Year: 2010
Contract: 5 years, $78 million ($40 million guaranteed)
Team: Washington Redskins

When the Washington Redskins gave a contract extension to Donovan McNabb worth $78 million and nearly $40 million guaranteed in the middle of the 2010 regular season, he was having his worst year ever. While he was on pace to eclipse the 4,000-yard mark for the first time in his career, his touchdown-interception ratio and practically every other statistical category was abysmal. At nearly 34 years old, it was probably time for the 'Skins to go in another direction and think toward the future, but instead, they handed McNabb a lucrative deal that he was not going to live up to.

One month later, head coach Mike Shanahan demoted Donovan to third string while making Rex Grossman the team's starting quarterback because that makes a whole lot of sense. But Shanahan and the rest of the front office making completely idiotic decisions aren't anything new, just look how they handled the whole RGIII injury situation.