5. Ryan Dempster

Cubs general manager Jim Hendry took a chance on Dempster, a starter coming off Tommy John surgery in 2003. Dempster proved a worthy gamble, coming back as the Cubs' closer, saving 85 games in three seasons before returning to the starting rotation. His best season was 2008, when he went 17-6 with a 2.91 ERA and made the All-Star team. (Mark J. Rebilas/US Presswire)