Zephyr Teachout's Quest to Become the Left's Newest Crusading Congresswoman

Zephyr Teachout wants people to get past her name.

"I did not know that Zephyr Teachout was a person," someone wrote on Twitter in late September, voicing a thought that a lot of people have when they hear or see her almost Pynchonesque monicker. "We're working on that!" she playfully responded.

For some New York progressives, Teachout is less a real human than a cause. Her claim to fame remains her challenge of New York governor Andrew Cuomo in the Democratic primary for the 2014 gubernatorial race, where she claimed a surprising 34 percent of the vote, despite being an unknown Fordham law professor going up against the state's most powerful politician.

It was a preview, in some ways, of the kind of Anti-Establishment left-wing challenge Bernie Sanders mounted against Hillary Clinton. Teachout was influential enough, and outspoken enough, that in March some Clinton allies worried about her being a "pain in the ass" by endorsing Sanders, according to campaign emails stolen in a hack and released by WikiLeaks.

But Teachout's foray into electoral politics wasn't a stunt, or an act of protest—she's obviously serious, and pragmatic, about becoming an elected official, and is now fighting to win a House seat in New York's 19th Congressional District, which spans 11 counties across New York's Hudson Valley. This region has skyrocketed in popularity over the past few years, for its small town aesthetics, farm-to-table restaurants, and "artisanal" Etsy-fied Renaissance (the tech company has an office here), especially among city folk looking for a greener (and cheaper) escape.

Teachout is one of these city folk. Her opponent, Republican John Faso, has called her a "liberal carpetbagger professor," and it's true that she is a recent transplant from Brooklyn—she hadn't lived in the 19th until March, a mere ten months before she announced that she would seek the House seat left vacant by three-term Republican representative Chris Gibson's departure. Though it's a local campaign, the core issue she's running on couldn't be more national—she wants to get money out of politics, which makes it fitting that her dead-heat race perfectly personifies the impact of Citizens United, the Supreme Court decision that ushered in a new age of corporate cash in elections.

At 44 years old, Teachout—who grew up on a farm in Vermont—seems like someone you'd run into at a craft fair, wearing a fluffy zip-up vest and sifting through homemade jams. When we met at a diner in Dover Plains on a recent Sunday morning, she arrived with her husband, Nick, fresh from a half-mile hike nearby. "So beautiful this time of year!" she exclaimed.

She insists that her move to the Hudson Valley wasn't a move of political calculation a la Hillary Clinton's move to Chappaqua before her campaign for Senate in 2000. "I moved here before I planned to run. It's closer to my folks, who are about two and a half, three hours north," she told me. "I'm a country person. I love it here." She mentioned anti-fracking campaigns and other causes in the region that she had worked on in the past.

"There are so many things that I see at a crucible moment in our country, and in this region—in the Hudson Valley, and Catskills," said Teachout. She added later, "We have a lot of pain throughout this district. There are really exciting bright spots, but there are a lot of places without jobs."

It was upstate areas like the 19th District—Ulster, Dutchess, and Sullivan counties—where Teachout dominated during the 2014 gubernatorial primary, but back then she was largely a protest candidate, a way for Democrats to register displeasure at the transactional politics of Albany under Cuomo. This campaign, on the other hand, feels more like a real contest, one removed from the echo chamber that has consumed this year's presidential election. (Cuomo endorsed Teachout in July, albeit in a pretty grudging manner—he didn't mention her name.)

When it comes to policy, Teachout sounds like an old-school 1930s populist wonk—perhaps a product of having a constitutional lawyer and a state judge as parents. She splits her district (and America, for that matter) into two camps: those who have money, and those who do not. And she often resists any talk about the right-left spectrum of ideology, or party politics, even if her own sympathies are pretty clear. Sanders has stumped for Teachout, who in turn has praised his own crusade. "Thank you Bernie Sanders for having the guts in leading all of us in standing up against the billionaires who are trying to take over our democracy," she said at a joint rally in September.

Teachout says she wants to represent independent farmers and self-employed workers on the House Agricultural and Small Business committees. Like Sanders, she supports a $15 wage, opposes trade deals like NAFTA and TPP, and wants to force big banks to lend to local businesses. One of her more notable proposals is to provide high-speed internet to rural America, which she described to the Huffington Post as akin to FDR's New Deal. "The Rural Electrification Act of the 21st century is broadband," she said.

She believes that she will have to take on Big Business (in her district, this means large farming conglomerates) to get anything done. And, aside from preaching campaign-finance purity, her remedy is to find common, if not shaky, ground with elected officials on specific pegs that unite rather than larger ones that divide. "I'd say, OK, so Mike Lee, the [Republican] senator from Utah, has done great anti-trust work. I'd reach out to him," she said. "OK, we disagree on other stuff. This is what we'll do."

To Teachout, the constant state of gridlock in Congress is no coincidence. Corruption and stalled governance feed off of each other, she believes—not getting anything done is exactly what Big Business wants, as both parties continue to line their pockets with huge sums of money from privately funded super PACs, which have the power to dramatically reduce the time it takes to actually campaign.

Faso, her opponent and former New York State assemblyman, represents the politician of this new "anything goes" age, she argues. "A career politician and lobbyist who thinks Citizens United is a good idea, and that there should be unlimited corporate speech, who's taken campaign cash to say that we shouldn't clean up the Hudson," is how she describes him.

In June, hedge fund billionaire Paul Singer donated $500,000 to a Super PAC supporting Faso. Robert Mercer, another wealthy hedge fund manager, has given half a million dollars to Faso as well. The influx of corporate cash prompted Teachout—who says her average donation is $19, and has benefited from Sanders's massive database of supporters—to challenge Mercer and Singer to a debate (they never responded, she said). "Sometimes I think this is a race against Paul Singer and Robert Mercer, and the other shadowy donors we don't know," she told me.

According to data compiled by ProPublica, Teachout's campaign has raised $3.3 million to Faso's $2.3 million, but outside groups opposing Teachout have spent $4.3 million compared to "just" $1.5 million spent by anti-Faso groups.

Faso is a conventional Republican candidate in most respects. This means he's a white guy, shifty when it comes to supporting Donald Trump, with a campaign website that has pictures of a gun, nefarious ISIS-esque symbolism, and an American flag on its "Issues" page.

In their most recent debate in mid-October, the two contenders fell into a predictable dynamic: Teachout went after Faso for his shady money sources, while Faso described Teachout as out of touch, a tax-and-spend liberal eager to impose cost hikes on Hudson Valley residents. He criticized Teachout's donations that came from from family members of George Soros, the notorious left-funding billionaire, as evidence that she, too, is not immune from big donors. (Faso's campaign did not respond to a request for comment.)

The 19th is that rare thing, an actual swing district. As we drove to a harvest fair where Teachout would introduce herself to voters who still might not know how to pronounce her name, we passed a decent number of Trump signs, as well as Teachout and Faso signs. No Clinton, though. "The bleeding heart is totally independent," Teachout said, referring to the district's split-even registration stats among Democrats, Republicans, and independents. "In this district, as one woman described to me, 'I vote like an EKG.'" Teachout flitted her finger. "Up and down."

For a relative campaigning neophyte, Teachout isn't too shabby at voter outreach. On a hayride with parents, Teachout talked about the best haunted houses for Halloween in the area, and joked with one boy that he was too young to be losing friends over politics. The farm itself was filled with the artisans and craftspeople that she hopes to represent come November. Before we left, I found Teachout talking alone with a guy forging horseshoes.

It seemed sleepy enough that you had to remind yourself that multiple millions of dollars are being spent on this single congressional race—something that was unheard of just a few cycles ago. Of course, it's not just in Hudson Valley; shadow donors behind super PACs are spending truckloads of cash nationwide, as the race for control of Congress tightens. By April of this year, it was already clear that this cycle's reliance on outside spending was set to surpass the 2012 numbers, making 2016 the most corporate-funded election year of our lifetime.

With Faso and Teachout in a statistical tie according to the polls, this race, like so many others this year, will solely depend on voter turnout. But Teachout hopes to push the populist tide in her favor—and in order to do that, she's focusing on something we all love to hate: Congress.

"I really think this whole year is about people versus powerful interests," she said. "And if you see it through a right-left lenses, you're actually missing how people are feeling."

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