Bert Olmstead's his first full season in the league was 1950-51, when he scored 20 goals and established himself as a bona fide NHLer with the Chicago Blackhawks. After a trade to Montreal Canadiens, Olmstead stayed with the Habs for the next eight years, and winning the Stanley Cup three straight years.

Olmstead played on the number one line for most of his time in Montreal, where initially he replaced Toe Blake alongside Elmer Lach and Maurice Richard on the famed scoring line. Later, Olmstead played the left wing on another prominent scoring line with Jean Beliveau and Boom Boom Geoffrion. Surprisingly, his more famous linemates credited Olmstead as the key to the combination.

Although he wasn't known as a scorer or point-getter, Olmstead did set an NHL record for most assists in a season with 56 in 1955-1956, a record that wasn't broken until Jean Beliveau collected 61 five years later. He also scored eight points in a game, tying a league record. But Olmstead was known mostly for his leadership qualities, for getting the most out of his teammates and inspiring those around him to better play.

After the 1957-58 season, the Montreal doctors told Olmstead he had no strength left in his knees and the Habs left him unprotected in the Intra-League Draft. Toronto coach Billy Reay pounced at the chance to claim him, and just like that Olmstead went from the Canadiens to the dreaded enemy, the Maple Leafs.

The Maple Leafs team made it to the finals in 1960 and two years later won the Stanley Cup, in large measure because of Olmstead's role on the team despite having missed two months during the season with a broken shoulder.

He was inducted into the Hall of Fame in 1985.