Bailey was born in Washington, D.C., and grew up in a violent household in a high-crime neighborhood in the suburbs of Maryland bordering D.C.
Bailey was raised Baptist. While playing basketball in Italy, Bailey decided to join The Church of Jesus Christ of Latter-day Saints. He was baptized by his father-in-law on 31 December 1995.
He is the father of six children. Bailey and his wife, Sindi (née Southwick), live in Salt Lake City, Utah with their three children.
Bailey has a daughter with his college sweetheart, and two sons from his first marriage.
Bailey currently is a public speaker, a broadcast analyst for the Utah Jazz and the University of Utah, an actor, and a singer/songwriter. 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.
Bailey is chairman of Big T Productions, Fertile Earth (which has a patent pending on a fertilizer that works through sprinkler systems), and FourLeaf Films.
He works with various charities — including Make-A-Wish, D.A.R.E., the Happy Factory.