#1 PPV quality bouts wasted on Nitro
One of the most head-scratching decisions WCW took was consistently giving away PPV quality matches on free TV.
WCW did this shtick so many times that it became a norm at one point. Eric Bischoff's reasoning for this was that he wanted WCW Nitro to be must-see TV. Eventually, WCW PPVs began registering low buyrates, which hurt business in the long term.
The match that immediately comes to mind while talking about WCW's ridiculous booking, is Goldberg vs Hollywood Hogan for the WCW World Heavyweight title on an episode of Nitro inside a packed Georgia Dome. Goldberg won the match and became the new World Heavyweight Champion, but the match was capable of main eventing a major PPV like Starrcade.
Bischoff's booking decisions didn't help WCW's cause and the inclusion of Vince Russo on the creative team made matters worse going forward.