In May 1990, Windham joined World Championship Wrestling (WCW) and re-united with the Four Horsemen which at that point consisted of Ric Flair, Arn Anderson, Sid Vicious, and Ole Anderson. At the time, Ole Anderson was only semi-active and permanently became their manager once Windham joined. He defeated Doug Furnas on June 13, 1990 "". He spent most of the time that year in tag team matches with the other Horsemen as partners. At Halloween Havoc 1990, Windham was involved in a controversial match between Sid Vicious and then NWA World Heavyweight Champion Sting. Vicious appeared to pin Sting and win the championship, but it was actually Windham who was dressed like Sting. Once the hoax was noticed, the match was restarted and the real Sting defeated Sid Vicious. Windham spent the rest of the year teaming with Arn Anderson in the continuation of a feud between the Four Horsemen and then NWA World Tag Team Champions, Doom. At Starrcade 1990: Collision Course, Windham and Anderson wrestled Doom to a no contest in a Street Fight when a member of each team was pinned.