Saikat Chakrabarti had grassroots potential and more money than God. Why did he lose?

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

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’s low name recognition and lack of political experience into assets. 

Despite spending at least $8.8 million, 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’s midterm election; Chan has subsequently received Chakrabarti’s backing, canvassers, and cash. 

So, what happened? 

With such a resounding loss, many factors likely contributed. For one, a key demographic that Chakrabarti courted, young voters, failed to show up at the polls.

The voters who did show up for June’s primary election cast votes that leaned conservative. Among other things, they emphatically shut down a proposal to raise taxes on large businesses.

San Franciscans did not throw their lot in with the upstart firebrand.

Chakrabarti also failed to get the support of any major local political groups, like unions, city politicians or voter guides. 

In conversations with political observers and campaign workers, many also attributed his loss to something else: Voters were initially excited about Chakrabarti’s campaign, but they lost trust in him in the final weeks. 

Senior staffers said that failing to obtain an expected endorsement from Chakrabarti’s former boss, Rep. Alexandio Ocasio-Cortez, was a fatal blow.

“Her non-endorsement,” Chakrabarti said, “was the clear turning point for us.”

Grassroots energy

When Chakrabarti opened his campaign office in July 2025, so many people showed up that they had to run the program twice, cycling in a couple hundred each time, according to Nadia Rahman, who joined as Chakrabarti’s political director in January 2026. 

That excitement was still there months later. In October 2025, more than 1,000 people RSVPed to his launch event at The Chapel, according to his campaign. Some 600 came.  

There was a “pulsating grassroots energy, excitement, momentum about his campaign,” Rahman said. 

Even a year out from the general election, dozens of volunteers were showing up each weekend to canvas for him. 

Energizing his supporters was a message of change.

Chakrabarti sharply criticized the Democratic Party for catering to corporations while failing to make people’s lives better. He spoke forcefully about the need for the United States to apply political pressure on Israel to protect the rights of Palestinians.

A transition to clean energy sources was on his agenda, as well as abolishing ICE, eliminating stock trading by members of Congress, and establishing Medicare for All.

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’s 2016 campaign for president, then as the 2018 campaign manager for Rep. Alexandria Ocasio-Cortez’s Congressional race and later as her chief of staff. 

Locally, however, Chakrabarti had committed an unforced error before his run: He had backed a moderate, Bilal Mahmood, with $10,000 during Mahmood’s run for the San Francisco Democratic Party on a well-funded, tech-backed slate. 

Mahmood subsequently unseated the city’s lone socialist supervisor at the time, Dean Preston, a champion of the city’s 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.

Still, he seemed to gain steam. Chakrabarti’s 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). 

Chakrabarti had the potential to peel away core constituencies from both his opponents — progressives from Chan and YIMBY urbanists from Wiener — but also the potential to end up without enough from either side.

But what made Chakrabarti a contender wasn’t just his politics; it was his money. In his 20s, Chakrabarti became a founding engineer 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. 

Initially, Chakrabarti’s star rose. 

He built a field team of more than 200 canvassers, touting it as “the largest grassroots field campaign San Francisco has ever seen.” 

He also spent heavily on digital and television ads to boost his name recognition.

“I’m Saikat Chakrabarti,” the ads went. “I left a career in tech to work for Bernie and AOC.” San Franciscans heard the message over and over and over again.  

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

‘I’m just not commenting on that race’

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. 

“What’s your stance on Saikat? Because you have a close relationship,” he asked. 

At this, Ocasio-Cortez launched into a minute-long non-answer.

“I’m trying to think about the role that I am trying to play more broadly in these things. We’ve got 435 seats in Congress and there is this moment — not just with this race, but with any race — once you go in, it’s like what about this, what about this, what about this one,” Ocasio-Cortez said to the reporter, laughing warily. “I’m one person with a pretty amazing crack, but also lean, team.”

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

“Some people said that you might have personal beef,” the reporter said, asking her about Chakrabarti. 

“I’m just not commenting on that race,” Ocasio-Cortez replied briskly, with a polite smile. 

The videos, put out a month and a half before the June election, set off a swirl of speculation about Chakrabarti’s time as her chief of staff.

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. 

Senior members of Chakrabarti’s team said they were completely blindsided by Ocasio-Cortez’s cold shoulder. They had been certain an endorsement was coming. 

Chakrabarti, the staffers said, was in communication with her team and had been thinking about flying to D.C. to meet in person. 

Confidence in Ocasio-Cortez’s 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. 

In retrospect, said Rahman, Chakrabarti’s political director, that was a mistake. “The endorsement would have been a bonus, instead of a factor that we had to live and die by.”

His opponents quickly capitalized. A political action committee supporting Chan sent out mailers about the non-endorsement. And Wiener’s campaign paid for a mass text message to San Francisco voters: “Saikat Chakrabarti is lying to you. He wants you to think AOC endorsed him. She didn’t,” the message said.

“He built his entire campaign on his experience working with her, and she just refused to endorse him. What else is he lying about?” 

The non-endorsement from Ocasio-Cortez reinforced the message from the attacks against Chakrabarti: That he was misrepresenting himself and was untrustworthy. 

Even before the videos, other missteps had called his character into question.

One March mailer, paid for by the Wiener-aligned PAC Abundant Future, spoofed a travel postcard, with loopy red letters saying “Saikat Chakrabarti sends greetings from Maryland.” 

The mailer pointed to an article 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. 

Chakrabarti claimed this was a paperwork mistake and that he bought the home for his parents. But it looked suspicious. Even if he wasn’t living there, perhaps he had been trying to avoid paying California taxes? 

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’s campaign colors with “Saikat lives in Maryland” written in big block letters on its side. 

After the Drop Site video, Johnston added a new accessory to it: A large sign that said “AOC fired Saikat.”

‘I don’t really know who to trust’

Chakrabarti’s canvassers soon began to hear concerns from voters. 

“It was almost like two phases of the campaign,” said field organizer Julianne Lempert. “People could start to feel a vibe shift.”

While residents still resonated with Chakrabarti’s message, they now had doubts about the man, she said. “They’d be like, ‘I love him, but now I got this hate mailer and I don’t really know who to trust.’”

Other doorknockers reported similar encounters, including Sasha Perigo, a longtime worker on progressive campaigns. “People were asking a lot of questions at the door that seemed pulled straight from the attack mailers,” she said. 

The campaign became concerned that its work was unraveling. It began rechecking with voters who had previously pledged their support. 

“We could tell that we’d lost them,” said Nate Allbee, the lead consultant on Chakrabarti’s team, who ran his canvassing operation.

Some in the campaign were still hopeful until days before the election that Ocasio-Cortez’s endorsement would come through. Chakrabarti said he was still in talks with her team.

When Representatives Rashida Tlaib and Ilhan Omar, two close allies of Ocasio-Cortez, endorsed Chakrabarti in late May, some hoped that would motivate Ocasio-Cortez to jump in.  

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.

“This 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,” Rahman said of their thinking at the time. 

The fallout extended beyond voters.

“I joined the Chakrabarti campaign because of his supposed imminent endorsements from AOC and Bernie Sanders. Those never came,” said one former staffer, who eventually quit. “It kind of became clear to me that his campaign was based on a premise that didn’t exist. He said a lot of stuff that he couldn’t back up.”

The final numbers 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 early the next day.

Despite the resounding defeat, folks at Chakrabarti’s election night party at the Chapel stayed upbeat, continuing to talk, dance and drink.

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’t they more upset? Was it naivete? Did his young supporters somehow not realize how total his loss had been?

Maybe it was hope. A few days after the election, Lempert answered a phone call from Mission Local sounding upbeat.

“Right now, I’m at a bonfire with all the volunteers and everyone, planning,” she said. “Initial tears, maybe, but we are like, ‘Okay, what’s next? How are we going to keep making life better for people?’”

“This campaign was never about Saikat specifically,” she added. “It was about the vision.”