David Flair never wanted to become a wrestler. He always wanted to be a State Trooper. He first appeared on camera backstage with his father at StarrCade '93 in WCW. His father was going to have to retire if he lost his match so they had the family appear to give it more emotion. In late 1998, David was back on WCW TV sitting front row and getting involved in some skirmishes with Eric Bischoff and the nWo. He eventually decided to become a wrestler and teamed with his father in his debut match at WCW/nWo Souled Out in Charleston, West Virginia on January 17, 1999. They wrestled Curt Hennig and Barry Windham and ended up losing the match. After the match, the entire nWo came out and Hulk Hogan lashed David with his belt until David's back was full of welts.

On February 21, 1999 at WCW's SuperBrawl, David turned on his father and joined the nWo WolfPac. He had Torrie Wilson by his side and used a taser on his father to help Hogan win their WCW World Title Match. He did not wrestle for awhile but did appear in vignettes with Torrie while he was training at the WCW Power Plant. He started to wrestle a regular schedule in May 1999. He made up with his father and Ric had the Four Horsemen help David to win matches. Ric, being the (onscreen) WCW President , stripped WCW United States Champion Scott Steiner of his title and awarded it to David. On July 11, 1999, David defeated Dean Malenko (with the help of Ric and Arn Anderson) to keep the title in his first defense on PPV.

In August, Ric had problems with Eric Bischoff backstage and was removed from TV along with Arn Anderson. David was left on his own and lost his US Title to Chris Benoit on August 9, 1999. In September, Torrie left David for Billy Kidman. Ric and Arn returned to TV and tried to help David. In October, Diamond Dallas Page and his wife Kimberly started a feud with the Flair's. Kimberly kept David distracted while Page "injured" Ric. David went nuts after seeing his injured father. David injured DDP in the WCW World Title Tournament that was being held on WCW Monday Nitro. He used the crowbar and only stopped when Kimberly got in between him and her husband. This got David started stalking Kimberly. She got one of her husband's teammates, Bam Bam Bigelow to help her but David used the crowbar on him too. He was a madman now.

Vince Russo finally scheduled a match between David and Kimberly for WCW Mayhem on November 21. Kimberly tried to seduce David and then "hit him low" but he had a cup on. DDP and his friend Chris Kanyon came to her rescue and laid David out. Arn arrived again but got laid out by David, who ran off into the fans.

David was joined by Daffney at StarrCade '99. He was joined a little later by Crowbar. They formed a team where they acted nuts and ended up winning the vacant WCW World Tag Team Titles in a tournament final on January 3, 2000 over Kevin Nash and Scott Steiner with Arn as the special referee. They lost the titles to Big Vito and Johnny the Bull, "The Mamalukes", on January 19. David soon split with Crowbar and in May 2000, joined Vince Russo's New Blood. He dumped Daffney and took Miss Hancock as his valet. He also turned on his father again which led to a match against him at The Great American Bash PPV. David lost but the next night, he won a match against his father to retire him and shave his father's head.

Near the end of 2000, David and Stacy were going to have an on-air wedding. Before that could happen though, it was revealed that Stacy was pregnant and that David was not the father. This led to David trying to figure out who the father was with the help of Ric, whom he had made up with, and Arn. He even had a match with Buff Bagwell to get Bagwell's DNA. This storyline ended abruptly and David left WCW without it ever being revealed who the father was.

David toured in the independent circuit for the first part of 2001. He teamed with Don Factor to win the NWA Tag Team Titles on March 21, 2001. They lost them on March 23. He then teamed with Romeo Bliss to win the NWA-Georgia Tag Team Titles on March 24. They lost them on April 21. In May 2001, the WWF picked up David's WCW contract and sent him to Ohio Valley Wrestling. He stayed there and feuded with Val Venis and had a brief tag team with Mark Jindrak until late 2002, when they dropped his development contract. He did make two appearances on WWE TV as he was beat up by Undertaker on March 4, 2002 and to wrestle Undertaker on March 14, 2002.

Flair joined Total Nonstop Action Wrestling in December 2002. He joined Vince Russo's S.E.X. group. He had a brief feud with Curt Hennig and the left S.E.X. to form Next Generation with Brian Lawler and Erik Watts. Together, they feuded with Dusty Rhodes and mocked him with an old NWA World Title belt. David left TNA in early 2003 and toured the independent circuit, winning the IWA Intercontinental Title from Ray Gonzalez on November 28, 2003. He lost it back to Gonzalez two days later. (Ric later had a confrontation with IWA promoter Victor Quinones over how David was treated in this promotion).

David became semi-retired after that to work for a medical supplies company. He occasionally returns to the ring for independent shows on weekends. He did do a tour for AJPW in 2004.