Bailey attended North Carolina State University and was a leader in the Wolfpack's miracle run to the 1983 NCAA Championship. That year, under head coach Jim Valvano, he led the Wolfpack in both scoring and rebounding. The Utah Jazz selected him as the 7th pick of the 1983 NBA Draft. Jazz management reported that he was selected for the quality of his character, as well as the quality of his game. This was the beginning of 16 years of his playing professional basketball, 12 of those years were with the NBA.
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. There he played for almost three seasons until 1994, when he left the NBA and played in the Greek League (playing for Panionios) for the 1994-95 season. From 1995 to 1998 he played in the Italian League for Polti Cantù in 1995-97 and Stefanel Milano in 1997-98, before returning to the Jazz as a free agent on January 21, 1999. He retired after the end of 1998-99 season.
Throughout his career Bailey has also been involved in community service. He has directed basketball camps for youth since 1984 in which he teaches young people lessons about life and basketball. Bailey's basketball camps often focus on students with serious illnesses or disadvantaged backgrounds. Bailey's record of service has resulted in numerous awards for leadership and contributions to the community. Included in his awards are: the NBA's prestigious Kennedy Community Award, the Utah Association for Gifted Children's Community Service Award, Sigma Gamma Chi fraternity's Exemplary Manhood Award, the Great Salt Lake Council of the Boy Scouts of America's American Champion Award and the Italian League's 1998 All Star Games Most Valuable Player.
Bailey currently is a public speaker, a broadcast analyst for the Utah Jazz and the University of Utah, an actor, and a singer/song writer. Bailey's music includes uplifting songs as well as a fusion of R&B and Nu Soul. His albums include Faith In Your Heart (1998), The Gift of Christmas (2001), and I'm Not the Same (2002). In addition to his music, he has appeared in a few films.