A Portrait of Dimitris Diamantopoulos
Posted by estiator at 14 July, at 14 : 03 PM Print
COVER STORY
The long-established restaurateur and Renaissance man knows the best is yet to come.
By Marianna Stephanou
“A name is a story.” If you know Dimitris Diamantopoulos— “Jimmy,” as many call him—you already know: He is kind, generous, and never without a smile. He embodies what it means to be a wonderful person. Diamantopoulos achieved what many call the American Dream, but he did it the Greek way—through hard work, persistence, and heart. He started his first restaurant, Andros Greek Restaurant, in 1988.
Later, he moved to South Florida, where he began collaborating with Miami Subs, along – side industry pioneers Gus Boulis and Gus Bartsokas. Eventually, he owned Miami Subs locations in four different states, operating them for more than 20 years.
But that was just the beginning. Diamantopoulos went on to open and operate several personal ventures: Gyro City Grill, City Diner, Wing City Grill, and Zeus Coffee Shops, among others. He also invested in and partnered with well-known franchises like BurgerFi, Taziki’s Mediterranean Grill, and The Great Greek.
Beyond business, Diamantopoulos is deeply involved in charity and community work. He has supported organizations such as the Salvation Army, veterans’ groups, local schools, colleges, and first-responder teams, including large police departments. His contribution to the community has been both wide-ranging and consistent.
A man of many talents, Diamantopoulos also once played minor league hockey for the Fayetteville FireAntz and minor league baseball for the Fayetteville SwampDogs. He’s always been passionate about Greek food and is now considering expanding City Diner—his 24-hour concept—to include a Greek menu corner.
“I’ve met a lot of good people in these 36 years,” he tells us. “I’m still learning. Every day is a new lesson. It’s a hard business—so many moving parts. You’re always changing gears.”
He speaks with pride about Estiator magazine, a publication that has been highlighting Greek-American restaurateurs for more than 40 years. “I get so excited when I see a new Greek restaurant open—even if it’s 1,000 miles away,” he says.
Still, success has come with sacrifice. He’s missed birthdays, holidays, and family time. But his family keeps him going. So does his strong bond with the church and AHEPA, and his loyal participation in Greek festivals, com – munity dinners, and dances.
As Diamantopoulos contemplates expanding City Diner to Florida, he’s honest about the challenge: “It’s one thing to succeed in one location. Scaling a restaurant chain is something else entirely.”
And still, he keeps going. The recipe for success, he says, has never changed: Good food. Good service. A clean place. Every day. Every second.
Many work eight hours and feel drained. Restaurateurs often work 24, and still say, “It’s nothing. Just running our business.”
For Diamantopoulos, the restaurant business is like a hospital—once you’re in, it’s hard to get out. He acknowledges that while all businesses operate for profit, restaurants have something extra: “There’s an unspoken, almost illegal feeling of pride and pressure. When a customer is happy, you feel it. When something goes wrong, you fix it—immediately.”
His daughter Eleni says that food shows and big events are her father’s favorite part of the business. “Like a kid going to a game,” she says with a smile. People often ask him, when will you stop? “I don’t know,” he says. “Maybe when I wake up one morning and don’t feel the drive. But that hasn’t happened yet. So, I keep going.”
Over the years, Diamantopoulos has met musicians, professional athletes, movie stars, and more. He’s won many awards for his innovations in the restaurant space. Most recently, in 2024, City Diner was honored as Restaurant of the Year.
In his words: “I am Dimitris Diamantopoulos. A giving man. A tired businessman. But above all, an admiral—and a family man.” As our conversation ended, he left us with this: “The best is coming.”
And to that, we say: We are Greeks. Children of Odysseus. The journey is in our blood. Keep going, Dimitris. You’re in a category of your own.
