Bailey was inducted into the Hockey Hall of Fame in 1975, 42 years after the Toronto Maple Leafs forward saw his career come to a sudden end after he was hit from behind by Boston Bruins defenseman Eddie Shore, fracturing his skull.

After growing up and playing junior hockey in Toronto, Bailey played two seasons of senior hockey with Peterborough before signing with the Toronto St. Patricks (who later became the Maple Leafs). He scored 15 goals as a rookie in 1926-27, then led the NHL in goals (22) and points (32) in 1928-29, finishing second in voting for the Hart Trophy as the NHL's most valuable player.

Bailey scored 22 and 23 goals respectively in each of the next two seasons, finishing with 43 and 42 points. His offense dropped off in 1931-32, when he finished with 13 points (eight goals, five assists) in 44 games. He scored one goal in the Stanley Cup Playoffs, but it was the series-winning goal in Game 3 of the Final against the New York Rangers.

He bounced back a bit in 1932-33, finishing with 18 points (10 goals, eight assists) in 47 games. Bailey had five points in his first 10 games of the 1933-34 season before his career came to an end on Dec. 12, 1933. Shore was angry after being knocked down by a hard check from Toronto's King Clancy; thinking Bailey had been the one who'd hit him, Shore retaliated. Bailey eventually made a full recovery but did not play again. An All-Star benefit game was held at Maple Leaf Gardens on Feb. 14, 1934, raising more than $20,000 for Bailey and his family. The highlight of the night came when he and Shore shook hands and embraced at center ice.

Bailey's No. 6 was retired at the benefit game; it was the first number to be retired by any North American professional sports team. He had 192 points (111 goals, 81 assists) in 316 NHL games.

He coached the Toronto Varsity Blues to three Canadian Interuniversity Athletics Union championships in the 1940s and was a timekeeper at Maple Leafs Gardens for more than four decades. Bailey died on April 7, 1992.