If the averages hold, Anna Di Maggio will have made more than 21,000 strombolis since Tony Di Maggio’s Pizza in San Jose reopened on June 13, after a fire destroyed the roof and temporarily closed the business.
At 80, Anna has been working at the family-owned restaurant since she and her husband, Tony, founded it 48 years ago. She makes 100 strombolis — a long, thin version of a calzone — on weekdays and 200 on weekends to meet demand for this popular item. Jack Di Maggio, her son and co-owner, said strombolis account for half of the restaurant’s sales.
“They’ve got the ham, the sauce, the salami, the American and the mozzarella cheese,” he told San José Spotlight. “There’s a little bit of mustard on the inside that adds a twist to the flavor. People love them.”
If the averages hold, Anna Di Maggio will have made more than 21,000 strombolis since Tony Di Maggio’s Pizza in San Jose reopened on June 13, after a fire destroyed the roof and temporarily closed the business. At 80, Anna has been working at the family-owned restaurant since she and her husband, Tony, founded it 48 years ago. She makes 100 strombolis — a long, thin version of a calzone — on weekdays and 200 on weekends to meet demand for this popular item. Jack Di Maggio, her son and co-owner, said strombolis account for half of the restaurant’s sales. “They’ve got the ham, the sauce, the salami, the American and the mozzarella cheese,” he told San José Spotlight. “There’s a little bit of mustard on the inside that adds a twist to the flavor. People love them.” Learn more at SanJoseSpotlight.com. #stromboli #pizza #italianfood #sanjose #SiliconValley
♬ original sound – San José Spotlight
Anna first met Tony when she was 14. When her father’s uncle came to visit her home in Palermo, Italy, Tony was with him — and after their first meeting Anna was asked what she thought of him.
“I told them he was cute,” she told San José Spotlight. Their future together was sealed.
Anna Di Maggio, who started the business with her husband Tony 48 years ago, makes 100 strombolis on weekdays and 200 on weekends to meet demand. Photo by Robert Eliason.
Shortly after, Tony relocated to the United States, and the couple kept their romance alive through letters until Anna followed him to New York three years later. Nine years after that, having married and settled in Middletown, New Jersey, they opened their first two pizzerias — Palermo and Naples.
“He was basically his own competition in that small town,” Jack said. “Then they got tired of the weather, came out to visit a cousin and fell in love with San Jose. They went home, sold everything and moved out here.”
The couple opened Tony Di Maggio’s Pizza in 1977 — and little has changed on the menu since then.
The stromboli is the signature dish. It’s made with the same hand-tossed dough used for the pizzas, but filled with a rich, tangy red sauce prepared fresh daily and slow-simmered for three hours in a 20-gallon pot. By contrast, the pizza uses a seasoned tomato sauce that cooks directly in the oven.
Customer Steve Schmidt has been coming to Di Maggio’s for more than 20 years and knew Tony, who he described as a “friendly old guy.” The stromboli is his favorite, but he said he was surprised the first few times he ordered it.
“It’s a little unusual, but it’s actually really delicious and gives it a little tang that it needs,” Schmidt told San José Spotlight. “It’s a little unique compared to the calzones that other people have.”
There is no list of exotic pizza variations beyond the Tony’s Combo, made with Italian sausage, pepperoni, salami, mushrooms, onions, sausage and bell peppers. Instead, customers can choose from 17 available pizza toppings to build their own special pie.
The Tony’s Combo pizza. Photo by Robert Eliason.
The pastas run the course of Italian standards: spaghetti, rigatoni, ravioli and manicotti, all served with the same stromboli sauce. Keeping things simple, there are no Alfredo or pesto sauces. There is also a house-made, crumb-encrusted eggplant available as a dinner or on the sandwich menu, along with meatballs, Italian sausage and a sub with ham, salami and American cheese.
There have been only two significant menu additions since the restaurant was founded. One is chicken wings, de rigueur in any pizza parlor. The other is pineapple as a pizza topping, banned by Tony for the restaurant’s first 15 years.
“There are so many things you can put on a pizza, so he just refused to use pineapple,” Jack said. “Until he noticed people were leaving the last few times he said, ‘No.’ He figured it didn’t make sense to lose business.”
Anna Di Maggio’s homemade strombolis account for half of the restaurant’s sales. Photo by Robert Eliason.
The restaurant suffered a double blow in 2012 with the death of Tony Jr. in April and Tony himself in November. Jack, who had been working at the pizzeria since he was eight, and his brother Tom, with a similar history, took over the business — a challenging but seamless transition.
Harder on the business was the July 2024 fire caused by melted insulation on the building’s roof air conditioner. Delays with permits kept Di Maggio’s from reopening until June 13, when it was overwhelmed by returning customers.
“We had a lot of people worried we were not coming back,” Jack said. “On that first weekend, we had lines from the door to the back of the building, and we ran out of food all three days.”
The customer response and deep loyalty they showed toward the business were gratifying, he said.
“I have never seen or been a part of anything like that,” he told San José Spotlight. “It felt like a sort of coming home, which is always what my dad tried to make people feel. He wanted his customers to feel like family.”
Contact Robert Eliason at [email protected].
Editor’s Note: The Biz Beat is a series highlighting local small businesses and restaurants in Silicon Valley. Know a business you’d like to see featured? Let us know at [email protected].
Tony Di Maggio’s Pizza
Located at 3852 Monterey Road in San Jose
(408) 629-7775
Hours:
Tuesday to Saturday 11 a.m. to 8 p.m.
Sunday 12-8 p.m.
Closed Monday