Diana Li Photo
Wynn speaks with neighbor June A. Williams.
If he loses next Tuesday’s Ward 10 aldermanic election, William Wynn said, he plans to keep canvassing the very next day: until he eventually wins the seat or seeks his next goal, to become New Haven’s first black Republican mayor, in 2019.
Next Tuesday Wynn squares off against Democrat Anna Festa to replace Justin Elicker as Ward 10 alderman. Wynn jumped into the race this past June, one of just three Republican candidates running for seats on the 30-member Board of Aldermen.
Ward 10 consists mostly of the northern half of the East Rock neighborhood. It also includes the Cedar Hill neighborhood. And then, way down Middletown Avenue, in an act of creative gerrymandering, it includes an orphaned slice of the Bishop Woods/Quinnipiac Meadows neighborhood near the North Haven border.
Wynn lives in that slice on Ward 10. He said he was inspired to run because previous aldermen have ignored and underrepresented his stretch of the ward. Despite his repeated attempts to get the city to solve local problems, he has seen little change over the years on his street. Truck drivers, such as those working for tow company Lombard Motors a few doors down from Wynn’s residence on Gando Drive, speed by at “a hundred miles a minute” down his residential street, he said. Garbage collectors often skip his house.
“They missed the garbage last week, but do they miss it on Cold Spring Street or Canner Street? No, but they do it here … They do it here frequently,” he said in an interview in his home on the side east of I‑91.
Anna Festa said she welcomes the challenge and that the “beauty of democracy” is that anyone can voice an opinion: Democrat, Republican, Independent, Green, unaffiliated, or any other label. (Click here to read a story about Festa’s candidacy.)
The “Forgotten Neighborhood”
Wynn was in for an unpleasant surprise when he found out that some of the houses he had canvassed for his campaign were actually part of Ward 12 and not his own Ward 10. Wynn’s very own residence and section of Ward 10 used to be part of Ward 12 before the once-a-decade redistricting process that took place last year.
A year later, confusion lingers for some of Wynn’s Gando Drive neighbors regarding what ward they actually live in. When canvassing, Wynn usually has to explain, often to people’s surprise, that his neighborhood is now in Ward 10.
Wynn with voter and neighbor Vera Gentile.
One of these neighbors, Vera Gentile, had no idea she was in Ward 10 and was not aware that Justin Elicker was her alderman. (Elicker is now running for mayor and has endorsed Anna Festa.) Like Wynn, she said she is concerned about the speeding traffic on their residential street, and recounted her own experiences worrying about her children safely crossing the street and getting to school amidst speeding industrial trucks.
As he canvassed on Sunday, Wynn told his neighbors that previous aldermen have “ignored us and this part of the ward.” Neighbor John Eldridge agreed. The ratio of North Haven cop cars to New Haven cop cars is anywhere from 5‑to‑1 to 10-to‑1 in the neighborhood, he said. For Eldridge, this part of town is ignored not only by aldermen, but by government in general.
“Here, we’re the forgotten neighborhood,” Eldridge said. “[Democratic mayoral candidate] Toni Harp? I haven’t seen her once around here recently. Only a few of her canvassers. Now, politicians think they don’t have to talk to us in person.”
Asked about these accusations, Elicker said that he has never heard from Wynn. He said that he has gone door-to-door in Wynn’s neighborhood. He added that he has been to community management meetings in Quinnipiac Meadows three times in the past half year. (Wynn acknowledged he has never personally reached out to Elicker.)
Eldridge, Wynn’s neighbor, called their part of town the “forgotten neighborhood.”
Running As A Republican
Wynn, who is 49 and was born and raised in the Quinnipiac Terrace housing complex (before they were demolished and rebuilt), said the hard work of his parents pulled his family out of the projects and enabled them to move to a home elsewhere in Fair Haven when he was a teenager. His dad, a machine operator, and his mom, a housekeeper, instilled in him the principles of hard work and personal responsibility.
Now, whenever he talks about issues ranging from school reform to community policing, he constantly uses the term “accountability”: School administrators who continue to get raises when student performance stagnates should be fired. Police officers need to interact more with neighbors. City Hall needs to spend more responsibly.
Wynn, who works as a business manager for the Board of Education, said he has an eye for dealing with finances and slimming costs. And his work as a lieutenant for the Department of Corrections through the 1980s, 1990s, and early 2000s has given him real-life experience with crime and safety issues, he said.
Wynn’s views about accountability reflect his belief in individual responsibility and merit, principles that he sees as Republican values. Although his immediate family members are Democrats, Wynn said, he decided that he was Republican early on in his teenage years. Growing up in the 1960s and 1970s, he felt the Democratic Party was “always finding ways to appease the unfortunate by welfare, government cheese, housing projects, and food stamps.” To him, the Republican Party represents individual hard work and merit.
“Granted, being a black Republican makes this very difficult to say, because the doors for a black man aren’t the same doors as for a white man. But my thing is everyone should be given a fair playing field,” Wynn said. “You can’t just say, ‘I’m going to take that handout. I’m going to take that welfare and be happy with that.’ You need to go out and make it happen.”
Wynn said much of the traffic on adjacent Middletown Avenue spills onto his street, Gando Drive, and wants the city to do something to calm the traffic.
Wynn argued that for the Democrats in New Haven, connections and insider information have become valued over merit and true qualifications. In particular, he criticized New Haven’s unions for advancing “their own agendas.” Though he is part of a union as an employee of the Board of Education, he said, he is “not a big union person.”
“New Haven has been one way for very long – for forever. New Haven needs change,” Wynn said. “New Haven has been orchestrated by individuals such as the Democratic Party to be not about what you know but who you know, and that needs to be changed.”
Running as a Republican obviously comes with its challenges in a largely Democratic city. When Wynn canvasses and meets voters, he never brings up the fact that is Republican. He will not deny he is Republican if asked. Wynn has found that voters do not always make the distinction between national and local Republicans. Wynn said the debt ceiling debate and the government shutdown crisis in the past few weeks have contributed to the “negative feedback” he gets when voters find out his party affiliation
Beyond Tuesday
At her home on Canner Street, Festa (pictured) talked about her involvement in the ward, from her role in organizing the East Rock Festival to efforts to get the Board of Education to reform school enrollment and sibling preferences.
Festa said that not a single voter she has canvassed has reported having heard of Wynn. She said she knocked on Wynn’s door last weekend but got no answer. She’s tried to find out what she could about him through Google.
Wynn said he has spoken to anywhere from 75 to 100 voters in the East Rock area. Wynn and Festa have yet to meet each other, though Wynn said he hopes the two candidates can have a debate before the election happens. He said he thinks Festa considers her candidacy a “shoo-in because of Elicker situation” (Elicker supports Festa’s candidacy). He did admit that winning the race will be a “tough nut to crack.”
Festa made it clear that running for alderman is not an indication of further political aspirations: as a neighborhood activist and mother of three children, ages 6, 8 and 10 all in New Haven Public Schools, she has a lot on her plate.
Wynn does have higher aspirations. Next year, he said, he plans on enrolling in law school; he is currently considering Brooklyn Law School, New York University, and Yale as his options. If he becomes alderman and enrolls in a New York area law school, he plans on commuting. His choice to go to law school is part of his grander plan to eventually run for mayor, he said; his aldermanic campaign has “taught [him] a lot.”
“As a Republican, this is a starting point for me. I don’t want to make it sound like I’m defeating myself already, but it’s a learning journey,” Wynn said. “I’m on the road to becoming the first black Republican mayor of the city of New Haven in 2019. … I will be making history.”
Coverage of other ward elections:
• Adam Marchand vs. Michael Pinto in Westville/ Ward 25
• Sarah Eidelson vs. Paul Chandler in Yale/Ward 1
• Andy Ross vs. Aaron Greenberg in Wooster Square/ Ward 8