Local Legacies- Businesses That Span The Generations

by Jill Cousins

Submarine sandwiches might not literally be in Rachel Milsom’s blood, but it’s not a stretch to say she was born to sell them. Her parents, Bob and Claudia Caplan, worked with Bob’s parents at their Super Sub Shop in Atlantic City, New Jersey, in the 1960s, and when Rachel was born in 1967, her birth announcement was actually scrolled across a picture of a sub sandwich. The sandwich was held by the diner’s mascot, Sammy Sub, who was changed into a girl for the special occasion.

The Caplan family, which also included younger sister Honey, moved to Central Florida in 1972, and a few months later, Bob bought Kappy’s Subs, a Maitland diner that was coincidentally owned by a man named Isadore Kaplan. When Bob retired in 2008, Rachel took over the business as president and now runs the beloved family-friendly diner along with her son Adam (Kappy’s general manager and chef) and daughter Maya (a part-time staffer).

“I literally was born into this,” says Rachel, 54, who lives with husband Justice Milsom in Altamonte Springs. “I’m not a proud person; I’m humble. But Kappy’s is part of my family, and if it weren’t here, it would make us very sad.”

Kappy’s is located on an unassuming strip of Highway 17-92 at Sybelia Parkway and is housed in an iconic Valentine diner building, which was delivered to its Maitland location on a flatbed truck from Wichita, Kansas, in 1964. The diner was originally a Whataburger before becoming Kappy’s in 1967.

When he moved his family to Florida, Bob sold annuities for an insurance company for a few months before discovering the original Kappy’s.

“I stopped into Kappy’s just out of curiosity and got into a conversation with the owner,” says Bob, now 79, who lives in Oviedo with his second wife of 40 years, Mary Ellen. “I had spent 13 years working with my parents in Atlantic City, and sub shops were something I was very familiar with. The owner let me know that he was trying to sell the store, and after about three visits with him, we made a deal. And that’s how it happened.”

Until his retirement, Bob was a fixture at Kappy’s, serving up some of the diner’s classics.

“Dad was the cook, and mom generally worked the sandwich board,” Rachel says of those early days. “And my mother was a people person – both of them were, but my mom really had the gift of gab.”

That personal touch – along with the food – kept the customers coming back. Neighborhood kids still ride their bicycles to Kappy’s and hang out there after school. Grown-ups sit on a stool at the counter and often have interesting conversations with a complete stranger next to them. College students, coming home for the holidays, have even been known to stop at Kappy’s for a milkshake before going home to visit their parents.

“Now that’s a tradition,” Rachel says with a laugh.

“I feel like we have a certain responsibility to the community to always be here and be relatively the same,” adds Adam. “We mean something to people.”

From the time she was in kindergarten, Rachel recalls hanging out at Kappy’s after school, and when she was old enough, she was put to work – peeling onions and portioning French fries and eventually working full shifts. When Rachel’s kids Adam and Maya were old enough, the tradition continued.

“I like to say I’ve been working here since I was five,” Adam grins. “I did the same things my mom did. Then when I was old enough to see over the counter, I would take orders, and when I was 16, I learned how to cook.”

The Kappy’s menu has evolved a bit with the times, but when it comes to changing the old-school look of Kappy’s diner, inside and out, that’s a touchy subject to its loyal customers.

“As much as we can leave it original, we have,” Rachel says. “We’ve replaced the grill and a fryer here and there, but the look is pretty much the same. When we reupholstered the stools, people got mad at us!”

Adam, 25, plans to make a career out of working in the restaurant business and hopes to keep Kappy’s going for as long as possible, which most certainly would make his grandfather (and great-grandfather) proud.

“No one knows what the future holds,” Adam says, “but I’m never going to give up Kappy’s.”