Wiley’s expertise flourished at the Salem Crescent Athletic Club in Harlem, where he developed numerous amateur champions.
In 1935, Wiley began mentoring a young Walker Smith Jr., who would later gain fame as Sugar Ray Robinson. Under Wiley’s guidance, Robinson achieved an amateur record of 85-0 and went on to secure multiple world titles in the welterweight and middleweight divisions. Their professional partnership spanned approximately 25 years, during which Robinson’s innovative and versatile boxing style was honed under Wiley’s tutelage.
Beyond Robinson, Wiley collaborated with other notable boxers, including Henry Armstrong, Lou Ambers, and Muhammad Ali. He briefly trained Ali for two fights later in Ali’s career, with Ali acknowledging Wiley as one of the best trainers he had ever worked with.
Wiley’s influence extended beyond the ring; he owned and operated Wiley’s Gym in Harlem, a hub for aspiring and professional boxers. He also managed several businesses, including a restaurant and nightclub, reflecting his entrepreneurial spirit.
Harry Wiley Sr. passed away in 1972, leaving behind a legacy as a pioneering and respected figure in the boxing community.
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