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As Nick Shalek ’05 decided during the summer whether to run for Ward 1 alderman, he knew that he had virtually no experience in New Haven politics, no knowledge about how to run a campaign in Ward 1, and few established contacts among the undergraduates who did.

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He also knew that an independent candidate in Ward 1 had not successfully defeated an incumbent Democrat in the modern history of the ward, and that his opponent had deep connections and allies within the local political scene, up to and including the support of Mayor John DeStefano Jr.

But by July, Shalek concluded that he might have a chance. To win, though, he would need to convince Yale’s campus that he was both a loyal Democrat and a more moderate alternative to the party’s nominee. In two months, he would need to register hundreds of voters who had never before been involved in Ward 1 politics, and then make sure they got to the polls.

Because of those challenges, supporters of both Shalek and his opponent Rebecca Livengood ’07 said they viewed him as an underdog even up until Tuesday’s election. But Shalek’s victory by a margin of 57 votes proved that the strategy he began developing over the summer could overcome the disadvantages that history and conventional Ward 1 wisdom suggested he would face.

“For every one person who knew about everything and was positive, there were 10 who were negative,” Shalek said. “People were rightfully skeptical.”

Doing the math

For both the Shalek and Livengood campaigns, 403 appeared to be the magic number. That was the final number of ballots cast for Alderman Ben Healey ’04 when he was reelected to the Ward 1 seat in a landslide in 2003 against independent Dan Kruger ’04, who received only 128 votes.

Livengood’s camp knew that the new alderwoman lacked certain advantages her predecessor had two years earlier. Unlike Healey, who had already served a full two-year term, Livengood only began serving on the board two months before Election Day, minimizing her advantage as an incumbent. And unlike Kruger, Shalek, a former president of the Yale Entrepreneurial Society and a former captain of the varsity hockey team, had a wide-ranging base of friends and associates on campus who might help him win over voters who would have supported Healey two years earlier.

But Shalek knew that a highly mobilized Livengood campaign might be able to make up for some of those lost voters. If Shalek was going to reach the 400-vote threshold, he would need to bring in voters who had not come anywhere near the Ward 1 polls before this November.

The different challenges the two candidates had identified were reflected in the differently styled campaigns each ran. Livengood’s approach was traditional, modeled after the larger campaigns she and many of her staffers had worked on in 2004. Her supporters worked on “visibility” — wearing green T-shirts with Livengood’s name on them and actively distributing posters and flyers. Volunteers worked in phone banks, repeatedly calling registered voters in their dorms, or went door-to-door to distribute voter registration forms and literature on Livengood.

“We had all worked on campaigns before, and I still think [canvassing] is the most effective way of reaching out to new people,” Livengood campaign manager Suzanne Kahn ’07 said.

Shalek’s campaign was no less aggressive in targeting the ward’s voters, but it used a markedly different approach that took advantage of established networks and groups, from sports teams to a cappella groups. Shalek campaign manager Brett Edkins ’06, who, like many of Livengood’s supporters, had worked with the Kerry campaign in 2004, said he doubted how effectively traditional campaign methods would work in Ward 1.

“They just transported those methods here,” Edkins said. “[But] this is Yale. Everyone knows everyone. Why are we still doing this sort of impersonal politics?”

With groups like sports teams, Shalek often worked through captains or other senior leaders, identifying at least one member of the team to work as a coordinator who could send out information about his campaign. The coordinator would then try to register the team at once, often at practice, while Shalek would personally contact anyone with questions. And on Election Day, vans were sent to several teams after practice, at the Gilder Boathouse, the Yale Bowl and Payne-Whitney Gymnasium.

“We made a couple of announcements to the entire football team when we had team meetings and said, ‘Listen, one of our buddies is going to be running for a local office, and for those of you who live in the ward … we’re going to have voter registration sign up sheets over by the cleats,” said Tyler Wells ’06, a friend of Shalek’s who helped him garner support among his football teammates. “After we pushed them a couple of times and got them registered and let them know this was a close friend of ours, they obliged, the younger guys especially.”

Wells said he would estimate that 30 to 40 of the team’s 100 members voted for Shalek.

Although Shalek’s inexperienced campaign made significant missteps — including the submission of an inaccurate campaign finance statement in September — it also found ways to take advantage of work done by the highly organized Livengood campaign. While Livengood’s supporters and her allies in the Yale College Democrats had registered hundreds of freshmen at the beginning of the semester, they did so with little regard to whom the new voters would support, leaving them open to persuasion from the Shalek camp.

But as many Old Campus residents said they felt overwhelmed by contact from Livengood supporters, Shalek said he was conscious of taking a more measured approach to door-to-door campaigning. Shalek knocked on doors every night during the last two weeks of his election, but his campaign also left fliers inviting freshmen to request that the campaign stop coming by.

A winning issue?

The battle on the Board of Aldermen regarding Yale-New Haven Hospital’s proposed cancer center had begun in earnest by the fall of 2004. On Yale’s campus, students affiliated with Community Organized for Responsible Development, a group closely aligned with labor organizers pushing for unionization at the hospital, were active in calling for certain conditions to be met before the cancer center moved forward. But for the most part, the issue inspired little open debate on campus.

By October, Shalek had changed that. He said his decision to run was inspired by thinking about economic development in New Haven and was cemented while watching a contentious aldermanic debate over the cancer center during the summer. When he returned in the fall, he made it the key rallying point for his campaign, knowing that Livengood believed the hospital needed to make further concessions before the city approved its plans.

For Shalek, the cancer center itself was a powerful issue: At stake, Shalek and his supporters argued, was not only millions of dollars of research funding and hundreds of jobs for a city institution, but also the lives of cancer patients.

But beyond the specifics of the project, the issue had a potent symbolic value in framing the race, both Shalek and Livengood supporters said after Tuesday, as it tapped into flashpoints in the candidates’ backgrounds. Contrasting his approach with what he called the “well-intentioned but impractical activism” of the Graduate Employees and Students Organization and the Undergraduate Organizing Committee, Shalek banked on the idea that he could convince voters that the cancer center proved Livengood was out of the Yale mainstream. By contrast, the charge that Shalek was too closely associated with the Yale administration due to his employment in the Investments Office never seemed to gain as much traction.

“[GESO and the UOC] are things that Rebecca has been supportive of, and for a lot of people on campus that helps them understand her campaign … and what her term on the board would represent,” Shalek said.

Dan Weeks ’06, who competed with Livengood in the spring for the Ward 1 Democratic Town Committee’s endorsement, said Shalek’s focus on the cancer center was unsurprising — particularly since the two candidates’ platforms on other issues, from gay rights to the environment and crime, were similar.

“It would have been too outrageous to brand her as paying fealty to the unions,” Weeks said. “The cancer center was an open door to raising a lot of the concerns that Nick’s campaign wanted to raise about Rebecca.”

In an interview on Thursday, Livengood said her campaign had succeeded in broadening its appeal well beyond the UOC, noting that she had key supporters came from other groups like the Roosevelt Institution, the Liberal Party and the Black Student Alliance at Yale. And Livengood took issue with the idea that her background limited her potential support, noting that the UOC had 375 members.

But she acknowledged that despite a visible presence of supporters — a group Edkins said he called the “green army” due to their trademark Livengood T-shirts — her campaign struggled to find a large group who would be guaranteed to support her on Election Day.

“Nick had a larger base than we did that offered automatic support,” Livengood said. “We had a large base in terms of volunteers, but not in terms of a cohesive group of people who are easy to bring out.”

The final surprise

By the time Nov. 8 rolled around, both campaigns were closely watching their “1’s.” As they canvassed, both campaigns used the common practice of voter identification, tracking how each registered voter might be expected to cast his or her ballot come Election Day. In the lingo of voter ID, a campaign marks a voter as a 1 if he is a definite supporter, a 2 if he is still on the fence and a 3 if he is definitely voting for the opposition.

Midway through Election Day, Edkins said, he noticed something that made him optimistic. The voters whom Livengood’s supporters had registered were showing up in much smaller numbers than he had expected. Meanwhile, many of Shalek’s 1’s were showing up — so much so that they were outnumbering all other voters combined.

But the two candidates’ campaigns offer different interpretations of why Shalek was able to win 57 more voters than Livengood. Livengood said her campaign hit two roadblocks: Shalek’s ability to tap into cohesive social groups like sports teams and fraternities, and a sense of inevitability among some of her potential supporters that an endorsed Democrat was destined to win. Livengood and her supporters said that because of the similarities between many of the two candidates’ positions, Shalek’s victory signaled more about campaign tactics than the political views of Yale’s campus.

“It’s not something based on an ideological difference,” said Helena Herring ’07, an active member of Livengood’s campaign. “It was based on personal relations.”

But Shalek and his supporters said Tuesday’s victory signified a desire among students to move away from the activist approach represented by the UOC.

“I felt positive all the time that we were giving Yale students a shot at the issues and another choice of Democrat,” Shalek said.

How closely Livengood’s supporters will choose to work with Shalek remains an open question. Livengood, whose term on the board ends in January, said she hopes her allies are galvanized by her defeat into working harder for the issues they care about at the city level. But with close contacts in City Hall and among other aldermen, that work may not be done through Shalek.

Shalek, on the other hand, will now turn to a new challenge: navigating the internal politics of the Board of Aldermen. Shalek is likely to be placed in the middle of a power struggle between two coalitions on the board looking to secure the seat of board president. Mindful that he may be a swing vote, Shalek has not yet committed to either side. Reflecting on a political career that had taken unexpected turns in just three months, Shalek said he was in no rush to make up his mind.