1. Jon Gruden. From the Oakland Raiders to the Tampa Bay Buccaneers, 2001
Arguably the most famous—and successful trade of a head coach in NFL history, the Oakland Raiders sent former head coach Jon Gruden to the Tampa Bay Buccaneers back before the 2002 season for first- and second-round picks in 2002, a first-rounder in ’03, another second-rounder in ’04 and some cash. While the Raiders went all the way to the Super Bowl in the first year without Gruden, they happened to lose to the team the coach was shipped to, the Tampa Bay Buccaneers. Talk about a back-fire.