After 80 years, family-owned Darien Sport Shop continues its evolution with a new generation and a distinctly personal approach to retail.
t‘s hard to wrap your head around a family business that has been
around for 80 years. In 1946, World War II had just ended, Frank Sinatra was dominating the radio, Joe DiMaggio was one of America’s biggest sports stars and the classic movie It’s a Wonderful Life had just been released. In Darien, a 22-year-old veteran, born and raised on Hecker Avenue, had just opened a little shop on the Post Road, selling a variety of goods.
A Born Merchant
Stephen F. Zangrillo (affectionately known as Mr. Z.) was working at Pitney Bowes in Stamford and hitchhiking to work while caddying at Wee Burn on weekends.
His father, a roofer, asked him: ‘What are you going do with your life? Hitchhike to Pitney Bowes every day? Why don’t you open a store?’
So he did.
He opened a small storefront on the Post Road near the train station and proved to be, in his daughter Gina’s words, “a born merchant.” He had an instinct for what people wanted and an ability to spot trends simply by watching his customers.
In those days, salesmen would arrive, open their trunks and show him merchandise. He would look it over and, according to Gina, say, “I’ll take three of those and six of those.”
The assortment expanded to encompass hunting, fishing, riding, golf and apparel for men and women. The store itself grew, too—moving across the street and doubling in size. Then, in 1954, he bought a piece of property at the corner of Post Road and Leroy Avenue, and built the first section of the store that still stands today.
The ski shop, added in 1963, was a particularly smart addition, Gina says, becoming a destination for families who came in not only for equipment, but for ski clothes, sleds and whatever else a New England winter demanded.
Mr. Z’s greatest talent, however, may have been knowing his customers.
In his later years, when a heart attack forced him off the sales floor, Mr. Z. would sit at his office window and watch people enter and leave the store. At night, he reviewed every sales ticket, making notes for employees: Thank a customer, follow up with someone who hadn’t been in recently, figure out what happened with a particular sale.
“He observed, he listened, he asked questions,” Gina remembers. It was customer service at its finest.
A Legacy of Her Own
Gina never intended to join the family business. She had been working in the city and had a good job in telecommunications when she stopped by the store in the mid-1990s, pregnant with her son, Doug.
Her father was sitting outside, contemplating a new expansion and some upcoming changes to his team, when he asked her to join the family business.
“I said, ‘I’m having a baby next week,’ and he said, ‘Oh, you know, whenever you get settled,’” she remembers. “And sure enough, I was home one week with the baby, and my father called the accountant, and said, ‘Is she coming?’ I literally came
n the next day for a meeting.”
She started in accounting and gradually took on more of the business. She brought in computers and spreadsheets, revamped the advertising and helped introduce a loyalty program in the late 1990s. Eventually, she was overseeing personnel, buying, merchandising and the overall direction of the store.
“He was almost like the Wizard of Oz,” she says of her father. So when his health began to decline, they created a routine that would allow him to stay involved while Gina took over the day-to-day business.
Eventually, she realized that some of his business instincts had become hers:“I feel like I have a little bit of my dad’s knack.”
She also learned through experience, while navigating two major crises—the 2008 financial crisis and COVID. Both gave her an opportunity to rethink the business and refocus on its core strength: the personal, in-person shopping experience.
After the pandemic, Gina refocused the business on what it does best: offering multiple brands and categories in one place, providing alterations and giving customers the kind of assistance difficult to replicate online. She also makes sure the store continually changes its merchandise and displays because local customers return frequently.
Next in Line
Now, the family story is coming full circle.
Doug Reilly—the son Gina was pregnant with when she first joined the business—spent eight years working in New York at a hedge fund after graduating from the College of Charleston. Although the family had talked about the possibility of him eventually joining the business, there was always one condition: He had to want it.
“We always talked about how this shouldn’t be a fallback. If you’re going to come in here, you have to want to be here. Not just because you got fired or your job’s too hard type of thing,” Gina says.
After marrying a Darien native and starting a family of his own, Doug began reconsidering his career and his commute. This spring, he joined Darien Sport Shop as its general manager.
His role is intentionally broad. Coming from outside retail, he is looking at the operation with fresh eyes, identifying ways to streamline systems, automate repetitive tasks and make better use of technology while leaving the parts of the business that work well alone.
“I don’t want to be the guy that comes, flips the tables upside down and says we’re changing the way we do things,” Doug says.
Instead, he is asking questions: Why is something done this way? Can a process be automated? Can employees spend less time on administrative tasks and more time finding the right merchandise, managing inventory and helping customers?
In some ways, he is following the same approach his grandfather and mother used before him: listen, observe and ask questions.
The More Things Change …
The store’s future will inevitably look different from its past. As the Corbin District changes the retail landscape in Darien and technology continues to evolve, customers will shop differently.
But the Sport Shop’s fundamentals will remain the same: offer a remarkably broad assortment while remaining the kind of small-town shop where people run into their friends and neighbors. And, above all, treat your customers like family.