Bailey is a local product, born in Voorhees, New Jersey and a product of Paul VI High School in Haddonfield, New Jersey. He was the 6th round choice of the Oakland Athletics in the 2006 MLB Amateur Draft out of Wagner College on Staten Island, New York.
Bailey made the A’s roster for Opening Day in 2009, and became an immediate phenom. For his season that included a 6-3 record, 26 Saves, a 1.84 ERA, a 0.876 WHIP, a 91/24 K:BB ratio, and just 49 hits allowed in 83.1 innings pitched, Bailey was named the American League Rookie of the Year.