Zephyr Teachout meets with potential voters in Ithaca, New York, August 9, 2014. Les Stone for Al Jazeera America

Editor’s note: This is the third in a series of profiles of people running for office in America who are unlikely to win, but who believe so strongly in their cause that they still try. The first profile, on Bruce Skarin's efforts in Massachusetts, can be read here. The second, on Joe Pakootas' campaign in Washington, can be read here. NEW YORK – One day in early June, Zephyr Teachout (pronounced ZEH-fur TEECH-out), a Fordham University law professor and aspiring governor of New York, made her way upstate to the small town of Rosendale. She needed time to think. She was coming off what seemed to be a major defeat: her failure in a (surprisingly close) referendum to get the endorsement of the Working Families Party. The newish progressive group was her natural base, but its members had decided to endorse incumbent Andrew Cuomo. So her friend and campaign manager, Mike Boland, invited her to his home for five days to figure out together whether she should run as a long-shot insurgent candidate anyway. They couldn’t make up their minds. Finally, they agreed to take a bus up to the state capital, Albany, where they would come to a decision. But they missed their connection in Kingston and found themselves stuck at an empty roadside bus station. Was it a sign? It was late. They asked if there was another way to get to Albany. There was an extra bus somewhere, someone at the ticket office said. And just like that, they were driven in the relative luxury of an empty bus to Albany. That, they decided, was the real sign. She was going to run anyway.

The candidate meets with local Democrats over breakfast in Ithaca. Les Stone for Al Jazeera America

A quick look at Zephyr Teachout’s resume shows a habit of taking on the establishment, often from the inside. The 42-year-old grew up in rural Vermont, went to Yale and got her first job as an aide to a special-education teacher. Soon after graduating from Duke Law School, she was representing inmates on death row in North Carolina. She worked on Howard Dean’s failed 2004 presidential bid – a campaign heralded for its groundbreaking web strategy – as head of online organizing. She also co-founded a group dedicated to breaking the power of Wall Street banks after the crash of 2008. Today, the anti-corruption Harvard academic Larry Lessig cites her campaign as “the most important money-in-politics race this year.” Teachout's main obstacle in this race so far has nothing to do with the issues: a recent Siena College poll found that 91 percent of Democratic voters didn’t know who she was or held no opinion of her. But if you want to run against the odds – and an unknown progressive candidate taking on an incumbent Democrat from the left is a true long-shot – then you need to at least be willing to hustle. Spend a day on the campaign trail with her, and you’ll see she’s hardwired for that particular challenge at least: from city hall to Queens to upstate New York, in cars and subways and on long-haul bus lines, her campaign is a rolling electoral insurgency against the powers that be. Five weeks into her campaign, on a hot and muggy summer morning in New York City, Teachout was addressing a dozen sweaty journalists alongside Republican challenger Rob Astorino in front of the Tweed Courthouse – the very spot where Cuomo had launched his own campaign four years ago. “I’m here today with a man I disagree with on almost everything,” she said, “because recent events show that Gov. Andrew Cuomo has not merely failed to clean up Albany; he has become part of the problem and an example of the very thing he once promised to fix.” Next to her, an aide brandished Cuomo’s campaign booklet from 2010. Teachout called it “a series of broken promises.” Her timing was perfect, as it turns out: the next day, the New York Times printed a two-page exposé on a panel set up by the governor last summer to look into allegations of corruption in state politics. The article detailed how investigators from the Moreland Commission faced constant interference from the governor’s office, which objected to their demands whenever they came too close to Cuomo. The commission was disbanded in March, nine months ahead of schedule, by the governor, who had vowed it would be “totally independent.” Morelandgate is Teachout’s backdoor into the race. Cuomo’s favorable rating has fallen to 53 percent, the lowest since he took office in 2011, according to a Wall Street Journal/NBC 4 New York/Marist poll conducted after the revelations. So she intends to walk right in. “I would challenge Gov. Cuomo to a series of debates on particular topics, including education, including immigration and including hydrofracking,” she said at the end of her speech. “But I will tell you that each one of those debates would end up being a debate about corruption in Albany.”

At a farmer's market in Ithaca. Les Stone for Al Jazeera America

A few minutes later, on the 6 train heading toward Canal Street, Teachout went over the day’s schedule, phone in hand. She was expected to speak in the courtyard of a Little Italy church with her running mate, Columbia University Professor Tim Wu, at 11:45 a.m., which meant she had 25 minutes for an important matter: lunch. “You know, I need to eat or my jaw will get stiff,” she reminded one of her two aides cheerfully. She had flown in from Buffalo on a 6 a.m. flight, but didn’t seem fatigued at all. Over a cappuccino, an assorted antipasti plate and a bowl of cheese soup on Mulberry Street, she immediately tackled a difficult subject with her aides: On July 21, the state Board of Elections received two objections to the campaign’s ballot petitions. But Teachout said she welcomes the challenge. Her volunteers have done a lot with very little. They collected 45,000 signatures, three times the number necessary, improvising a campaign headquarters at a Wall Street atrium that once served as the Occupy movement’s headquarters. Teachout said she has complete trust in their work. Indeed, the Board of Elections later ruled the petitions were valid. At the small church, Wu was already speaking to a crowd in Mandarin. “Jacket on or off?” she whispered to an aide as a reporter pointed a mic at her face. The answer was on. “It’s just so damn hot,” she said, smiling Wu is a renowned lawyer and a leading light in the world of Internet policy, and by picking a New Yorker of Taiwanese descent as her candidate for lieutenant governor, Teachout is sending a message to the state’s Democratic base. “Where has Gov. Cuomo been on immigration issues?” he said after a brief introduction. He went on, criticizing the incumbent for his failure to pass the Dream Act and for choosing Kathy Hochul, “a famously anti-immigrant ex-congresswoman” as his running mate. Teachout nodded.

Campaigning in Ithaca Les Stone for Al Jazeera America

At 2 p.m. the Elmhurst-Jackson Heights Senior Center smelled like chicken cacciatore. Over a hundred people were gathered to eat and celebrate Peruvian Independence Day. A large batch of keys in hand, director Lucy Garcia greeted Teachout and the campaign team. Her bright-blue shirt matched her eye makeup and the five rings stacked on her index finger. “In this senior center it has been our tradition to celebrate ethnicity,” Garcia explained in the large room filled with red and white balloons. She grabbed a mic and turned toward the audience. “Can we have some quiet, please?” she called out, translating everything into Spanish as she went. “I want to introduce a lady that is running for governor of New York.” A group of women in bright dresses sitting at the front table cheered. “Happy Peruvian Day!” Teachout shouted after being introduced as “la futura governadora.” “My name is Zephyr Teachout ...” There was a collective “huh?” That often happens when she first says her name. When she was younger, Teachout thought it would be an obstacle to a career in politics. But it may have served just the opposite purpose, she said, prepping her to face derision from an early age. Even her middle name, Rain, doesn’t disappoint. “Zephyr! Repeat after me, Ze-phyr!” she said. “And I want you all to remember that the Statue of Liberty is a woman welcoming people from all over the world.” After her speech, women asked for photos with Teachout. She danced out of the senior center and caught a cab back to Manhattan. “Campaigning is so much fun,” she said. A few hours later, in an air-conditioned room in a midtown building where her headquarters are located, she compared herself to the jazz musician Rahsaan Roland Kirk, who used circular breathing to play more than one instrument simultaneously. “It was the only way he could play the harmony and the melody at the same time,” she explained, crushing sushi between two chopsticks. “Campaigning is like that. The job is to play these different instruments, like fundraising and press and community meetings, and at the same time maintain strategy and the capacity to listen, so that you’re not just sort of blowing out things that you’ve heard before.” Her voice was starting to break a little, but she still showed no sign of fatigue.

At the breakfast event in Ithaca. Les Stone for Al Jazeera America