net worth is difficult to pin down. But using midpoint estimates, including an assumed $50 million stake in Stripe, puts it at roughly $150 million. His primary residence in San Francisco and a Maryland property that he says was purchased for his parents do not generate income and are exempt from financial disclosure requirements.

His disclosure shows two rental properties generating between $10,000 and $30,000 annually. Additionally, he invested $100,000 in a gym; he told The Standard he was helping a friend start a business.

Chakrabarti has been outspoken on supporting green energy and ending wars and said he has divested (opens in new tab) since entering the race, instructing his wealth manager to “invest ethically,” avoiding fossil fuels and military-related companies.

Meanwhile, his wealth could explode at any moment: Should Stripe go public, as reports suggest (opens in new tab), he could become a near-billionaire overnight.

Despite his commitment to spending a San Francisco mansion’s worth of money on his race, Chakrabarti is opposed to privately financed political campaigns. If elected, he will work to ensure that no one else can retrace his path. 

“My goal very clearly has been to tax the ultra-rich, including myself. To get rid of the influence of corporate money and big money in politics,” he said. “That means no private money in elections.” 

After he wins, that is.