Alder Challenge Charts Changing Wooster Sq

A bridal business owner with local political history roots has filed to run against Wooster Square’s two-term, union-affiliated incumbent alder in a Democratic race that sheds light on a neighborhood in flux.

Ellen Cupo, a Democrat who represents Ward 8 on the Board of Alders, is running for a third term this year on a platform of affordable housing and job creation for working-class New Haveners. 

For the first time since her election in 2019, Cupo faces an opponent in this September’s Democratic primary: small business owner Andrea DiLieto Zola, who’s prioritizing safety and cyber-security in her challenger campaign.

Both lifelong New Haveners, the two candidates reflect different facets of a changing Wooster Square — a neighborhood that has lately seen an influx of high-end apartments bringing a host of new residents.

While both Cupo and Zola live in Wooster Square, the ward also includes Jocelyn Square, the Mill River District, and parts of Fair Haven and the Annex. 

As a result, Ward 8 crosses multiple parks and rivers. It encompasses clusters of grand brownstones, industrial buildings, and low-income housing. It includes a hub of widely-used social services and nonprofits as well as many of the city’s most well-known, tourist-attracting pizzerias.

Challenger: "A Little Brooklyn" Grows

Zola, 36, first moved to the Wooster Square neighborhood about a year ago, renting an apartment in the newly-constructed Olive and Wooster luxury apartment building at 87 Union Ave., which falls just outside the bounds of Ward 8 and in the Hill/City Point/Ninth Square/Long Wharf/Wooster Square-crossing Ward 6.

A few months ago, Zola moved into Ward 8 proper with her partner and six-year-old in a brownstone on the corner of Court Street, where colorful front doors and carefully-tended plants adorn a rare pedestrian-centered block in the city. She and her family love to grill on their Court Street patio, with their fluffy dog Teddy.

“Wooster Square is like a little Brooklyn,” Zola said during a recent interview with the Independent.

Though Zola is a relatively new Wooster Square resident, she has built a stake in the area for years. She has operated a beauty bar and bridal business on Wooster Street, recently renamed Bridafy, since 2017. 

The pandemic slowed business dramatically — but Zola has no plans to leave her storefront at 208 Wooster St. Instead, she has recently applied for a zoning special exception to transform the storefront into a plant-based cafe called The Little Dandelion, partnering with Edge of the Woods grocery co-owner Justin Dodge. Zola expressed enthusiasm about bringing ​“healthy options” to Wooster Square.

A lifelong New Haven resident, Zola has lived in a number of neighborhoods. She grew up in Morris Cove, where she went to Nathan Hale Elementary School. She would later live in the Corsair, a luxury apartment building in East Rock. Throughout her time living in New Haven, she said, she was ​“always visiting Wooster Square.”

Zola’s motivation to run for alder is tied to her family, especially her great uncle, Biagio ​“Ben” DiLieto, who served as the city’s police chief from 1970 to 1976 and as mayor from 1980 through 1989. 

Zola said she’s inherited her great uncle’s ​“love for his family and the city and each person in the city,” adding, ​“I know that New Haven is going to keep thriving and I want to be a part of it.”

If elected alder, one of Zola’s priorities would be to double down on safety issues in the ward. 

“I’m passionate about public safety because of being a mom,” Zola said. She praised Wooster Square’s active block watch, and called for more of a police presence in the neighborhood. ​“Since Wooster Square is becoming more populated, things are developing quickly. We need more police.”

Zola later added, ​“I think the new developments are beautiful,” that the new residents in the neighborhood will help bring vibrancy and economic activity to Wooster Square. She noted that she doesn’t want the new buildings to encroach on the neighborhood’s historic character.

Zola’s focus would also include traffic safety. A car recently zoomed down Olive and struck a pedestrian right outside her apartment, she said. When asked about specific measures she would take to improve street safety, Zola responded that she would support ​“adding a stop sign where a stop sign is needed” and, more broadly, ​“talking about new ideas.”

Another passion of Zola’s is cybersecurity. She is currently enrolled in a Southern Connecticut State University course on the subject, and hopes to ​“advance the conversation” about resilient technology in the city.

So far, Zola has no criticisms of incumbent alder Cupo, or of the Board of Alders and city leadership as a whole. She likes to say that the current climate is a ​“VUCA World” — an environment of Volatility, Uncertainty, Complexity, and Ambiguity — and she said she avoids criticizing elected officials for doing their best to navigate challenging and unfamiliar terrain.

Zola served on the Wooster Square Monument Committee, helping to select a replacement for the Columbus statue that formerly stood in the park. ​“I was all for it being taken down,” Zola said of the Columbus statue. The new monument is ​“a nice way to celebrate immigrants” and make the neighborhood ​“welcoming for all.”

Zola took a stance on one controversial question that has long brewed throughout the city, and especially in Wooster Square. ​“We get Sally’s at least once a week,” she said — usually a bacon and onion pizza.

Incumbent: Working Families Focus

Meanwhile, Cupo, 35, is running again for her third consecutive two-year term as alder.

Cupo grew up in Fair Haven, born to labor activists who co-founded Yale’s UNITE HERE Local 34 union. She would later find work at Yale through the New Haven Works job pipeline program. 

Now a proud organizer with the union her parents helped form, Cupo said she continues to believe in the priorities that her fellow union-affiliated alders champion: promoting affordable housing development, creating working-class jobs, and pressuring Yale to contribute more funding to New Haven.

Cupo maintained that being an alder entails representing not just one neighborhood, but the entire city. ​“You cannot do this job if you do not absolutely love every neighborhood in New Haven,” she said. 

At the same time, she has brought her community activism skills to advocate for outcomes in her ward on a grassroots level.

That approach proved effective in 2022, when a strip club was proposed for Jocelyn Square to the dismay of neighbors who remembered the owner’s previous nightclub as a riotous and sometimes violent establishment.

Cupo convened community meetings, a protest, and a letter writing campaign to fend off the proposal. Eventually, the proposal was withdrawn.

“A strip club would never go here, right out in Wooster Square” where residents generally have more resources, Cupo said. ​“I’m so proud that we were able to organize and get people to say no.”

Cupo currently serves as chair of the alders’ Legislation Committee, having taken over for former East Rock Alder Charles Decker when he moved out of the city last year. As vice-chair and then as chair, Cupo has helped to pass a number of zoning regulations, among other kinds of legislation — including laws governing the sale of cannabis and an agreement paving the way for the former Strong School’s transformation into a queer-friendly affordable housing complex.

In addition to affordable housing, Cupo is working with the city to implement traffic calming measures on Wooster Street. 

She next hopes to adjust the city’s noise ordinance to deter drag racing. ​“I want it to be an equitable conversation,” she said. ​“Most of the folks [driving illegal ATVs] are Black and Brown people. I want to make sure we enact legislation that is not discriminatory, but still effective.”

This term, Cupo was absent from a number of alder meetings, which she attributed to a combination of maternity leave after the birth of her daughter Ada and illnesses in her family; as of now, she’s attended about 69 percent of full Board of Alders meetings in 2022 and 2023 so far. 

“It’s really important to have working parents on the board,” Cupo said — to have people viscerally experiencing the challenges of that balancing act helping to make decisions that will affect the whole city.

She was first elected in 2019 — the same day her son, Hunter, was born. Juggling a baby with a new political role, a full-time job as a senior administrative assistant in Yale’s Women’s, Gender, and Sexuality Studies department, and a commitment to union organizing on the side has affected the mindset she brings to the job. 

Since 2019, Cupo said, time has flown by. Hunter is now nearly four years old, and he’s an older brother to baby Ada. Photos of him adorn the walls at Kaiyden’s coffee shop, where Cupo and her family are regular customers. 

In that time, Wooster Square has changed, too. Multiple luxury buildings have flown up on Olive Street since her first election — and have added a new focus to her sense of purpose as an alder: affordable housing.

Cupo argued that due to the new luxury apartment buildings in the neighborhood, ​“the price of rent skyrocketed” in the area. ​“It worries me when these large luxury apartments go up, because that takes a toll. We need to build more housing for regular people.”

Anecdotally, she said, many of her neighbors have been priced out of Wooster Square, and some friends have left the city altogether due to a rising cost of living. 

“This is the place I grew up in,” Cupo said. ​“I want my children to stay here. I want New Haven to be an option.”