Bernie Sanders wanted a “revolution.” He ended up sparking a civil war inside the Democratic Party.
When the Vermont senator launched his first presidential bid in April 2015, he said it was designed to take on two major targets; the “immoral” and “unsustainable” economic system where “the top one percent owns almost as much wealth as the bottom ninety percent” and a “political situation where billionaires are literally able to buy elections and candidates.”
Sanders knew his mission was dicey. At his very first announcement, he openly wondered whether it would even be possible for a candidate who railed against the rich and corporations to succeed in a time when presidential campaigns typically cost over a billion dollars and relied on wealthy backers. Sanders also alluded to the fact that, as an avowed socialist and the longest serving independent in Congress, he was operating outside of the two-party system that had dominated American elections for over a century.
“You are looking at a guy—indisputably—who has the most unusual political history of anybody in the United States Congress,” Sanders said to the small throng of reporters and curious onlookers who came to see his first announcement on a lawn outside the US Capitol.
However, the idea that a grumpy socialist in rumpled suits who relied on small-dollar donors could catch fire and shock the country’s corporate establishment turned out not to be the most audacious aspect of Sanders’s campaign. Sanders, who had caucused with the Democrats since he entered the Senate in 2007 but was not technically a party member, was trying to wrest the Democratic nomination from the party’s leadership without throwing a punch.
At his announcement, the reporters pressed Sanders to criticize Hillary Clinton, who was widely seen as President Obama’s chosen successor and the choice of the party elite. Sanders declined. He stressed that he detested “ugly thirty-second ads and vigorous personal attacks.”
“I believe that, in a democracy, what elections are about are serious debates over serious issues, not political gossip, not making campaigns into soap operas,” Sanders said.
Despite starting with those lofty aspirations, less than eight months later, before the voting even had begun, the Sanders campaign was feuding with Clinton’s camp and the Democratic National Committee over debate scheduling and access to voter data. One late 2015 dispute saw the party committee lock Sanders’s team out of some of its own files. The move led Sanders’s campaign manager, Jeff Weaver, to hold a fiery press conference where he declared the “Democratic establishment” was engaged in “a heavy-handed attempt to undermine this campaign” in order to have a “coronation” for Clinton.
Amid the conflicts, Sanders put aside his initial reluctance to engage in arguments outside of the policy realm. Once the primary voting began in the first months of 2016, Clinton pulled ahead and Sanders himself described the race as unfair. He suggested that the DNC chair, Florida congresswoman Debbie Wasserman Schultz, needed to be removed and that the party needed to change its direction.
“Frankly, what the Democratic Party is about is running around to rich people’s homes and raising obscene sums of money from wealthy people,” Sanders said in a late May 2016 interview with CBS. “What we need to do is to say to working-class people—we are on your side.”
Sanders had also begun to attack Clinton more directly. He criticized her on issues of criminal justice, on economics, on her past remarks that he said were “racist”—a strategic shift his advisers credited with achieving his late victories, particularly in Michigan, and prolonging the primary. Clinton fired right back.
The fight cracked a deep rift down the middle of the Democratic Party that led to ugly scenes at the national convention in July 2016. An email hack linked to Russian intelligence spilled the DNC’s private communications into public view just ahead of that gathering, where Sanders was set to formally cede the nomination to Clinton. The trove of messages revealed Wasserman Schultz and her aides mocking Sanders’s team, rejecting an offer to schedule an extra debate, and considering sending reporters negative narratives about Sanders’s campaign operation. Sanders supporters reacted by staging loud protests outside the venue and on the convention floor.
Sanders ultimately lost the nomination to Clinton. However, his political revolution didn’t entirely end in defeat. Under pressure from the scandal, Wasserman Schultz resigned as the convention began. The party’s new leadership acceded to several reforms proposed by Sanders and his allies.
In the general election, Donald Trump, a businessman and reality TV star who ran on racially charged attacks on immigrants and minorities, took advantage of the Democrats’ infighting to eke out a narrow victory over Clinton.
Exit polls from multiple news organizations indicated roughly nine out of ten Republicans voted for Trump and roughly nine out of ten Democrats voted for Clinton. In a starkly polarized nation, there was very little crossover. This landscape meant the infighting on the left was likely decisive. The division persisted after Trump took office.
Unlike the Republicans, who emerged from the cataclysmic campaign as, unquestionably, the party of Trump, Democrats came out of 2016 defeated and adrift. Trump’s win had effectively prevented the race from being a definitive referendum on whether Clinton’s politics or Sanders’s should guide the party in the post-Obama era.
With the future of the party in question and the progressive movement galvanized by Sanders’s run, a wave of socialist candidates staged their own battles against Democratic incumbents in the midterm elections two years later. Their most dramatic victory came in New York when Alexandria Ocasio-Cortez, who had been a volunteer on Sanders’s 2016 campaign, took down a Democratic Party boss.
Ocasio-Cortez was not entirely a political neophyte. Before working on Sanders’s race, she interned for the late Massachusetts senator Ted Kennedy, the old liberal lion of New England. However, her insurgency didn’t start with Kennedy or even with Sanders.
It began with her little brother.
Gabriel Ocasio-Cortez enjoyed listening to progressive commentators on YouTube. As the left reeled from Sanders’s 2016 primary loss and Donald Trump’s subsequent victory in the general election, Gabriel watched two prominent digital rabble-rousers, Cenk Uygur and Kyle Kulinski, co-found a new political action committee: Justice Democrats. The group was explicitly designed to carry on Sanders’s mission by recruiting progressive candidates who would reject corporate donations, primary incumbent Democrats, and shift Congress to the left. Gabriel latched onto the idea and nominated his sister for the project.
At the time, Alexandria Ocasio-Cortez was in the midst of a quarter-life transition. She’d graduated from Boston University and returned to New York City stuck in neutral, living in her mom’s old apartment in the Bronx while serving cocktails at a bar in Manhattan. But she was, as anyone who met her could see, a superstar—brilliant, beautiful, engaging, and relatable. All she needed was a spark.
Corbin Trent, who was one of Justice Democrats’ leaders and would go on to join Ocasio-Cortez’s staff, remembered Gabriel’s nomination.
“It got noticed,” Trent said, in an interview for this book.
Justice Democrats fell short in several respects. They fielded far fewer candidates than they had initially hoped and lost almost all their races. Nevertheless, their impact was massive. Ocasio-Cortez won her race. Along with her, the organization also helped elect three other House members—Ilhan Omar, Rashida Tlaib, and Ayanna Pressley. The quartet joined together to form the progressive “Squad.” With just those four victories, Justice Democrats had unquestionably transformed Congress.
Like the candidates they hoped to elect, the leaders of Justice Democrats came from unusual backgrounds. Along with Uygur and Kulinski, the group’s founders included Zack Exley and Saikat Chakrabarti, who met while working for Sanders in 2016. The two campaign aides had started another group, Brand New Congress, as it was becoming clear that Sanders would lose to Clinton. By March 2017, they brought that organization into Justice Democrats.
The group’s operations were led by Chakrabarti, Exley, and Trent. The three had met on Sanders’s “distributed organizing” team, which used digital tools to encourage volunteers to knock doors and make phone calls.
Trent was a self-described “semi-right-winger from East Tennessee.” He initially captured the attention of Sanders’s team with cash.
“We had donation data for Bernie. And for the longest time, Corbin was one of four or five people that maxed out,” recalled Chakrabarti, who was already working for the campaign. “So, we just assumed he was this super-rich heir of some southern billionaire or something.”
That assumption turned out to be a mistake. Trent had grown up just outside the Smoky Mountains and worked in a factory that made furniture parts. That job vanished in the wake of the recession, along with so much of the region’s manufacturing industry. Trent tried to reinvent himself as a trained chef. He went to New York for culinary school and ended up working in some of the most exclusive restaurants in the city and its suburbs.
Trent only had a casual interest in politics, but serving outrageously expensive cuisine to indifferent diners instilled in him a seething class rage. His tipping point came when he poured a thousand-dollar bottle of pinot noir only to watch it go to waste.
“It’s one of my favorite grapes, one of my favorite wines, one of my favorite regions,” Trent said, his drawl speeding into a staccato. “I’m kind of excited about it. I’m telling them about it all.… Then, when I’m clearing the table after a few hours, I notice they didn’t even fucking take a sip of this wine.”
He soon quit his job and returned home to open a food truck. When Trent came back to Tennessee, he found a community that had “collapsed.” Many of his friends and family were using opiates to fill the holes left by the economic downturn. The pill demon would eventually climb onto his back too. Yet as Sanders caught on around the country, Trent saw reasons for hope and threw himself into the campaign.
“When Bernie showed up, he was living in a trailer,” Chakrabarti said of Trent. “He sold his food truck … and basically just used the savings to start driving around Tennessee, just organizing Tennessee, whatever he could do.”
Chakrabarti had assumed Trent’s money flowed from a family fortune, but it was just earned selling street food.
Unlike Trent, Zack Exley actually had political experience prior to working for Sanders. A tall, slender man with windblown white hair, Exley had a résumé that included work on John Kerry’s 2004 White House run and at the progressive organization MoveOn.org. But even as he moved within the more traditional apparatus, Exley longed to subvert it. According to Trent, Exley was “like this mad scientist dreamer” who had pitched the idea of a congressional insurrection within the Democratic Party for years.
Exley had just needed a backer. Now, he had found one. Chakrabarti was a multimillionaire, a coder who left Silicon Valley to hack the political system.
The son of Bengali immigrants, Chakrabarti grew up in Texas. His grandfather was a professor whose work as an engineer at a nuclear power plant paved the family’s path to America. Chakrabarti went to Harvard, where he studied computer science.
After school, Chakrabarti made his way to a hedge fund and, ultimately, to the West Coast where he started his own company before becoming the founding engineer at Stripe, a payments-processing firm. That made him one of the first few employees to earn equity at a business that’s valued at over $50 billion as of this writing.
For Chakrabarti, the startup world was “amazing” because he could create something and see a real impact.
“I’m never going to downplay how much I enjoyed working at Stripe or doing my own company because it’s so much fun to build stuff,” Chakrabarti explained. “You feel like you’re doing something that’s helpful.”
But while he liked starting businesses, Chakrabarti didn’t necessarily enjoy running them. As he put it in an interview, “I wasn’t really the guy to figure out like, you know, corporate culture and how to do management correctly and all that stuff.”
However, after Chakrabarti founded Justice Democrats in the wake of Sanders’s defeat, he and his colleagues would soon be managing a dozen political campaigns all at once.
In early 2017, as Donald Trump was remaking the right in his own image, Justice Democrats set out to build a new left. From its headquarters in Corbin Trent’s home state, Tennessee, the group began trying to build a progressive alternative to the consulting firms, advocacy groups, and alphabet soup of committees at the heart of the Democratic Party apparatus.
With Brand New Congress, Trent, Exley, and Chakrabarti initially sought to back an army of about four hundred candidates who would run for almost every seat in the House.
“We were trying to run in every primary,” Chakrabarti said. “We were going to run people as Republicans, as Democrats, Independents.”
The trio wanted to leverage multiple races to solve what they called the “spotlight problem”—the challenge of getting voters to pay attention outside of a presidential election year. Compared to the high-wattage, eleven-figure frenzy of the presidential election, local and congressional elections are often dimly lit affairs, plagued by low interest and low turnout. Chakrabarti and his team were hoping that operating a slate of hundreds of candidates could turn congressional elections into a similarly big, captivating campaign. Attention was vital because they hoped to counter incumbents backed by the establishment donor network and expensive ads with digital organizing tools like the ones Sanders pioneered and a full-court media press.
“I think those are the only two things that matter,” Trent said.
As Chakrabarti told Rachel Maddow in a 2016 interview, Brand New Congress would be “a single, unified, presidential-style campaign that’s going to look a lot like the Bernie Sanders campaign.” Like Sanders, they were hoping to galvanize an army of small-dollar donors.
It was a grandiose dream that would have to be scaled back multiple times. Their first wake-up call came when the group discovered that, amid the hyperpolarization of the Trump era, they could make no inroads into conservative areas. As the trio of strategists brought Brand New Congress under the umbrella of Justice Democrats, they abandoned the plan to take on the couple hundred staunchly red seats in Congress.
Instead, they narrowed the focus to blue districts, but Justice Democrats still thought they might be able to recruit hundreds of primary challengers. Armed with funding and resources from the organization, these progressive champions would primary “corporate Democrats,” hoping to knock them out, win the general election, and establish a beachhead for the left on Capitol Hill.
The group was collecting nominations, meeting with candidates, and bringing the most promising recruits together at weekly retreats. These gatherings were held in Frankfort, Kentucky, where a Sanders campaign alum who volunteered for Justice Democrats, Mary Nishimuta, ran a coffee shop.
“She had space,” Chakrabarti explained.
Chakrabarti described the multistep vetting process as “grueling as hell.” In the end, though Justice Democrats would endorse over seventy House hopefuls in the 2018 midterms, they decided to cut back their ambitions again and focus on working with a dozen of the most promising prospects. It was the number they had ready to go when money—and time—started to run out.
“We couldn’t keep funding doing those retreats,” Chakrabarti said. “So we had what we had, and started basically announcing campaigns in the summer of 2017 because we didn’t want to get to a point where we’re at the end of 2017 and we haven’t even launched a campaign yet.”
Ocasio-Cortez would later say attending a Justice Democrats retreat in Frankfort convinced her to run for Congress. But not every candidate that the group wanted to back was committed. Justice Democrats didn’t wait for them to pull the trigger.
According to one source, the activists at Justice Democrats filed declarations of candidacy with the Federal Election Commission without authorization from the candidates in question—forms that they falsely represented as signed by those candidates.
This certainly seems to have happened at least in the case of Ocasio-Cortez, since public records show that she filed in one district and then filed in a different district five days later.
“We filed Ocasio’s paperwork to run against Serrano initially in New York,” Trent said, referring to Jose Serrano, the member of Congress then representing the state’s Fifteenth District.
Serrano was hardly an ideal opponent for her. Like Ocasio-Cortez, he was Puerto Rican and an icon of that community. The pair were also both to the left of the Democratic establishment. Serrano was one of the most reliably progressive House members, and, for that reason, never a figure in Democratic leadership.
An FEC filing made for Ocasio-Cortez to campaign against Serrano on May 10, 2017, confirms Trent’s account. Ocasio-Cortez was ready to run, but she had her own idea about where to fight. Her paperwork was refiled in the Fourteenth District five days later, on May 15, 2017. She had set her sights on a far more natural enemy—Joe Crowley.