Tough Guy. War Hero. Mogul: The rags-to-riches tale of Highland Park’s Larry Klairmont

From flushing Japanese soldiers out of pillboxes in Saipan, to staring down union thugs and machine operatives in Chicago, to building a mammoth Chicagoland real estate empire, to amassing a world-class classic and antique car collection, Larry Klairmont has lived the uncompromising life of a can-do tough guy with a broad smile, a love of country, and a mastery of the art of the deal.

“Once I have determined to do something, nobody is ever going to talk me out of it,” said Klairmont, who for fifty years has lived in a house he built high atop a Highland Park bluff overlooking Lake Michigan. Actually, there is one exception to that assertion. More than once, he’s declared, “By God, I’d re-enlist!” At ninety, even though he can still fit into his Marine Corps dress blues, they might say no.

Raised in poverty and some weeks eating nothing but potatoes, Klairmont was carved with strong will that showed itself early on. At sixteen, he wanted to “get even” with the Japanese and enlisted in the Navy. Soon he was in the Pacific on a ship being attacked by kamikazes. After he and another sailor pulled an American pilot out of a burning plane, and were badly burned themselves, he was officially recognized for bravery.

When the ship returned to Pearl Harbor, he was stuck in a desk job, but not for long. “I told them I want to join the Marines. I want to fight,” he said. In short order, he was a Marine on a ship bound for Saipan and one of the bloodiest battles of the war.

Naval bombardment had not destroyed the heavily fortified pillboxes, and tanks equipped with flamethrowers had proven ineffective, too. “They couldn’t get to the top of the hills to get close enough, so we had to go in manually,” said the five-foot-four-inch soldier. “I was a gung-ho guy. Even in high school, nobody messed with me. I was small and strong and aggressive. I volunteered to be a flamethrower because that was the only way we were going to get (them).”

Klairmont next saw hand-to-hand combat on Iwo Jima, where he took a bayonet thrust to the neck and shrapnel to the knee and kept on fighting. For his bravery in the Pacific, he was awarded two Silver Stars, a Bronze Star, and two Purple Hearts.“We did what we had to do, and I have tried to put all that behind me,” said Klairmont, And yet, once a Marine, always a Marine. On July 4th this past summer, he led the Highland Park parade in his dress blues, glistening with medals earned more than six decades ago.

After the war, Klairmont enrolled in law school at DePaul, but after his stepfather died, he dropped out and went into the dry-cleaning business to support his mother and learning-disabled sister. Building racks and counters from scrap, and working day and night, he grew Imperial Cleaners from one store into an operation with one hundred ten retail stores, forty-seven retail routes, and ten wholesale routes before selling the business in 1962.

Chicago being a tough union town, Klairmont flashed his inner Jimmy Cagney more than once during those years. On one of those occasions, he was yanked into a limo between “two gorillas” and reminded that he was infringing on Teamsters territorial laundry route rights. “I was told, ‘You know you are a very bad boy.’” His response: “I am no boy. I am a &%#@ warrior, and you better believe it.”

Three days later, one of his delivery trucks was set on fire, so he went to see the attorney for his competition, brought along a one-hundred-dollar bill and a loaded gun, and made the guy an offer he couldn’t refuse. Option A: “I told him we are going to do one of two things. You and I will take this hundred-dollar bill to have a nice lunch, and you will call off your gorillas.” Then, with the gun to the man’s face, Klairmont offered Option B. “I said, ‘If you don’t want to do that I’m going to blow your head off, pick you up, and I’ll throw you out the tenth-story window.’”

“Let’s go have lunch,” the attorney responded, and there was never another problem.

While operating Imperial Cleaners, Klairmont had also started Imperial Realty. His first purchase was a commercial property in downtown Highland Park, which he renovated and which paid for itself in three years. Larry’s son Alfred joined the company in 1978 and now is president. Together, the father-son duo has acquired and redeveloped more than one hundred fifty commercial properties and have never defaulted on a mortgage or been forced to renegotiate a purchase contract. Currently, they manage more than three thousand tenants in more than ten million square feet of office, industrial, retail, and residential space, making them one of Chicagoland’s largest office space and property managers.

Last year, they became the first father-son duo inducted into the Chicago Association of Realtors Hall of Fame. “I never dreamed we would someday be in the Hall of Fame. I was just tying to make a successful company,” said Klairmont, who also has two grandchildren in the business.

The secret to his success? “My word is my bond. You shake hands with me and it doesn’t have to be in writing. When I say it’s a deal, it’s a deal.”

Klairmont’s mental toughness has helped, too. Like when he purchased a half-mile-long dormant industrial property along Knox between Belmont and Diversey in Chicago in the nineteen eighties. Neighborhood groups, backed by Mayor Harold Washington, wanted the zoning to remain industrial. He said the only way to viably develop the property was mixed use. “They fought me tooth and nail,” he said. “I persevered.” In the coming years, Wal-Mart opened its first Chicago store there, along with numerous other job- and tax-revenue-producing businesses.

These days, Klairmont calls himself “semi-retired” from the real estate business, as his son takes care of the “day-to-day” problems. “But as far as the deals go, I am involved in  every deal,” he said. Having just bought a “real nice piece in Highland Park,” Imperial now owns north of fifteen commercial properties there.

Never one for half-measures, roughly fifteen years ago, Klairmont began amassing a classic car collection that is now one of the largest and most significant collections in the Midwest. The Klairmont Kollections, as it is now known worldwide, consists of roughly five hundred classics housed in a block-long one hundred fifty thousand square-foot building he owns in Chicago. He is now only buying “extremely rare and valuable cars in excess of a million dollars,” he said. His most recent purchase was a 1948 Tucker, one of only fifty-one made in Chicago. “It gives me pleasure because I periodically enjoy looking at the cars,” he said.

Every car is started at least once a month by a staff that includes three full-time mechanics. There are also two planes hanging from the ceiling, a re-creation of a drive-in movie theatre, a turn-of-the-century gas station, a nineteen twenties fire engine, the model train layout displayed at the 1939 New York World’s Fair, a room filled with Titanic memorabilia, and another room dedicated to the Marine Corps. There’s even the electric chair used in Sing Sing prison to execute six hundred felons.

The museum is now available for charity fundraising and other events as a means to help pay overhead costs and perhaps justify its continued operation and thus the furtherance of Klairmont’s legacy in the future. “What I have done is create something that is unique, and that is what I have enjoyed doing,” he said.

Klairmont and his wife, Elaine, built their home in Highland Park fifty years ago. There are no interior ninety degree angles, only forty-fives and twenty-twos. And every room is paneled in a different kind of wood. “That’s what I wanted,” he said.

The couple had five children, and there are now twelve grandchildren and one great-grandchild. Elaine died eight years ago.

His significant other for the past seven years has been Joyce Oberlander, who came up with the idea of gathering all his classic cars into one central location and who has been instrumental in cataloging them. She has also had the time to get at the root of what makes him tick. “He came from such a poor background,” she said, “and he figured out at a very young age, ‘I’ve got to take care of myself.’ And then he saw boats and cars and said, ‘I want to work so I can have that.’”

“He is a very determined person,” she continued. “If he starts something, what he doesn’t finish today he finishes tomorrow. It is beyond him to let something go, and if he knows this is something he should do, he does it. At this age, he could afford to just lollygag around, but that is not his work ethic.”

He can also be quite unassuming, she said. For example, his children did not know anything about his military career until they unearthed a wooden box years later filled with his dress blues, medals, and memorabilia. Nor do he and Joyce lead a pretentious lifestyle, preferring quiet evenings at home and meals on the porch. “He does not need a lot to be comfortable,” she said.

Still, that drive to create and to produce is never far beneath the surface.

Asked to evaluate his life, he paused, then said: “What has given me some sense of personal satisfaction is that in 1946, when I got out of the Marine Corps, I had two hundred dollars and my uniform. And from that, I have created this empire. And it is an empire.”

About the author

Alan P. Henry is a New York Times bestselling author, six-time national fiction contest prize winner, and thirty-five-year newspaper veteran with the Chicago Sun-Times, Boston Globe, Boston Herald, and now, 22nd Century Media.

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  • Eugene Salganik December 28, 2016 at 1:51 pm

    What would he say about college “safe spaces”?

    Reply