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Rogelio V. Solis/AP

It’s tough to break in to entrenched political systems, even at the local level. Here’s how four women navigated these dynamics in Queens.

This story was produced in collaboration with WNYC.

Even as the last presidential election ignited a wave of activism across the country, with droves of scientists and other non-politicians vowing to run for office, the September primaries in New York City showed that politics is still an insider’s game. Incumbents won every race they ran, reinforcing a populist sentiment across the political spectrum that the system is rigged.

For first-time or outsider candidates, that feeling can make navigating the insular world of local politics daunting. What may strike newcomers as particularly rigged are political machines. At best, these organizations funnel resources to specific candidates. More often, their goal is to hold onto power within a select group, instead of bringing new people into the fold.

In the deep-blue borough of Queens, where 130 different languages are spoken, the Democratic Party speaks largely with one voice. Here, a powerful political machine protects its turf by tapping handpicked candidates and throwing roadblocks up against insurgents who mount a challenge.

It doesn’t happen just in Queens—or in New York City. Machines exist across the country. They come in every ideological stripe, up and down the political food chain. How can first-time candidates ever be victorious against the entrenched—and territorial—establishment? There are broad lessons to draw from four women’s tussles as they tried to enter politics for the first time, learning to work both inside and outside of the machine.

You’ve got to pay your dues

As Donald Trump delivered his ‘American Carnage’ inaugural address this January, 30 women gathered on the 17th floor of a law office in downtown Brooklyn for lessons in running for office. The event was sponsored by Eleanor’s Legacy, a nonprofit that supports pro-choice, Democratic women candidates. But catharsis kept interrupting the curriculum.

One woman raised her hand to say the Democratic party had failed them. Another complained the national operation only talks about raising money.

Kimberly Roberts chimed in from her seat toward the back of the room. Democrats needed to do some self-reflection, she said, about divisions that exist among them. “I take the train from Queens, and you can see the racial division as you travel through Queens—despite the fact that it is the most diverse borough in New York City, a diverse city,” she said.

A few days later, over plates of curried goat and fried calamari at her favorite neighborhood restaurant, Roberts told me why she’s thinking about a career in politics. “There's nobody coming to save us,” she said.

We were in Springfield Gardens, a mostly middle-class neighborhood in southeast Queens, where she was born and raised. She’s 36 years old, the daughter of Jamaican immigrants, a graduate of New York University with a Master’s in education from the University of Connecticut.

Kimberly Roberts took a step back from politics when she ran into stickiness with the machine. (Brigid Bergin)

Before the election, she was a Peace Corps volunteer in Guyana. That assignment was cut short last fall due to a security threat. Suddenly, Roberts found herself back home at her parents’ house, just as Trump’s Access Hollywood tape emerged.

Roberts was shocked by the state of the campaign. As the reality of Trump’s election sank in, she said there was too much at stake for someone like her in a place like New York City to sit on the sidelines any longer.

So she recalibrated her plans: Instead of dedicating her time to the developing world, she focused on her community at home. Roberts left that Inauguration Day workshop inspired to learn more about running for office. She also met a woman there from her neighborhood—someone who knew more of the rules about how the system works.

Adrienne Adams is the chairperson of the Community Board in Roberts’s neighborhood. There are 59 community boards across New York City, each with up to 50 volunteer members. These are the places where the most hyper-local civic concerns are addressed. Adams encouraged Roberts to apply to be a community board member. You submit an application to the borough president’s office and hope for the best.

Adams has been the Community Board chair for going on five years, and she’s learned a few things along the way. One of the hardest lessons came last year, when she ran for State Senate against an incumbent, James Sanders.

The race was complicated. When Adams announced she was running, it was supposed to be an open seat. Sanders had already indicated plans to challenge his local congressman, but then changed his mind. Even with the backing of the Queens County Democrats—the Queens machine—Adams lost to Sanders.

Political watchers say Adams was just a pawn in a political chess game. The machine sent a message to Sanders, because he wanted to run against an incumbent who was higher up the ladder—Congressman Gregory Meeks. The machine wanted Sanders to know, even though he was also an incumbent, they’d back an outsider to challenge him. The move forced Sanders to run a harder race. The machine doesn’t like it when you mess with one of its own.

In February, Roberts and Adams drove up to the annual gathering of the Black and Latino Caucus in Albany. It was a chance to schmooze with elected officials and power brokers from across the state.

When we spoke by phone after she got back, Roberts sounded deflated. Her ambition and idealism were replaced by questions: She was learning just how hard it is to break in. “Adrienne raised an enormous amount of money, she had an enormous amount of backing. She did a whole lot...and still lost,” said Roberts.

I had lunch with Adams a few months later. She’s a former corporate trainer with close ties to lots of institutions in her community. And she’s been building her network for years.

“It's tough to penetrate what some call the Queens machine,” said Adams. But she is playing the long game, making sure that those in power knew she was willing to run again.

And sure enough, the next month, she got her chance. When her local City Council member Ruben Wills was convicted of corruption, the Queens County Democrats picked Adams to replace him on the ballot. She won a tough primary in September and is the favorite in this year’s general election.

As for Roberts, she was turned down for that appointment to the community board. The news came in a form letter with no clear explanation as to why. Roberts opted to go back to school to study urban affairs at The New School and volunteer for the Adams campaign. She decided she just wasn’t ready to pursue a career in politics, yet. “That's the reality,” she said. “But I'm not defeated.”

Whether she knows it or not, she’s started to pay her dues.

Don’t forget the little details

Eryka Montoya is a potential spoiler in a Queens City Council primary; Frank Bolz is the lawyer for the Queens Democratic Committee. So, last summer, Bolz headed to a hearing of the New York City Board of Elections to formally object to her presence on the ballot.

Listen to more of Eryka Montoya’s story, from WNYC:

Tune in to the full podcast here.

Montoya is 35 years old and a first-time candidate. Her hopes rest with 10 elections commissioners—men and women, black and white and brown, one Democrat and one Republican from each of the five boroughs. But they all have one thing in common: Under state law, they are the last and only officials at any city agency who are handpicked by the party bosses.

To appear on the ballot, Montoya needed 450 valid signatures on her petitions. She submitted 1,084. But the Board of Elections—which is controlled by the parties—has invalidated more than half of them, leaving her 22 signatures short. This hearing is her last chance to prove she has enough valid signatures. If she loses, she can take it to court—but that means hiring a lawyer, plus other expenses.

Eryka Montoya’s name was scratched from the ballot because she was missing some of the fine print. (Brigid Bergin)

“I believe she didn’t have a fax number on her coversheet,” said Bolz, the lawyer for the Queens machine. “[The] rules are very specific that that’s one of the considerations.”

Montoya is pleading with the Board to preserve her candidacy. But they are already making the motion to remove her. And it was true—she was missing a fax number, and she didn’t bring a list to refute the tossed signatures. She said if she had to do it over again, she would have brought her own lawyer—and of course, she would have included that fax number.

Get an early start

For some first-time candidates, the big race comes next year. That’s the case in the 14th congressional district, which spans parts of Queens and the Bronx. It’s 50 percent Hispanic—nearly half its residents are foreign-born. Even though the race is months away, savvy candidates are getting a head start.

Congressman Joseph Crowley secured the seat nearly two decades ago and hasn’t had a primary challenger in 14 years. He’s currently the Chair of the House Democratic Caucus, which makes him the fourth-most powerful Democrat in Congress. His colleagues see him as someone with even higher leadership potential. He’s also the leader of the Queens Democratic County Committee—the machine boss.

Alexandria Ocasio-Cortez, 27, and a progressive Democratic candidate, is in a quixotic pursuit to challenge him. She explained this to me one Sunday in early October at a park in North Corona, Queens where she planned to go canvassing door-to-door. Her race is not until June 2018.

Alexandria Ocasio-Cortez is challenging Joseph Crowley’s seat in Congress. (Brigid Bergin)

Ocasio, who worked for the Bernie Sanders campaign in the Bronx, is now taking on the city’s strongest political boss on his home turf. She said Crowley is beholden to Wall Street and real-estate interests, and that he’s out of touch. “The way the Queens Democratic Party machine has worked, they operate on a politics of exclusion,” said Ocasio.

I asked Crowley what he says to people who see how the local party operates and say, the system is rigged.

“I think ‘rigged’ is an interesting word to use when the judges in this county are elected by the people,” Crowley replied. That’s technically true, but slightly misleading: Judicial candidates are nominated by the party. In a one-party town, voters don’t have much choice at the polls.

Crowley has a few questions for anybody who thinks their voice is not being heard.

“Do they belong to a Democratic club? Do they understand what a primary is? Do they know that's not necessarily the end all, that there was a general election? How sensitive is that district to a general election?” asked Crowley, rattling off other questions.  

In other words, whether you’re just starting out in politics or in line to be the next Speaker of the House, you have to understand the machine works—and do so as early as possible.

How to fight City Hall, and win

These stories may read like cautionary tales: The first-time candidates inspired to make a difference are sucked under by political machinery that, instead of welcoming them in, responds with a shrug, or worse.

But these are just beginnings. Roberts is building on her experience with the Adams campaign. Despite being booted from the ballot, Montoya still spends her evenings phone-banking for candidates. And Ocasio’s race is still months away. She knows it’s a steep uphill battle. But even if she loses, she said her campaign will be a success if it accomplishes another goal.

“If [my congressional district] can be more educated, more organized, more invested than we were a year ago,” said Ocasio, “then this campaign will have been 100 percent worth it.”

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