How Indian-American Saikat Chakrabarti became AOC’s chief of change


On a Wednesday morning in late May, emissaries of two of the strongest political voices on climate change convened at a coffee shop a few blocks from the U.S. Capitol. Saikat Chakrabarti, chief of staff to Rep. Alexandria Ocasio-Cortez, D-N.Y., was there to meet Sam Ricketts, climate director for Washington Gov. Jay Inslee, D, who is running for president almost exclusively on a platform of combating global warming.

Saikat Chakrabarti, Ocasio-Cortez’s chief of staff, in the Cannon House Office Building in Washington, D.C., in June. (Photo for The Washington Post by Mary F. Calvert)

A newly released plank of Inslee’s climate change agenda had caught the attention of Chakrabarti and his boss, who had tweeted that Inslee’s “climate plan is the most serious + comprehensive one to address our crisis in the 2020 field.”

Pleased by the positive reception from the demanding Green New Deal wing of the climate struggle, Ricketts had set up this meeting with Chakrabarti to establish a personal connection and share approaches to climate advocacy.

“Congrats on the rollout,” Chakrabarti told him as they sat down. “That was pretty great.”

“Thank you again for the kudos you guys offered,” said Ricketts. “We wanted to be pace-setting for the field, and I think we’re there now. . . . I want to ask you for input . . . in addition to hearing what you guys are working on.”

Chakrabarti had an unexpected disclosure. “The interesting thing about the Green New Deal,” he said, “is it wasn’t originally a climate thing at all.” Ricketts greeted this startling notion with an attentive poker face. “Do you guys think of it as a climate thing?” Chakrabarti continued. “Because we really think of it as a how-do-you-change-the-entire-economy thing.”

“Yeah,” said Ricketts. Then he said: “No.” Then he said: “I think it’s, it’s, it’s, it’s dual. It is both rising to the challenge that is existential around climate and it is building an economy that contains more prosperity. More sustainability in that prosperity – and more broadly shared prosperity, equitability and justice throughout.”

Chakrabarti liked the answer. “The thing I think you guys are doing that’s so incredible is . . . you guys are actually figuring out how to do it and make it work, the comprehensive plan where it all fits together,” he said. “I’d love to get into a situation where everyone’s trying to just outdo each other.” But Chakrabarti couldn’t help adding: “I’ll be honest, my view is I still think you guys aren’t going big enough.”

Ricketts seemed unfazed by the critique. “Well, you know, we’re not done. When it comes to a nationwide economic mobilization, there’s more to come on this front, for one. And other key components we’re going to be rolling forward speak to some of the key justice elements of this . . . ensuring every community’s got a part of this.”

Nationwide economic mobilization. Justice. Community. Ricketts kept laying down chords in Chakrabarti’s key. It was an acknowledgment of just how far inside establishment Washington the progressive movement has reached. Everything is intersectional now – including decarbonization.

Ocasio-Cortez’s priorities and approach offer the purest expression of the progressive movement in Congress. And as her gatekeeper and chief of staff – the COS to AOC – Chakrabarti is a new type on Capitol Hill: the movement chief of staff. It’s what you become when your boss is invested with the hopes of millions of Twitter followers and painted with the prejudices of countless haters. Your job involves both scheduling for the next week and planning for the ages.

Chakrabarti played a major role in helping to produce the Green New Deal resolution introduced by Ocasio-Cortez and Sen. Edward Markey, D-Mass., in February 2019. (Photo for The Washington Post by Mary F. Calvert)

“I like to show my cards and see people’s reactions,” Chakrabarti told me after we left Ricketts. “I just wanted to get a sense of where they’re coming from. . . . They seem open and hungry and want to do stuff. . . . In my mind, an ideal situation is we have a president surrounded by a bunch of people who are constantly thinking how could we go bigger, bolder, faster, better on everything. . . . I don’t know if Inslee’s going to be president, but if he runs a really good campaign, maybe he ends up running a big agency. What’s the mind-set he’s going to bring to that agency?” Coffee with Ricketts was a way of peering over the political horizon – which is exactly what a movement chief of staff wants to do.

Almost as remarkable as the rise of Ocasio-Cortez has been Chakrabarti’s trajectory. When we met, Chakrabarti, 33, arrived with his customary backpack and white button-down shirt stretched over a torso that has spent a lot of time in a gym. Because I was interested, he began telling the story of how he went from politically disengaged techie to fired-up activist to insurgent insider. He didn’t mention that he also deserves much of the credit for recruiting AOC to run in first place.

“To me, there wasn’t a difference between working for her and working for the movement as a whole,” he said. “The whole theory of change for the current Democratic Party is that to win this country we need to tack to the hypothetical middle. What I think that means is, you don’t take unnecessary risks, which translates to: You don’t really do anything. Whereas we’ve got a completely different theory of change, which is: You do the biggest, most badass thing you possibly can – and that’s going to excite people, and then they’re going to go vote. Because the reality is, our problem isn’t that more people are voting Republican than Democrat – our problem is most people who would vote Democrat aren’t voting.”

The son of immigrants from India, Chakrabarti grew up in Fort Worth, Texas. He graduated from Harvard with a computer science degree and went to work on the tech side of a hedge fund in Connecticut. After saving enough money to start his own company, he moved to San Francisco in 2009 and co-founded Mockingbird, a Web design tool.

In 2011 he became one of the earliest employees of Stripe, the online payments platform. Chakrabarti and Ross Boucher, one of his colleagues on the Stripe product team, would work 70-hour weeks, eat dinner every night in the office, then go work out. “He’s someone who actually cares about the thing being done and not whatever credit he might get,” Boucher told me. “He’s interested in the outcome, and doing the work.”

At first Chakrabarti shared the idealism of those lured to the Bay Area to change the world through tech. But San Francisco was a shock. “You see, like, holy crap, is this the dystopian future we’re signing up for?” he says. “I mean, it’s just huge amounts of wealth and some very rich people, and then just poverty and homelessness very visually and very viscerally. That was a lot of why I ended up quitting Stripe. I loved the people I worked with – I just didn’t feel like I was actually solving any real problems. And I wanted to figure out how to do that. And you know, yes, climate change is an existential threat, but there’s also kind of this existential issue of why is it that as our society is progressing . . . things seem to be regressing and getting worse for a large number of people? Why is that happening? How do we fix that?”

Initially, he doubted the answer lay in political engagement – a learned cynicism, he thinks, of his generation having grown up watching wars, recession and bank bailouts. “We’ve only ever seen the establishment win,” he says. What changed his mind was the enthusiastic mass reaction to Bernie Sanders’ campaign four years ago. He contacted Zack Exley, a senior Sanders adviser, and said he’d do anything to help. Exley was in charge of the campaign’s distributed organizing team, which was trying to use the Internet to harness the tremendous volunteer energy.

“He saw how our organizing worked, and he was able to imagine the [software] tools that we needed and just build them himself,” Exley told me. “He was just a super-humble, super-level-headed guy. I always used to joke that he was the only emotionally healthy person in politics.”

In the spring of 2016 – even before Sanders conceded the primary race – Chakrabarti, Exley and other Sanders organizers, including Alexandra Rojas and Corbin Trent, were thinking of next steps for the movement. To enact change, they reasoned, it was vital to transform Congress. They formed a group called Brand New Congress with the mission to recruit hundreds of community leaders and working-class candidates to run on a vision of getting corporate money out of politics, tackling climate change, transforming the economy, providing health care for all, standing for racial justice and stemming mass incarceration. They sifted through more than 10,000 nominations to find the best recruits. “Our biggest criteria was, basically, find someone who had a chance to sell out and didn’t,” Chakrabarti says.

Ocasio-Cortez, who was then a bartender from the Bronx, was nominated by her brother. It was Isra Allison, another member of Brand New Congress, not Chakrabarti, who had a key initial recruiting interview with her. But Chakrabarti drove the overall effort. In the recent Netflix documentary “Knock Down the House,” which follows four of the candidates, Chakrabarti can be seen declaring to a gathering of the recruits, including Ocasio-Cortez, “We actually want to create that grass-roots-funded machine that can be a real opposition to the current institutional powers.”

Nasim Thompson, who also helped recruit candidates, told me: “It was clear from the very beginning that the ship was moving with his guidance. . . . He was so focused that it naturally created a gravitational pull. . . . He was sort of relentless in that, and simultaneously just so pleasant, it was shocking. Almost not human. I used to say, ‘How do you stay so Zen?’ ”

In the end, the project “was a spectacular failure,” Chakrabarti tells me, laughing. They managed to recruit only a dozen candidates because, as it turned out, many good people doing strong community work didn’t see the point of running for Congress. Of the 12, only one won: Ocasio-Cortez. Chakrabarti ended up helping to manage Ocasio-Cortez’s campaign, while Trent handled media and Rojas worked on field operations. Under the auspices of a new group, Justice Democrats, also co-founded by Chakrabarti, they endorsed dozens more, including progressive winners such as Reps. Ilhan Omar of Minnesota, Ayanna Pressley of Massachusetts and Rashida Tlaib of Michigan.

“It was a total failure, but we also had no idea that one or two victories would have as much of an earth-shattering impact like AOC’s victory did,” Chakrabarti says. “It was a learning experience to find out that Alexandria, but also Ilhan, Rashida and Ayanna, just by being strong leaders within Congress and continuing to act the way they did during the campaign, to a large extent, can actually move stuff so fast and so massively and so big. . . . One of my favorite things Alexandria said recently was: We’re not just changing the Democratic agenda, we’re changing the Republican agenda. Because now there’s Republicans putting out climate plans.”

Trent has joined Chakrabarti inside Ocasio-Cortez’s office, as communications director, while Rojas and Thompson remain on the outside, as executive director and candidate recruitment director, respectively, of Justice Democrats. The movement now has an inside game, as well as an outside game. “That’s what building power looks like,” Thompson says.

After she was elected, Ocasio-Cortez said in a video to recruit a new crop of Justice Democrats: “I’ve literally been movement-first and accountable to social movements the entire time I’ve been running for office.” The office Chakrabarti manages in the Cannon Building operates in that spirit.

“We think of ourselves as an office that’s . . . a component to a larger infrastructure,” he says. “Literally, our mission statement in the office talks about what do we, as a movement, want to do in the long run, and that’s how we set our goals.” A draft of the mission statement brainstormed at a staff retreat begins: “To boldly and decisively spur a people-led movement for social, racial, environmental and economic justice.”

Not everything has run smoothly. Chakrabarti played a major role in helping to produce the Green New Deal resolution introduced by Ocasio-Cortez and Sen. Edward Markey, D-Mass., in February. Yet the measure’s rollout was marred by an FAQ that included controversial language not in the resolution, such as providing economic security to those “unwilling to work.” Conservative critics gleefully pounced. “An early draft of a FAQ that was clearly unfinished and that doesn’t represent the GND resolution got published to the website by mistake,” Chakrabarti wrote on Twitter. “Mistakes happen when doing time launches like this coordinating multiple groups and collaborators.”

In March, meanwhile, a conservative group filed a complaint with the Federal Election Commission highlighting more than $1 million paid by Brand New Congress and Justice Democrats to a corporation set up by Chakrabarti. Chakrabarti and an attorney for the groups said none of the money went to Chakrabarti but was to support the multiple campaigns seeking to transform Congress.

On a typical day in late May, Chakrabarti’s schedule is split between conventional management chores and tending to the movement. In a room with the rest of the staff, he sat at a desk that he has not had time to decorate with photos or anything personal. On his computer, Chakrabarti showed me the automated system he programmed to process the overwhelming volume of requests for Ocasio-Cortez’s time. Work in the office paused occasionally to watch Ocasio-Cortez on television questioning witnesses at a hearing on facial recognition technology.

After meeting with Ricketts and attending a briefing on caste prejudice in America, Chakrabarti was visited by a class of political communications students from Syracuse University. They quizzed him on the office’s social media strategy. “If this was a newsroom, she’s our editor in chief,” he said. “We’re constantly trying to find interesting frames we can take to connect issues that don’t usually get connected.”

He added: “It’s not just a media strategy, but the office strategy boils down to: Where do we actually want to see the world move to and the country move to . . . and how do we get from here to there?”

Chakrabarti grew up in Fort Worth and was a politically disengaged techie in San Francisco before becoming involved in politics, first with Bernie Sanders’ 2019 presidential campaign. (Photo for The Washington Post by Mary F. Calvert)

Chakrabarti is a student of America’s past economic mobilizations in the face of crisis, such as Franklin Roosevelt’s original New Deal during the Great Depression, and the industrial retooling necessary to build the material to win World War II. In my conversations with him and in the conversations I watched him have with others, he often circled back to one of his core convictions, which is that voters really will turn out for bold ideas scaled big enough to tackle today’s crises of climate and inequality. What he needed – what the movement needed – was more data to convince skeptics, especially centrist Democrats.

Later that afternoon, he walked to a park near the Capitol for a pair of conference calls with pollsters. As Hill worker bees in blazers and blouses bustled past, he sat on a bench and kicked around a calculus of change with those on the calls. “The basic argument of the progressive wing versus the centrist wing of the Democratic Party right now is the centrists think the way to win is tack to the middle, try to convince Republicans,” he said on the first call. “Progressives think the way to win is mobilizing and convince people to vote for something. So how do you actually test that hypothesis before the actual election?”

The idea under discussion would be to go into swing districts held by centrist Democrats and survey views on progressive proposals, such as Medicare-for-all, pieces of the Green New Deal, caps on credit card interest rates. It would be a rigorous analysis, with the ideas matched against counterarguments and also tested for their potential to motivate people to vote. The results would be shown to reluctant representatives, to get them onboard.

“Part of it is about pressuring these congresspeople and presidential candidates to go big, but also giving them the cover to do so,” Chakrabarti said to me between calls with the pollsters. “How do we help people develop a bit more of a backbone?”

It seemed to me that Chakrabarti’s worldview is founded on his utter certainty not just that the progressive vision is good for America – but that it is what most Americans actually want. Yet what if he is wrong?

After the calls, I asked him what happens if the polling shows the centrists are correct – that these ideas are too much, too fast, for most folks. “I don’t want it to be false propaganda,” he said. “So if it turns out that our hypothesis is wrong, that just means we need a different strategy. . . . If the answer is no, then I think the strategy would be: OK, how do we reach the people in their district in a different way to present the ideas and try to persuade people that these are good ideas.”

He paused for a long moment and then added drolly: “And, you know, if after everything, it turns out we’re just totally wrong, then hopefully I’ve been convinced of the error of my ways.”



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