“As soon as you shake his hand, he’s got you hooked…. That’ll always be the gold standard for politicians if you’re young or old, progressive or moderate.”

This is how Ben Florsheim ’14, the 27-year-old mayoral candidate for Middletown and Wesleyan alumnus, was described to me at a Democratic fundraiser this past weekend by an older common councilman and former school principal, who sports more wrinkles than Ben has years of age. It was the kind of statement echoed unanimously by Florsheim supporters over the course of this private event, held on the riverfront patio at the Mattabesett Canoe Club—an unofficial meeting spot for Democratic party officials in Middletown.

This characterization of the young candidate came after Florsheim briskly walked into the Canoe Club, waved at the table of young progressives—most of whom work for his campaign—and immediately went over to the councilman’s table. He shook his and his wife’s hand, asked them about their children, and inquired about his re-election campaign. 

Now granted—this was a fundraiser, and those in attendance were supporters of Florsheim’s campaign. But there is something substantive to the councilman’s description, something that I’ve heard in different iterations over the past weeks covering the campaign. It’s not every day that you get a room of veteran politikos, hardened to the realities of local city government, parroting the same praise that’s also being sung by newcomers to the political system—especially when that candidate is one of the youngest and most progressive political figures that Middletown has seen in recent years. It fits the manner in which Florsheim wades through the political waters.

Florsheim is trying to bring to Middletown a grassroots style of campaigning that’s emerged all around the country in recent years, challenging conventional campaign orthodoxy.

Florsheim, a fervent progressive, is the only one of the four candidates on the Democratic primary ballot that has pledged not to accept campaign dollars from city contractors or lobbyists. His manner of politicking—straddling multiple political terrains of support—has drawn comparisons to South Bend, Ind.’s presidential hopeful, Pete Buttigieg. The comparisons aren’t unfounded. Florsheim sheepishly admits that he read Buttigieg’s autobiography cover-to-cover after a friend gave it to him around the time he was considering running for mayor. 

Supporters of Florsheim see in him an uncanny ability to speak to different demographics of voters, young or old, moderate or progressive, and resolve contradictions without changing the message or coming off as phony. 

“What you hear from voters everywhere in Middletown is Ben listens to everyone who has the opportunity to talk to him,” said Bobbye Knoll Peterson, Florsheim’s campaign manager. “He really listens to them, he doesn’t listen to respond, he listens to absorb information, and figures out how to move forward together. He doesn’t just agree for the sake of agreeing. He has integrity, honesty, and real willingness to say what he’s going to do and then stick to it.” 

Like the opponents of Buttigieg’s campaign on the national level, however, Florsheim’s critics might see this style as ineffectual, a fruitless attempt to smooth over inherent conflicts. After hearing Florsheim’s staffers criticize mayoral race competitor, Bill Russo, for comments he made about Hispanic voters at a mayoral forum the previous night, I asked Florsheim how he thought the forum went.

“I think it was a good conversation,” he said. “We all dug into the issues, and no one was taking swings at each other.” 

Through an extensive social media presence, Florsheim’s team has branded him as a grassroots street fighter, “THE CURE FOR THE COMMON MIDDLETOWN POLITICIAN.” His campaign wants to broadcast to the world images of him knocking on doors in low voter turnout parts of town that politicians historically have written off. For this reason, there is something surprising, almost jarring, about seeing him at a more buttoned-down, traditional political event such as a waterfront fundraiser. It’s almost like seeing Bernie Sanders in a tuxedo at the Met Gala. But maybe this discrepancy means that the Beto O’Rourke-esque Facebook live streaming and active social media campaign strategy, broadcasting the daily grind of bottom-up politics, is working. 

With the exception of the bartender and two Middletown High School students, who are part of the Mayoral youth cabinet, and this reporter, Florsheim is the youngest person at the waterfront event. Originally from Wisconsin, he carries himself with a distinctly Midwestern earnestness, mingled with a cerebral and stiff wonkishness when he starts talking about public policy. He wears New Balances, dons an Oxford white shirt that covers a tattoo on his right bicep, and has short sleek dark hair, parted sharply to one side. He has an Apple Watch on his left wrist, which he monitors frequently to make sure he’s keeping up with the strict schedule that Peterson has set for him.


“If you want me to get any sleep at all tonight, Ben, we have to hit 1300 IDs of ones and twos by this evening,” she’d shouted at him earlier that day back at their campaign headquarters. On the campaign trail, IDs refer to primary voters that the campaign still needs to contact, with ones and twos indicating support for Florsheim. 

At the time, Florsheim had been taking too long for her liking to show me the primary precincts they needed to win on a color-coded electoral map they have hanging up on the wall. Scheduling posters with allotted timing slots down to the minute, all neatly scribbled in Sharpie, were strewn on the floor and walls of their campaign headquarters. 

Peterson is a Renaissance woman of Middletown politics, who, along with managing Florsheim’s campaign, is also running her own bid for Common Council. She sits as the vice chair of the Democratic Town Committee (DTC) and once acted as the co-director of the North End Action Team. Florsheim appears far more reserved than Peterson, whose role for the candidate, as his strategic guru, could also be interpreted as expressing latent frustrations during moments in the campaign when Florsheim is too filtered to speak openly. 

“I hate that guy’s guts, he’s dead to me,” Peterson belted across the HQ office in between sips of a Red Bull when a campaign staffer reported that one of their best canvassers wouldn’t be able to knock on doors that day.

In fairness, this was three days until the primary election, tensions were running high. Not everything was going to plan. The campaign scheduler was out for the afternoon with a possible ear infection. 


Symbolically, the riverfront could not be a more perfect setting to encapsulate this mayoral race. As parking on overcrowded Main Street has become scarce, the riverfront is soon to become the new site of development, another source of capital flow and investment into the city. This has caused friction within the Middletown community and, in large part, has acted as a fault line between the candidates. Mayoral candidates Director of Public Works Bill Russo and Councilwoman Mary Bartolotta argue that opening the riverfront for commercial business will stimulate economic growth. But Florsheim is more skeptical that rapid development will be in the best interest of all Middletown residents. He is running on a “riverfront for all” platform, which insists that the city take the long-term view to ensure that businesses who want to stake out the waterfront are actually invested in the longevity of the Middletown community and that all members will benefit from the prosperity that development will bring.

Generally, if you read the Democratic candidates’ stated positions on the big issues from their websites, you might feel like you were parting hairs to find distinctions, but a staffer on any of the four campaigns—whether Florsheim’s, Russo’s, Bartolotta’s, or Geen Thazhampallath’s—will tell you that there’s a vast sea differences between them. The primary race—fairly or not—has been made into a conflict of insiders and outsiders, old guard and new guard. The riverfront has been a flash point of this tension in the Democratic race. 

It’s long term, those are long-term issues, the decisions we make now will have huge impacts 50years down the line—the riverfront is a project [which], for better or worse, will form the identity of the city,” Florsheim said to me in an interview last Wednesday. “We, as a community, have a good sketch of what we want the riverfront to look like…. We want public buy-in and developers to actually be invested in our lives with long term viability. We don’t want to see empty buildings in 20 years.” 

This future-oriented approach has also defined Florsheim’s candidacy with regard to his proposal for revamping the public school system, the issue that motivated him to enter the race. 

“I think for a long time there has been a sense that instead of funding the schools, we need to put economic development front and center, and that’s how we’ll raise tax revenues to fund the schools,” he said. “But we reached the point where there was a diminishing returns on that. We have good schools and teachers, but we can do better and be more proactive in funding our school system, because that’s what makes families want to come live here.”

“Inadequate schools is a downward pressure on economic development,” he went on. “If we make the right investments in schools, businesses will also want to come here because they look at these kind of things, where are my employees going to want to live. I wasn’t sure why people weren’t shouting from their rooftops how exciting this is—we need to put education front and center of who we are.”

Slotted as the progressive opposition in the race, Florsheim’s already unorthodox grassroots approach is even out of the norm for standard progressive campaigns, in that it refuses to be merely oppositional. In the same breath that he calls attention to the issues that the town faces—such as homelessness and an opioid crisis that has claimed record high overdoses in recent years—Florsheim lauds the city’s potential and achievements with a kind of local pride.

“There’s a lot of positive things happening in this city, and I see that as an opportunity and responsibility to build the future for this town, and I didn’t think anyone was giving a clear vision for where Middletown would be in 10, 20 years,” said Florsheim. “A lot of people are happy here. I knock on doors, and people say, ‘I don’t have major complaints, and I like living in Middletown.’ But a lot of the positive things have been happening without the full proactive involvement of city government. The theme is to be proactive, to think about where we want to be in 10, 20, 30 years, and have that big picture, and make sure, then, that we’re executing, but you need to have that vision.”

Florsheim’s enthusiasm for Middletown was born when he arrived at Wesleyan University to start college in 2010. Coming off high school experience working on Democratic campaigns in Wisconsin, he immediately got involved with the Middletown DTC as an organizer. 

However, on a campus where student politics tend to center more around activism than establishment party politics, his work for the DTC was met with skepticism from his activist peers in the College of Social Studies.

“My thinking has changed on this over the years,” Florsheim explained. “I was very entrenched in establishment party politics at the time. I think electoral politics are really important, obviously, since I’m running for office, but being out in the field for the past years you see how drastically the system isn’t working for everyone, why people are cynical, and in the last few years a lot of meaningful change, I truly believe, has occurred through direct action.” 

Florsheim mentioned that two courses in particular—“Wealth and Poverty,” taught by Associate Professor of Economics Wendy Rayack, and “The History of the Welfare State”—opened his eyes to certain issues that he’d overlooked and shifted his politics to a more left-leaning perspective.

“These classes showed not just in the abstract but very tangibly, the way we in this country have very intentionally set up a system that makes it very hard for working people to break out of poverty, and that really shaped my views,” he said. “The way we criminalize and punish people with a lack of access to opportunity has deep intractable connections with race, gender, immigration status.”

Even though Florsheim stayed in Middletown after graduating, working as an aide to Senator Chris Murphy and within the DTC, his lack of home-grown roots in the city has been used as a wedge against him by opponents.

“I don’t think it matters that much to people, the current mayor wasn’t born here and many haven’t [been],” he said. “I get the sense of feeling deeply connected to the place you’re from, but I also think that there’s got to be room for all voices.”

While working for Murphy, traveling around the state talking to other mayors and local leaders, Florsheim saw the need for policy-oriented and localized campaigns. This experience has formed the bedrock of his current platform.

“Local level is where you can change things and improve people’s lives,” Florsheim argued. “If it isn’t happening in Washington…then it’s our responsibility to lead on the local level…. I think mayor is the most exciting job in politics. I always thought this was the dream job, and you get to make a difference in so many ways.”


After the fundraising event, I pulled into the parking lot of the campaign headquarters some minutes after Florsheim and Peterson had arrived. On my way into the office, I walked past a homeless veteran stationed outside the HQ on the street whom Florsheim has befriended. The campaign keeps bottles of water refrigerated for him in the office. Just outside the office are trash bags full of IPA beers and Chipotle wrappers from late nights of phone banking and canvassing. Inside the office, the Florsheim staff is a ragtag team of young politically engaged progressives. One staffer has a coffee mug that reads “Give me a refill, the patriarchy isn’t going to fight itself,” and there’s a “crafts corner” in the back of the office. With the range of tattoos, dyed hair, and “Sons of Anarchy” references thrown around, the staffers may seem more like a group of millennials at Klekolo or Perkatory Coffee than people hard at work on the campaign trail. 

But, as I walk into the office, Florsheim has already launched into a policy discussion with two local Middletown residents who have stopped by the office. They animatedly debate the need for sustainability efforts and green spaces on the riverfront development. Peterson fumes in the background. They’re only at 1000 IDs and it’s already 5 p.m. The primary voting was to start in two days, on Tuesday, Sept. 10.


Correction: A previous version of this article included a quote taken out of context. The article has been edited to remove it. 

Peterson was referred to as a co-founder of NEAT, but she was in fact once a co-director. 

Luke Goldstein can be reached at lwgoldstein@wesleyan.edu.

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