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At age 100, Larry Simon ‘doing pretty good’

Chuck Stinnett by Chuck Stinnett
June 14, 2025
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At age 100, Larry Simon ‘doing pretty good’

Larry Simon (Photo furnished)

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Larry Simon celebrated his 100th birthday last Tuesday as straight-forwardly as he could.

“I stayed alive,” he quipped.

In truth, there was a bit more celebration than that. There was a family dinner for him last Saturday night with his four children and his six grandchildren.

And there was a happy birthday Facebook post that in less than 24 hours attracted more than 500 comments, many from customers and former employees of Simon’s Shoes, where he worked for some 65 years.

“Mainly I never retired. I never retired up here,” Simon said, tapping his head.

“He never said, ‘I’m done,’” his son Bruce, who now owns the store, said. “… He calls me at the store to remind of things to do that I forgot.”

On a recent afternoon, Larry Simon is seated in an easy chair in the den of his home on North Main Street. He’s dressed in his trademark blue-striped dress shirt with button-down collar. He’s wearing khaki slacks and comfortable Skechers shoes.

The ranch-style house has been his home since he bought the lot for $4,000 in about 1959 and had it built from a design by an Evansville architect.

But his memories go back much further than that.

“I remember the old railroad bridge,” he said, referring to the span that stood from 1885 until late 1933, a year after the current train bridge opened.

His father, Jacob W. “Jake” Simon, immigrated from Lithuania in 1910, following two brothers who made Henderson their home years before. Like many immigrants without a trade, he became an itinerant peddler, going from farmhouse to farmhouse packing wares such as buttons, combs and bedspreads. He slept in farmers’ barns until they trusted him enough to let him sleep in their homes; he walked until he could afford a horse and buggy.

In 1919, Jake Simon and a partner opened a small shoe and clothing store at First and Main streets. He bought out his partner a year later, and Simon’s has been there ever since.

Larry Simon served as a machine gunner in the army in Europe during World War II, writing numerous descriptive letters home to his mother, who kept them; the family has had them reproduced in a book.

Larry joined his father’s business in 1949 and, despite resistance from Jake, nudged the business toward specializing in footwear.

A few years later, he approached an attractive young woman at then-new Nautilus Hotel in Miami Beach and informed her, correctly, that she was wearing the wrong size shoes. It was a peculiar introduction, but effective. He went on to wed Lois, a New Jersey girl; they were married 64 years until her death in 2020.

Eventually, Larry bought and expanded his father’s business, later acquiring the former J.C. Penney building next door, which helps house the store’s large inventory. (Simon’s became fameds for stocking shoes in more sizes than competitors, which drew customers from far beyond Henderson.)

In 1996, Larry Simon received the second-ever Heart of Downtown award from the Downtown Henderson Project.

When Simon ran the store, he had a string of bright young students working for him after school or during summers.

One such student worker was David Springer, who went on to become a NASA engineer in Florida.

Another was Ronnie Crenshaw, who became vice president of research and development for Bristol Laboratories in Syracuse, New York.

There was David Crawford, a longtime manager for SAS (San Antonio Shoemakers) in Texas. “He just called,” Bruce Simon told his father. “He said you told him that he’d be an old shoe dog. He said you gave him the best training.”

One Simon’s alum assembled the team to perform a heart transplant at Jewish Hospital in Louisville; another did medical research at Vanderbilt.

“What kids say they learned is respect and responsibility,” Bruce Simon said. “That’s why most of them turned out the way they did.”

These days, Simon stays on top of the news, reading The Wall Street Journal, the Hendersonian and The Evansville Courier, and watching CNN.

“He uses an iPhone and an iPad,” Bruce said.

He watches reruns of “The Rifleman,” “Gunsmoke” and “The Andy Griffith Show,” satisfying his sweet tooth with Peanut M&Ms or ice cream.

Or he watches videos of trains. “I love everything on tracks,” Simon said. He grew up at 410 N. Main St., just doors away from the railroad overpass. “I knew every passenger train that went over that bridge.”

He goes for walks and lifts hand weights. “That reminds me,” he said. “I need to get back on that (stationary) bike.”

Simon has around-the-clock caregivers, and Bruce is just a five-minute drive away from the shoe store.

“I’m doing pretty good,” Larry Simon said. “I don’t have any complaints.”

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