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In late 1998, David was back on WCW TV sitting front row and getting involved in some skirmishes with Eric Bischoff and the n Wo.
He eventually decided to become a wrestler and teamed with his father in his debut match at WCW/n Wo Souled Out on January 17, 1999.
In October, Diamond Dallas Page and his wife Kimberly started a feud with the Flairs.
They wrestled Curt Hennig and Barry Windham and won the match.
After the match, the entire n Wo came out, and Hulk 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.
In his autobiography, Ric Flair alleges that Hogan took liberties with his son by whipping him far more times than agreed upon and that he would never forgive Hogan for this.
During a storyline in September, Wilson left Flair for Billy Kidman.
Ric and Anderson returned to TV and tried to help David.
Kimberly tried to seduce Flair and then "hit him low", but he had a cup on.