Damon Bailey was born on October 21, 1971, in Indiana. Damon was a 6'3" guard. He went to Bedford North Lawerence High schoool, where he was outstanding. Damon is the career point leader in Indiana High school basektball with3,134. Damon Bailey -- a household name among Indiana basketball fans since Bob Knight mentioned him as a hot prospect when Bailey was a mere eighth-grader -- solidified his reputation as a Hoosier hoops legend on March 24, 1990. That evening in the Hoosier Dome (now RCA Dome), the talented senior from Heltonville led Bedford North Lawrence to its first state championship. In 1990 the most ever to watch a high school game in Indiana, 41,000, watched him in the state finals He was the Mr. Basketball in 1990.. Hie scored a game-high 30 points including the Stars' final 11 -- and the game-clinching free throws with 0:24 on the clock. Bailey's late-game heroics gave BNL a hard-fought 63-60 victory over previously unbeaten Concord
"High school basketball is pure," said living icon Damon Bailey, the leading scorer in Indiana boys' high school history. "That's fun. Once you play college ball at an Indiana, a Kentucky or a North Carolina, or you play professionally, that's a job. You happen to get an education, but you're there to play basketball, I don't care what anybody says. "Playing high school basketball was definitely one of the most enjoyable times of my life. It is the highest level of what basketball is meant to be."
Damon played his college ball at Indiana Unviersity for Bobby Knight.At IU he scored 1,741 career points putting him seventh and the all time list at IU. He was named first-team All-Big Ten his senior year.
In 1994 Bailey was drafted in the second round of the NBA draft by the Indiana Pacers, but spent just one year in the league on the Pacers' disabled list.Damon stayed in Indiana and played several yearrs in the CBA. He was selected to the 1997-98 All-CBA First Team, while ranking 3rd in the CBA with 7.3 apg He was named American Conference Player of the Week three times in his CBA career