Bailey has been a broadcast analyst for the Utah Jazz and the University of Utah— in addition to work as an inspirational speaker, singer, songwriter, and film actor.

Bailey attended North Carolina State University and was a leader in the Wolfpack's miracle run to the 1983 NCAA Championship.

[2] On November 25, 1991, he was traded by the Jazz along with a 1992 second-round draft pick to the Minnesota Timberwolves for Tyrone Corbin.

[3] From 1995 to 1998, he played in the Italian League for Polti Cantù in 1995–97 and Stefanel Milano in 1997–98,[3] before returning to the Jazz as a free agent on January 21, 1999.

Bailey and his wife, Sindi (née Southwick), live in Highland, Utah with their three children BreElle, Brendan, and Bryson.

[9] While playing basketball in Italy, Bailey decided to join the Church of Jesus Christ of Latter-day Saints.