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After Democrats lost the White House, the Senate, and the House of Representatives in last year’s election, Saikat Chakrabarti waited for the party’s leaders to acknowledge — if not address — their mistakes.
“I was sort of expecting the Democrats to have a big realization that, ‘Oh my Gosh. We did something wrong. We’ve got to figure out what that was,’” he tells Rolling Stone. “Especially when they’re confronted with the fact that Trump increased his vote share amongst a bunch of working-class coalitions and demographics.”
Instead, just days after the election, he listened to his representative in Congress, former Speaker Nancy Pelosi, do a podcast interview with The New York Times where she argued against the idea that the American electorate had rebuked the Democratic Party.
“She basically made the case for how the Democrats don’t really need to change,” Chakrabarti says. “You know, that they ran a great race, did their best, and nothing needs to change. That was the first warning sign to me. I really feel like the Democrats actually need to become a party that’s fighting tooth and nail for the working class and middle class right now.”
Chakrabarti is no stranger to American politics, especially those of insurgents. The 39-year-old tech millionaire, who was a founding engineer at Stripe, first entered politics by working on Sen. Bernie Sanders 2016 presidential campaign. He then went on to help start Justice Democrats, a progressive PAC, before working as Rep. Alexandria Ocasio-Cortez’s chief of staff.
Two months after hearing that Times interview, Chakrabarti watched as President Donald Trump came into office and began delivering on the far-right agenda he promised his supporters.
“My second concern right now is that Trump is sort of doing the coup that he’s been promising he’s going to do all through the election, that the Democrats warned us he was going to do all through the last election,” he said.
Chakrabarti said the muted Democratic response to Trump’s actions so far quickly made him realize, “Oh the Democrats actually don’t get it.”
He views their overall plan as waiting to rely on growing backlash to Trump and hoping the pendulum swings back in their favor so they can secure some sort of victory in the 2026 midterms or 2028 general election.
“I really believe at the end of the day, for most people in America, their lives have just been getting harder and harder,” he said. “Wages have been stagnating or barely creeping up for decades. The big expenses — housing, health care, education, child care — that stuff has been skyrocketing in cost. And the combination of these two factors has made people feel stuck for a long time. It’s making people feel like their kids are not going to have a life that’s as good as theirs, or their life’s not going to be as good as their parents.”
That feeling of stagnation and decline, Chakrabarti said, has led people to vote for change candidates in most presidential elections since 2008.
If the Democrats can’t counter with an actual transformative economic vision, Chakrabarti predicts that even if the pendulum may swing back their way next time, it will likely swing back toward Republicans the time after that, with even more extreme results.
That’s why he says he decided to primary Pelosi, who led Democrats in the House of Representatives for two decades, in California’s 11th congressional district. (Pelosi has since passed the torch to Hakeem Jeffries.)
“Leadership doesn’t know how to act right now tactically to stop the coup, and leadership doesn’t know or doesn’t believe that we should even have any sort of a vision to pitch to Americans for how to make their lives better,” says Chakrabarti. “And, actually, I don’t even know if they believe everything I was just saying about how, for most Americans, their lives have been getting harder and harder.”
Despite his critiques of the party and its leaders — he says explicitly that the current leadership team is not the right leadership — Chakrabarti is still quick to state how respects Pelosi’s service and accomplishments.
“I’ve talked to so many people in San Francisco now who respect Nancy Pelosi for her career, and the glass ceiling that she shattered, but they can’t believe she’s running again,” he said. “They really feel like it’s time for something new.”
Rising anger at Democratic leaders for failing to stand up to Trump is beginning to generate conversations about a potential Tea Party-esque anti-incumbent movement on the left. As such, Chakrabarti believes Democratic voters are more open to somebody new, and to change more broadly, than they would have been even two or four years ago.
Nonetheless, Chakrabarti knows this is not going to be an easy race — which he says is why he announced his campaign so early. Pelosi is a fundraising powerhouse with national name recognition and has been serving in Congress for nearly four decades.
Chakrabarti sees the length of her congressional career as a liability.
“When Nancy Pelosi first got the seat back in 1987, that was when I was one-years-old,” he says. “You could rent a place in San Francisco for a few hundred bucks a month.”
He also points out that at that period of time, the gulf between mainstream Republicans and Democrats on major issues was often much more narrow than it is today, and the overall tenor in Congress was much less polarized.
“I think Nancy Pelosi and a lot of Democrats from that generation, they grew up in that political environment, and so, they still believe any day now their Republican colleagues are going to come around and they’re going to come to their senses,” he says.
All of this, Chakrabarti argues, has left many of the Democratic leaders, including Speaker Pelosi, as being “completely out of touch” with the realities of the political environment we find ourselves in today.
Pointing to the Iraq War, the 2008 financial crash, and both of Trump’s presidential victories, Chakrabarti says many people in his generation have grown up with America’s politicians and democratic institutions failing them over and over again.
“We sort of grew up in this era where the adults in the room were shown not to have any idea what to do,” he says. “And then when we asked them ‘What’s your plan? How do we actually get out of this mess?’ they’ve got no ideas.”
The only way forward, for Chakrabarti, is massive transformational change.
To make that argument, he harkens back to the 1930s when President Franklin Delano Roosevelt, who was also politically battling against an authoritarian far-right, defeated their movement for decades by improving the lives of everyday Americans through the New Deal’s expansion of the social safety net.
“That’s what we need to be doing now,” Chakrabarti states before laying out a list of policy priorities — including universal guaranteed health care, raising the minimum wage, and making childcare affordable.
Beyond that, he says the bigger piece of what FDR did that often gets missed is that through a mobilization for World War II, America built up and expanded its massive industrial base.
He sees the modern day version of that as being the response the United States could be having to climate change.
“There’s this transition that’s happening globally, with or without us, towards clean technology,” he said. “It’s a $100 trillion global transition that’s going on, and it would be absolutely insane for us not to be a big part of that.” Trump, of course, wants to remove the United States from that clean energy transition.
Chakrabarti is desperate for a wave of leaders who will send the country on a shared mission to fight the climate crisis the same way FDR sent the country on a mission to both win World War II and defeat the Great Depression.
“I think Democrats need to really transform people’s economic lives, not just make people a few extra bucks,” he says.
He continues: “We need people to run all across the country who are interested in a sort of a transformative economic vision. Right now, I’m in a place where I’m just calling for people to run and to get in touch with me.”
To that end, his campaign website has a “Run With Me” tab, where he is trying to recruit and build a progressive wave.
His vision is to have a presidential candidate who runs in 2028 on a big vision who is backed up by dozens, if not hundreds, of people running for Congress on this shared vision.
“We need something new,” Chakrabarti says.
