Michael Vick (Falcons)
Toward the tail end of the 2004 season, the Falcons gave Vick a nine-year, $130 million extension. He finished second in the MVP voting that year, so he seemed worth it at the time. On the other hand, he played just five games the previous year due to injury, calling Vick’s durability into question. That should have made the Falcons at least a little nervous to give him a nine-year extension.
Of course, Vick didn’t get close to fulfilling the years of that contract. He went 15-16 over the next two seasons despite rushing for over 1,000 yards in 2006. Vick then spent some time in prison and was suspended by the league, keeping him out of the NFL for two years. The Falcons managed to get out of that huge contract extension, although it’s still a rather regrettable contract for both parties.