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Searching for a miracle in Cleveland: The story of Winston Willis

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Winston Willis (left) and Dizzy Gillespie (right) in rear of Jazz Temple Building. Gillespie was making one of several appearances at the club when this photo was taken in 1963. (Courtesy Gayle Photography/Willis Family Photographs)
Winston Willis (left) and Dizzy Gillespie (right) in rear of Jazz Temple Building. Gillespie was making one of several appearances at the club when this photo was taken in 1963. (Courtesy Gayle Photography/Willis Family Photographs)

On his way to Hollywood, a young Black man named Winston Willis stopped in Cleveland in 1959 to shoot a little pool and walked away $35,000 richer.

For a time, Willis was a multi-millionaire, the largest employer of Black people in the Midwest and a bold business mogul with a big reputation.

In this first of two excerpts of a Last Seen podcast, Cleveland writer and race educator Ajah Hales explores Willis' legacy.

This segment aired on May 30, 2022.

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