Bill O'Brien had the best quarterback in NFL history during his time as New England's quarterback coach and offensive coordinator around the turn of the decade, and he did an amazing job of turning around the Penn State program (making Christian Hackenberg look serviceable in the process) before he took the Texans' head coach position in 2014. His time with Tom Brady may have been any coach's version of heaven, so perhaps it's fitting that O'Brien now finds himself firmly in quarterback purgatory.
The franchise's decision to sign former Broncos backup Brock Osweiler to a four-year, $72 million contract before the 2016 season will go down as one of the worst free-agency moves in league annals.