Can New York Democrat Zephyr Teachout Stop Governor Andrew Cuomo?

Zephyr Teachout lives in a fifth-floor walkup in Fort Greene, Brooklyn. She also wants to be New York’s next governor. First she has to get by the guy with the $30 million war chest.

When Zephyr Teachout announces herself to a room, the first thing she addresses is the most striking thing about her.

“My name is Zephyr Teachout!” she shouts to a roomful of would-be supporters sipping white wine and drinking Coronas, her eyebrows darting upward in a look that says, “Can you believe the ridiculousness of that?!”

“I am not an app!” she continues, by way of clarification. “Or a train! I am a Deaniac!”

This is met with cheers, as the wine- and beer-sipping members of this crowd are attending a fundraiser celebrating the 10th anniversary of the local New York City chapter of Democracy for America, a progressive organizing outfit that arose out of the fervor of the Howard Dean presidential campaign.

But though Teachout got her start in politics 10 years ago with much of the crew gathered last week at the loft in the Chelsea section of Manhattan and was the chief Internet organizer for the Dean campaign in 2003, there does not seem to be much enthusiasm for her latest project. She faces a steep uphill climb in a Democratic primary for governor of New York in less than a month against Andrew Cuomo, he of the more than $30 million war chest, famous last name, and, earlier this year at least, some of the highest approval ratings of any governor in the country.

The organizer of the anniversary event took pains at its start to tell reporters that even though Teachout was attending, her appearance did not signify an endorsement of her campaign by Democracy for New York City. Nor would Howard Dean, who headlined the event, be endorsing one of the architects of his own political rise. (“I can’t speak about the race because I don’t know much about it,” he told one reporter.)

“I am for her challenging Cuomo,” said one activist in the back of the room, “But in terms of being for her because of her, well, I’m not sure I am there yet.”

Another, when asked what brought her to a Teachout event, sounded surprised that she was attending one.

“Oh, this is for Zephyr?” said the activist, who said she had known Teachout for a decade. “I didn’t…I thought…I didn’t realize this was about that. Sure, I guess I’m a supporter, but I haven’t given it much thought, to be honest. I’m really here to see Howard Dean.”

Ever since the former Vermont governor’s campaign, but more seriously over the past two years, the Democratic Party has been undergoing a kind of slow-burning revolution. Just as the Tea Party has wrested control of the Republican Party from the Beltway establishment, progressives have been trying to pull Democrats to the left and purge the party of pols too willing to coddle corporate interests. These progressives have cheered the victories of Elizabeth Warren in Massachusetts and Bill de Blasio in New York City, and taken heart in a smattering of congressional wins around the country.

“There is a rising economic populist tide in America, and Elizabeth Warren is the personification of that movement,” said Adam Green, the head of the Progressive Change Campaign Committee, which has been on the front lines of that fight. “And Zephyr Teachout is going to be a big part of it, as well.”

But in dethroning, or even denting, Cuomo, this nascent movement is facing its greatest test. The governor has conducted a master class in manipulating the levers of power in notoriously dysfunctional Albany, even as he has enraged progressives. He helped engineer a state Senate that is held together with a coalition of Republicans and conservative Democrats, keeping the more unruly members of his own party relegated to the minority. He reversed promises to permit nonpartisan redistricting and to clean up state government by enacting meaningful campaign finance reform. He let a tax on millionaires expire, and he outmaneuvered de Blasio to prevent a new tax for paying for universal pre-kindergarten in New York City. A host of progressive priorities—banning fracking, raising the minimum wage, legalizing marijuana, curbing the growth of charter schools, and more abortion rights—stalled, although the governor did get gay marriage and more restrictions on guns passed. Then came recent revelations that some of the governor’s string pulling around a commission he created to root out Albany corruption may have been a string pulled too far, with a U.S attorney investigating whether the governor overstepped his limits to protect allies and aligned lawmakers.

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That this is all happening in New York, one of the most liberal states in the union, has been particularly galling.

So along came Teachout. A constitutional law professor specializing in corruption and trust-busting, a death row lawyer, a transparency-in-government advocate, and an activist with organizing experience in various parts of the progressive movement, she was lured into the race by the Working Families Party, an umbrella group of labor unions and liberal groups that has helped push the state’s and the city’s politics profoundly to the left over the last 10 years (Mayor de Blasio is a founding member.)

But just as the WFP was set to give its endorsement to Teachout, Cuomo made a few promises to push for the liberal agenda in Albany, including helping to secure a Democratic-controlled state Senate and raising the minimum wage (albeit tepidly, appearing only on video at the WFP convention). So, despite loud grumblings from rank-and-file activists, the WFP, the biggest organizing force in progressive politics in the state, announced that despite it all, it was for Cuomo, too.

And so Teachout has been left to soldier on, alone.

But sitting in a café around the corner from her apartment in the Fort Greene neighborhood of Brooklyn on a rainswept morning the night after her appearance alongside Dean, Teachout seemed buoyed. The last couple of days had been good ones. The Cuomo campaign had challenged her residency in the state, but the case had been dismissed. (Her landlord, she said, had been served with a subpoena.) The New York Times had editorialized about “A Teachout Moment” and accused the governor of bullying. A few days earlier, the centrist Democrat slayers over at the Progressive Change Campaign Committee announced they were going all in for her, the only battle against a Democratic incumbent they would engage in this year.

“The divide in the Democratic Party is as real as peanut butter and jelly,” Teachout said, drinking a latte underneath a wall-scale painting of the World Cup bracket, which put the flag of the victorious Germans just above her head. “This is a very serious fight about priorities and who you are fighting for. It’s about whether you are fundamentally serving the middle class or not. The corporate Democrats, I don’t think they are Democrats. And Andrew Cuomo is the archetype of this. His economic theory is tax breaks. Now tell me the difference between that and Ronald Reagan.”

Teachout says that as governor, she would be “a dog on a bone” about campaign finance reform. She would gut the Common Core educational standards and pour money back into schools by raising taxes on the rich and on the financial services industry, dismissing concerns that deep-pocketed individuals and companies would flee if taxes were raised. “I want to hold a campaign event at the Goldman Sachs tower in Jersey City,” she joked.

Teachout doesn’t see herself as a top-down, big-government type of Democrat but rather, she took pains to point out, a “trust-busting Democrat” who wants decision-making to take place at the community level as much as possible. She sees the decline of small business in New York as a damning indictment of Cuomo.

“I am a progressive, populist Democrat,” she said. “But I am a traditional Democrat. Andrew Cuomo would prefer to characterize me as far to the left, but on issue after issue I am much more in the mainstream of this state than Andrew Cuomo. I would be right at home in Mario Cuomo’s Cabinet. Andrew Cuomo has wandered off into the Republican Party. He looks like he is running for president of a conservative country.”

Asked what kind of Democrat she was, Teachout responded without missing a beat, “A Teddy Roosevelt Democrat.”

“No! Franklin Roosevelt. FDR!” she corrected herself. “I just stopped by Hyde Park. Sherrod Brown, Elizabeth Warren. These are the people I really admire. They are mainstream, populist Democrats.”

Teachout seemed nonplussed by the fact that the largest progressive organizing force in New York, the Working Families Party—an organization she considered herself a proud, dues-paying member of—was now ostensibly working to defeat her. Cuomo, she suggested, had created an almost Nixonian-level culture of fear around Albany; she described campaign staff who declined to work for her because they feared it would irreparably harm their careers. Before she eventually decided to tap Tim Wu, a fellow law professor and one the leading theories of Internet policy, she reached out to lawmakers she thought would be interested in running statewide with her. They declined. “I am afraid of what it would mean to my constituents,” one told her. Teachout is up for tenure at Fordham Law in January, and she has been warned by some supporters not to be surprised if she is denied in light of her gubernatorial campaign.

“I have three piles of fundraising,” she said, pushing aside a sliced egg and avocado salad to demonstrate. “Here is the pile of people who have given me money. Here is the pile of people who won’t. And here is the biggest pile—the people who tell me they want to donate to the campaign but want to do it anonymously because they are afraid what might happen if the governor finds out.”

If the Working Families Party’s endorsement of Cuomo was supposed to rip apart the progressive coalition in New York State, it has not happened yet, even though as Adam Green, the head of the PCCC, put it, “Andrew Cuomo is one of the worst corporate Democrats in America.” Members of the WFP rank and file understood why the leadership maneuvered to back Cuomo, even as the impending ethics investigation into his administration made that decision look worse and worse. Some labor unions that are a part of the WFP would need Cuomo’s support in upcoming labor contracts; others were able to get long-sought tangible victories out of it, like a promise to raise the minimum wage. Others saw the endorsement as part of the group’s ability to make short-term transactional deals while playing a long game. This is a group, after all, that started plotting de Blasio’s eventual mayoral run back when he was a lowly school board member in Park Slope.

People close to the WFP leadership said the group seemed quite pleased, meanwhile, to watch Teachout scratch out ways to make the campaign a real race. They had already gotten a few concessions out of Cuomo when they endorsed him, after all; the better Teachout did, the more likely Cuomo would need their grassroots army of supporters and the more likely they would be able to hold Cuomo to his commitments next term.

“There is definitely a sense right now of buyer’s remorse, of ‘Oh shit, what did we do?’” said one party member. “Of course Cuomo is going to be reelected, but maybe now we can get him to deliver on what he promised.”

After she finished her salad, Teachout returned to her cramped but charming fifth-floor walkup apartment overlooking Fort Greene Park, making clear along the way what was to be considered on and off the record in her domicile (Off: Anything that depicts any lack of order in the apartment, and any of the usual nonsense used to dismiss female politicians. On: The piece of the Marcellus Shale sitting on her kitchen table/desk and Arthur Schlesinger’s Roosevelt biography. Unclaimed: The daisies sitting in an Honest Tea bottle by the door, the copies of Ibsen and Plato resting on her bookcase.)

She had an interview with Fred Dicker, a fiery and feared talk radio host and New York Post columnist whom Cuomo smartly neutralized but who had since turned against the governor. Dicker—a devoted advocated of fracking, the Second Amendment, and low taxes—and Teachout were an unlikely pair, but now they at least had a common enemy, and so Teachout turned off the air conditioning in her apartment (“We are turning the heat up in our politics! It’s the long, hot summer of our democracy!”) and called around to a few friends to go over that she should say to Dicker, who has a reputation of being a bulldog of an interviewer. (In 2010, he was physically attacked by Cuomo’s Republican opponent.) A recent poll had shown that more New Yorkers believed Cuomo makes decisions based on what is best for his own political future than what is best for the state and that Cuomo had wasted energy and resources on the ultimately fruitless effort to kick her off the ballot.

Instead, Dicker mostly wanted to talk about whether Teachout would support Cuomo in the general election should she lose the primary and her thoughts about the Israeli-Palestinian conflict. Wrong answers to either are fatal. Teachout deftly deflected, trying to change the subject to Cuomo’s unwillingness to debate her and the failure of his appeal to challenge her residency: “Sometimes I think he’s scared, and sometimes I think he just can’t help himself.”

Afterward, though, she was clearly deflated.

“Ahh, I should have known,” she said. “I didn’t anticipate there would be so much about Israel.”

After the interview, Teachout walked to an art space in Brooklyn, where she met with Wu, her running mate, for a Reddit AMA. They gathered in a small conference room surrounded by a couple of aides and divided up who would take which questions. Wu took one on net neutrality: “Net neutrality is like’s women’s suffrage in the teens or ’20s. It’s its own little issue. In the ’20s, most people didn’t care about women’s issues, except for women’s groups. That’s what it’s like with net neutrality.”

But the AMA, too, was a little slow to catch on.

“We are competing with a Park Ranger AMA,” reassured one aide. “It takes some time.”

Another asked Teachout if she had considered how much better their fundraising would be if they had a public financing system that rewards small donors.

“Every fucking morning,” Teachout said.

Teachout took a question on redistricting and another on her favorite kind of bagel. Wu answered one about whether he would prefer to fight 100 “duck-sized Gov. Cuomos, or one Gov. Cuomo-sized duck.”

“I gave this a lot of thought,” Wu wrote, “And I still stand by my old answer that the one Cuomo-sized duck would be easier because the 100 duck-sized Cuomos would get behind you and kick you off the ballot.”

One of the oddities of politics in New York is that although the governor and lieutenant governor are a ticket, they run separately, which presents the possibility that Cuomo could best Teachout and face the Republicans in November with Wu as his lieutenant governor. (The Republican side faced such a scenario in 2010.) Teachout said she picked Wu in part because he was a contrast to Cuomo’s chosen running mate, Kathy Hochul, a former congresswoman from western New York most known among progressives for being open to gun rights and closed to undocumented immigrants’ rights.

“It is very clear that Andrew Cuomo did not expect a Democratic primary for governor, or he never would have picked her,” Teachout said. “He picked Kathy Hochul because he wanted to send a signal to Republicans around the state—or around the country. I don’t know if he is running for president.”

In the days since our talk, things have started to look up for the Teachout campaign. An influential Manhattan political club rescinded its endorsement of Hochul and backed Wu. The state’s second-largest public employees union announced that it was backing the ticket, too, and Lawrence Lessig, the Harvard professor and campaign finance reform advocate, pushed his network of supporters to donate more than $50,000 to the campaign.

After losing out on the WFP backing, “I know Andrew Cuomo just thought I would vanish,” Teachout said. “But I actually have it easy. Most insurgents have to convince voters to change their minds. I just have to convince people to know that I exist.”