A Crab Orchard High School and Marion High School graduate, Bailey was an outstanding pitcher for Southeastern Illinois College from - and was named to the All-Region team. Selected by the Boston Red Sox in the draft, he pitched for four Major League clubs in part of eight seasons, filling relief roles coming out from the bullpen as a middle reliever and as a set-up man as well. In a spring training game on April 2, 1993, Frank Viola and Bailey combined on a no-hitter as the Red Sox defeated the Phillies 10-0 at Jack Russell Memorial Stadium in Clearwater, Florida.