With his barrel chest, ruddy-faced grin, and thin remnants of blond hair, Joe Crowley was the prototypical glad-handing political jock. But, other than appearances at parades and in back rooms, he had little presence on the ground in the parts of Queens and the Bronx that he represented. Nevertheless, he was a local party boss and a formidable figure in Washington.
As chairman of the House Democratic Caucus, Crowley was fifth in line in the party’s leadership structure and a contender to succeed Nancy Pelosi as Speaker of the House one day. Crowley was also entrenched in New York City’s power structure as chair of the Queens County Democratic organization, the local party apparatus that held sway over political offices and appointments in the borough.
The county party was one of the final vestiges of the old boss and machine system that powered the city’s infamous Tammany Hall years. Crowley had an uncle, aunt, and cousin who also had positions in the local government.
The circumstances of his first election to Congress show the machine in action. By 1998, Crowley had spent a decade in the New York State Assembly when the sitting congressman, Thomas Manton, who had already filed paperwork to run for reelection, abruptly announced his retirement.
At the time, Manton was chair of the Queens County Democratic Party, which means he ran the committee that would select his replacement. Crowley was his handpicked successor. By dropping out at the last minute, literally one day before the deadline, Manton had blocked anyone else from running for the open seat. Crowley’s name replaced Manton’s on the ballot. The maneuver led to criticisms from the local press and politicians on both sides of the aisle, but Crowley won without much contest and was effectively installed in Congress. Soon after, Crowley assumed the Queens County chairmanship.
Crowley was emblematic of the aging leadership and anti-democratic party structures progressives often blamed for blocking popular reforms. He was also out of step with the changing face of the district. Manton and Crowley both had the Irish roots that were predominant in Queens and the Bronx for much of the last century. Yet, in more recent times, the area had seen an influx of immigrants from Africa, South Asia, and Latin America. The streets of the district teemed with halal butchers, South American food carts, and Caribbean restaurants. These new residents needed access to better health care, jobs, and an immigration system that worked—and they wanted leadership that looked more like them.
While Crowley and his traditionally moderate politics were becoming a bad fit for the district, he was still a fearsome rival. He had a million-dollar war chest and alliances with officials and unions who could put boots on the ground for him in a primary race.
Justice Democrats provided Ocasio-Cortez with impetus and infrastructure, but their capabilities were limited—particularly with a dozen candidates around the country. The group’s Tennessee headquarters was nearly a twelve-hour drive from Ocasio-Cortez’s district. She initially pounded the pavement herself, weaving in and out of brown brick apartment buildings and elevated train tracks without professional staff by her side.
“I was bartending. I was going out in my community. The very first canvass that I did was out of a Trader Joe’s bag,” Ocasio-Cortez said to an audience of college students a year later.
For all her modesty, Ocasio-Cortez proved a solid strategist. She had identified Crowley’s central weakness—he did not live in the district and owned a home in the DC suburbs with his wife and daughters. At local events and forums, Ocasio-Cortez blasted Crowley as disconnected and in thrall to corporate donors.
Back in Tennessee, some of the Justice Democrats’ leaders were beginning to see unusual promise for her race. Few people outside of the organization believed Crowley could be seriously challenged. A relatively sleepy race usually favors the incumbent. But Ocasio-Cortez’s backers saw low turnout as a potential asset.
“We don’t gotta move that many people,” Trent said of the race. “The win number was so low.”
Eventually, Justice Democrats dispatched a veteran of the Sanders campaign, Waleed Shaheed, to join Ocasio-Cortez in September 2017.
Their first meeting was at a café in Union Square that had a long line to get in.
“And so I pointed to a restaurant across the street that looked empty and I was like, why don’t we just go there?” Shaheed said in an interview for this book.
Ocasio-Cortez declined.
“Oh, I, uh, work there,” she replied sheepishly.
It was the site of her now-famous job as a bartender. She was meeting her first staffer between shifts.
Even while working a day job, Ocasio-Cortez threw herself into the race. She initially struck Shaheed as highly motivated but new to the mechanics of campaigning.
“She was just learning a lot,” he said.
A quick study, Ocasio-Cortez displayed a clear knack for messaging. The budding candidate was “doing her own oppo” and eager to share her own research about her chosen opponent.
“She was like, ‘Oh, and I just found out this thing about Joe Crowley’s record, or … this donation he got from this bank,’ ” Shaheed recalled. “She was just so excited.”
But even with a uniquely talented candidate and the compelling narrative of a twentysomething taking on a party boss, Ocasio-Cortez’s campaign struggled to gain traction. To make matters worse, by the end of 2017, the Justice Democrats organization was facing a crisis.
According to Trent, the group’s leadership realized “we can’t back twelve people. We’re out of money and we’re only bringing in … $50,000 a month or whatever.”
The group would have to scale back its grand ambitions one more time. They needed to go from a dozen candidates to one who really had a chance.
“We had to pick the right one,” Trent said. “We end up deciding in December … to go all in with Ocasio.”
Within about a month, in early 2018, Chakrabarti headed to New York, taking on a full-time role as Ocasio-Cortez’s campaign manager. That meant Justice Democrats would be largely abandoning the other candidates they had promised to support. This decision led to resentment behind the scenes. And Chakrabarti found a new crisis when he stepped off the plane. Just as they were pinning all their hopes on Ocasio-Cortez, she was thinking of quitting.
“It hadn’t turned around yet,” Trent explained.
After nearly a year of hard work, she had gained little visible traction. With Chakrabarti throwing himself into the race, Ocasio-Cortez decided to soldier on. Yet even her allies believed a victory was impossible.
Sean McElwee, a progressive pollster, was host of a weekly happy hour that functioned as a social hub of sorts for New York City’s leftists. He bragged about having Ocasio-Cortez come by in the early days “when she had 8,000 Twitter followers.”
“Even on the day of the election, I don’t think anyone really thought she was serious or was going to win,” McElwee said.
Ocasio-Cortez’s campaign staff was looking at grim numbers put together by the respected Democratic pollster Celinda Lake. According to Trent, Lake’s data never showed her within thirty-five points of Crowley.
Crowley seemed to share that dim view of Ocasio-Cortez’s chances. He didn’t rouse himself to catch the Acela back to the city for an initial debate with Ocasio-Cortez, and instead sent a surrogate to appear in his place. Ocasio-Cortez turned the occasion into a rout, politely dismissing the stand-in and pouring criticism on Crowley that he wasn’t present to answer. Ocasio-Cortez’s campaign had a fresh face and well-produced videos. People started to notice. The next time they were set to debate, Crowley actually showed up.
Ocasio-Cortez almost certainly could not have made it to Congress without the Democratic Socialists of America.
While nowhere near the size of the major parties, the DSA boasted of being the largest socialist organization in the country. With roots in early twentieth-century union movements and sixties radicalism, the organization blended the old left and the new. In May 2017 when Ocasio-Cortez launched her campaign, the DSA was enjoying a period of explosive growth fueled by Bernie Sanders’s run the prior year and backlash to the subsequent election of President Trump. Many of the group’s new members were younger, more modern progressives who were focused on identity and social issues.
In 2015, the DSA only had about six thousand members. Two years later, its ranks had swelled to roughly twenty-five thousand. That surge was being felt on the ground in Queens.
Prior to Trump’s election, the Democratic Socialists of America had no outpost in the borough. In January 2017, as the Queens-bred Trump took office, the organization formed a local branch and held its first meeting organized by veterans of the Sanders campaign.
Aaron Taube, who would go on to briefly work for Ocasio-Cortez, was present for the first DSA meeting in Queens. His story is emblematic of how Sanders, and then Trump, drove the group’s rise in New York City.
For Taube, a skinny, self-described “Jewish kid” who grew up in a Long Island suburb and wasn’t politically active, Sanders’s White House bid caused something to click.
“Oh wow, there’s this thing beyond being a Democrat or even a progressive. There’s this thing that’s democratic socialism,” Taube said of Sanders. “He spoke to a lot of these issues that I cared about and he showed me that there’s this thing beyond liberalism.”
While Taube supported Sanders and donated money, his admiration for the candidate didn’t translate into in-person activism. That all changed after Trump’s victory in the presidential race.
“I have to do something,” Taube thought. “Everything is burning and bad.”
Along with “abject fear,” Trump’s ascent added to Taube’s dissatisfaction with the Democratic Party establishment.
“The Democrats had failed their one purpose, which is to protect us from the Republicans,” Taube said. “Seeing this fall apart you’re like, ‘Oh yeah, actually everyone who is running the Democratic Party is a huge idiot.’ ”
Taube joined the DSA on November 9, 2016, the day after Trump was elected. He felt the Democrats were “not fit to stand up to this crisis.”
“We need something stronger and better that really speaks to people,” said Taube.
The DSA’s national leadership similarly saw Trump’s ascent as an indictment of the Democratic establishment. In 2018, when asked about the organization’s post-Trump membership surge, DSA National Director Maria Svart described it as being motivated by opposition to both the Republicans and the mainstream left.
“People are excited by a bold vision and they’re willing to fight for it. Neoliberal Democrats are afraid of what might happen if we build the powerful multiracial working-class movement that it will take to stand up to Trump because they know that this movement will also stand up to them, too,” Svart said at the time.
Vigie Ramos Rios, a Puerto Rican woman who grew up as an “Army brat” and found her way to Sanders’s organization after a layoff, was one of the initial organizers. Ramos Rios, who went from having not voted for over a decade to serving as one of Sanders’s delegates at the 2016 Democratic National Convention, was eager to stay involved after Trump’s victory. Nevertheless, she had moderate ambitions for that first Queens DSA meeting.
“There ended up being like ten of us who were planning it and we were like, ‘If we get another ten people, this would be great,’ ” Ramos Rios remembered in an interview for this book.
The event exponentially exceeded her expectations. Ramos Rios said over 130 people showed up. Taube, who was one of the attendees, said the place was “packed.”
At the meeting, people listed their priorities and concerns on oversize pads of paper. For Ramos Rios, the main takeaway was that they needed to establish an organization capable of exerting “political pressure” to help people achieve these goals. They also recognized the need for diplomacy since, as Ramos Rios put it, despite socialism’s popularity with young people, “for Boomers and Gen Xers—the word socialist had been demonized.”
“We needed to be able to establish an organization that could get people in our local communities involved,” she said, adding, “When you talk about the aims and the goals of socialism, the vast majority of people in Queens agree but when you talk about it using that language, you alienate a good portion of the population.… So from what I recall, the group that was organizing things was really about how do we get people to come back?”
Ramos Rios ended up becoming Queens’s representative to the citywide DSA steering committee. However, the initial momentum didn’t last.
“There was a big drop off after that,” Taube said of that first meeting. “It felt like there was a lot of people there and excitement, and then, it sort of fizzled.”
Taube was one of the ones who stuck around, even though he was a newcomer to activism.
“I had sort of a limited understanding of political possibilities,” explained Taube. “I was kind of like, well, you can have a revolution or an election and I don’t know how to shoot a gun and probably would be really bad at that.… I’m going to go do this electoral thing.”
Taube became a chair of the Queens DSA’s electoral working group. The position made him a key figure in Ocasio-Cortez’s rise. It also thrust him into one of the organization’s main internal schisms.
When Taube and the other new chairs took over the electoral operation, they figured endorsing candidates would be a natural first step.
“We were like, ‘Oh, I guess we’re leading this working group, I guess we should do a campaign,’ ” Taube said.
But the question of electoral participation was fraught within the DSA. Some members of the group prefer to prioritize other forms of activism like union and tenant organizing rather than campaigns for office. And, if the DSA was going to back a candidate, there were extensive questions about what kind of platform they should have and how closely tied to the organization that candidate should be.
Alexandria Ocasio-Cortez had joined the DSA, but she didn’t have a long history with the group. Nor was she in lockstep with the policy positions the DSA included in its endorsement questionnaire. Namely, while she defended the movement to boycott and sanction Israel over the Palestinian occupation on free-speech grounds, Ocasio-Cortez did not explicitly support it. Lastly, she was running on the Democratic Party line.
All of these issues were controversial within the DSA. Still, when Taube and his colleagues first met Ocasio-Cortez in early 2018, they were completely sold.
“We were just blown away by what everyone sort of knows about her now, which is that she’s this incredible public speaker who comes across as very sincere, and passionate, and smart,” said Taube.
Along with being drawn to the candidate personally, the electoral working group liked the idea of an underdog taking on a Democratic Party machine. They also appreciated how Ocasio-Cortez stacked up against her initial opponent, Joe Crowley.
“You know, you have this dynamic young woman of color running against this really just totally frumpy old white guy with no swag,” Taube said, adding that they thought, “She’s got this, she’s going to be the youngest woman elected to Congress.”
While Taube and his cohort saw Ocasio-Cortez as an ideal future “ambassador for DSA,” others in the organization had what he diplomatically described as “concerns.” Mainly, some worried that the candidate was “a Democrat.” Others wondered whether Ocasio-Cortez was “a real socialist” since she hadn’t publicly identified as such before pursuing the group’s endorsement.
Many DSA skeptics of Ocasio-Cortez balked at backing any candidate who was also on the major party line. They complained that the Democrats are “a party of capital,” and, as a result, it didn’t make sense for an anti-capitalist group like the DSA to back them in any way. According to Taube, the debate over endorsing was a microcosm of the larger questions among leftists over whether to work with more mainstream allies or make a more radical, and ideologically pure, stand. However, the radicals’ reservations did not prevail this time. Ultimately, Taube said he and the Queens working group “led the process of convincing the New York City DSA to endorse her, which we did a little over two months before her election.”
“It was a harder sell than it should have been,” Taube added with a wry laugh.
The process took time due to the DSA’s internal debates and the fact Ocasio-Cortez’s district spans parts of both the Bronx and Queens. The DSA prides itself on democracy. For the city organization to support her, she would need to win at least 60 percent of the vote in either the Queens DSA branch, or the so-called “BUM Branch,” which represents the Bronx and Upper Manhattan. Ocasio-Cortez fell short in the BUM Branch. However, she crossed the 60 percent threshold in Queens.
“We got what we needed,” Taube said.
Ramos Rios was frustrated by the DSA’s hand-wringing over whether to back Ocasio-Cortez and other potential candidates.
“I’m trying not to be disparaging, but I often think of it as navel-gazing because I’m like, we are so far from truly pulling in the vast majority of voters,” Ramos Rios said. “It’s part of the frustration of why I’m not as active a member anymore.”
Rather than looking for perfect allies, she suggested the growing organization should “talk to people who are not members to continue to invite people in and welcome them once they’re there.”
“I hate the litmus test. I hate the arguments of who’s a true socialist and who isn’t,” she explained. “Like how about we hold up what are our basic values on helping the community on universal health care, these sorts of things. And we can get back to the argument when we actually have political power.”
Once the group decided to endorse, the DSA provided Ocasio-Cortez with over one hundred volunteers, which Taube said was about one-fifth of her ground game. The organization also helped connect her to Ramos Rios, who became her campaign manager.
Ramos Rios said she got the job after a call from Chakrabarti, who she knew “from the Bernie days.” He reached out in early February 2018, just four months prior to the primary. Ramos Rios thought he was asking for her help organizing volunteers since it was late enough in the game that “they must have a campaign manager already.”
“I realized three questions in, he was interviewing me to be her campaign manager,” Ramos Rios said.
Once she was brought on to the team, Ramos Rios had questions about the campaign operation since deadlines were fast approaching. Was there a lawyer? Did they have a team to collect the signatures from voters that were needed to get on the ballot? The answer was no to all of the above.
“I’m like, okay, we have a lot of work to do in two weeks,” Ramos Rios recalled.
Along with Ramos Rios and the team from Justice Democrats, Ocasio-Cortez’s fledgling campaign had another key adviser: Alexandria’s romantic partner, Riley Roberts.
The pair, who became engaged in 2022, initially began dating in college. During Ocasio-Cortez’s 2018 campaign, they lived together in her Bronx apartment. Since-deleted webpages show Roberts dabbled in a variety of projects prior to Ocasio-Cortez’s race. Roberts’s personal home page described him as an “entrepreneur, sociologist, and contrarian.” The site said Roberts had helped set up something called the “Cop Out Collective,” which he called “a social project with the mission of shifting the public opinion about the role of cops in society.”
“The influence of certain bureaucratic pressures creates some cops that abuse their power and dehumanize the members of society who [they’re] supposed to be protecting,” Roberts wrote, adding, “High end hemp t-shirts with our logo will be available for sale on our website.”
Roberts also once built a website for a venture selling a brand of high-priced coffee culled from the droppings of the civet, a cat-like Indonesian mammal. His page for the exotic excrement brew featured a testimonial from Ocasio-Cortez alongside her smiling photo.
“I was skeptical at first, but this Civet coffee has a unique, smooth and full-bodied flavor that I really enjoyed trying,” Ocasio-Cortez declared, according to the page.
A source close to the couple described the site as a mock-up that Roberts, who was freelancing at the time, made to build his web design portfolio.
Roberts’s digital experience came in handy as Ocasio-Cortez ran for Congress. According to Ramos Rios, the campaign manager, Roberts was Ocasio-Cortez’s “major adviser and supporter.” She also said he was “the linchpin” of their digital fundraising operation. Ramos Rios described his contributions as “vital” and “integral.”
While Roberts’s presence was felt on the campaign, the staff rarely interacted with him in person.
“He was a force and he was active, but … I think Riley’s an extreme introvert,” Ramos Rios said. “He’s really quiet. In fact, he worked out of their apartment.… Riley was like, Boo Radley, half the time you didn’t see Riley. You didn’t hear Riley.”
Ramos Rios and multiple other veterans of that campaign said Ocasio-Cortez also had a shy streak.
“She’s a writer, she’s an introvert,” Ramos Rios said of Ocasio-Cortez. “Introverts lose their energy talking to people. So if she’s done a big rally or talking to a bunch of people, she needs time alone to recoup that energy.”
This personality trait meant Ocasio-Cortez was absolutely overwhelmed by what happened next.
Ocasio-Cortez and her campaign were set to spend election night at a pool hall in the Bronx. Pink neon lights blared down from the ceiling as volunteers and supporters weaved between the bar and scuffed billiards tables. As the polls closed, a local news station, NY1, had a camera trained on Ocasio-Cortez when the first results filled the television screens. She was crushing Crowley.
Her reaction was instantly iconic. Her jaw dropped, she shook, screamed, and covered her open mouth with her hands. Her eyes remained locked on the screen, blazing out utter shock and delight.
“She’s looking at herself on television right now,” the NY1 reporter, Ruschell Boone, explained to the audience at home.
Ocasio-Cortez was literally reeling. A smiling woman put a hand on her back to help her keep steady.
“How are you feeling?” Boone asked. “Can you put it into words?”
“Nope,” she answered instantly, shaking her head with her jaw still half dropped. “I cannot put this into words.”
Ocasio-Cortez’s eyes stayed wide, riveted by the numbers that were coming in. Her breath was ragged as though her astonishment had knocked the wind from her small frame.
“This was a grassroots campaign. Can you believe these numbers that you’re seeing right now?” Boone asked.
“I cannot believe these numbers right now,” Ocasio-Cortez replied. But even in her apparent shock, she pulled herself on message. “But I do know that every single person here has worked their butt off to change the future of the Bronx and Queens. That’s what I know.”
Boone pointed out that she had gone up “against the Queens machine.”
“Well you know what?” Ocasio-Cortez answered, “We meet a machine with a movement.”
The eyes of the world were on her now. That dramatic first interview kicked off an avalanche. Reporters who had not planned to cover the long-shot challenger rushed up to the pool hall. Camera flashes broke through the lights with a disorienting rhythm as the mix of press and supporters surged towards the woman of the hour.
Trent, Ocasio-Cortez’s communications director, remembers seeing Ocasio-Cortez try to huddle with Roberts in a roped-off area by the pool tables.
“The thing that happened instantly was … now she had become a magnet,” Trent recounted in a series of interviews for this book. He described the people in the crowd as a “sea of iron shavings” that were flying at Ocasio-Cortez.
“They’re just drawn to her,” Trent said. “And they all want a little bit.”
People crushed around her asking for selfies, autographs, interviews, and hugs.
“She had to, like, take a break,” Trent said. “It’s such a physically draining, and mentally and emotionally draining experience for her to do this with people.”
And it wasn’t going to stop any time soon.
As the waves of admirers came down on Ocasio-Cortez, Trent had a major problem of his own. Throughout the campaign, he had been struggling with an opiate addiction. Trent put it more bluntly.
“I was hooked on fucking pain pills,” he said.
He had not told Ocasio-Cortez any of this. And as election night approached, Trent ran out of the medication he had come to rely on.
“I was on Suboxone, which is the shit you take to get off of Oxycontin and opiates, until election night—until, literally until, the night that Ocasio won her primary,” said Trent.
If she lost, Trent’s time in New York would have been over, but the shocking upset victory meant he couldn’t return home to Tennessee the next day to refill his prescription. He was wracked with withdrawal symptoms as he and Ocasio-Cortez dealt with an onslaught of media requests and press coverage. But the whir of international attention afforded to America’s rising socialist star was its own kind of buzz.
“I got off Suboxone with fucking adrenaline,” Trent said.