Jon Gruden (Tampa Bay Buccaneers)
Things started great for Gruden when he arrived in 2002. He revamped a listless Tampa Bay offense and let what was a generational defense do its thing. That got the franchise its first Super Bowl championship. It was a strong coaching job, but many believe Gruden simply took advantage of an ideal situation established by his predecessor, Tony Dungy. They wanted to see how he’d once he had to start forming his own team down the line.
In fairness, Gruden inherited some difficult situations in terms of salary cap and draft capital, but even so, his subsequent years with the Bucs were lukewarm at best. He failed to even make the playoffs in 2003 to defend the crown and from that year to his last in 2008, Tampa Bay reached the postseason just twice. His reign became pockmarked by a steadily disintegrating core and a stubbornness on his part to favor older veterans rather than grooming younger players.
A problem that he hasn’t seemed to grow out of.