Cynthia Nixon (left), Alessandra Biaggi (top right), Bill Lipton & Jumaane Williams (bottom)

The Working Families Party celebrated its 20th anniversary last month at Brooklyn Bowl in Williamsburg, with its rank-and-file cheering on a line up of politicians that have served as standard bearers, past and present. But it’s the future of the party that is especially uncertain as the upstart liberal organization lays it all on the line in backing insurgent candidates in state elections this year.

In doing so, especially in its decision to take on Governor Andrew Cuomo by backing Cynthia Nixon, some the party’s longtime allies have turned adversaries, portending a potentially diminished presence in the state’s political landscape if its gamble does not pay off over the next several weeks. At the anniversary celebration, which featured Mayor Bill de Blasio, among others singing the party’s praises for its push to create a more fair and equal New York, there was little sign of uneasiness about its bold choices this election year; an atmosphere of revelry prevailed, possibly the sign of progressive activists happy to be going for it all instead of triangulating with Cuomo and other more centrist Democrats as it had in the past.

There is also a sense among WFP leaders and supporters that the party is already where the Democratic Party is heading, and where it needs to be, with a more progressive vision of left politics reflective of a new post-Clinton, post-Cuomo Democratic era.

Created by community advocates and labor unions with a vision of pulling Democrats to the progressive left, the WFP has played a prominent role in championing the bread-and-butter issues that most affect working, low- and middle-income Americans. Through activism and advocacy around policy and funding, the party battles inequity, whether it be in housing, employment, wages, criminal justice, education, environment, or electoral access. In local and state elections, Democrats eager to brandish their progressive bonafides have coveted and sought the WFP’s endorsement, and the party’s vocal leaders and active network of members and volunteers.

But after years of being let down by elected officials they propped up, the WFP’s leadership made a drastic decision this year to endorse underdogs in key Democratic primaries. They backed Nixon’s challenge to Cuomo, a two-term incumbent seeking reelection, and New York City Council Member Jumaane Williams in his attempt to unseat Lieutenant Governor Kathy Hochul; and they are fiercely rallying behind progressive candidates who are trying to replace Democratic state Senators who until recently made up the Republican-allied Independent Democratic Conference (IDC).

The reaction to the WFP’s moves has been significant, and potentially crippling. Several unions that had filled the party’s coffers for years pulled their support for fear of angering the governor, who made explicit threats against anyone who would stay, according to a WFP leader. But advocacy groups and a progressive activist base rallied, resolute to take on Cuomo, whom they no longer trusted after a 2014 deal went bad, and the former IDC members, who had betrayed their Democratic party-mates.

While acknowledging its newfound vulnerability, WFP leaders and supporters also had a sense that they were on the right side of history, pursuing their true vision of where the Democratic Party should be (with the necessary help of the WFP), representative of the national trendlines -- the WFP did back Bernie Sanders in the 2016 Democratic presidential primary -- a feeling only bolstered in recent weeks by events like the shocking congressional primary victory of Alexandria Ocasio-Cortez, whom the WFP had not endorsed over Rep. Joe Crowley, but quickly sought to align with thereafter.

“I think the unions are dismayed by the way the Working Families Party has chosen to operate this cycle,” said Stuart Appelbaum, president of the Retail, Wholesale and Department Store Union, in a phone interview. RWDSU was among those unions that left the party this year and Appelbaum is one of several labor leaders who say that Cuomo deserves to be reelected.

“They’re diverting energy and resources from the effort to send more Democratic congresspeople from New York to Washington, [and] our prime responsibility is to work to take back the House of Representatives…Our concern is that the WFP no longer is representing, in its current rendition, the interests of working men and women, despite their name, and that is why unions felt it was necessary to disassociate themselves.”

WFP leaders and allied elected officials say the party made a calculated wager, riding a groundswell of progressive sentiment that has moved the state’s political center, and that no matter how the chips fall on September 13, primary day, the party has already won.

“This is the party they founded 20 years ago...to pull the Democratic Party to the left and with a coalitional approach to building power,” Brooklyn City Council Member Brad Lander told Gotham Gazette at the WFP’s anniversary gala. Lander spoke of the “radical but also practical vision” of Jon Kest, the progressive organizer who founded the WFP as well as the advocacy groups New York Communities for Change and its predecessor, the now-defunct Association of Community Organizations for Reform Now (ACORN).

“The WFP’s always contained this dynamic tension,” Lander said, between “the strength of voice of grassroots activists” and “established but still progressive” institutions such as labor unions. “At this moment, given shifts in the broader zeitgeist...and of course because of the way the governor has approached this, the party is in a more activist movement space,” he said. Like the WFP, Lander is backing Williams for lieutenant governor and several of the challengers to the former IDC members.

Surely, if the WFP notches wins in the many primaries it is involved in -- the WFP offers a general election ballot line, but does much of its work backing its preferred candidates in their Democratic primaries -- it will strengthen the party, and conversely, losses will set them back, Lander said. Though, given the state of New York’s politics, “There’s no choice,” Lander said.

For nearly eight years, the WFP has cried foul about Democratic recalcitrance as key progressive policies have failed to pass the state Legislature. The WFP continues to advocate for issues that include healthcare for all, ending the school-to-prison pipeline, fair wages, fixing the city’s subways, increasing funding to under-resourced schools, the DREAM Act, campaign finance and voting reform.

Cuomo and the members of the erstwhile IDC largely claim to support that agenda and have repeatedly blamed the Republican-controlled Senate for thwarting its planks. But Cuomo tolerated, if not supported, the presence of the IDC, and critics hold its members up as a major obstacle to full Democratic control of both legislative chambers. Democrats have a comfortable majority in the 150-seat Assembly but, with the return of the IDC to the mainline Democratic conference, hold 31 seats in the 63-seat Senate.

And though the State Democratic Party, at Cuomo’s behest, is focused on recapturing the Senate, which necessitates flipping seats in the general election, groups like the WFP insist on replacing rogue Democrats with candidates who better embody progressive values and they trust to not flee for a deal with Republicans.

The party is taking a “big risk,” Dorothy Siegel, WFP treasurer, conceded on the sidelines of the gala, where Nixon, Williams, de Blasio, and Ben Jealous, the WFP-backed Democratic nominee for governor in Maryland, took the stage one by one to celebrate the WFP’s history. “Because, the power structure doesn’t like to be challenged...and the WFP is a really small organization,” Siegel said. “The people who control the levers of power win. Individual people never win.”

Siegel lamented her belief that the state’s politics, the governor, and state Legislature are powered by special interests, largely real estate developers and Wall Street executives (she left out the extensive influence of labor unions). “The WFP is not powered by any of those powerful people. We’re only powered by people who pay us $5 a month,” she said. “It’s a true David and Goliath situation. If we lose the governor’s race, we run the risk of very powerful people being very angry. They can do a lot of things to us that would make our lives difficult.”

Siegel pointed to the investigation involving the WFP that stemmed from alleged campaign finance violations in the election of City Council Member Debi Rose on Staten Island in 2009. Two campaign workers were accused, and later cleared, of charges that they worked with the WFP’s consulting firm, Data and Field Services, to circumvent campaign finance law. The years-long episode cost time and money that the WFP could ill-afford. “Lots of people got laid off. We almost went out of business,” Siegel said. “They could do that again. Do not underestimate the power of super-wealthy people to trample people who want to take away their power.”

Is it worth the risk? “Absolutely. 100 percent,” she said.

One of the most consequential possible effects of the WFP backing Nixon over Cuomo -- who they endorsed in 2014 after he promised to bring the IDC to an end and enact many of the same policies he’s promising again this year, which he did not follow through on -- is that it could cost the party automatic ballot access. A “third party” like the WFP needs at least 50,000 votes for its candidate for governor to maintain its ballot line into the future, which Nixon could easily attain in the general election. But Nixon losing the Democratic primary would put the WFP in a tough spot. Its leaders claim they won’t play spoiler and risk electing a Republican by drawing general election votes away from Cuomo. The party could feasibly get behind Cuomo while removing Nixon from the gubernatorial ballot line. A back-up plan is in place to move her to an Assembly race, in which she would not run, they say.

[Read: The Cynthia Nixon-Working Families Party Back-up Plan]

“We’re confident that Cynthia’s going to win and that the insurgents running against the IDC are all going to win,” said Bill Lipton, NYWFP political director, in a phone interview. “There’s a progressive wave coming. In the unlikely event that she loses, Cynthia’s agreed to meet with the leaders of the WFP and we’ll have an important decision to make. We’re very confident about any of the possible scenarios.”

A Nixon win would shock the political world, and catapult the WFP to never-before-seen power for a minor party. While initial polls show Nixon losing badly, her campaign argues that polling has been skewed and that polls are unable to capture the insurgent energy among Democrats and behind her candidacy. On the other hand, polling shows Williams to have a very real shot at unseating Hochul, which would also strengthen the WFP and cause major headaches for Cuomo (candidates for governor and lieutenant governor run separately in the primary, but as a ticket for the general election).

If Lipton had concerns about the WFP’s undertaking in this election cycle, he betrayed none of them. “We’re not taking a risk. We’re fulfilling our mission. The risk would be for us if we stray from our mission,” he said, critiquing the Democratic establishment for relying on the same wealthy donors as their Republican opponents. “The mission of the WFP is to break up that cozy relationship between these parties and these oligarchs and demand that there be a party that is truly fighting for working people,” he added. “And Cuomo and the IDC fundamentally made the problem worse by not just taking money from the same wealthy donors that fund the Republican attacks on working people but actually openly supporting and aligning themselves with the Republicans. The danger for us would’ve been not standing up to these Trump Democrats. That would’ve been the greater danger.”

The WFP hasn’t been a pure supporter of every progressive candidate, as evidenced by its choice of Cuomo over Zephyr Teachout in 2014, among others. Though the party derived momentum after the recent primary victory by Ocasio-Cortez, the young democratic socialist who defeated ten-term incumbent Rep. Crowley in Queens, its backing of Crowley left many questioning the WFP afterward. Lipton said the party was now fully behind her and that their earlier decisions owed to the fact that Crowley was moving to his left and the party had already committed to challenging former IDC state senators. “In retrospect, we clearly made a mistake. Alexandria Ocasio-Cortez has inspired us and working people around New York and the nation,” Lipton said.

The party also hasn’t made an endorsement in the state Senate District 18 race where Julia Salazar, also a democratic socialist, is posing a primary challenge to Democratic Senator Martin Dilan, an eight-term incumbent. Although, Lipton did not close the door on the prospect of an endorsement. “As of now, the WFP has made no endorsement in the race,” he simply said. The party is backing Andrew Gounardes in a competitive Brooklyn Democratic primary with Ross Barkan, the winner of which will try to unseat one of the few Republican elected officials in the city, Senator Marty Golden.

[Read: Running for State Senate, Julia Salazar Attempts Progressive Primary Upset]

Karen Scharff, co-chair of the NYWFP and, until recently, longtime executive director of Citizen Action of New York, an activist group and member of the WFP, insists the party will come through September 13 with several victories, similarly citing Ocasio-Cortez, among other progressives, who prevailed in the congressional primaries.

“The headline that came out of June 26 was not ‘Democratic establishment wins big.’ It was quite the opposite,’” Scharff said in a phone interview. “I think really that Cuomo and the IDC and the establishment Democrats took a major risk themselves by ignoring the growth of the progressive movement as it really built up steam over the past seven years going back to Occupy Wall Street and then Bill de Blasio’s election in New York City, the Black Lives Matter movement, the Bernie Sanders momentum, and they’re showing that they realize it.”

She noted that Cuomo has moved to his left in the last few months on several fronts, owing to the shifting dynamics of the Democratic base. “I think that the risk we’ve taken in our endorsements this year have already paid off in moving the dominant issues in our state in a direction that is gonna meet the needs of working families instead of the needs of hedge fund donors and real estate donors,” she said, insisting that the governor and state Legislature, no matter who wins, can ill-afford to ignore the WFP’s agenda next year. “I think this is the direction the electorate is moving in and the Democratic Party’s going to have to either move with it or risk being left behind,” she said.

“I don’t think WFP is out on a limb by itself here,” Scharff continued. “This is really part of the establishment versus the entire progressive and resistance movement….We’re definitely acting as part of a broader movement with a lot of allies.”

Public Advocate Letitia James, who first got elected to the City Council on the WFP line in 2003, also attended the 20th anniversary gala, though her presence was more muted. Despite being a longtime WFP poster star, she did not speak to the gathering, choosing to mingle on the sides. James is running for attorney general with the governor’s support and eschewed the WFP’s endorsement, which the party has reserved for either James or one of her primary opponents, Zephyr Teachout, hoping that one of the two prevails September 13. Asked about the party’s risky endeavors this year, which include the challenge against Cuomo, James demurred. “I was with WFP when they had fundraisers at churches and if you didn’t get there early enough, all the cheese and crackers were gone. They’ve come a long way,” she said.

“They took a chance on me several years ago,” she said, “and they are voting their values. I just wanted to come because they are my friends and because when I needed a party to run on, the Working Families Party was there and that’s something I’ll never forget.”

Theodore Hamm, associate professor and chair of journalism and new media studies at St. Joseph’s College and longtime Brooklyn politics watcher, struck an optimistic note about the state Senate candidates that the WFP has endorsed, though he said that Nixon and Williams are unlikely to win. “The question, I guess, is if those people win but Cuomo holds on, then how will the new state Senate take shape with the some of the IDC figures no longer there and the challengers now taking those seats,” he wondered. “But that would certainly give the WFP influence, to a much greater degree than they’ve had thus far in the state Senate. That really should be where they put their energy.”

Even Hamm admitted, though, that after Ocasio-Cortez’s shocking upset, “There’s no certainties anymore of what will happen in the future. In the wake of her victory, even though they didn’t support her, it made it seem like their gamble was worth at least pursuing.”

At the WFP gala, Mayor Bill de Blasio spoke early and eagerly. His association with the party goes back to his years as a City Council member from Park Slope. “People try and bet against the Working Families Party all the time, the status quo loves to discount them,” the mayor said to whoops and applause. “But guess what? The Working Families Party is here to stay.”

[Read: New York Democrats’ Season of Choosing]