A true gentleman: Oak Lawn barber retiring after 50 years

You may have met barber Jim De Simone. But if you haven’t, maybe you heard about his legendary feats.

He kicked a game-winning, 81-yard field goal for St. Laurence High School. He was the secret weapon for the 1985 Super Bowl Champion Chicago Bears. He can bench press 850 pounds. He dunked over Michael Jordan. Remember any of them? You probably missed the victory parades that were thrown for him —just him— on Western Avenue. He won’t let you forget about it, either.

I bought these stories without question as a kid. The adults in the barbershop, including my dad, knew better. I should have picked up on the stifled laughter after the tenth visit.

His tall tales, some redefining the art of deadpan bravado, are entering their final chapters. "Barber Jim" is retiring. After nearly 50 years in the business, he will cut his final head of hair on Dec. 31 at Gentlemen’s Preferred (10240. S. Kenton). A native of Chicago’s West Lawn neighborhood, De Simone hadn’t exactly planned on working in the tonsorial field.

"I was supposed to be here for two weeks, DeSimone said. "I never planned on {cutting hair}. I graduated from St. Laurence High School in 1968, went to Molar Barber College and took a liking to the trade."

De Simone’s opened his first shop at 4630 West 103rd Street in March 1972, footsteps from the Jewel-Osco and Arena Bowl. In 1992, he moved a block east to his current location. Both locations were called Gentlemen’s Preferred, although the name came by accident.

"It was never supposed to be called 'Gentlemen’s Preferred.' It was supposed to be called 'Gentlemen Jim’s barber shop,' named after the boxer Gentleman Jim Corbett. But when I was applying for my license, I needed a name. I actually forgot about the 'Gentleman Jim' part and had to come up with something. And I just came up with ‘Gentlemen’s Preferred.'"

But his customers rarely, if ever, went to get their haircuts at “Gentlemen’s Preferred.” The name was, more or less, an administrative formality. They went to get their haircuts from “Jim.” And like barbershops that would now qualify as “old school,” Jim's shop never had an appointment calendar. No web site. No influx of Yelp reviews. No buy-one-get-one coupons. No add-ons. Just a good, quality haircut and conversation. His customer base frequently included generations of families. I was one of them. My dad, a school teacher in the area brought me there as a kid. I brought my own two-year old there recently as well.

The decor at De Simone’s shop was atypical of what you would find at a Great Clips or Super Cuts. It was reminiscent of a relative’s basement on the South Side: orange-tiled floors, wooden coffee tables, a 1970s General Electric wall-unit air conditioner and fluorescent lighting. It was like a good pair of slippers: comfortable and predictable.

There was also a corner trophy case adorned with various momentos, specifically from athletic teams in the Chicago Catholic League. If you went to Brother Rice, Marist, Mount Carmel, St. Laurence or Leo, there was a good chance that a hat or t-shirt was in the case. On a recent Saturday, several customers (all of whom went to St. Catherine in Oak Lawn), gathered in the shop to reminisce about conversation, “Super Trooper” buzz cuts and good-natured insults.

"It was like an event when we came here," longtime customer Jim Winters recalled. "Everyone would plan their haircuts around the same time and we would all hang out and shoot the {breeze}."

Fellow loyal customer Brian Tansey also reflected on his childhood.

"We would always come in together before basketball games and he’d race to get us all done before the games…a lot of good times with my buddies here."

And like his dedicated customers, many of them who maintained loyalty after moving away from Oak Lawn and the South Side in general years ago, De Simone has redefined dedication to his job and customers. He moved to the Lake Geneva, WI area years ago. His commute still consists of driving south to the Metra line across the border to Harvard, IL. From there, we would take the train downtown, walk to the CTA Orange Line, take that train south to Midway, jump on a southbound Cicero Ave. bus south to 103rd Street and walk the rest of the way.

"It’s taxing at times but this is where I belong," De Simone said. "On Chicago’s South Side."

De Simone was formally recognized and given a proclamation for his life's work recently by Oak Lawn and Village Clerk Jane Quinlan. Several of his customers, who frequented the barbershop as kids and now serve as Oak Lawn police officers, were in attendance for the ceremony.

De Simone has a son (Todd) who lives in Buffalo Grove and a wife (Susan) who has supported those long commutes and dedication to the business and his customers.

"My wife is the most important entity in my life," De Simone said. "She believed in me when I didn’t believe in myself."

His last haircut will be at 4:00 p.m. on New Year’s Eve. It’ll be with Michael Curtin, a longtime customer who has been coming to see Jim for many years.

American barbershops have long been an impromptu therapy session, of sorts. No couch involved, of course. Just a chair that pedestals up and down. Customers have sought advice from their barbers and talked out the troubles of their day and Jim was no different. In fact, there is a sign that demonstrates this in De Simone’s office— channeling his offbeat humor: "Listen to my troubles: no charge. Listen to your troubles: 50 cents." He provided a service with a slice of psychology. He'll miss those relationships the most.

"Without a doubt, the people. In the time that I’ve spent here, it was like a Charles Dickens novel. It was the best of times, it was the worst of times. You enjoyed life with the people and you shared their problems. I’m going to miss it."