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Known as “The Entertainer”, Eddie Shack played for the New York Rangers for two years. In 1960, the Rangers shipped him to Toronto where he fit in instantly. In his first full season with the Leafs, he won the Stanley Cup. He would win two more in the next two years and scored the Cup-winning goal in 1964. Shack won another in 1967 before he was traded to Boston. Over the next seven seasons, he moved to Los Angeles, Buffalo and Pittsburgh before returning to the Leafs and retiring in 1975. A three-time All Star, Shack has involved himself in several business ventures over the years.