In 1987, Windham ventured to World Championship Wrestling (WCW), where he teamed with The Italian Stallion. He never got above preliminary status and went to WCCW briefly at the end of 1988. In January 1989, he was back in WCW teaming with another second generation wrestler, Dustin Rhodes, as the "Texas Broncos". In a match aired on January 28, 1989, Kendall teamed with Eddie Gilbert against his brother Barry and James J. Dillon of the Four Horsemen. Kendall turned on Gilbert and joined Barry and held up the four fingers to the camera. Before the next show, Dillon left the promotion and the Horsemen name was dropped. The Windhams and Ric Flair were given a new manager, Hiro Matsuda, and a new stable name, "Yamasaki Corporation". Kendall stayed with the stable (which grew to include Butch Reed and Michael Hayes) until the summer, when he left WCW.
Windham returned to WCW in 1997 with his head shaved and feuded with Chris Adams and Jim Duggan. In 1999, when WCW created a hardcore division, he entered it briefly and feuded with Hardcore Hak. In June, Windham joined The West Texas Rednecks in what would be the biggest push of his career. The Rednecks were his brother Barry, Curt Hennig and Bobby Duncum, Jr.. They were supposed to be heels feuding with Master P's rappers, the "No Limit Soldiers", but the southern fans of WCW cheered the Rednecks instead. The angle was quickly dropped and they moved on to a feud with Harlem Heat (Booker T and Stevie Ray). Kendall and Barry defeated Harlem Heat for the WCW World Tag Team Title's but lost them back to Harlem Heat three weeks later. By the end of 1999, Windham once again left WCW.