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By Ajah Hales
These are the views expressed solely by the writer and not necessarily those of The Cleveland Observer.
This three-part series explores the rise, destruction, and ongoing fight for justice surrounding Winston Willis’ lost empire:
Part 1: The Rise of a Black Business Titan – How Willis built his fortune, overcame racial terrorism, and created a thriving Black business district.
Part 2: The City’s War Against Willis – The media smear campaign, legal battles, and political attacks that led to the dismantling of his empire.
Part 3: The Erasure of Winston Willis – How the City seized his properties, erased his legacy, and why Cleveland still refuses to acknowledge what was taken from him.
The Sankofa Series: Winston Willis Part 1.
Winston Willis came to Cleveland from Detroit in 1959, stopping briefly on his way to Hollywood to gamble. On his first night in town, he won $35,000 at a pool hall and decided to stay, investing in real estate.
“You’ll never be able to do the things you’re talking about doing in Cleveland…it ain’t that kind of city.”
That’s what Willis’ cousin Bo told him when he shared his vision for urban revitalization led by Black Clevelanders, for Black Clevelanders. But Willis refused to believe that. By the 1960s and 70s, he had built a multimillion-dollar empire at the corner of Euclid Avenue and East 105th Street—a place they called Inner City Disneyland.
So, what happened to Winston’s empire? And why don’t more Clevelanders know about this living legend? Why was Winston Willis’ legacy erased, and by whom?
From Detroit to Cleveland: A Businessman Is Born
Willis’ first business, Detroit Carpet and Tile, came naturally. Growing up, he worked in his father’s carpet store, rubbing elbows with jazz legends like Miles Davis and John Coltrane when they stopped by to shop.
That early experience gave him the confidence and skills to open the first of many successful businesses in Cleveland’s East Side.
The Jazz Temple: A Cultural Landmark Under Siege
With his gambling skills and business acumen, Willis had enough money to open a jazz club in University Circle—a bold move in a city where Black entrepreneurs faced constant opposition.
He leased a former auto showroom at Mayfield and Euclid, directly across from Case Western Reserve University, and turned it into The Jazz Temple, a liquor-free lounge that welcomed all races. Willis knew the relationships he built in Detroit’s jazz scene would make the club successful—even without alcohol. And he was right.
The Jazz Temple became a cultural hotspot, drawing legendary musicians like John Coltrane, Freddie Hubbard, and Herbie Hancock. Celebrities like Redd Foxx, Richard Pryor, and Malcolm X frequented the venue, along with influential Black Clevelanders—including a rising politician named Carl Stokes.
But success came with a price. The Jazz Temple became a target of racial terrorism.
University Circle was already earmarked for redevelopment, and city officials had no intention of letting a Black-owned club thrive in the heart of the district.
According to Willis’ sister, Aundra, threats poured in every night: racist prank calls, bomb threats, and constant intimidation.
Freddie Hubbard recalled performing one night when another bomb threat came in. “We were playing Three Blind Mice,” he said. “This will take people’s minds off the bomb threat—and it did.”
But the threats weren’t just empty words. Two weeks later, The Jazz was destroyed by a bombing.
Dynamite planted in an exhaust vent blew the club apart after hours. No one was arrested, and the police called it an ‘educational warning.
The club’s location at the edge of Little Italy fueled suspicions that its residents played a role. Other Black-owned and interracially mixed establishments—like Towne Casino Club and Mount Zion Congregational Church—were also bombed around the same time.
Many Black business owners gave up. But Winston Willis refused to back down.
Look for Part 2 next month is The Cleveland Observer.
