Turns out it does get worse and more painful than not winning a game.
In the NFC Championship game in 2000, the Bucs were trying to put up just enough points, as the defense had held down the Rams offense (which was no small feat). Driving at the end of the game, Shaun King connected with Bert Emanuel for a key first down conversion, only to have it wrongfully overturned, and force the NFL to rewrite the rules the next season due to the controversy caused by the call. This is the same rule that would later famously frustrate Calvin Johnson and many other receivers.
The catch will more importantly be remembered as the idiotic reason the Buccaneers don’t have two Super Bowls. Anyone who thinks that 1999 Buccaneers team wouldn’t have mopped the turf with the Titans clearly isn’t familiar with how dominant that team truly was. But thanks to that call, Tony Dungy never won a Super Bowl in Tampa and was eventually fired for falling short of NFL immortality.
Both Dungy and the Bucs separately got the last laugh.