Dinsmore began his career in 1996 and was assigned to NWA-Ohio Valley Wrestling, later becoming Ohio Valley Wrestling. OVW became WWE's farm territory and, during his time there, Dinsmore won a record of eight times the OVW Heavyweight Champion as well as the OVW Southern Tag Team Champion eleven times. When he was called to the main roster, he debuted as Eugene Dinsmore, Eric Bischoff's nephew. Eugene was involved in a storyline with Evolution, facing Triple H at SummerSlam. He also won the World Tag Team Championship with William Regal. Eugene would stay with WWE until 2007, including a feud with Kurt Angle where he won his gold medal, having a match against him at SummerSlam.