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Barber Retiring after Half a Century in Stroudsburg

STROUDSBURG, Pa. — His shop is still tucked off Main Street in Stroudsburg. His barber tools still line this stone shelf.  But it’s the end of an era for longtime barber Leonard Dempsey.

“55 years, wonderful years, I have to thank all the customers, too,” said Leonard Dempsey, Dempsey’s Barber Shop.

Leonard or “Dempsey” as he’s known by his loyal customers, didn’t want it to end here.   However, last month, the 88-year-old suffered a stroke and knew it was time.

“Three weeks ago, if you asked me, was I going to retire? Hell, no, I wasn’t going to retire. I didn’t think what was going to happen would happen. When it happened, it happened, boom, right then and there,” said Dempsey.

Leonard’s longtime business neighbor Kathy Rodgers, who runs a dry cleaning and tailoring shop on North 6th Street, decided to use her annual customer appreciation day, as Leonard’s retirement party.

The whole community came out to wish him well.

“I just thought it was a good way for him to be able to talk to the people who come over there all the time and they can share in it. It’s a neighborly thing,” said Kathy Rodgers, Kathy’s Dry Cleaning and Tailoring.

“Dempsey cut my hair for years. He is a fabulous barber. We are all going to miss him so much here in Stroudsburg. I mean he really is a staple in the community,” said Kurt Visser.

“I didn’t do nothing. I am just happened to here. I am just a bystander, so to say,” said Dempsey.

Staying in the same building for more than 50 years is no easy task, so we asked Dempsey how he did it.

“You got to love your work. If you don’t love your work, then you won’t do good,” said Dempsey.

Leonard’s father was a barber, but it was his wife who landed him this job in Stroudsburg all those years ago.

While he can’t recall his first customer from 1970, he certainly remembers his last.

“My son was my last customer. Of course, I didn’t get paid for it,” said Dempsey.

Leonard plans to spend some time down south with family.  For now, he will enjoy the company that kept him going for five decades.


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