The centimillionaire congressional candidate hopes to bring his no-holds-barred approach to national politics — again
by Io Yeh Gilman May 5, 2026 (MissionLocal.org)
On the homepage of congressional candidate Saikat Chakrabarti’s campaign website there is no criticism of Republicans or President Donald Trump.
Instead, his choice words are for the Democrats: “I’m running for Congress because Democratic Party leaders in D.C. are unfit to lead the world as it is today.”
That’s not because Chakrabarti supports Trump; far from it. It’s because he thinks establishment Democrats are at fault for allowing Trump’s rise and return.
“People want something different,” Chakrabarti told Mission Local, pointing to a March 31 poll that showed that the Democratic Party as an institution polls worse than Trump — 35.3 percent approval for the Democrats, 41.1 percent for Trump.
“I believe the way you win in this moment is not to present something that’s a compromise, it’s to present a different vision of a future that goes bigger.”
His vision is of a Democratic Party that ends funding for wars and weapons, provides healthcare for all Americans, funds free public college, transitions America to clean and renewable energy sources, and more.
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But his plan for achieving that is through confrontation: Primarying moderate Democrats, including party leaders; pressuring representatives to hold firm against funding for Immigration and Customs Enforcement and cuts to Medicaid; and going around House leadership to force votes on “popular” issues, like banning Congressional stock trading (though House Democrats including Minority Leader Hakeem Jeffries are already working on a plan for that).
It’s an aggressive strategy that’s already familiar to many on Capitol Hill. During his tenure as chief of staff to Rep. Alexandria Ocasio-Cortez, he frequently made national headlines for his scathing criticisms of fellow Democrats.
But Ocasio-Cortez preferred a less confrontational approach and, after eight months, Chakrabarti departed.
“I left AOC’s office at the end of 2019 after ruffling a few too many feathers in D.C,” he told Jacobin Magazine last July.
A former colleague of Chakrabarti, who declined to be identified because his current employer has not authorized him to speak to the press, said that he, Chakrabarti, and other staff members had the “wrong expectations” coming into the job.
“We came in like, ‘We’re here to call people out on their bullshit and burn this place to the ground and be radicals and be flamethrowers and call it like we see it,’” he said. Ocasio-Cortez “had a different strategy that involved not pissing everybody off, her colleagues and leadership, which is entirely reasonable.”
“After a while, it became clear to [communications director] Corbin [Trent] and Saikat that they weren’t going to be able to practice politics the way that they thought they would and the way that they wanted to,” the staffer added. “They sort of gradually made their way out.”
Now Chakrabarti’s hoping to get back to Washington, D.C., this time as the representative himself. He’s using the millions he made in tech in his 20s to self-finance his campaign against State Sen. Scott Wiener and Supervisor Connie Chan. If he makes it to D.C, though, he has no plans to ease up on the Dems.
“I am running to change the Democratic Party,” Chakrabarti said at a recent debate, “and that’s going to ruffle some feathers. If you want someone who’s going to get along to go along, then I’m not your guy.”
Ocasio-Cortez, for her part, has repeatedly declined to endorse her former staffer or even comment on the race. ❮❯
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‘You’re about to blow up your entire political career’
Chakrabarti’s start in politics came in 2015 at the age of 29, when he joined Bernie Sanders’ presidential campaign. He had just quit his job as one of the first engineers at the financial-technology company Stripe after becoming disillusioned with tech.
Chakrabarti and some of his Bernie colleagues soon realized, though, that Sanders’ platform would need allies in Congress. So they founded Justice Democrats to replace moderate and corporate-aligned Democrats with progressives, and in 2018 recruited candidates across the country to primary Democrats.
Justice Democrats soon concentrated resources on one: Ocasio-Cortez. Chakrabarti became her campaign manager, and she won 57-43, beating Joe Crowley, one of the most powerful congressional Democrats at the time.
When Ocasio-Cortez arrived in Washington later that year — with Chakrabarti working as her chief of staff — she cemented her reputation as a political firebrand before she was even sworn in. Ocasio-Cortez walked into Pelosi’s office to join a climate-change protest arranged by the Sunrise Movement, which had been organizing for years.
“As a member, I want to thank you all because you are giving us as a party the strength to push,” she said, standing in the center of Pelosi’s office surrounded by a ring of seated protesters holding bright yellow signs.
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It is the kind of action Chakrabarti hopes to emulate if he’s elected. As he sees it, a direct line can be drawn between Ocasio-Cortez calling for a Green New Deal at that protest and the climate provisions in Joe Biden’s Inflation Reduction Act in 2022.
“It made a huge difference, because that’s what blew it up in the media,” he said. From there, Ocasio-Cortez introduced the Green New Deal, which influenced the climate policies of candidates in the 2020 primary, he said.
But joining the sit-in came with risks.
“Everyone was telling her, ‘you’re about to blow up your entire political career by doing this,’” Chakrabarti said.
And indeed, the protest did not earn Ocasio-Cortez any fans in Pelosi’s office, who felt that they had already agreed to protesters’ main demand: creating a congressional climate-change committee.
“Showing up at a Pelosi protest, it was not thought out,” said Drew Hammill, who was Pelosi’s deputy chief of staff at the time.
‘Who is this guy?’ the Democratic caucus demanded
As Ocasio-Cortez settled into her new role, Chakrabarti and her other staffers kept up the aggression. Chakrabarti himself made a habit of firing off provocative tweets about other Democrats.
That included attacking the Blue Dogs, a moderate Democratic caucus, which backed a bill providing $4.6 billion in emergency humanitarian aid to the U.S.-Mexico border — but without provisions that other Democrats wanted, including reducing funding for ICE and requiring the administration to provide a higher standard of care in detention centers housing migrant children at the border.
“Instead of ‘fiscally conservative but socially liberal,’ let’s call the New Democrats and Blue Dog Caucus the ‘New Southern Democrats,’” Chakrabarti tweeted. “They certainly seem hell bent to do to black and brown people today what the old Southern Democrats did in the ’40s.”
He deleted that tweet within an hour, but soon followed up with others that were no less provocative.
“Can we stop calling the Blue Dog Caucus ‘fiscally conservative but socially liberal?’ I missed the part of fiscal conservativeness or social liberalness that includes wasting $4.5 billion of taxpayer money to put kids in concentration camps,” he tweeted, calling out Sharice Davids, a Native American congressperson from Kansas.
“You can be someone who does not personally harbor ill will towards a race, but through your actions still enable a racist system. And a lot of New Democrats and Blue Dogs did that today.”
“Who is this guy and why is he explicitly singling out a Native American woman of color?” the official Twitter account of the House Democratic Caucus replied.
Meanwhile, Chakrabarti also had a few choice words about Pelosi. “All these articles want to claim what a legislative mastermind Pelosi is, but I’m seeing way more strategic smarts from freshman members like @AOC, @IlhanMN, @RashidaTlai and @AyannaPressley,” Chakrabarti tweeted July 6.
“Pelosi is just mad that she got outmaneuvered (again) by Republicans.”
Chakrabarti’s tweets set off turmoil within the Democratic caucus that went on for weeks — with some calling for Chakrabarti’s firing, according to Politico reporting from the time.
Chakrabarti stands by those tweets. But to Hammill, they were counterproductive.
“If you’re just pissing on people who are on the same side of the aisle as you, you’re not going to get support in committee, on the floor,” he said. “You’re going to make your own political grandstanding a liability for your constituents.”
Infuriating other Democrats, Hammill added, could make it hard to get desired committee assignments. And as bills work their way through committee, those Democrats — plus their allies — may be reluctant to entertain amendments or funding requests.
Chakrabarti, for his part, thinks that many will be grateful that he is willing to be the one to stick his neck out.
“They’re excited to see somebody take the first step,” he said.
A true believer
Ocasio-Cortez eventually decided that a confrontational approach on every issue was not what she wanted.
She and another representative were all set to oppose a 2019 bill favored by Intuit and TurboTax that included a clause preventing the IRS from creating free tax-filing software, for example, until they realized that Rep. John Lewis, the civil rights icon, was the bill’s sponsor.
“They kind of realized that they were going to have to stand up and debate John Lewis and object to his bill and accuse John Lewis of carrying water for H&R Block and TurboTax,” the former staffer said. “They both just kind of were like, ‘I don’t want to do that.’”
If Chakrabarti makes it back to Congress, though, people who worked alongside him think that he would stick to the confrontational approach. Several called him a “true believer.”
Chakrabarti, for his part, said he would have handled that tax bill differently. His plan, he said, would be to incite public outrage to counter the companies’ lobbying efforts.
“Create pressure on the outside, actually get people to notice this and then get that amendment out” would be the plan, he said.
That confrontational approach has its pitfalls, warned Peter Loge, a longtime congressional staffer and associate professor at George Washington University’s School of Media and Public Affairs.
“If you want to win a primary, especially a crowded primary in a liberal area, you want to sound as liberal and righteous as you can,” he said. “But once you get to Congress, self-righteousness doesn’t tend to get you very far.”
“What he will do is demonstrate he’s somebody the Democrats can’t rely on and the Republicans can’t trust,” Loge said. “Because he’s the one who’s always shouting into the wind.”
The equation could change, Loge said, if Chakrabarti can build a coalition. “The power that he could have is, if there are enough members of Congress who agree on an issue to hold something up that matters,” Loge said.
Loge pointed to the Freedom Caucus, a group of far-right Republicans who have forced their way on a number of issues, including the removal of Kevin McCarthy as Speaker of the House.
Chakrabarti has been working on just that. One of his big lessons from his stint with Ocasio-Cortez, he said, is that it’s important to go into Congress with relationships already in place with like-minded Democrats. He’s been connecting with other progressive Democrats running for Congress, like Nate Blouin in Utah, to create a plan of action.
Still, he acknowledges, his plan is risky.
“If I do go after party leadership, I try to do the political revolution there, and it doesn’t work then, yeah, I’m not going to have a long career in Congress,” he said. “But I think that’s okay.”
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Io Yeh GilmanStaff Reporter
Io is a staff reporter at Mission Local covering city hall and S.F. politics. She is a part of Report for America, which supports journalists in local newsrooms.
Io was born and raised in San Francisco and previously reported on the city while working for her high school newspaper, The Lowell. She studied the history of science at Harvard and wrote for The Harvard Crimson.
You can reach Io securely on Signal at ioyg.10More by Io Yeh Gilman
