Not known as the best skating forward, Olmstead used a physical playing style to compensate for that weakness, earning the nickname "Dirty Bertie."

Olmstead spent his first three NHL seasons with Chicago Black Hawks (1948-51), who traded him and forward Vic Stasiuk to the Detroit Red Wings for forward Steve Black and defenseman Lee Fogolin Sr., on Dec. 2, 1950. Less than three weeks later, the Red Wings traded Olmstead to the Montreal Canadiens for forward Leo Gravelle.

Olmstead played eight seasons with the Canadiens, spending most of his time on the top line, first with Elmer Lach and Maurice Richard and later with Jean Beliveau and Bernie Geoffrion. On Jan. 9, 1954, Olmstead joined Richard as the only Canadiens player to score eight points in a game when he had four goals and four assists in Montreal's 12-1 win against the Black Hawks.

Olmstead's most productive season came with Montreal in 1955-56, when he had 70 points (14 points, 56 assists) in 70 games. He had 383 points (103 goals, 280 assists) in 508 games with the Canadiens, and was part of their Cup championships in 1953, 1956, 1957 and 1958.

Olmstead's time in Montreal ended abruptly. Doctors told the Canadiens that Olmstead had no strength remaining in his knees, so they left him unprotected in the Intra-League Draft. Olmstead was claimed by the Toronto Maple Leafs, where he was briefly a player assistant before focusing solely on playing. Olmstead had 165 (56 goals, 109 assists) in 246 games with the Maple Leafs, with whom he won the Cup in 1962.

He was claimed by the New York Rangers in the 1962 Intra-League Draft. After refusing to report to the team, Olmstead retired at age 35. He spent several seasons coaching, including one with the NHL expansion Oakland Seals in 1967-68; he was 11-37 with 16 ties in 64 games before he resigned.

Olmstead was inducted into the Hockey Hall of Fame in 1985. He died on Nov. 16, 2015, at age 89.