Olmstead began his career with the Black Hawks in 1949. In December 1950, he was traded to the Montreal Canadiens via Detroit. Olmstead had his best statistical years playing for Montreal, leading the league in assists in 1954–55 with 48, and setting a league record for assists with 56 the following season. Olmstead was claimed in an Intra-League Draft by Toronto Maple Leafs in 1958, and played there until his retirement in 1962. 