Pizza-Making Alumnus Takes Slice of City with Election Win

As Ben D’Allesandro ’05 climbed the stairs to the Craftsman house on Darlington Avenue in the Wagener Terrace section of downtown on a warm October day, he paused to listen to the beautiful melody coming through the screen door. After the 95-year-old woman at the piano stopped playing, D’Allesandro knocked on the door, introduced himself as a candidate for City Council and asked if he could listen to another tune. She obliged, even signing this time. A month later, her grandson messaged him on Facebook to say thanks for taking the time to chat with her.

“There were very few people who didn’t want to chat, especially elderly folks,” he says. “And there are a lot of elderly people out there that we aren’t aware of because they don’t really go out. You don’t really see them until you go and knock on a bunch of doors, and then you realize that there is this fairly large amount of people out there that are kind of just living alone most of the time.”

That’s how D’Allesandro – co-owner of D’Allesandro’s Pizza and now the council member-elect for Charleston’s District 6 – won an upset over longtime incumbent William Dudley Gregorie: one quietly earnest conversation at a time.

“I think my getting out there and just getting to know a lot of folks was probably where I was able to make the most impact,” he says when asked for the key to his victory as he sits in a booth at his restaurant one recent morning.

District 6 covers the West Side of the peninsula from Calhoun to Mount Pleasant streets. It’s dense weave of neighbors, parks and busy corridors like Rutledge Avenue. After knocking on hundreds of doors, D’Allessandro refined a platform that pairs big-picture support – affordable housing, flooding mitigation – with touchable, near-term wins: free community events, park amenities and immediate detours around chronically flooded intersections. What he heard behind those doors sharpened the urgency.

Civic Sensibility, Entrepreneurial Spirit

Friends have jokingly called D’Allesandro, who has a very local civic sensibility, the unofficial mayor for years. He served on the constituent school board 16 years ago, ran an underfunded council bid 12 years back (“not a great campaign,” he concedes), then spent seven-plus years on the Accommodations Tax Board.

“I’ve always been involved with local government,” he says. “That’s the best place to make an impact for everyday people.”

D’Allesandro studied urban studies with a concentration in city planning at the College, training he’s ready to finally use in the formal arena.

“I’m very excited to do this,” he says. “I have this overwhelming feeling of responsibility.”

He’s also a small-business owner with a practical streak. He and his brother, Nick, opened their namesake pizzeria in 2006 by scraping together college fund leftovers from their grandmother, running up some credit card debt and eventually buying the building when it went up for sale in 2009. They’ve since expanded to two other locations in the state, in Summerville and Greenville.

“It’s an Xs-and-Os business,” says D’Allesandro, who worked at Gilroy’s Pizza Pub on King Street during college. “Sell pizza, keep ingredients fresh, make sure your expenses are less than your revenues – and keep your employees happy.”

All the Right Toppings

He still plans to be there every morning, making dough before council work. A trusted manager, Christen Frazier, runs the day to day.

The personal and the public keep blending for him, which may be the point. The kid from Bala Cynwyd, Pennsylvania, near Philly, learned to juggle (and yes, ride a unicycle) from his dad, Andy, a union HVAC serviceman who founded the Philadelphia Jugglers Club and gathered weekly in public spaces to practice. His mom, Suzanne, is a registered dietitian who helped children throughout Philly with cystic fibrosis before she and Andy moved to Folly Beach about 12 years ago, when Ben and his brother started having children.

Today, D’Allesandro and his wife, Jennifer ’05, whom he met during the pizzeria’s first year when she came to work there, are raising four children in the heart of District 6 on Rutledge Avenue. On Jan. 13, 2026, he’ll be sworn in. After rolling the dough each morning, he’ll then roll up his sleeves to go to work for his constituents/customers.

“After almost 20 years, we’ve established a great name in town and a great identity that really embraces community,” he says. “The pizzeria has always supported the community, and people have always supported us. It’s not like I had to really change much for the campaign. I turned the volume up a little bit, but it was basically just an extension of the pizzeria and the people that my parents have raised us to be.”