He played for the Toronto Maple Leafs, Detroit Red Wings, and Chicago Black Hawks of the National Hockey League between 1953 and 1958.

In the American Hockey League Bailey flourished, playing in 54 games, amassing 46 points and a team-high 115 penalty minutes.

Throughout the game Richard repeatedly tried to renew his attack on Bailey and even refused to leave the ice after a slash when ordered by the referee.

[1][2] The following two seasons would be much less dramatic as they saw Bailey splitting time between the Maple Leafs and the Hornets, never really finding his scoring touch when brought up to the big leagues.

While playing for the Hornets in 1956, Bailey was suspended from the remainder of the playoffs and fined US$575 for assaulting referee Jerry Olinski on April 2.

He would only play in 28 games before again being traded, this time with Jack McIntyre, Nick Mickoski and Hec Lalonde for Earl Reibel, Billy Dea, Lorne Ferguson and Bill Dineen on December 17, 1957.

The following season saw Bailey playing only five more games for the Barons before being traded for Bill Dineen once again, this time to the Buffalo Bisons on October 20, 1959.

Bailey, Glen Skov, the rights to Danny Lewicki, Terry Gray and Lorne Ferguson went to the Montreal Canadiens for Cecil Hoekstra, Reggie Fleming, Ab McDonald and Bob Courcy.

In his final season, Bailey was suspended after slugging referee Billy Purcell in a game at Fort Wayne on December 9, 1967.

Long time Fort Wayne General Manager Ken Ullyot called him "the last of the great stick handlers."