BY JACK SHORT - Wentworth Caldwell grew up immersed in Civil War history and groceries, though he’s involved more with the former than the latter since moving to Boca Grande 10 years ago. He also volunteered at the lighthouse museum until last year, and now spends his days with his wife, Barry, and dog, Bentley, soaking up the small-town feel and history of the island.
Before moving to the island, Barry knew her way around the Gulf of Mexico. She grew up in Alabama, but Wentworth’s familiarity with Florida began and ended in Stuart on the east coast, where his grandfather owned property. When that property was sold, he and his wife began looking for a new vacation spot.
“We came, really, not with the intent of buying, but after a couple of visits we said, ‘let’s just look around, it won’t hurt,’” he said.
They ended up buying an island house built in 1946. It had been a two-story apartment house until a few years before.
He said he prefers the village area of Gasparilla Island because he likes being in the middle of the action.
“We liked being in the village, and the more we stayed here the more we liked it,” he said. “It’s close enough to the beach where the grandkids can walk or ride bikes to the water, and it’s just so convenient living here. It’s a joy.”
Some, or all, of his eight grandkids and four daughters fill up the house from time to time, and he said he expects them later in the week for a spring break vacation. At the time of the interview, though, it was just him and Bentley. Bentley, a lab-ish sort who is possibly the friendliest dog of all time, was snoring in the corner.
Wentworth speaks in an accent unmistakably born of a Tennessee upbringing. His grandfather started the family’s grocery business, H.G. Hill Food Stores, in the state.
“He built it up from one little store and he lived up over it,” he said. “It was a small neighborhood grocery, and he developed it into a fairly nice-sized chain in the middle of Tennessee.”
Wentworth got his start in the family business as a teenager picking up whatever odd jobs he could around the stores – from bagging groceries to sweeping up the parking lot. In 1965, he assumed a more official position organizing and setting up newly opened locations, but only after “doing just about everything there is to do” in a grocery store.
“I did it all,” he said. “There wasn’t anything I didn’t do, and there’s a lot to it – it’s a big business.”
His experience in all facets of the grocery business was no accident, either. Wentworth knew from a young age that was the trade he wanted to go into, and felt that he’d be a more effective part of it if he knew it from the ground up.
“Your employees can relate to you,” he explained. “You know what they’re dealing with every day. It makes you a better executive if you’ve done all the various jobs. Now, a lot of the new thinking is that you don’t need to do all that stuff; you learn it in school … and then you step into an executive position. But a lot of these guys miss – they can’t relate to the agony of being a checker or dealing with the public every day when you’re there on the firing line. You have to be able to talk their language.”
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