In the early 80's, Dillon spent some time wrestling for the World Wrestling Federation (WWF). He made his Madison Square Garden debut on April 23, 1984 when he challenged Tito Santana for the WWF Intercontinental Heavyweight Championship, losing by pinfall after a flying elbow by Santana.
He is most remembered as a manager in pro wrestling. He guided many wrestlers to singles and tag titles in WCW. Dillon achieved his greatest success as the manager of the Four Horsemen, which consisted of Ric Flair, Tully Blanchard, Arn Anderson , Ole Anderson, Lex Luger and Barry Windham. After leaving WCW in February 1989, Dillon served as a front office executive for the WWF until 1997. On April 21, 1997, he returned to WCW as an on-camera commissioner, which he lasted until fall 1998.
In 2012, Dillon was inducted into the WWE Hall of Fame along with the Four Horsemen (Flair, Blanchard, Anderson, and Windham).