5. Deion Sanders, Washington Redskins (2000):
Make no mistake about it, Sanders is arguably the best cornerback in NFL history. But his free agent deal with the Washington Redskins is still one of the worst decisions in NFL history.
Following an illustrious career with Atlanta, San Francisco, and Dallas, “Primetime” signed a ridiculous seven-year, $56 deal with the splurging Redskins in 2000. He rewarded them with 38 tackles, four picks, and a forced fumble and then retired after the end of the year. He would resurface with the Baltimore Ravens years later. Despite his status as a true NFL legend, his short, disastrous tenure in Washington will remain anything besides legendary.
