He played baseball in college for Southwest Missouri State University, and on January 12, 1982, was drafted by the Texas Rangers in the 7th round.

[1] He joined the Indians Major League roster for the start of the 1986 season, and made his pitching debut against the Baltimore Orioles on April 9, 1986.

He threw 5 complete games and 2 shutouts, yet was moved back into the bullpen late in the season and finished with a 9–14 record.

On January 9, 1990, Bailes was traded to the California Angels for Jeff Manto and minor league prospect Colin Charland.

[1] He signed on with the Toronto Blue Jays farm system on April 25, but could not make it past the Syracuse Chiefs at the AAA level, and after being released in January 1995 he retired.

[4] After spending some time in the business field and playing for a semi-pro league in Springfield, Missouri, Bailes signed on with the Texas Rangers after the 1996 season in hopes of making a comeback.

He made his first major league appearance in over four seasons on August 8, when he pitched 0.2 innings against the New York Yankees.