Bailey was one of the top left wingers of his day, but his career came to an abrupt end on December 12, 1933, when he was viciously checked from behind by Eddie Shore of the Boston Bruins, apparently in retailiation for a hit he had received from King Clancy moments earlier. Bailey's body was hurled across the ice, and it was feared that he would not survive after severely injuring his head. Bailey did recover, and an All-Star game was held at Maple Leaf Gardens for his benefit on February 14, 1934, now recognized as the forerunner of the NHL's modern All-Star Game. Bailey and Shore shook hands and embraced at center ice before the game began. Bailey never played hockey again, but did continue to work for the Maple Leafs as a coach and in the front office until late in life.

In his seven and a half seasons, Bailey totaled 111 goals and 82 assists in 313 games. His #6 jersey was the first ever to be retired by an NHL team, and is one of only two to have been permanently retired by the Maple Leafs. Bailey was inducted in to the Hockey Hall of Fame in 1975.