Bailey began his career in the Canadian Amateur Hockey Association (CAHA) and was a member of the Toronto Aura Lee team. He then joined the Toronto Canoe Club in the National Hockey Association (NHA) and was a member of the Toronto Blueshirts.
Bailey was a key member of the Toronto Maple Leafs when they joined the National Hockey League (NHL) in 1926. He was a top scorer for the team and was known for his aggressive style of play. He was also a leader in the locker room and was respected by his teammates.
Bailey was forced to retire in 1934 due to a career-ending injury. He was hit in the head by Eddie Shore of the Boston Bruins and suffered a fractured skull. Bailey was hospitalized for several weeks and never returned to the ice.
Bailey was inducted into the Hockey Hall of Fame in 1975 in recognition of his career accomplishments. He was remembered for his leadership, skill, and dedication to the game of hockey. He was a true pioneer of the sport and his legacy continues to live on.
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