It’s the end of an era. Rep. Nancy Pelosi, D-Calif., who counts among her legacies in Congress successfully undercutting the push for Medicare for All, announced last week that she is retiring from Congress. The two-time former speaker of the House made her announcement after Democrats made remarkable gains in nationwide elections, campaigning on affordability and standing up to the Trump administration.

“We are in this era where we need new ideas, we need new leaders, we need people who are going to push the party in a new direction,” says Saikat Chakrabarti, who is running to replace Pelosi and represent San Francisco in Congress, making economic inequality and corporate power the focal point of his politics. This week on The Intercept Briefing, host Akela Lacy speaks to Chakrabarti, the co-founder of the progressive outfit Justice Democrats who helped run the primary campaign of one of its first candidates, Rep. Alexandria Ocasio-Cortez, becoming her first chief of staff.

Answering Lacy’s question as to how he’ll get it done, Chakrabarti says, “In the 1930s, we had a really powerful, far right in this country. We were actually seeing Nazi rallies in Madison Square Garden, it was filling the stadium. And the way we defeated that was FDR came in with the New Deal movement. He built this whole new economy and a whole new society that improved people’s lives so dramatically, it just killed this idea that you need an authoritarian to do it for you.” FDR “wasn’t advocating for going back to a pre-Great Depression era. He was advocating for something new. So that’s the way we get it done, and I see some movement towards that.”

Chakrabarti has been openly calling for House Minority Leader Hakeem Jeffries, D-N.Y., to be primaried and tells The Intercept that Senate Minority Leader Chuck Schumer should be too, following the end of the longest government shutdown in U.S. history, after eight Democratic senators — none who are up for reelection — joined forces with Republicans to pass a spending package.

“My goal, honestly, is to replace a huge part of the Democrat establishment,” says Chakrabarti. “I’m calling for primaries all across the country. … I think we actually have to get in there and be in a position of power where we can do all that, so it’s not going to be this constant compromising with the establishment, trying to figure out how we can push.” He adds, “I tried the pushing strategy — that’s what Justice Democrats was: We were trying to elect people to try to push the Democratic Party to do the right thing. It’s not going to work. We have to replace them.”

Listen to the full conversation of The Intercept Briefing on Apple Podcasts, Spotify, or wherever you listen.

Transcript

Akela Lacy: Welcome to The Intercept Briefing, I’m Akela Lacy.

It’s the end of an era.

Nancy Pelosi: I will not be seeking reelection to Congress.

AL: U.S. Representative Nancy Pelosi, who counts among her legacies in Congress successfully undercutting the push for Medicare for All, announced last week that she’s retiring from Congress. The Democrat and two-time former speaker of the House represents one of the country’s most liberal districts: San Francisco, California. And she has done so for nearly 40 years.

Pelosi made her announcement after Democrats made remarkable gains in nationwide elections. One takeaway, as we discussed in last week’s episode, is that voters want leaders who will fight for affordability and stand up to the Trump administration.

The race to replace Pelosi began before she publicly shared that she would not run for reelection. And although the California primary is seven months away, it’s already looking like a crowded and competitive field.

Saikat Chakrabarti was the first to jump into the race for Pelosi’s seat, setting up a challenge from her left.

Chakrabarti co-founded the progressive outfit Justice Democrats and helped run the first campaign and office of one of its first candidates: Rep. Alexandria Ocasio-Cortez.

He’s running on a campaign promising to push for universal health care and child care, enact a stock trading ban for members of Congress, cost-of-living issues, and to “stop funding the genocide in Gaza.”

He’s also criticized some of his colleagues in the progressive movement. So how is he positioning himself amid a wave of other primary challengers? And how would he actually fulfill his campaign promises? Saikat Chakrabarti joins me now. Saikat, welcome to the Intercept Briefing.

​​Saikat Chakrabarti: Hey, thanks for having me.

AL: ​​Saikat, you’ve been described as a bit of a contradiction. You’re independently wealthy; you’re a founding engineer at the payment processing company Stripe; and Business Insider has said, you may be wealthier than Nancy Pelosi, one of the wealthiest members of Congress.

You’ve also made economic inequality and corporate power the focal point of your politics. You ran Alexandria Ocasio-Cortez’s campaign, became her first chief of staff, and co-founded Justice Democrats.

Most tech millionaires aren’t necessarily also progressive anti-establishment politicians. How do those two identities fit together for you?

Most tech millionaires aren’t necessarily also progressive anti-establishment politicians. How do those two identities fit together for you?

SC: I’d say most tech millionaires are really working toward their own demise as well in the long run. Because, I mean, look, I’ll give you my whole background. I grew up middle class in Texas. I grew up going to public schools. My parents actually grew up fairly poor. My parents are from India. They immigrated here in the 1970s, and my dad was a victim of partition, which was a catastrophic event — we basically split up India along religious lines after the Indian Revolution. And so his family were refugees that had to flee overnight from Bangladesh over to India. And so I grew up with the stories of their struggles. My dad grew up with a family of 12 in a one-bedroom apartment, often didn’t know where his next meal would be coming from.

“The way our economy is set up and has been set for so long is a lottery.”

I’d say my values really come from that — in two ways. Like one, it’s both these values that are shaped by how hard people who are totally capable have to actually work when they get a bad plate handed to them in life. But also just the way our economy is set up and has been set for so long is a lottery. Because at the end of the day, my dad struggled, but he won a lottery ticket; he got a visa to come to America. And I go back to Calcutta and I meet his friends and his family who all had it just as hard or just as hard-working, just as capable people who never made it out.

And so I joined the tech industry back in 2007, or 2009, actually, after college. And it was a time when tech really was being pitched as a solution to a lot of the big problems in the world. I was a completely apolitical person, and I bought it. I did think I was going in to try to solve some big issues. At the time like Muhammad Yunus was doing microfinance to alleviate poverty, yada, yada. And living in San Francisco and seeing unhoused people on the streets while I’m going to my tech job — it just gave me the feeling that maybe I’m actually not solving the problems I really want to work on.

So it sounds really cheesy now, but I quit the tech industry and I wrote a list. I was like, I want to work on inequality, poverty, and climate change. Again, I was not political at all — I was looking at mainly working in nonprofits. And that was around the time Bernie Sanders started running for president. I didn’t know if he had all the answers, but he was talking about those things in a very compelling way.

And so I joined that, and I ended up working on the Bernie campaign. I started a group — Justice Democrats — to recruit people to run on progressive values all around the country. And that’s how I ended up recruiting AOC to run, and ran her campaign, and ended up as her chief of staff.

“I worked hard, but I did not work harder than a teacher or a nurse or the people cleaning our offices did every single day. I just won the startup lottery.”

But I really believe at the end of the day, like a fundamental thing — and this is why I don’t think it is a contradiction — I experienced that lottery economy, that the startup economy really is in San Francisco. It’s this system where you can just hit it big if you just happen to be in the right place at the right time.

That’s what happened to me. And like I worked hard, but I did not work harder than a teacher or a nurse or the people cleaning our offices did every single day. I just won the startup lottery — and that to me is wild to have an economy set like that where you can just win a lottery and never have to work again.

While most people actually running society, working hard to run society, we’re saying, “You’re never going to be able to afford a house. You’re never going to be able to have a secure retirement.” I think a society and economy set up like that is doomed to fail. I think that is the ultimate demise of America.

And I’d say to people who are in my position, who have wealth, who don’t see it that way, who aren’t willing to just accept some taxes on themselves to make an economy that actually works for everybody — you’re being shortsighted because this won’t end up good for you either, if you end up in a society that’s a complete dystopia, that’s completely unequal.

“You’re being shortsighted because this won’t end up good for you either, if you end up in a society that’s a complete dystopia.”

AL: Speaking of the people on whose backs the society runs, as we’re speaking, the longest government shutdown ever is on the verge of ending after eight Democratic senators decided to join forces with Republicans to pass a spending package.

For years, you’ve been critical of Democrats, saying they’re too weak, too compromising, too establishment. Do you think they should have ended the shutdown without a healthcare guarantee?

SC: No. I mean, this has been my main critique of the party for so long. A lot of my critique is on the policies and what they actually want to do and what they want to stand for.

“ Strategically, they preemptively cave.”

But a big part of my critique is, strategically, they preemptively cave, and this was a prime example of that. I mean, not through any leadership by Schumer or Hakeem Jeffries, but we were actually winning on this fight. And it’s not like, I don’t think this is a political fight. We were actually fighting for once to deliver something real for people who are suffering in this economy right now.

This economy sucks, and we’re talking about doubling or tripling people’s health insurance premiums in the middle of this, right? So Democrats were winning that messaging. You saw it in the polling, you saw public sentiment on the shutdown going towards Democrats. And then we’re coming off the back of a massive electoral victory last Tuesday where Donald Trump actually went on TV and said, you know, he was saying part of that was because Republicans were losing the messaging on the shutdown fight. So, I mean, call me naive but honestly, I thought like, “OK, finally we have the leverage, we have the upper hand. Maybe Democrats will realize they can push.”

So watching them cave, I mean, oh my God, why? Like, why? You’re winning. You could have actually delivered something and then you could have gone into the next election and said, “We fought Trump and we won.” Because right now, I think the main reason people don’t want to vote for Democrats — part of it’s the policy, but part of it’s, they’re weak! Do you want to vote for people who aren’t going to get shit done for you? No. So this just proved, I think, that image to a bunch of people.

“I’m not seeing Democrats go out there and persuade the public in the way that I saw Dick Cheney and George Bush persuade the public to go to war in Iraq, which was an actually an unpopular thing to do.”

So no, they absolutely should have kept fighting. I think they could have won. And honestly, my opinion, if we had seen Hakeem Jeffries and Schumer and some of the Democratic leaders actually fighting way more — because my big critique of this whole fight was, I’m not seeing it be front-page news every single day. I’m not seeing Democrats go out there and persuade the public in the........

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