Bailey attended Broomfield High School in Broomfield, Colorado , and he pitched for the school's baseball team. During the summer between his junior and senior years, he tore the ulnar collateral ligament in his pitching elbow. He underwent Tommy John surgery , causing him to miss his senior year. Bailey enrolled at Gonzaga University and played college baseball for the Gonzaga Bulldogs. He signed with Oakland and spent his first professional season with both the AZL Athletics and the Vermont Lake Monsters , posting a combined 3—1 record and 2.