Don Cherry won four Calder Cups during his extensive professional playing career in the American Hockey League (AHL), capturing the championship with the Springfield Indians in 1960 and three times with the Rochester Americans in 1965, 1966, and 1968. His playing career also included securing the Memorial Cup with Barrie in 1953, a single NHL game with the Boston Bruins in 1955, and earning the Lester Patrick Cup with the Vancouver Canucks of the Western Hockey League (WHL) in 1969 before retiring as a player in 1970. Cherry transitioned to coaching in 1971 with the Rochester Americans in the AHL, where he was recognized as AHL Coach of the Year during his tenure from 1971 to 1974. This success led to his appointment as head coach of the NHL’s Boston Bruins in 1974.

He notably co-hosted the iconic ‘Coach’s Corner’ segment on ‘Hockey Night in Canada’ alongside Ron MacLean from 1986 to 2019, making him one of Canada’s most recognizable sports figures. Concurrently, he hosted the long-running radio program ‘Don Cherry’s Grapeline’ from 1984 to 2019 and produced the highly popular direct-to-video series ‘Don Cherry’s Rock’em Sock’em Hockey’ from 1989 to 2018. His commentary expertise also extended to joining ESPN as a commentator for the NHL playoffs in 2008. Cherry’s significant impact on Canadian culture was recognized when he was ranked 7th in CBC’s ‘The Greatest Canadian’ poll in 2004.

He received the Canadian Forces Medallion for Distinguished Service in 2008 and was honored with a star on Canada’s Walk of Fame in 2016. Following his departure from ‘Hockey Night in Canada’ in 2019, Cherry continued his media presence by launching a new ‘Grapevine’ podcast the same year, before announcing his retirement from podcasting in 2025.