He is best known for being the strategic leader of the original Four Horsemen that consisted of Nature Boy Ric Flair, Tully Blanchard, Arn and Ole Anderson. He is most remembered as a manager in pro wrestling. He guided many wrestlers to singles and tag titles in the NWA. In the early 1990s Dillon served as a front office executive for the WWF before returning to a similar, albeit on-camera role with WCW.
In late 1985, Dillon was switched to managing Tully Blanchard. It was a move upward as Blanchard was fresh off a run as NWA United States Champion at the time and one of the major heels of the promotion. They did an angle where Tully and JJ, as he was called, kicked Baby Doll out of their little group, which got them even more heat as heels. They also started to hang out with Ric Flair and his "cousins," Ole and Arn Anderson. They "broke" Dusty Rhodes' leg and were soon called the Four Horsemen. They won most of the titles in the NWA and were dominant for the next couple of years.
In 1987, Dillon acquired Lex Luger as an "associate" member of the Four Horsemen. Soon, they pushed Ole out and Luger was made a full member. Dillon was involved in the first "War Games" match with the Four Horsemen against the Road Warriors, Paul Ellering, Nikita Koloff, and Rhodes. He ended up submitting in the match due to an injured shoulder, a shoulder that he really dislocated when he landed wrong after a Road Warriors double team.
In 1988, Dillon wrestled a few bullrope matches against the Midnight Rider, who was Rhodes under a mask.
Luger left to be replaced by Barry Windham in 1988, and most wrestling insiders thought this incarnation was the best technical wrestling group of the Four Horsemen. It only lasted four months, as Arn and Blanchard left for the WWF in August. Dillon attempted to build the Horsemen back to full strength. He hired Butch Reed as his thug and even got Barry's brother Kendall Windham to join, but they were never called the Horsemen because Dillon was let go shortly after that. To explain Dillon's sudden disappearance, Flair said on TV that he fired him because he let Ricky Steamboat sneak back into the NWA.
As the Four Horsemen dissolved in late 1997, Dillon began supporting Sting in his battle to win the WCW Championship back from nWo leader Hollywood Hogan. He was one of the most prominent figures in pleading with Arn Anderson to re-form the Horsemen in late 1998 and stood alongside the other members when Ric Flair made his surprise return. This event launched their re-formation in October of that year and their subsequent retaliation on Bischoff's abuse of power. The Horsemen vs. nWo storyline eventually had Bischoff "firing" Dillon from WCW. Dillon was also responsible for bringing in Vince Russo and Ed Ferrara to WCW.
In February 2006, Dillon made an appearance as a manager for the team of Darin Corbin and Ryan Cruz, the North Star Express at the Chikara Tag World Grand Prix, a 32-team, Tag Team tournament held over 3 days, culminating in the final night at the New Alhambra Arena in Philadelphia, Pennsylvania.
Dillon appeared at the March 31, 2008 edition of WWE Raw where he came out with three other Horseman (Blanchard, Windham & Arn Anderson) during Ric Flair's retirement party, his first ever appearance with World Wrestling Entertainment.