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The Challenger

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A few decades before Justin Elicker decided to run for mayor of New Haven, he stole a shopping cart. “I don’t know what we were thinking, but we stole a shopping cart and threw it in the woods,” he told me. Elicker remembers lifting the grocery-store staple as a singular moment of rebellion in his sheltered young life in the wealthy suburb of New Canaan, Connecticut. “It was really exhilarating,” he reflected, smiling sheepishly. “I still feel bad about it.” 

Elicker came of age in a community that regularly tops the charts for highest median family income in the United States. Just a forty-five minute drive from New Haven, New Canaan is 95 percent white and looks strikingly different from the majority-minority city he’s hoping to run. “It was in one way very wholesome,” Elicker told me, “and in another way, devoid of a lot of the realities of the world.” Before moving to New Haven, he attended Middlebury College, then taught English in Taiwan, worked as a Foreign Service Officer in the U.S. State Department, and taught elementary school, high school, and college in Connecticut. He moved to New Haven in 2007 to attend Yale’s School of Forestry and the School of Management, and graduated in 2010. Now, nine years after graduating, he lives with his wife, Natalie, and their two kids on the top floor of a three-family house on Orange Street.

After outgrowing his days of snatching shopping-carts, Elicker ran for mayor of New Haven for the first time in 2013, when he was 37 years old. He’d lived in New Haven for six years, and served as alder for the East Rock and Cedar Hill neighborhoods for four. His platform centered around “fresh solutions,” which he posted one by one for seventy-five days on his campaign website. The solutions touched on everything from police reform to vocational training programs to the bureaucracy of the preschool enrollment process. Hartford Courant reporter David Holihan wrote that he ran as “New Haven’s equivalent of Bernie Sanders, only younger and with better hair.” 

He had big plans and not much experience. His relationship to the city was shaped by his time at Yale, and some constituents seemed to feel that he hadn’t spent time in the neighborhoods he was hoping to represent. The unions staunchly backed his opponent Toni Harp, a fellow Yale graduate and a popular state senator. At one debate, Paul Bass, editor of the New Haven Independent, asked Elicker how he would succeed as mayor with “no appreciable support” from people of color in the city. 

In the 2013 election, his supporters looked very much like the people he’d grown up around: most of the 23 percent of the votes he accumulated in the Democratic primary came from the affluent, predominantly white neighborhoods of East Rock and Westville. After his loss in the primary, he ran as an independent in the general election against Harp. She became the first woman to be mayor of New Haven; he went back to the drawing board.

Elicker’s 2019 campaign wasn’t entirely a departure from his campaign in 2013; both were grassroots-based and issues-centered. Each time, he emphasized his commitment to taking only donations that fell within the limit set by the Democracy Fund, New Haven’s public financing system ($370 in 2013 and $390 in 2019). But on the night of the 2019 primary election, something was different. An underdog from the beginning, Elicker won with 2,048 votes more than Harp. In 2013 he won in just seven wards, five of which included East Rock, downtown, and Yale’s campus. This year, he took fifteen. Though predominantly white neighborhoods remained a large portion of his support, New Haveners from all corners of the city turned out to vote for Elicker. At debates he received enthusiastic cheers. The city celebrated him. So what changed?

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On a Monday night in the middle of September, one week after he’d come out on top of the Democratic primary that many doubted he’d win, Elicker threw a “campaign kick-off.” The mood was both celebratory and expectant. Supporters and friends from across the city filled the back room of BAR, a pizza restaurant on Crown Street. Bro-hugs were exchanged and backs were slapped and kids were fed New Haven-style pizza. Gage Frank, Elicker’s campaign manager, took down names and emails as supporters filed in. Violet string lights gave the room an optimistic glow.

Many people at the campaign kickoff had voted for Harp in past elections, or had worked with her in different capacities throughout her terms. Criticism of Harp was at an all-time high following her cost-cutting relaxation of lead paint regulations, her involvement in hiring an unpopular superintendent, and accusations of corruption in her administration. Maria Tupper, an Elicker supporter in attendance, said, “As a woman, it’s hard for me not to support another woman.” But, as many of his supporters agreed, the city needed transformation, and Elicker promised change.

By the time speeches started, the room was full. Ties were loosened; tables were packed; and those without seats stood. State representatives for Connecticut shared the stage, each talking for a few moments about their support for Elicker to gentle applause. Then Urn Pendragon, a former mayoral candidate, took the floor. “Unity is more than a five-letter word,” she insisted, and received a lukewarm “woo.” When Elicker stepped up onto the table and grabbed the microphone, he thanked every speaker. The crowd roared for each name. Tables shook. Kids stomped their feet. 

Nearly a week after the event, when I walked into Elicker’s campaign headquarters on the first cold day of September, the room was quiet. It was the first floor of a small building on Whalley Avenue, nestled between an auto body shop and a hair salon. The bricks were painted daffodil yellow. On the walls, butcher paper hung underneath a question: “What are your hopes for New Haven?” 

“Equity in all schools for all kids,” one message written in block letters insisted. “Let’s start with honesty and transparency,” suggested another. “Police accountability” huddled next to a large “Tax Yale,” with “I second that” and “So do I!” written carefully in faded green marker underneath. The WiFi password, NewLeadership2019, was pasted on each wall, along with a sign denoting how many shifts campaign volunteers and staff had taken for the week. “Justin: 18” was at the top of the most recent one. The only person who completed more shifts—his campaign manager, Gage—did so only by one. 

Kevin Alvarez, Elicker’s field manager, greeted me with a warm smile as I walked into campaign headquarters. I recognized him as the “Kevin” from Elicker’s encouragements to “email Kevin” in the videos that he posts on Facebook, Beto O’Rourke-style, shot from the front-facing camera on his iPhone. Like Beto, Elicker demonstrates his fluency in Spanish in the videos—a skill he has mobilized to mixed responses while debating and knocking on doors throughout his campaign. In the same tradition as Beto’s performance at the first presidential debate, Elicker’s willingness to speak in Spanish could be interpreted as a sign that he’s focused on communication and accessibility in governance—or, to some ears, it could ring as inauthentic.

One of the successes of Elicker’s 2019 campaign is the variety of ways he’s created relationships with voters. He engages with millennials online and with the elders of his city on their front porches. And his willingness to reveal his personality in his public presence shows—from his SoundCloud cover of The Rainbow Connection in the style of Kermit the Frog, to his storied Justin Bieber impression the Independent deemed “credible,” to the way he gives out his phone number freely online and in speeches.

But on the night of the 2019 primary election, something was different. An underdog from the beginning, Elicker won with 2,048 votes more than Harp.

Elicker wore his signature cornflower-blue shirt and held a Klean Kanteen gingerly with both hands as we spoke. He had a bad cold, but he talked through it in a soft and serious way, stopping when a story he told made him chuckle. I asked him why he would be the best person to be mayor. “I don’t think I’m the best person. Barack Obama would be better than me,” he said solemnly. (Many supporters applaud his humility.) He believes that the knowledge he’s gained over the past five years as executive director of the New Haven Land Trust and the perspective he’s gained from living in New Haven for more than a decade will set him up for success. 

Elicker took leadership of the Land Trust, a non-profit organization focused on local land stewardship and environmental education, in February 2014. Around that time, an embezzlement scandal involving Elicker’s predecessor racked the organization. Elicker moved the Land Trust forward,  spearheading a youth jobs training program, revitalizing Schooner Camp, and championing a series of community gardens—which, five years later, are going strong.

While sharing a beer with her wife at Elicker’s campaign kickoff, Sally Esposito, a former educator who has watched the Land Trust evolve under Elicker’s leadership, told me that Elicker has gotten to know the city through his work in community gardens. She recalled watching him turn the Land Trust’s struggling finances around and shift it from an organization focused on wealthy neighborhoods into one that served her neighbors in Fair Haven who needed more help. She saw Elicker get his hands dirty in gardens across New Haven, growing familiar with neighborhoods he hadn’t spent much time in before. 

“I never knocked on doors in East Rock,” Elicker said about his most recent campaign. “I knocked on doors everywhere else in the city.” He found the process fulfilling, and it changed the way he campaigned. “It’s interesting how many things come up over and over and over again on the doors,” he said, mentioning affordable housing and free after-school programs as common topics of concern. The focus of his campaign shifted substantially from the neighborhoods that had supported him in 2013 to the neighborhoods he felt needed more attention, but his closest supporters remained committed—Elicker didn’t spend his canvassing time near his home, but he attended fundraisers in East Rock, and stayed close to his friends and supporters there. 

At the Land Trust, more than any place else, Elicker learned how to lead with his ears first. “It’s really important to not just show up, even if you’re pretty sure it’s the right thing to do, not just show up and tell people ‘we gotta do this,’ but to listen, and engage, and build trust,” he said. Elicker looked up at the ceiling quizzically while we talked, as if he were presently absorbed in the process of figuring out how he felt and what he should do. He repeated this gesture many times throughout our conversation, especially while reflecting on his relationship with one community gardener in particular, Alonzo Bryan. 

Bryan (whom Elicker calls “Mr. Alonzo”) tended a community garden on Hazel Street in Newhallville, for which he’d been caring alone for a couple of years. When the Land Trust approached him to ask if other Newhalville residents could garden in the plot, Bryan felt frustrated. “And it was fair for him not to be happy about that,” Elicker said, gazing upwards. But Elicker, no stranger to distrust, was persistent. He felt that the community in Newhallville should have an opportunity to cultivate their own soil, and benefit from the harvest. “Over time, we developed a relationship with him,” he said. Then, recently, Bryan welcomed a woman and a group of young children to Hazel Street to garden alongside him. 

Another thing that Elicker learned from his work with Bryan is that time can be an ally. “Things take a lot of time. And sometimes time is all it takes,” he said. Time has been good to Elicker; the six years between his campaigns account for half of his time living in New Haven. Part of his recent success is tied to the roots he’s put down in those years. 

She saw Elicker get his hands dirty in gardens across New Haven, growing familiar with neighborhoods he hadn’t spent much time in before.

Elicker has worked in the past years to distance himself from Yale. But Elicker’s engagement with New Haven, like incumbent Toni Harp’s, has been shaped by his time as a Yale student. When I asked him about how he would tax Yale, he paused, then placed two fingers on the table between us, in parallel lines. “What’s important is exploring those options at the same time that you build a relationship,” he told me. “Like two business that are potentially collaborating, but potentially competitive.” He turned a searching gaze upward once again.

Elicker has an instinct for collaboration. “The way I’ve learned how to make those decisions in life in general is to incorporate other people who I trust,” he said. “I don’t think one person is ever good at making all the best decisions.” Part of the shift in Elicker’s appeal from 2013 to 2019 is that he surrounded himself with a more diverse campaign team. “It was important to get leadership from many different backgrounds to be visibly part of the campaign,” he said, “both to guide some decisions on the campaign, but also to show the city that our campaign was inclusive of many people, and prioritize that.” 

Elicker’s consciousness of the ways his whiteness has shaped his candidacy takes various forms. At worst, he seems prone to tokenizing the people around him. At best, his reflections encourage him to engage more humbly and more intentionally with the city. 

“My administration will be really accessible,” he said with a hopeful smile. “A lot of people want to be listened to and want to be heard.”

Elicker proved throughout the 2019 campaign his chameleonic skill of shifting tactics in order to meet the expectations of the city he hopes to govern. He recognizes his blind spots. He pays attention to what New Haveners tell him they need, and incorporates their conversations into his platform. How he’ll transition into office, if elected, remains to be seen. “I think being mayor is a constant campaign,” Elicker told me. He’s been working to win the trust of New Haveners over the last six years; perhaps, come January, we’ll be seeing more front-facing iPhone videos and hearing more of his knocks on our doors. 

Mara Hoplamazian is a senior in Grace Hopper College.

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