Olmstead began his career with the Calgary Stampeders of the Western Hockey League in 1948. He was a prolific scorer and was named to the WHL First All-Star Team in 1951. He was then signed by the Montreal Canadiens in 1952 and went on to become one of the most successful players in Canadiens history. He was a key member of the team that won five Stanley Cups in a row from 1956 to 1960.
Olmstead was traded to the Toronto Maple Leafs in 1960 and went on to help the team win the Stanley Cup in 1962. He was then traded to the Chicago Black Hawks in 1964 and was named to the NHL Second All-Star Team in 1965. He was traded to the Oakland Seals in 1967 and retired after the 1967-68 season.
Throughout his career, Olmstead was known for his physical style of play and his ability to score goals. He was also known for his leadership and his ability to motivate his teammates. He was inducted into the Hockey Hall of Fame in 1985 and his number 3 was retired by the Montreal Canadiens in 2009. Olmstead was one of the most successful players in NHL history and his legacy will live on for many years to come.
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