According to his economic disclosure form, Chakrabarti, who officially launched his campaign against Pelosi earlier this year, is worth at least $167 million, much of it equity in Stripe, the payment processing company where he was a founding engineer. If elected, he would be one of the wealthiest members of Congress.

Wiener, who opened his congressional campaign committee last year, reported raising more than $1 million in his most recent filing with the Federal Election Commission, with $867,105 cash on hand at the end of September.

By comparison, Chakrabarti’s FEC filing shows total contributions of just under $1 million, about half from personal loans to his campaign. After spending on infrastructure, he reported $95,384 cash on hand and$755,000 in outstanding loans and debts. But given his net worth, he can presumably self-fund this campaign going forward.

Pelosi, long one of the Democratic Party’s most prolific fundraisers, reported contributions of just over $2 million for 2025, including at least $450,000 transferred to the Democratic Congressional Campaign Committee. She reported $1.5 million cash on hand through September.

Expect Wiener to cast Chakrabarti as a kind of political dilettante with weak ties to San Francisco and little experience governing.

“It’s not enough just to say, ‘Oh I want to challenge the establishment and do all these things,’ when you don’t necessarily have the track record of showing that you know how to do that,” Wiener said, without mentioning Chakrabarti by name.

Chakrabarti responded in a statement: “I have experience turning big ideas into reality even in a gridlocked Congress. Scott has experience tinkering with regulations in an overwhelmingly Democratic Sacramento.”

Pro-Palestinian activists attempt to block access to the Port of Oakland in September. A bill languishing in the House would block the sale or transfer of certain bombs and other weapons to Israel. (Juan Carlos Lara/KQED)

One issue that could separate Chakrabarti from Wiener, who is Jewish, is Gaza. Israel’s war there has drawn widespread condemnation for the devastation and deaths of tens of thousands of Palestinians following Hamas’ Oct. 7 attack on a music festival in Southern Israel that killed hundreds and took about 240 civilians hostage.

A bill currently languishing in the House, H.R. 3565, would block the sale or transfer of certain bombs and other weapons to Israel. Chakrabarti has aired ads calling on Pelosi to support the bill, which has not passed out of committee. Interviewed this week, Wiener twice declined to say how he’d vote on H.R. 3565, but said, “I do not think that we should be selling offensive arms to Israel under this government or any government like it. We need to get a government that’s committed both to democracy and to peace and not to this devastation.”

Veteran San Francisco political consultant Eric Jaye said while he disagrees with many of Wiener’s policy positions, he acknowledges his effectiveness.

“Scott Weiner has been one of the most productive legislators we’ve ever seen in San Francisco, and in many respects he’s the Nancy Pelosi of his generation. He’s the Willie Brown of his generation. He’s the Phil Burton of his generation,” Jaye said.

When this congressional seat became vacant after the death of Rep. Sala Burton, Pelosi received a deathbed endorsement from Burton’s widow but she was relatively unknown beyond Democratic Party insiders. More than a dozen people ran including four San Francisco supervisors. Jaye doubts there will be that kind of candidate stampede this time.

“(Pelosi) didn’t scare anybody out. Now, if it’s Weiner and Pelosi, I don’t think others will look at that and say, ‘I could beat one of those two,’” Jaye said. At the same time, he added that Pelosi “suffers from a suspicion that grew in the American electorate about octogenarian leaders, based on what happened with former President Biden.”

Still, an open House seat is too enticing for politicians to ignore. Supervisor Connie Chan is reportedly considering a run. Pelosi’s daughter, Christine, has also considered running.

Whoever enters the race, Jaye said, will face “a moment in San Francisco politics, California politics, national politics where voters are pretty frustrated with the slow pace of change. So it’s a very, very roiled political environment.”