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by\u00a0Io Yeh Gilman<\/a> <\/strong>May 5, 2026 (MissionLocal.org)<\/p>\n\n\n\n![\"\"\/](\"https:\/\/i0.wp.com\/newspack-missionlocal.s3.amazonaws.com\/mission\/wp-content\/uploads\/2025\/10\/100825_MMG_Saikat-4-scaled.jpg?fit=780%2C520&ssl=1\")
On the homepage of congressional candidate<\/a> Saikat Chakrabarti\u2019s campaign website there is no criticism of Republicans or President Donald Trump.<\/p>\n\n\n\n Instead, his choice words are for the Democrats: \u201cI\u2019m running for Congress because Democratic Party leaders in D.C. are unfit to lead the world as it is today.\u201d<\/p>\n\n\n\n That\u2019s not because Chakrabarti supports Trump; far from it<\/a>. It\u2019s because he thinks establishment Democrats are at fault for allowing Trump\u2019s rise and return. <\/p>\n\n\n\n \u201cPeople want something different,\u201d Chakrabarti told Mission Local<\/em>, pointing to a March 31 poll<\/a> that showed that the Democratic Party as an institution polls worse than Trump \u2014 35.3 percent approval for the Democrats, 41.1 percent for Trump.<\/p>\n\n\n\n \u201cI believe the way you win in this moment is not to present something that\u2019s a compromise, it\u2019s to present a different vision of a future that goes bigger.\u201d <\/p>\n\n\n\n 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. <\/p>\n\n\n\n <\/a><\/p>\n\n\n\n \u2190\u2192<\/p>\n\n\n\n 4 \/ 6<\/p>\n\n\n\n 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 \u201cpopular\u201d issues, like banning Congressional stock trading (though House Democrats including Minority Leader Hakeem Jeffries are already working on a plan<\/a> for that).<\/p>\n\n\n\n It\u2019s an aggressive strategy that\u2019s 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. <\/p>\n\n\n\n But Ocasio-Cortez preferred a less confrontational approach and, after eight months, Chakrabarti departed. <\/p>\n\n\n\n \u201cI left AOC\u2019s office at the end of 2019 after ruffling a few too many feathers in D.C,\u201d he told Jacobin Magazine<\/em><\/a> last July. <\/p>\n\n\n\n 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 \u201cwrong expectations\u201d coming into the job. <\/p>\n\n\n\n \u201cWe came in like, \u2018We\u2019re 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,\u2019\u201d he said. Ocasio-Cortez \u201chad a different strategy that involved not pissing everybody off, her colleagues and leadership, which is entirely reasonable.\u201d<\/p>\n\n\n\n \u201cAfter a while, it became clear to [communications director] Corbin [Trent] and Saikat that they weren\u2019t going to be able to practice politics the way that they thought they would and the way that they wanted to,\u201d the staffer added. \u201cThey sort of gradually made their way out.\u201d<\/p>\n\n\n\n Now Chakrabarti\u2019s hoping to get back to Washington, D.C., this time as the representative himself. He\u2019s using the millions he made in tech in his 20s to self-finance<\/a> his campaign against<\/a> 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. <\/p>\n\n\n\n \u201cI am running to change the Democratic Party,\u201d Chakrabarti said at a recent debate, \u201cand that\u2019s going to ruffle some feathers. If you want someone who\u2019s going to get along to go along, then I\u2019m not your guy.\u201d<\/p>\n\n\n\n Ocasio-Cortez, for her part, has repeatedly declined to endorse her former staffer or even comment<\/a> on the race. \u276e\u276f Enjoy craft martinis, live DJ nights, and dance in a unique retro-salon setting. Open daily from 2pm to 2am. Swing by during the day or join us at night for music, drinks, and unforgettable memories!Club \u2022 Trending \u2022 5K viewsDiscover the Vibe<\/p>\n\n\n\n Chakrabarti\u2019s start in politics came in 2015 at the age of 29, when he joined Bernie Sanders\u2019 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. <\/p>\n\n\n\n Chakrabarti and some of his Bernie colleagues soon realized, though, that Sanders\u2019 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. <\/p>\n\n\n\n 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.<\/p>\n\n\n\n When Ocasio-Cortez arrived in Washington later that year \u2014 with Chakrabarti working as her chief of staff \u2014 she cemented her reputation as a political firebrand before she was even sworn in. Ocasio-Cortez walked into Pelosi\u2019s office to join a climate-change protest arranged by the Sunrise Movement, which had been organizing for years. <\/p>\n\n\n\n \u201cAs a member, I want to thank you all because you are giving us as a party the strength to push,\u201d she said<\/a>, standing in the center of Pelosi\u2019s office surrounded by a ring of seated protesters holding bright yellow signs.<\/p>\n\n\n\n Cleaner Streets, Stronger Community<\/strong><\/p>\n\n\n\n After 5 years of working to fix SF’s litter problem, Clean Streets – a Mission-based, community-funded, litter pickup workforce has funded 1,236 hours <\/strong>of living-wage work and cleaned 617 miles <\/strong>of neighborhood streets. As little as $5 makes a difference. Click here to help us clean the Mission. <\/em><\/strong><\/p>\n\n\n\n 148<\/strong><\/p>\n\n\n\n It is the kind of action Chakrabarti hopes to emulate if he\u2019s 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\u2019s Inflation Reduction Act in 2022. <\/p>\n\n\n\n \u201cIt made a huge difference, because that\u2019s what blew it up in the media,\u201d he said. From there, Ocasio-Cortez<\/a> introduced the Green New Deal, which influenced the climate policies of candidates in the 2020 primary, he said.<\/p>\n\n\n\n But joining the sit-in came with risks.<\/p>\n\n\n\n \u201cEveryone was telling her, \u2018you\u2019re about to blow up your entire political career by doing this,\u2019\u201d Chakrabarti said. <\/p>\n\n\n\n And indeed, the protest did not earn Ocasio-Cortez any fans in Pelosi\u2019s office, who felt that they had already agreed to protesters\u2019 main demand: creating a congressional climate-change committee<\/a>. <\/p>\n\n\n\n \u201cShowing up at a Pelosi protest, it was not thought out,\u201d said Drew Hammill, who was Pelosi\u2019s deputy chief of staff at the time. <\/p>\n\n\n\n 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<\/a> about other Democrats. <\/p>\n\n\n\n That included attacking the Blue Dogs, a moderate Democratic caucus, which backed a bill providing $4.6 billion in emergency humanitarian aid<\/a> to the U.S.-Mexico border \u2014 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. <\/p>\n\n\n\n \u201cInstead of \u2018fiscally conservative but socially liberal,\u2019 let\u2019s call the New Democrats and Blue Dog Caucus the \u2018New Southern Democrats,\u2019\u201d Chakrabarti tweeted. \u201cThey certainly seem hell bent to do to black and brown people today what the old Southern Democrats did in the \u201940s.\u201d <\/p>\n\n\n\n He deleted that tweet within an hour, but soon followed up with others that were no less provocative. <\/p>\n\n\n\n \u201cCan we stop calling the Blue Dog Caucus \u2018fiscally conservative but socially liberal?\u2019 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,\u201d he tweeted, calling out Sharice Davids, a Native American congressperson from Kansas.<\/p>\n\n\n\n \u201cYou 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.\u201d<\/p>\n\n\n\n \u201cWho is this guy and why is he explicitly singling out a Native American woman of color?\u201d the official Twitter account of the House Democratic Caucus replied.<\/p>\n\n\n\n Meanwhile, Chakrabarti also had a few choice words about Pelosi. \u201cAll these articles want to claim what a legislative mastermind Pelosi is, but I\u2019m seeing way more strategic smarts from freshman members like @AOC, @IlhanMN, @RashidaTlai and @AyannaPressley,\u201d Chakrabarti tweeted July 6.<\/p>\n\n\n\n \u201cPelosi is just mad that she got outmaneuvered (again) by Republicans.\u201d<\/p>\n\n\n\n Chakrabarti\u2019s tweets set off turmoil<\/a> within the Democratic caucus that went on for weeks \u2014 with some calling for Chakrabarti\u2019s firing, according to Politico<\/em> reporting<\/a> from the time. <\/p>\n\n\n\n Chakrabarti stands by those tweets. But to Hammill, they were counterproductive. <\/p>\n\n\n\n \u201cIf you\u2019re just pissing on people who are on the same side of the aisle as you, you\u2019re not going to get support in committee, on the floor,\u201d he said. \u201cYou\u2019re going to make your own political grandstanding a liability for your constituents.\u201d<\/p>\n\n\n\n Infuriating other Democrats, Hammill added, could make it hard to get desired committee assignments. And as bills work their way through committee, those Democrats \u2014 plus their allies \u2014 may be reluctant to entertain amendments or funding requests. <\/p>\n\n\n\n Chakrabarti, for his part, thinks that many will be grateful that he is willing to be the one to stick his neck out. <\/p>\n\n\n\n \u201cThey\u2019re excited to see somebody take the first step,\u201d he said.<\/p>\n\n\n\n Ocasio-Cortez eventually decided<\/a> that a confrontational approach on every issue was not what she wanted. <\/p>\n\n\n\n She and another representative were all set to oppose a 2019 bill<\/a> 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\u2019s sponsor. <\/p>\n\n\n\n \u201cThey 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,\u201d the former staffer said. \u201cThey both just kind of were like, \u2018I don\u2019t want to do that.\u2019\u201d<\/p>\n\n\n\n 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 \u201ctrue believer.\u201d <\/p>\n\n\n\n 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\u2019 lobbying efforts. <\/p>\n\n\n\n \u201cCreate pressure on the outside, actually get people to notice this and then get that amendment out\u201d would be the plan, he said.<\/p>\n\n\n\n That confrontational approach has its pitfalls, warned Peter Loge, a longtime congressional staffer and associate professor at George Washington University\u2019s School of Media and Public Affairs. <\/p>\n\n\n\n \u201cIf 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,\u201d he said. \u201cBut once you get to Congress, self-righteousness doesn\u2019t tend to get you very far.\u201d<\/p>\n\n\n\n \u201cWhat he will do is demonstrate he\u2019s somebody the Democrats can\u2019t rely on and the Republicans can\u2019t trust,\u201d Loge said. \u201cBecause he\u2019s the one who\u2019s always shouting into the wind.\u201d<\/p>\n\n\n\n The equation could change, Loge said, if Chakrabarti can build a coalition. \u201cThe power that he could have is, if there are enough members of Congress who agree on an issue to hold something up that matters,\u201d Loge said.<\/p>\n\n\n\n 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. <\/p>\n\n\n\n Chakrabarti has been working on just that. One of his big lessons from his stint with Ocasio-Cortez, he said, is that it\u2019s important to go into Congress with relationships already in place with like-minded Democrats. He\u2019s been connecting with other progressive Democrats running for Congress, like Nate Blouin in Utah, to create a plan of action. <\/p>\n\n\n\n Still, he acknowledges, his plan is risky.<\/p>\n\n\n\n \u201cIf I do go after party leadership, I try to do the political revolution there, and it doesn\u2019t work then, yeah, I\u2019m not going to have a long career in Congress,\u201d he said. \u201cBut I think that\u2019s okay.\u201d<\/p>\n\n\n\n Mission Local<\/em> is growing its local coverage: We\u2019ve long covered the whole city but we are now designating reporters to five neighborhoods<\/strong> \u2014 the Tenderloin, Richmond, Sunset, and Bayview \u2014 and keeping one in the Mission District, which has been our home for the last 18 years.<\/p>\n\n\n\n Having reporters on-the-ground and asking questions is what makes Mission Local stand out \u2014 it\u2019s our biggest strength and what we intend to bring to every neighborhood we cover. <\/p>\n\n\n\n Our goal is to raise $125,000<\/strong> \u2014 the price of adding coverage in one neighborhood for one year<\/strong>. If you donate to our fundraiser today, your gift is doubled thanks to the match.about:blank<\/p>\n\n\n\n Double my donation!<\/a><\/p>\n\n\n\n io@missionlocal.com<\/a><\/p>\n\n\n\n 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.<\/p>\n\n\n\n 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.<\/p>\n\n\n\n You can reach Io securely on Signal at ioyg.10More by Io Yeh Gilman<\/a><\/p>\n","protected":false},"excerpt":{"rendered":" The centimillionaire congressional candidate hopes to bring his no-holds-barred approach to national politics \u2014 again by\u00a0Io Yeh Gilman May 5, 2026 (MissionLocal.org) On the homepage of congressional candidate Saikat Chakrabarti\u2019s campaign website there is no criticism of Republicans or President Donald Trump. Instead, his choice words are for the Democrats: \u201cI\u2019m running… Continue reading ![\"\"\/](\"https:\/\/cdn.broadstreetads.com\/uploads\/s_800_4fd70d53-4875-486e-a6c8-83198c0b53f3.png\")
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<\/p>\n\n\n\nBeauty Bar is Back! Revitalized!<\/h1>\n\n\n\n
\u2018You\u2019re about to blow up your entire political career\u2019<\/strong><\/h3>\n\n\n\n
![\"Image\"](\"https:\/\/cdn.broadstreetads.com\/uploads\/s_800_b6166a7e-6647-4be5-a379-7ca3f07b8d9c.png\")
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<\/figure>\n\n\n\n\u2018Who is this guy?\u2019 the Democratic caucus demanded<\/strong><\/h3>\n\n\n\n
A true believer<\/strong><\/h3>\n\n\n\n
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<\/figure>\n\n\n\nThis May we have a $50K match!<\/strong><\/h4>\n\n\n\n
Latest election coverage<\/h2>\n\n\n\n
![\"Meet](\"https:\/\/i0.wp.com\/newspack-missionlocal.s3.amazonaws.com\/mission\/wp-content\/uploads\/2026\/02\/District-2-Banner.png?resize=800%2C600&ssl=1\")
<\/a><\/figure>\n\n\n\nMeet the District 2 candidates: Do you support layoffs this budget cycle?<\/a><\/h3>\n\n\n\n
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<\/a><\/figure>\n\n\n\nAt debate, District 2 candidates part ways on housing<\/a><\/h3>\n\n\n\n
![\"Here\u2019s](\"https:\/\/i0.wp.com\/newspack-missionlocal.s3.amazonaws.com\/mission\/wp-content\/uploads\/2026\/04\/042026_ZM_SFCityHall-09-scaled.jpg?resize=1200%2C900&ssl=1\")
<\/a><\/figure>\n\n\n\nHere\u2019s what\u2019s on the ballot for San Francisco\u2019s June 2 election<\/a><\/a><\/h3>\n\n\n\n
Io Yeh GilmanStaff Reporter<\/a><\/h2>\n\n\n\n