The five worst quarterback contracts of all-time

Drew Bledsoe, New England Patriots, 2001

10 years, $103 million (2001-2010)

The New England Patriots and the year 2001 will always be connected, but it’s not because of this megadeal.

Bledsoe was the first overall pick in 1994, and in the first six years of his career, the big-armed quarterback led the team to a Super Bowl appearance, but generally played more like a middle-of-the-road QB than an elite one.

Still, prior to the 2001 season, the Patriots paid Bledsoe like he was the best in the game, extending the former top pick for 10 years and more than $100 million.

Incredibly, Bledsoe only played two games for New England under this contract, suffering an injury in his second game that changed the course of the NFL for the next 15 years. A fellow named Tom Brady took his job, and…well, you know the rest.

Bledsoe was traded to Buffalo after the season (if you can believe it, there was actually a debate at the time about which quarterback the Pats should start). In Buffalo (and later in Dallas), Bledsoe continued his career-long tradition of being good but not great.

Bledsoe was never a bad player (and he’s certainly the best QB the Bills have had since Doug Flutie, which says more about the Bills than Bledsoe), but he was never worthy of the elite status that this contract suggested for him.

Next: Michael Vick