Bailor was born in Connellsville, Pennsylvania, the fifth of Robert and Agnes Bailor's six children. Meanwhile, Law applied to discharge himself as Yee's bailor. The owner giving up custody is the "bailor" and person who takes is "bailee". Bailor signed with the Orioles upon graduation from Geibel Catholic in . Bob Bailor played in the MLB and also went to Geibel. Bailor played baseball with the Connellsville American Legion team. On April 2, 1986, the Dodgers released Bailor. From until , Bailor served as a coach with the Toronto Blue Jays. Bailor had batted a record 51 times before striking out for the first time.