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Remembering Oliver "Pudge" Henkel, key player behind Playhouse Square's rebirth

Oliver Henkel was one of the driving forces behind the resurrection of Cleveland's theater district.
Playhouse Square
Oliver Henkel was one of the driving forces behind the resurrection of Cleveland's theater district.

The curb along Euclid Avenue in front of Playhouse Square was saved by one man: Oliver Henkel. It was the first move in his decades-long quest to preserve Cleveland’s theater district.

“He was the greatest gentleman I ever met,” said veteran Cleveland theater director Joe Garry. “He was the smartest man I ever met. He was a diplomat of the first order. What really saved the theaters was clearly Oliver Henkel.”

Henkel died August 25 at the age of 88 at his home in Cleveland Heights. The Mansfield native was born in White Plains, New York, and nicknamed "Pudge" due to his rotund appearance as a newborn. He came to Cleveland in 1964, setting up a legal practice that eventually involved the city’s civic and cultural endeavors.

In the early 1970s, he was an attorney with Jones Day when the Loew’s building – home of the Ohio and State Theatres - teetered on the brink of destruction. Yet theater operator Ray Shepardson had a vision to save the venues.
“He didn't have any answers to save it,” Garry said. “’For what? How will we save it? Where will we get the money?’ He just knew it had to be saved.”

Henkel found a legal loophole barring heavy equipment from entering the sidewalk, delaying the demolition and allowing Shepardson and Garry to mount a wildly successful production of “Jacques Brel is Alive and Well and Living in Paris.” That led to renewed interest in the theaters both from audiences and philanthropists.

“I was a hippie with Afro hair, and I would hardly get into the major offices in the city,” Garry said. “All Oliver had to do was make a phone call and the head of any company, any organization, would see Oliver.”

From 1973-1980 Henkel led the Playhouse Square board, applying for nonprofit status and making legal maneuvers to keep the lights on.

“Most of the money we made from the bar was the major part that helped us get through those first difficult years,” Garry said. “When we were going to open a show in the Palace Theatre, he discovered that it would be very expensive to buy another liquor license. He found the technicality in the law that if the buildings were connected, you could use the same liquor license.”

That led to some impromptu construction, creating the opening between the Palace and the State that remains to this day.

“It was done in a drunken night when everyone was just pounding into the wall … so we could say we were connected,” Garry said. “That, I think, speaks to his brilliance.”

A brilliance that took root during his upbringing in Mansfield and studies at Yale Law School. That’s where he met future Colorado Senator Gary Hart. The two-time presidential candidate penned a remembrance of Henkel last month, calling him “a loyal friend and remarkable American.” Hart tapped Henkel to run his first presidential campaign in 1984.

At about the same time, with Playhouse Square’s renovation in full swing, Art Falco came aboard as finance director. By 1991, he was promoted to become the theater district’s third CEO. He can’t recall a single disagreement or cross word during his decades of friendship with the man many called “Pudge.”

“He was a very warm individual,” Falco said. “Very likable, very intelligent, high integrity. There was no elitism to Pudge. He was so articulate that he could tell a story in a way that you would understand.”

Falco said that resurrecting a derelict stretch of Euclid Avenue was a special kind of challenge for the man who had served aboard the U.S.S. Mahan as a guided missile officer and later played semi-professional football for the Ansonia Black Knights.

“I think Playhouse Square attracts a certain type of individual,” Falco said. “Pudge was the first, but there were others that followed him. And I think it was this sense of pride that you could actually take something that few thought would actually ever succeed and see it grow. If Pudge was not involved those theaters wouldn't be here today, and we would have wonderful parking lots.”

Instead of parking lots, the second-largest theater district in the country is now presided over by Craig Hassall. He took the helm at Playhouse Square in 2023. Soon after, he was invited to dine with Henkel and his wife of 62 years, Sally.

“The whole lunch was designed to help me meet important people in Cleveland,” Hassall said. “Pudge and Sally, they're so hooked into Cleveland folk and their heart remained of Cleveland. They didn’t move away. They were so passionate about the city.”

In later years, Henkel chaired the Gateway Economic Development Corporation, which led to the construction of today’s Progressive Field and Rocket Arena. He served as chief external affairs officer at the Cleveland Clinic from 2006-2013. He continued attending Playhouse Square board meetings as emeritus chair for the past several years, staying connected to the legacy he helped create.

"He was never there to take the front-page story," Garry said. "What interested him was really making the city and the world we live in a better place."

A memorial service is scheduled for Oct. 20 at 3 p.m. at Plymouth Church in Shaker Heights. The service will also be livestreamed on the church’s website.

Kabir Bhatia is a senior reporter for Ideastream Public Media's arts & culture team.