STROUDSBURG, Pa. — After 47 years, Leonard Dempsey is convinced the only thing that’s going to put him out of business is his customers dying before he does. Actually, no — Dempsey doesn’t think he’s even going to die.

“I think I’ll just live forever,” Dempsey said. “I’ve never felt old, or depressed. Business is going down. They’re dying every day.”

It’s a morbid joke wrapped in a frank truth, a specialty from the 85-year-old Stroudsburg barber who has learned two rules in his trade: people have to like you, and you have got to behave yourself. He likened his one-on-one customer conversations to that of working for a newspaper, only better — you get the full details.

“But when you get six customers in here, you change your tune,” Dempsey said. “You’re back in church.”

With its big, painted front window and walls adorned with dated books, photos and artifacts — including a century-old child’s stool still in use today — Dempsey’s Barber Shop on North Sixth Street has the natural lighting of a cathedral, but that’s where the similarities end. It’s preserved in lineage history, with granite countertops from Dempsey’s father’s barbershop in the 1920s and a red brass barber chair from the location’s previous owner, Russell Swingle.

The nostalgic items are only amplified by Dempsey’s storytelling. Six-plus decades in the trade have only sharpened his ability to tell a story about nearly anything and draw a laugh from it.

“Anybody who says anything, I have a story on it,” Dempsey said.

There’s the story of how he thought he failed his barber’s test in the early 1960s when he was excused from the exam after shaving a man’s face with two single strokes — when in reality, the instructor was confused as to how he did it so well.

There’s another story of marrying his wife, Mary, in his hometown of Carbondale in 1965. It was “the biggest wedding in Carbondale history,” Dempsey said, with 350 invited dinner guests costing him about $1,300. The newlyweds counted their monetary gifts afterwards and found out they received $1,300 — “I broke even,” Dempsey jokes.

Then there’s the story of the first time he went to the hospital — 12 years ago, at 73. Dempsey had indigestion from a lunchtime cheesesteak and was surprised to hear that he was actually suffering from a heart attack. He underwent a two-hour open heart surgery, and hasn’t felt a pain since.

“If someone asked me what a heart attack is like, I’d say it’s a piece of cake,” Dempsey said. “I’ve had toothaches that were more painful.”


For a father of six who has been working for 70 years and has cut hair for — by his count — well over 1,000 customers, Dempsey said he’s been blessed with remarkable health. His only medication is for his heart, and he only needs glasses to read.

Mary, a former maintenance employee at East Stroudsburg University for 25 years, has only been to the hospital to deliver children, Dempsey said, and doesn’t take any medication.

“We’re blessed beyond dreams,” Dempsey said.

His regrets are minimal.

Dempsey is business-savvy. He was once a landlord and auctioneer, and has sold treadmills, barber chairs, tires, guns, other barbershops and even horses before. He wishes he could have owned a pawn shop.

Though he takes time off twice a year to visit two children and four of his seven grandchildren in Florida, he wishes he vacationed more. He recalls driving cross country to California to visit his daughter a few years ago, then not taking any stops on his way back home.

“I wanted to get back to my customers,” Dempsey said. “I should’ve went to the Grand Canyon, I should’ve taken a vacation at the time. I made a big mistake.”

And he misses how Stroudsburg once was. An East Stroudsburg resident for the past 40 years, Dempsey said the borough was once “really a town.”

“Brodheadsville was nothing, Mount Pocono was nothing,” Dempsey said. “Stroudsburg was the hub of everything.”


But there isn’t much room for complaint for the union barber who once charged $1.25 for a cut. His youngest daughter, Kathryn, has been apprenticing under him for a year and is taking her licensing test this month. Kathryn also manages the shop’s beautician services and is a licensed cosmetologist. A college graduate who studied theater and communications, Kathryn never thought she’d become a barber alongside her dad.

“I think it runs in the blood,” Kathryn said.” I wasn’t even aware it could be a career.”

Dempsey never expected it either, saying he always assumed a son would take over the family business. He said Kathryn could become a manager after five years of work, and praised his daughter’s abilities and energy. He quoted a sign she put up on the wall in the mostly antiquated shop: “Follow your dreams, for they know the way.”

“Kathryn is phenomenal,” Dempsey said. “She can be anything she wants to be.”

Dempsey never sat down with Mary to talk about what he wants to do, because he’s still happy with what he’s doing now. He pities younger generations trying to start small businesses today, noting he never had that first year’s-worth of anxiety that’s applied to practically every business now. Instead, what he remembers is a young man coming into the shop at about 10 a.m. on April 13, 1964 — his first customer.

That customer, now a Nazareth man in his late 60s, still comes to Dempsey’s. Most of his customers are lifelong ones at this point, which led to Dempsey’s joke in the first place — he’s only going out of business if they die first.

“It’s been an interesting life,” Dempsey said.


Information from: Pocono Record,