The Greatest Insult to Injury NFL Moments in History

New York Giants #21 running back Tiki Barber blows a kiss to the fans after scoring a touchdown in the first quarter during the Philadelphia Eagles vs New York Giants game on December 17, 2006 at Giants Stadium Philadelphia Eagles 36 New York Giants 22 (Photo by Tom Berg/NFLPhotoLibrary)
New York Giants #21 running back Tiki Barber blows a kiss to the fans after scoring a touchdown in the first quarter during the Philadelphia Eagles vs New York Giants game on December 17, 2006 at Giants Stadium Philadelphia Eagles 36 New York Giants 22 (Photo by Tom Berg/NFLPhotoLibrary) /
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#2:  Jon Gruden returns to haunt the Raiders

The Oakland Raiders’ handling of their head coaches over the past two decades has been bizarre. Late owner Al Davis used to have the utmost confidence in his coaches but that changed by the early 2000s. His decision to trade Jon Gruden to the Tampa Bay Buccaneers was the height of the absurdity since the young coach had turned them into contenders the past two years.

At first the decision seemed favorable enough. Oakland was one of the best teams in 2002 and had a bounty of draft picks to get even better moving forward. They cruised to the Super Bowl where they expected to claim their fourth Lombardi trophy. Only there was one problem. The man who built them and knew them best was waiting with an even better team.

Gruden and his Tampa Bay Buccaneers crushed the Raiders 48-21 including three interceptions returned for touchdowns. Gruden knew everything they were going to do and took full advantage. Oakland has been to the playoffs just twice total since he left.