{"id":370107,"date":"2026-06-22T12:49:11","date_gmt":"2026-06-22T12:49:11","guid":{"rendered":"https:\/\/www.newsbeep.com\/us-ca\/370107\/"},"modified":"2026-06-22T12:49:11","modified_gmt":"2026-06-22T12:49:11","slug":"saikat-chakrabarti-had-potential-and-money-why-did-he-lose","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/us-ca\/370107\/","title":{"rendered":"Saikat Chakrabarti had potential and money. Why did he lose?"},"content":{"rendered":"

When Saikat Chakrabarti launched his campaign for Congress last October, so many people showed up<\/a> that it spooked state Sen. Scott Wiener<\/a> into entering the race before Speaker Emerita Nancy Pelosi had bowed out.\u00a0<\/p>\n

At the time, it looked like Chakrabarti had a real shot. Less than a year earlier, Daniel Lurie had run a successful campaign to become mayor of San Francisco by using his considerable personal wealth to launch a well-funded, well-researched campaign that turned Lurie\u2019s low name recognition and lack of political experience into assets.\u00a0<\/p>\n

But despite spending at least $8.8 million<\/a>, Chakrabarti came in third, with 18 percent of the vote. Now, Supervisor Connie Chan, who got 30 percent of the vote, and Wiener, who got 41 percent, will square off in November\u2019s midterm election; Chan has subsequently received Chakrabarti\u2019s backing<\/a>, canvassers<\/a>, and cash<\/a>.\u00a0<\/p>\n

So, what happened?\u00a0<\/p>\n

With such a resounding loss, many factors likely contributed. For one, a key demographic that Chakrabarti courted \u2014 young voters \u2014 failed to show up<\/a> at the polls. The voters who did show up for June\u2019s primary electorate cast votes that leaned conservative \u2014 among other things, they emphatically shut down<\/a> a proposal to raise taxes on large businesses<\/a>. San Franciscans did not throw their lot in with the upstart firebrand.<\/p>\n

Chakrabarti also failed to get the support of any major local political groups, like unions, city politicians or voter guides.\u00a0<\/p>\n

But in conversations with political observers and campaign workers, many also attributed his loss to something else: While voters were initially excited about Chakrabarti\u2019s campaign, they lost trust in him in the final weeks.\u00a0<\/p>\n

Senior staffers said that failing to obtain an expected endorsement from Chakrabarti\u2019s former boss, Rep. Alexandio Ocasio-Cortez, was a fatal blow.<\/p>\n

\u201cHer non-endorsement,\u201d Chakrabarti said, \u201cwas the clear turning point for us.\u201d<\/p>\n

Grassroots energy<\/p>\n

When Chakrabarti opened his campaign office in July 2025, so many volunteers showed up that they had to run the orientation program twice, cycling in a couple hundred each time, according to Nadia Rahman, who joined as Chakrabarti\u2019s political director in January 2026.\u00a0<\/p>\n

That excitement was still there months later. In October 2025, over 1,000 people RSVP\u2019d to his launch event<\/a> at The Chapel, according to his campaign. Some 600 came.\u00a0\u00a0<\/p>\n

There was a \u201cpulsating grassroots energy, excitement, momentum about his campaign,\u201d Rahman said.\u00a0<\/p>\n

Even a year out from the general election, dozens of volunteers were showing up each weekend to canvas for him.\u00a0<\/p>\n

Energizing his supporters was a message of change. Chakrabarti sharply criticized<\/a> the Democratic Party for catering to corporations while failing to make people\u2019s lives better. He spoke forcefully about the need for the United States to apply political pressure on Israel<\/a> to protect the rights of Palestinians. A transition to clean energy sources was on his agenda, as well as abolishing ICE, eliminating stock trading<\/a> by members of Congress and establishing Medicare for All.<\/p>\n

\"\"Supporters of Saikat Chakrabarti listen intently during the politician\u2019s speech at The Chapel during his campaign kickoff on Wednesday night. Photo by Mariana Garcia.<\/p>\n

He had national bona fides: Chakrabarti had worked with some of the most famous progressives in national politics, first as director of organizing technology for Sen. Bernie Sander\u2019s 2016 campaign for president, then as the 2018 campaign manager for Rep. Alexandria Ocasio-Cortez\u2019s Congressional race and later as her chief of staff.\u00a0<\/p>\n

Locally, however, Chakrabarti had committed an unforced error before his run: He had backed a moderate, Bilal Mahmood<\/a>, with $10,000 during Mahmood\u2019s run for the San Francisco Democratic Party on a well-funded, tech-backed slate<\/a>.\u00a0<\/p>\n

Mahmood subsequently unseated<\/a> the city\u2019s lone socialist supervisor at the time, Dean Preston<\/a>, a champion of the city\u2019s Democratic Socialists of America chapter. Chakrabarti was, from the get-go, persona non grata to the chapter and its members. It cost him possibly hundreds of young canvassers capable of blanketing the city, and local leftists persistently dogged his campaign.<\/p>\n

Still, he seemed to gain steam. Chakrabarti\u2019s politics straddled the line between progressive and moderate on municipal issues. He supported measures to increase taxes on certain types of business (like Chan) but also favored upzoning and making it easier to build housing (like Wiener).\u00a0<\/p>\n

Chakrabarti had the potential to peel away core constituencies from both his opponents \u2014 progressives from Chan and YIMBY urbanists from Wiener \u2014 but also the potential to end up without enough from either side.<\/p>\n

But what made Chakrabarti a contender wasn\u2019t just his politics \u2014 it was his money. In his 20s Chakrabarti became a founding engineer<\/a> for the financial technology company Stripe. That made him a centimillionaire, meaning that he could spend more on his campaign than either Chan or Wiener and did not have to curry favor with donors.\u00a0<\/p>\n

Initially, Chakrabarti\u2019s star rose.\u00a0<\/p>\n

He built a field team<\/a> of over 200 canvassers<\/a>, touting it as \u201cthe largest grassroots field campaign San Francisco has ever seen.\u201d\u00a0<\/p>\n

He also spent heavily on digital and television ads to boost his name recognition. \u201cI\u2019m Saikat Chakrabarti,\u201d the ads went. \u201cI left a career in tech to work for Bernie and AOC.\u201d San Franciscans heard the message over and over and over again.\u00a0\u00a0<\/p>\n

In the polling, he appeared to be doing well: They showed him gaining a lead<\/a> over Chan; one<\/a> released by his campaign had him 15 points ahead of her, and within striking distance of Wiener.<\/p>\n

The campaign was feeling confident, but the narrative began to change on April 16, when a reporter from the media outlet Drop Site News caught Ocasio-Cortez in the basement of a Capitol Hill building.\u00a0<\/p>\n

\u201cWhat\u2019s your stance on Saikat? Because you have a close relationship,\u201d he asked.\u00a0<\/p>\n

At this, Ocasio-Cortez launched into a minute-long non-answer<\/a>. \u201cI\u2019m trying to think about the role that I am trying to play more broadly in these things. We\u2019ve got 435 seats in Congress and there is this moment \u2014 not just with this race but with any race \u2014 once you go in it\u2019s like what about this, what about this, what about this one,\u201d Ocasio-Cortez said to the reporter, laughing warily. \u201cI\u2019m one person with a pretty amazing crack, but also lean, team.\u201d<\/p>\n

The video<\/a> went viral, garnering 840,000 views on X and almost 300 retweets. And so did the next video<\/a>, posted four days later, showing Ocasio-Cortez addressing the issue of Chakrabarti again.\u00a0<\/p>\n

\u201cSome people said that you might have personal beef,\u201d the reporter said, asking her about Chakrabarti.\u00a0<\/p>\n

\u201cI\u2019m just not commenting on that race,\u201d Ocasio-Cortez replied briskly, with a polite smile.\u00a0<\/p>\n

Rep. Alexandria Ocasio-Cortez (D-NY), who has yet to endorse her former campaign manager and chief of staff Saikat Chakrabarti in his bid to succeed Nancy Pelosi in representing California\u2019s 11th district, told Drop Site\u2019s Julian Andreone that she is \u201ctrying to think about the\u2026 pic.twitter.com\/A2t9naEMXW<\/a><\/p>\n

\u2014 Drop Site (@DropSiteNews) April 16, 2026<\/a><\/p>\n

The videos \u2014 put out a month and a half before the June election \u2014 set off a swirl of speculation about Chakrabarti\u2019s time as her chief of staff<\/a>. In particular, rumors started that, when he left her office in 2019, Chakrabarti had been forced to step down by Ocasio-Cortez because his confrontational approach against moderate Democrats was damaging her ability to get things done in Congress.\u00a0<\/p>\n

Senior members of Chakrabarti\u2019s team said they were completely blindsided by Ocasio-Cortez\u2019s cold shoulder. They had been certain an endorsement was coming.\u00a0<\/p>\n

Chakrabarti, the staffers said, was in communication with her team and had been thinking about flying to D.C. to meet in person.\u00a0<\/p>\n

Confidence in Ocasio-Cortez\u2019s endorsement was, in fact, part of why they had made his work with her such a central part of the campaign. Ocasio-Cortez was a central part of many of his advertisements and a picture of them together adorned his flyers.\u00a0<\/p>\n

In retrospect, said Rahman, Chakrabarti\u2019s political director, that was a mistake. \u201cThe endorsement would have been a bonus instead of a factor that we had to live and die by.\u201d<\/p>\n

His opponents quickly capitalized. A political action committee supporting Chan sent out mailers about the non-endorsement. And Wiener\u2019s campaign paid for a mass text message to San Francisco voters: \u201cSaikat Chakrabarti is lying to you. He wants you to think AOC endorsed him. She didn\u2019t,\u201d the message said. \u201cHe built his entire campaign on his experience working with her, and she just refused to endorse him. What else is he lying about?\u201d\u00a0<\/p>\n

The non-endorsement from Ocasio-Cortez reinforced the message from the attacks against Chakrabarti: that he was misrepresenting himself and was untrustworthy.\u00a0<\/p>\n

Even before the videos, other missteps had called his character into question.<\/p>\n

One March mailer, paid for by the Wiener-aligned PAC Abundant Future, spoofed a travel postcard, with loopy red letters saying \u201cSaikat Chakrabarti sends greetings from Maryland.\u201d\u00a0<\/p>\n

The mailer pointed to an article<\/a> published by the San Francisco Standard in November 2025, which showed that Chakrabarti had declared a property in Maryland as his primary residence in 2018.\u00a0<\/p>\n

Chakrabarti claimed this was a paperwork mistake and that he bought the home for his parents. But it looked suspicious \u2014 even if he wasn\u2019t living there, perhaps he had been trying to avoid paying California taxes?\u00a0<\/p>\n

Perhaps the most memorable attack, though, was carried out by San Francisco politico Conor Johnston, a Wiener-supporter, who began driving around a van decked out in Chakrabarti\u2019s campaign colors with \u201cSaikat lives in Maryland\u201d written in big block letters on its side.\u00a0<\/p>\n

After the Drop Site video, Johnston added a new accessory to it: a large sign that said \u201cAOC fired Saikat.\u201d<\/p>\n

\u2018I don\u2019t really know who to trust\u2019<\/p>\n

Chakrabarti\u2019s canvassers soon began to hear concerns from voters.\u00a0<\/p>\n

\u201cIt was almost like two phases of the campaign,\u201d said field organizer Julianne Lempert. \u201cPeople could start to feel a vibe shift.\u201d<\/p>\n

While residents still resonated with Chakrabarti\u2019s message, they now had doubts about the man, she said. \u201cThey\u2019d be like, \u2018I love him but now I got this hate mailer and I don\u2019t really know who to trust.\u2019\u201d<\/p>\n

Other doorknockers reported similar encounters, including Sasha Perigo, a longtime worker on progressive campaigns. \u201cPeople were asking a lot of questions at the door that seemed pulled straight from the attack mailers,\u201d she said.\u00a0<\/p>\n

The campaign became concerned that its work was unraveling. It began rechecking with voters who had previously pledged their support.\u00a0<\/p>\n

\u201cWe could tell that we\u2019d lost them,\u201d said Nate Allbee, the lead consultant on Chakrabarti\u2019s team, who ran his canvassing operation.<\/p>\n

\"\"Saikat Chakrabarti talking with his campaign volunteers on election day June 2, 2026. Photo by Zoe Malen.<\/p>\n

Some in the campaign were still hopeful until days before the election that Ocasio-Cortez\u2019s endorsement would come through \u2014 Chakrabarti said he was still in talks with her team. When Representatives Rashida Tlaib and Ilhan Omar, two close allies of Ocasio-Cortez, endorsed <\/a>Chakrabarti in late May, some hoped that would motivate Ocasio-Cortez to jump in.\u00a0\u00a0<\/p>\n

But she never endorsed him, nor did she ever say no. The uncertainty made the campaign unwilling to address the lack of support head on.<\/p>\n

\u201cThis is the most consequential endorsement that we can get ahead of Election Day. We are not going to do or say anything to jeopardize that, no matter what is happening around us, no matter what the attack mailers say, no matter what the press is writing about these videos,\u201d Rahman said of their thinking at the time.\u00a0<\/p>\n

The fallout extended beyond voters.<\/p>\n

\u201cI joined the Chakrabarti campaign because of his supposed imminent endorsements from AOC and Bernie Sanders. Those never came,\u201d said one former staffer, who eventually quit. \u201cIt kind of became clear to me that his campaign was based on a premise that didn\u2019t exist. He said a lot of stuff that he couldn\u2019t back up.\u201d<\/p>\n

The final numbers<\/a> were devastating: In the initial vote drop on June 2, Chakrabarti had around 14 percent of the vote, Chan had 28, and Wiener led with 43. Though the numbers improved to 18 percent by the final tally, the results were clear. Chakrabarti conceded<\/a> early the next day.<\/p>\n

Despite the resounding defeat, folks at Chakrabarti\u2019s election night party at the Chapel stayed upbeat<\/a>, continuing to talk, dance and drink.<\/p>\n

\"FourSaikat Chakrabarti\u2019s campaign supporters on stage during his campaign party after the 8:45 results on June 2, 2026. Photo by Zoe Malen.<\/p>\n

Chakrabarti eventually emerged from backstage and wandered into the crowd bearing a large grin that seemed a bit forced. When he came on stage to speak, the crowd screamed deafeningly. Why weren\u2019t they more upset? Was it naivete? Did his young supporters somehow not realize how total his loss had been?<\/p>\n

Maybe it was hope. A few days after the election, Lempert answered a phone call from Mission Local sounding upbeat. \u201cRight now, I\u2019m at a bonfire with all the volunteers and everyone, planning,\u201d she said. \u201cInitial tears, maybe, but we are like, \u2018Okay, what\u2019s next? How are we going to keep making life better for people?\u2019\u201d<\/p>\n

\u201cThis campaign was never about Saikat specifically,\u201d she added. \u201cIt was about the vision.\u201d<\/p>\n

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