Centimillioinaire Chakrabarti has a lofty progressive agenda | Politics

“I think they’re falling flat on the job of actually stopping this authoritarian coup I believe we’re in the middle of,” said Chakrabarti, who as of March 31 had spent nearly $5 million on his campaign based mostly on loans from himself — more than all of his rivals combined in the race.

Chakrabarti’s outspoken approach to other Democrats has been evident in his campaign for the District 11 seat — particularly concerning his chief opponent, state Sen. Scott Wiener.

It also featured prominently in a notable controversy in 2019 when he was chief of staff to liberal firebrand Rep. Alexandra Ocasio-Cortez of New York, whom he helped to elect.

That incident has gained currency this month because Ocasio-Cortez has not endorsed Chakrabarti, though Chakrabarti says he would “love” to have it and “of course, I’m going through the process.” An email from The Examiner sent to Ocasio-Cortez’s office did not receive a response.

Her reticence has prompted speculation about her relationship with Chakrabarti, who frequently invokes his past work with her in support of his campaign and uses photographs of himself with her in campaign materials.

In particular, Chakrabarti in an interview with The Examiner drew a clear line from his work supporting Ocasio-Cortez on the Green New Deal to President Biden’s Inflation Reduction Act, which produced the largest climate and energy investments in U.S. history.

Chakrabarti was Ocasio-Cortez’s campaign manager and then campaign chair during a 13-month period. When she took office, he became her chief of staff in Washington, D.C.

That arrangement came to an end after eight months following a controversy over a message Chakrabarti posted on social media comparing some Democrats to “new Southern Democrats” based on their votes on a border-control bill.

“Instead of ‘fiscally conservative but socially liberal,’ let’s call the New Democrats and Blue Dog Caucus the ‘New Southern Democrats,’” Chakrabarti wrote in the message, according to The Washington Post. “They certainly seem hell bent to do to black and brown people today what the old Southern Democrats did in the 40s.”

The subsequently deleted message drew an online rebuke from the House Democrats Twitter account run by the office of Rep. Hakeem Jeffries, according to The Intercept. Jeffries, another House member representing New York, is the legislative body’s current minority leader.

Pelosi — who was speaker of the House at the time — encouraged members not to air grievances with other Democrats in public, The Post reported.

Asked about the controversial message this week, Chakrabarti reiterated his disappointment over the vote in Congress.

“Trump was putting children into cages,” Chakrabarti said. “I believe the thing I said is the system of immigration that Trump is implementing is a racist system. That made a lot of people mad. But it’s true, it was.”

Despite the dustup, The Intercept reported in 2019 that Ocasio-Cortez’s office said Chakrabarti’s departure had been planned. It quoted Ocasio-Cortez as saying she was “extremely grateful for his service to advance a bold agenda and improve the lives of the people” in her New York district.

Chakrabarti also said this week his exit was planned, that he trained his replacement, and that he was expecting a baby.

Wiener spokesperson Joe Arellano, however, recently said Chakrabarti was “trying to cover up the skeletons in his closet” from his time in the nation’s capital.

“San Franciscans want a representative who fights for our values and also delivers for our city and country,” Arellano said this week. “That requires building coalitions and passing real laws.”

Asked about Wiener’s voluminous legislative record, Chakrabarti questioned how much effect his laws have had.

“If voters believe the thing that we’re really lacking in D.C. right now is more experienced state and local legislators, then, yeah, I’m not your guy,” he said. “But if you think what we need to do is actually change the party, take the political risk to do that, then that is what I’m offering.”

Julie Edwards, a spokesperson for San Francisco Supervisor Connie Chan, another candidate in the race, said, “Saikat attacks people who could be allies.”

Though she said Chan would call out “corporate Democrats” who “cave to billionaires,” Edwards said Chan “looks forward to joining all the Democrats, using all leverage from their different roles and perspectives, to get the best deal for the working Americans nationwide.”

Chakrabarti, meanwhile, said he thinks Democrats need a “fundamental reset.” He said the nation is in a moment similar to the 1930s, when many people were attracted to fascism but President Franklin Roosevelt showed how the government could work for the good of common citizens.

“You have to be willing to blow up your future political career if you want to make real change happen today — and that’s what I’m willing to do,” he said.

Raised in Fort Worth, Texas, by parents who from India, Chakrabarti said he grew up “middle class,” attending public schools. He graduated from Harvard University in 2007 with an undergraduate degree in computer science.

Chakrabarti had two three-month internships and spent a year as a technology associate in Connecticut at a large investment firm before co-founding Mockingbird, a web-design firm that he was part of for the next eight years amid other pursuits.

In February 2011, Chakrabarti became a founding engineer at the payments-technology company Stripe, based at the time in San Francisco. The role quickly catapulted him into the ranks of the ultrawealthy. Chakrabarti left the company after two years and four months, and his fortune today is worth more than $160 million, according to federal disclosure forms.

A tech boom was blossoming in San Francisco while Chakrabarti was at Stripe, and he said he quit because he became disillusioned watching people get “pushed out” of The City.

“When I went through that experience of hitting the startup lottery, that to me, felt like I need to give back,” Chakrabarti said. “Because, yeah, like I worked hard, but I didn’t work harder than a teacher or a nurse or the janitors cleaning our offices.”

“They would never be able to afford a home, would never be able to afford a secure retirement,” he said. “And that’s frankly why I quit, and I started looking around for how to solve the actual problems people were facing.”

Chakrabarti said he was not political at the time, but he was attracted to the messaging of U.S. Sen. Bernie Sanders — “and that’s how I ended up spending the next 10 years of my life trying to unrig this broken economic system by passing taxes on the rich, including myself, by trying to actually create an economy that will work for working people and not just the wealthiest few.”

“It’s not just a question of fairness,” he said.

“I believe it’s a question of whether our country is doomed, because I do believe when you see levels of inequality like we’re seeing today, that is how nations fail,” he said. “It’s an existential crisis for this nation.”

In 2015, Chakrabarti worked as director of organizing technology in Sanders’ first presidential campaign. Then in April 2016, he co-founded Brand New Congress, which he ran as executive director for nearly a year and a half to support progressive candidates.

Chakrabarti also co-founded Justice Democrats in 2017, and he led that organization — which played a prominent role in the election of Alexandra Ocasio-Cortez and other progressive politicians — as executive director for 18 months.

After leaving Ocasio-Cortez’s office, Chakrabarti became congressional policy director for New Consensus, a think tank he co-founded that develops and promotes progressive public-policy ideas for a clean economy.

Its “Mission for America” is something of a progressive version of the conservative Heritage Foundation’s highly influential Project 2025, a “plan of how exactly do you build up an economy that will create prosperity for everybody and reverse the decline we’re seeing today,” Chakrabarti said.

Chakrabarti said he has “a lot of respect for Nancy Pelosi” — particularly for her advocacy for HIV/AIDS research, care and prevention — and said she was a better leader and opponent of Trump than Jeffries. But he criticized Pelosi for voting in favor of an $890 billion defense budget last December.

“I’m not going to vote for another dollar for any defense spending,” he said. “In fact, I believe we need to slash our military budget.”

“We’re getting dragged into World War III, looking at AI potentially replacing half of all of our jobs,” he said. “At the same time, wealth and power is being concentrated into the hands of a few at a scale that we haven’t seen since the Gilded Age. And in the face of these monumental challenges, I think a lot of what most Democrats are offering are kind of the same old, same old.”

A spokesperson for Pelosi responded by providing a memo from Democrat Rep. Adam Smith, the ranking member of the House Armed Services Committee, stating that, among other things, the package included measures to strengthen congressional oversight.

Wiener has said Chakrabarti had a negligible presence in San Francisco before his candidacy, and his campaign has attacked Chakrabarti’s residency and voting history, highlighting the fact that Chakrabarti voted in San Francisco in 2010 and then not again until 2020.

Chakrabarti said he has owned different homes in San Francisco since 2013 and currently lives with his wife and daughter near Duboce Park.

He said he has given “millions” of dollars to local nonprofits, particularly those providing housing and food assistance. He served on the Friends of Duboce Park board of directors for about a year until leaving to pursue his campaign, according to the organization’s president.

Wiener’s camp has hit Chakrabarti on the residency issue following a news report that said he claimed a house in Maryland was his principal residence for seven years in conjunction with property-tax payments. Chakrabarti has said it was a mistake not repeated on other documents and that he bought the home for his parents.

He countered that campaign mailers highlighting the Maryland story were funded by Abundant Future, a committee that has received hefty donations from tech bigwigs and other wealthy figures, including cryptocurrency billionaire Chris Larsen and Y Combinator CEO Garry Tan. He noted that Larsen’s company, Ripple Labs, made a large donation to Trump’s inauguration, though Larsen has personally made large donations to Democrats as well.

Chakrabarti said he wants to get all corporate money out of elections and to move toward public financing of elections.

He said he sees Congress as corrupted and wants to restrict lobbying by former members. In addition, he vowed to file something called a “discharge petition” in order “to force a vote on banning congressional stock trading” by representatives, which he believes the public overwhelmingly supports.

“Leadership doesn’t like it because you’re going around their power,” he said. “I don’t care about that.”

Meanwhile, he attacked Wiener for not immediately joining him and Chan during a January debate in labeling Israel’s war against Hamas in Gaza a “genocide.”

Wiener refused to answer a lightning-round question on the charged subject and was booed by the audience. Later, in a video he posted online, he did use the term to describe Israel’s actions in the conflict and explained his hesitance given the word’s origins in the wake of the Holocaust — but not before Chakrabarti posted his own video featuring Wiener and asserting, “When you can’t call out a genocide when the whole world sees one, how can we trust you in D.C.?”

Politically, Chakrabarti said he has mostly been active at the federal level. He gave $7,000 in November to New York City Councilmember Chi Osse shortly before Osse backed off a run against Jeffries.

Chakrabarti has also made some contributions to San Francisco candidates, including most recently $500 to Natalie Gee, who is running for District 4 supervisor.

But Wiener and Chan both have far more extensive lists of endorsements from politicians, political groups and unions.

Chakrabarti said he has had about 3,000 people who signed up to volunteer. Some of those he hired, and his campaign currently employs more than 200 people in various capacities, including as canvassers, some making $45 an hour.

“I’m going to force Democrats to fight this moment,” he said. “And I believe that’s what people want, too.”