21. Bill Parcells
A New York Giants’ icon and NFL Hall of Famer, Parcells is one of the league’s all-time great head coaches. But even the very best are capable of making implausible decisions from time to time. His moment of poor judgment while in charge of the New York Jets in 1997. To be fair, the toxic nature of that franchise is enough to bring anybody down, so it’s difficult to blame him too much.

The Jets were behind with seconds left on the clock against the Detroit Lions. They were at the Lions’ nine-yard line with the opportunity to kick a field goal and send the game to overtime. But instead, Parcells ordered a halfback pass. Of course, the Lions intercepted it and ended the Jets’ postseason dreams. One kick could have changed the entire course of history.