The global financial system was said to be on the brink of a complete meltdown. From the press gallery overlooking the House floor, Rep. Joseph Crowley’s glistening dome could be seen above the crush of lawmakers deciding whether to bail out Wall Street. It was September 29, 2008, and as the votes of those rejecting the demand for $700 billion began adding up, Crowley’s voice could be heard above the din. “600 points!” he shouted across the aisle, with his thumb down. As the Dow Jones industrial average continued to crash, Crowley, a New York Democrat, continued to loudly update his Republican colleagues on the market carnage being unleashed by the shock populist rejection.

The resistance was ultimately broken and the bailout was approved days later. But as the debate about what it would look like went on through the winter, Crowley found himself caught up in an ethics probe, having taken campaign money from lobbyists representing financial firms just before voting against imposing tougher restrictions on Wall Street. The Office of Congressional Ethics, which was created that March by Democrats in the wake of the Jack Abramoff scandal, looked into Crowley’s fundraising and referred it to the House Committee on Ethics for further investigation. The panel, comprised of fellow lawmakers, eventually cleared Crowley of any wrongdoing.

Photo: Bill Clark/CQ Roll Call/Getty Images

When the New York Daily News reported on the unfolding scandal, it noted that Crowley, when he was first elected, relied heavily on labor union money, but had since shifted to Wall Street cash. “I think I’ve matured here both personally and in terms of my assignments,” Crowley explained at the time. “Many people here in Washington view me as an important figure.” At the time, Crowley was the vice chair for finance at the Democratic Congressional Campaign Committee, his fundraising generosity a way to win the favor of colleagues and rise in the ranks. He’s been on a steady climb since and has only gotten better at hauling in cash. So far this campaign season, Crowley has raised $2.8 million and has $1.6 million cash on hand, according to Federal Elections Commission filings. Now the chair of the House Democratic Caucus, he has spent much of 2017 and 2018 doling out checks to moderate and conservative Democratic candidates around the country, part of a behind-the-scenes bid to be in a position to replace House Democratic Leader Nancy Pelosi, D-Calif., if she’s ousted by her colleagues after the November elections. But for the first time since 2004, Crowley will have to get through a primary first.

Congressional candidate Alexandria Ocasio-Cortez poses for a picture in the Bronx borough of New York, on April 21, 2018. Photo: Andres Kudacki for The Intercept

Alexandria Ocasio-Cortez is the first Democrat in years to challenge Crowley’s reign over New York’s 14th Congressional District, which includes parts of Queens and the Bronx. A 28-year-old community organizer, her drive to enter public office was shaped by a series of events that began to unfold at the height of the 2008 recession, she told The Intercept in an interview at a diner in Queens. That fall, she was a 19-year-old undergrad at Boston University. She remembers getting an emergency call from her mother while sitting in an economics class. She hopped in a taxi, took the next flight home, and went straight to the hospital to see her father. He died on September 9, and she felt she could only take a week off of school. “I come from a working-class background, so you don’t really get a ton of time to mourn,” she said. As the economy collapsed, she found herself “deeper and deeper underwater,” she said. Her family became locked in a years-long probate battle with the Westchester County Surrogate’s Court, which processes the estates of people who died without a will, as Ocasio-Cortez’s father had. She witnessed firsthand how attorneys appointed by the court to administer an estate can enrich themselves at the expense of the families struggling to make sense of the bureaucracy. The family was barely getting by on her mom’s income as a housecleaner and bus driver, and after Ocasio-Cortez graduated in 2011, she began bartending and waitressing to pitch in. She also started working as educational director with the National Hispanic Institute, a nonprofit that aims to cultivate leadership in Latino youth. Back in New York, she was fighting to stave off the banks, which were eyeing the family home. “We just couldn’t afford to keep our home, and we had bankers going up to the curb of our home and taking photos of our house,” she recalled. In 2012, four years after her father’s death, they finally shook free of the surrogate’s court, property records show. In 2016, as Ocasio-Cortez campaigned for Sen. Bernie Sanders, her mother and grandmother, falling further behind, sold the home before it was lost. They moved to Florida, while Ocasio-Cortez stayed behind in New York. Fending off foreclosure and being able to ride the New York real estate market back up had allowed the family to sell the home for more than $300,000, which Ocasio-Cortez knew had not been the fate of millions who’d fallen victim to the financial crisis. When the young organizer entered the race to challenge Crowley, New York political observers assumed she’d fall short of the 1,250 signatures she needed to get on the ballot, because New York’s arcane, machine-driven electoral system means that most of them can be disqualified for one technicality or another. By the April 12 deadline, she had collected more than 5,000 names. She has raised about $200,000, according to her campaign. Despite the financial disadvantage, Ocasio-Cortez cautioned against discounting a candidate based on their war chest: “You can’t really beat big money with more money,” she said. “You have to beat them with a totally different game.” She’ll face off against Crowley on June 26.

Photo: Chip Somodevilla/Getty Images

Crowley doesn’t just sit atop the House Democratic machine: His influence in New York Democratic circles has only grown since he became a member of Congress in 1999, after more than a decade in the state legislature. He dominates the political machine in Queens, holding the official title of chair of the Queens County Democratic Party. The county party — the visible expression of the Queens machine — projects power throughout the borough in a number of overlapping and interlocking ways. It holds tremendous sway over judicial elections, where the Democratic judges allowed on the ballot are elected nearly automatically. For years, party leaders have been able to keep challengers off the ballot by enforcing arcane election laws, which are then adjudicated by judges who themselves came up through the machine. By acting as the gatekeeper for making it onto the ballot, the machine effectively ensures that its chosen judicial or political candidates will be elected in the heavily Democratic county. As the New York Daily News wrote in 2017: For 30 years, the same three men have effectively controlled one of the largest Democratic organizations in America. They are Gerard Sweeney, Michael Reich and Frank Bolz, the powerful attorneys who serve Rep. Joe Crowley, the chairman of the Queens County Democratic Party. Reich is the executive secretary of the party, a spokesperson and wrangler of district leaders. Bolz is the law chairman, entrusted with keeping county-approved candidates on the ballot and knocking their rivals off. And then, there’s the Queens County Surrogate’s Court, which has a long history of corruption. Ocasio-Cortez had only a faint impression that something was off in the Westchester Surrogate Court where her family did battle for four years. The more she learned about the Queens one, the more convinced she was that her hunch about the lawyers who profited off of probate proceedings had been correct. Here’s how the New York Times described the Queen’s court in a 2011 account, in which Crowley is dubbed “the party boss in Queens”: Power and money are found not so much in the voting booth as in the machine-controlled judicial conventions that pick judges, and in the courthouse on Sutphin Boulevard. That is where you find Surrogate’s Court, otherwise known as widows and orphans court. This court appoints guardians who make handsome fees processing the estates of those Queens residents who die without wills. To enter this court is to stumble upon Ponce de Leon’s own spring, an eternal source of easy money for the politically wired. Sweeney’s office, according to the Daily News, made $30 million as counsel to the public administrator of the court from 2006 to 2017, administering the estates of people who died without wills. He did not respond to The Intercept’s request for comment, and he declined to comment to the Daily News last year about his work. Scott Kaufman, who served as Crowley’s campaign treasurer for 17 years, made almost half a million dollars from assignments by the court from 2006 to 2017, the New York Post reported last June. Kaufman’s haul prompted a state probe into possible pay violations. He did not return The Intercept’s request for comment, but he told the Post last year that he was in compliance with state rules on court appointments. “Any review will conclude that the rules have been complied with,” Kaufman said. A spokesperson for the Office of Court Administration declined to comment on the investigation, but noted that “Scott Kaufman is currently eligible for appointments,” meaning he is still able to accept court appointments as a public administrator. Crowley’s allies in the machine, Ocasio-Cortez charged, “defend him in court and they bump his opponents off the ballot,” referring to ballot challenges filed with the Board of Elections against candidates Crowley did not support or who oppose the machine. Last year, as DNAInfo reported, a candidate in a City Council primary was booted from the ballot for not having enough valid signatures; she said she was bullied for not “kissing the ring” of the party boss, Crowley. In that race, Crowley supported Assemblyman Francisco Moya, who went on to defeat Hiram Monserrate, a former council member and state senator who was expelled from the legislature after a 2009 conviction for assaulting his girlfriend. The machine has a tight relationship with developers. Ocasio-Cortez noted in a follow-up email that Crowley’s organization reaped large sums of real estate money before the Queens machine installed the new City Council speaker, Corey Johnson, who has since “led the council in rezoning neighborhoods for luxury developments — pricing out local families and constructing high rises when the city already has 275k vacant units.” A spokesperson for Crowley said the incumbent was “proud” of his support for Johnson and Moya. “Joe Crowley is proud to have supported Corey Johnson for Speaker and to have helped him make history as the first openly gay man and the first HIV+ person to serve as Council Speaker,” the spokesperson said in an email. “Similarly, he is proud of his work to defeat convicted domestic abuser and thief Hiram Monserrate in last year’s Council race, just as he is proud to have helped lead efforts to stop Monserrate’s election to the State Senate and City Council.” But the nepotism within the Democratic machine makes for “an extremely unethical arrangement that impacts families like mine,” Ocasio-Cortez said, referring to her family’s working-class roots. “It really is a David versus Goliath situation where you have someone that has, in my opinion, abused their power, abused their position to further marginalize working families. And now we’re challenging him.” Given the recent volatility of American politics, there’s likely to be at least one stunning upset this November that rocks the establishment and that nobody saw coming. Could it be Crowley?

Congressional candidate Alexandria Ocasio-Cortez high-fives a child during a campaign event at St. Paul’s Evangelical Lutheran Church in the Bronx borough of New York, on April 21, 2018. Photo: Andres Kudacki for The Intercept

The safe money on a race in a machine-dominated district is to bet on the boss. And, to be sure, Crowley is likely to be the favorite. But Ocasio-Cortez has a few plausible reasons to believe there’s a path to victory: She has more than 8,000 individual donors; that’s a pool she’ll continue to grow and can keep tapping into if her campaign gains momentum. It suggests that the 5,000+ signatures she turned in were no fluke.

Primaries are very low-turnout affairs, meaning the absolute number of votes she needs to win is quite low, in the high-four figures or low-five figures.

Crowley is the king of Queens, but he represents the Bronx from a distance. If Ocasio-Cortez can organize and run up her numbers in the Bronx, while holding her own in Queens, she can win. The case against her isn’t based on substance, but on raw politics. Crowley is a very good old-school politician: engaging on the stump, charismatic, and diligent about building relationships. He has close relationships with the bosses of the Bronx machine, which can turn out votes. And, for many Democratic voters, he’s not that bad. The political differences between Ocasio-Cortez and Crowley are on issues of economic and racial justice. But, even for a corporate, Wall Street-funded Democrat, Crowley — like all good politicians — is flexible. With Ocasio-Cortez giving him a real challenge from the left, Crowley came out and endorsed “Medicare for All.” “When I launched my campaign on an unapologetic advocacy for ‘Medicare for All,’ within two weeks, he co-sponsored the legislation,” Ocasio-Cortez said. “That’s when people first started noticing how sensitive he was to our race, how sensitive he was to this challenge.” A Crowley campaign aide told The Intercept that the decision to co-sponsor “Medicare for All” had nothing to do with Ocasio-Cortez, adding, “She’s not making him any more progressive; he’s always been a progressive advocate.” Ocasio-Cortez has also joined the chorus of voices calling for the abolition of U.S. Immigration and Customs Enforcement. Crowley has gotten noticeably more critical of the agency. She also has the backing of the New York City Democratic Socialists of America and Black Lives Matter, while Crowley, whose district includes the notorious Rikers Island jail, has done little on criminal justice reform. In fact, as Ocasio-Cortez argued, former New York City Mayor Michael Bloomberg is fundraising for Crowley, “so we got the guy who created stop and frisk, who’s paying the representative of Rikers Island to continue this racket of incarcerating black and brown people in New York City.” An invitation for the fundraiser Bloomberg hosted at his Manhattan home on May 2 suggested contributions of $1,000, $2,700, and $5,400. From Ocasio-Cortez’s perspective, the race is not about electing “just any old Democrat.” Democrats beholden to corporate interests are not representing their constituents and, oftentimes, “take the very same money as Republicans,” she said. Indeed, Crowley’s second biggest donor, the Blackstone Group, is a close ally of President Donald Trump. “This is actually about electing Democrats whose financial interests are aligned with their communities’ interests,” Ocasio-Cortez said. And Crowley’s financial interests, she maintained, “are at odds with everything that this community needs,” so you can’t really trust his recent policy shifts “to be anything deeper than face value, anything deeper than a re-election bid.”

Congressional candidate Alexandria Ocasio-Cortez has dinner with supporters of her campaign at a Latin American restaurant in the Bronx borough of New York, on April 21, 2018. Photo: Andres Kudacki for The Intercept

But for many rank-and-file Democratic voters, even some who are inclined to back Ocasio-Cortez over Crowley, the possibility that Crowley could become speaker of the House — assuming Democrats wrest back control in the midterms — is alluring. With Trump in office, “Medicare for All” isn’t going to be implemented just yet, and dismantling ICE is a far-fetched dream. But a congressional representative who is House speaker might be able to bring home the kind of bacon that the impoverished district needs. Ocasio-Cortez faces the challenge of countering that assumption. Her argument is that, yes, Crowley’s power — both locally and nationally – could theoretically be used for the benefit of the people of the district. In reality, though, Ocasio-Cortez said he’s used it to benefit Wall Street and luxury real-estate developers, who are gentrifying the district and pushing working-class people out. Crowley’s support extends beyond Wall Street, though: He is backed by two dozen labor unions, including some of the state’s most powerful. Among his supporters are the Communications Workers of America, New York State AFL-CIO, 32BJ SEIU, and 1199SEIU. New York City Central Labor Council President Vinny Alvarez said in a statement that “throughout his tenure in Congress, Rep. Crowley has demonstrated steadfast support for organized labor, working people, and for the issues affecting their families and communities.” New York State AFL-CIO President Mario Cilento said Crowley is a champion for the cause of workers, and that he has a record of standing up for the middle class. “From securing health benefits for 9/11 responders and survivors, to fighting for increased access to health care and housing and delivering federal funding to improve the Bronx-Queens community, he has demonstrated his commitment to working families,” Cilento said. Despite Crowley’s labor backing, Ocasio-Cortez argues that the race is winnable because her opponent, a 56-year-old white man, does not reflect one of the most diverse districts in the country. About 40 percent of his stomping ground, after a 2012 redistricting, is now the Bronx. Half of the district’s residents are immigrants and 70 percent are people of color, his constituents don’t tend to work in the industries he takes money from, and he hasn’t lived in the district in years, she noted. (Nearly 75 percent of Ocasio-Cortez’s donations are small individual contributions, while less than 1 percent of Crowley’s funds are small donations, according to OpenSecrets.) “The people of Queens and the Bronx have elected Joe Crowley to represent them in Congress by an overwhelming majority each and every time his name has appeared on the ballot,” Crowley’s campaign manager, Vijay Chaudhuri, said in an emailed statement. “This year will be no different.”

Congressional candidate Alexandria Ocasio-Cortez leaves a campaign meeting in the Bronx borough of New York, on April 21, 2018. Photo: Andres Kudacki for The Intercept