One of Boston’s Most Legendary Restaurant Spaces Gets New Life as a Swanky Italian Steakhouse

Charlestown’s 10 City Square holds a special place in Boston restaurant history. For nearly two decades, it was the site of notorious celebrity chef Todd English’s landmark restaurant Olives, at one time a line-inducing spot that drew people to Charlestown from all over the city. After a subsequent turn as Legal Oysteria — an Italian restaurant run by the ubiquitous seafood chain Legal — and years of pandemic vacancy, the building is once again drawing crowds of eager diners.

The crew behind Charlestown hangouts Monument and Waverly — as well as a small South Boston empire that includes brunch hotspot Lincoln and Italian restaurant Capo — has launched Prima, an Italian steakhouse with veal chops, piles of pasta, a mozzarella bar, and a dream to once again become a restaurant that everyone can’t stop talking about.

For the resurrection, the restaurant group tapped Erica and Michael Diskin of Assembly Design Studio. The two groups have a long-running partnership that dates back to the design of Lincoln a decade ago. (Some of Assembly Design Studio’s other projects have included chef Jason Santos’ spots Buttermilk & Bourbon and Citrus & Salt, as well as restaurants further afield like the acclaimed Shipwright’s Daughter in Mystic, Connecticut.)

The front dining room was designed with reclaimed wood, leather, cracked subway tiles, and other elements to make the space feel aged, in a sophisticated way. “We wanted it to feel old but not shabby, like a piece of Boston that had been there forever,” Erica says.

Assembly Design Studio

Assembly Design Studio

Assembly Design Studio

Assembly Design Studio

Head down a long hallway, past the kitchen, and you’ll end up in the Rose Room, a second dining area that switches up the old-world feel for something more sultry. The room, which was previously a tiny, tucked-away private dining area, was a challenge to redesign, Erica says. “How do you make the worst seat in the house the best?” Step into the room now and there’s a pink marble fireplace, an eight-seat bar with a matching pink countertop, and plush, rose booths with fringed lamps hanging overhead. (It can be rented out as a private dining room, but is otherwise open for regular dinner service.)

“It was supposed to be a turnkey restaurant project,” the group’s culinary director Nicholas Dixon says with a laugh. “And then it turned into a very long, detailed project.”

Assembly Design Studio

Assembly Design Studio

Assembly Design Studio

Chef Jacob Mendros, who has worked everywhere from former fine-dining legend L’Espalier to Loco Taqueria and Oyster Bar, which is backed by the same owners as Prima, leads a menu that includes pasta, pizzas (made in Olives’ original pizza oven), seafood, and steaks carved from their in-house butchery downstairs. Mendros was also adamant that the restaurant needed a mozzarella bar — “He was like, I’ll do this project, but I want the mozzarella,” Dixon says — and the resulting menu section includes fresh mozzarella balls, stracciatella, and creamy ricotta. Marissa Hart, Capo’s pastry chef, dreamed up the desserts, which include gigantic cannoli, strawberry tiramisu, and more.

Assembly Design Studio

Assembly Design Studio

Assembly Design Studio

Other key players in the opening include managing partner Jon Sweeney, who oversees all three of the group’s Charlestown restaurants between Monument, Waverly, and Prima; wine director Jeronimo Ramales, a longstanding Capo veteran; and general manager Andrew Colgan, who formerly managed the dining room at Monument and Waverly.

Dixon is aiming to pull off a dining experience that pays homage to Olives and the place it holds in the city’s restaurant history, he says. “When I was 20, I was a line cook in the city, and people would talk about Olives, and how great of a restaurant Olives was, and that there was always a line to get into Olives,” Dixon says. “I just always remember that being, like, one of my first [moments of] what is that place?”

It was also an early training ground for many of Boston’s current bold-faced restaurant names, including Neptune Oyster owner Jeff Nance, celebrity chef and restaurateur Tiffani Faison, and Michael Serpa, the chef and owner behind seafood spots Select Oyster Bar, Little Whale, and Atlántico.

“It once was a great restaurant,” Dixon says. “The neighborhood needs a great restaurant [again].”