When the Indians were owed a player from Pittsburgh in mid-1985, they chose Bailes, a Double-A reliever with sharp breaking stuff. He jumped to the majors the next spring and went 10-10 with seven saves, setting a Cleveland rookie record for most relief wins (eight). Though unable to throw too often, making him better suited to starting, he continued to be shuttled between the rotation and the bullpen.
Bailes was traded to California in January 1990, where he spent three seasons. He tried to catch on with Toronto in 1993, but retired when he couldn’t make it past Triple-A Syracuse. He came out of retirement in 1997 (he had pitched the year before in a semi-pro league in Springfield, Missouri) to spend two final seasons with the Rangers.