A highly touted prospect, Benson was drafted first overall by the Pittsburgh Pirates in 1996. He followed a strong rookie season in 1999 with an even stronger season in 2000, but those would prove to be the two best seasons of his career, as he underwent Tommy John surgery after the 2000 season. He posted three more good seasons from 2004 to 2006 with the Pirates, the New York Mets, and the Baltimore Orioles, but then underwent rotator cuff surgery, after which he was never again an effective Major League pitcher.