
Flair first appeared on camera backstage with his father, Ric Flair, at Starrcade 1993 in World Championship Wrestling. In the storyline, his father was going to have to "retire" if he lost his match, so his family appeared to increase the emotion. In late 1998, David was back on WCW television 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 on January 17, 1999. They wrestled Curt Hennig and Barry Windham, and won the match. After the match, the entire nWo came out, and Hollywood Hogan lashed David with his belt until David's back (and stomach where the belt whipped around and struck) was full of welts while his father was handcuffed to the ring ropes.
On February 21 at SuperBrawl IX, David turned on his father and joined the nWo Wolfpac. He used a taser on his father to help Hogan win their WCW World Title match. He did not wrestle for a while but did appear in vignettes with Samantha.
Flair started to wrestle a regular schedule in May 1999. He made up with his father who then had the Four Horsemen help Flair win matches. Ric, being the on-screen WCW President, stripped WCW United States Champion Scott Steiner of his title and awarded it to Flair. On July 11, at Bash at the Beach, Flair defeated Dean Malenko, with the help of Ric and Arn Anderson, to keep the title in his first defense on pay-per-view.
In August, Ric was removed from television. Flair was left on his own and lost his United States Title to Chris Benoit on August 9. During a storyline in September, Samantha left Flair for Billy Kidman. Ric and Anderson returned to television and tried to help David. In October, Diamond Dallas Page and his wife Kimberly started a feud with the Flairs. Kimberly kept Flair distracted while Page, in storyline, injured Ric. In response, Flair went insane after seeing his injured father. Flair injured Page in the WCW World Title Tournament that was being held on WCW Monday Nitro. He used a crowbar and only stopped when Kimberly got in between him and her husband. This led to a storyline where Flair stalked Kimberly. She got one of her husband's teammates Bam Bam Bigelow to help her, but Flair used the crowbar on him too. Vince Russo finally scheduled a match between Flair and Kimberly for Mayhem on November 21. Kimberly tried to seduce Flair and then "hit him low", but he had a cup on. Page and his friend Chris Kanyon came to her rescue and laid Flair out. Anderson arrived again but got laid out by Flair, who ran off into the crowd.
Flair was joined by Daffney at Starrcade in December 1999. He was joined a little later by Crowbar. They formed a team and won the vacant WCW World Tag Team Titles in a tournament final on January 3, 2000 over Kevin Nash and Scott Steiner with Anderson as the special referee. They lost the titles to Big Vito and Johnny the Bull, The Mamalukes, on January 19. Flair 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. Flair 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, Flair and Keibler were going to have an on-air wedding as part of a new storyline. Before that could happen though, it was revealed that Stacy was pregnant and that David was not the father. This led to Flair trying to figure out who the father was with the help of Ric, whom he had made up with, and Anderson. He even had a match with Buff Bagwell to get Bagwell's DNA. This storyline ended abruptly when Miss Hancock returned to television with Shawn "The Star" Stasiak and a baby carriage in the ring. Instead of a baby, however, it was revealed that there were 8x10 pictures of Shawn in the carriage. After this angle, Flair was no longer seen in WCW as a competitor.
On the February 12, 2001 edition of Nitro, as on-screen CEO Ric Flair and the Magnificent Seven were trying to discuss things inside the ring, Kevin Nash appeared on the Turnertron and told Ric that he had his son David in his locker room. Nash told Ric that his number one priority was to become the number one contender to the WCW World Heavyweight Championship, which was held by Scott Steiner. His number two priority was getting a rematch for Dustin Rhodes against Rick Steiner, who was WCW U.S. Champion at the time. Nash felt like Ric had wronged Rhodes, and he felt Rhodes could beat Steiner in a rematch. Out of concern for his son's safety, Ric granted all of Nash's requests. Nash would get his title shot against Scott Steiner for the WCW World Heavyweight Championship later that night, and Rhodes would get his rematch against Rick Steiner. Later that night, Nash came to the ring with Ric's son David. As they started coming to the ring, Nash punched David. Ric Flair and WCW security came out as Ric begged Nash to stop assaulting his son. Nash did not listen and gave David a Jackknife Powerbomb. Ric and WCW security came to the ring to pull David out as Scott Steiner was coming down to the ring alongside Midajah.
Flair made two appearances for the World Wrestling Federation (WWF) during 2002, as he was beaten up by The Undertaker on March 4 and wrestled the Undertaker on March 14 as part of the build-up for his father's match against Undertaker at WrestleMania X8.