On December 13, 1933, during a game between the Maple Leafs and the Boston Bruins, Bailey was hit from behind by Eddie Shore of Bruins and hit his head on the ice, fracturing his skull. Bailey had severely injured head and it was feared that he would not survive. Bailey would eventually recover from his injury but he was never able to play hockey again. There was an all-star benefit game that was held at Maple Leaf Gardens on February 14, 1934, which raised $20,909.40 for both Bailey and his family. Bailey and Shore shook hands and embraced at centre ice before the start of the game. The NHL introduced the annual all-star game thirteen years later.