16. Rex Grossman (2003, Pick #22)
The old joke about Rex Grossman was his undying love of the deep ball, with virtually no regard for where his long throws would end up (or whether the offense or defense was the recipient of said passes).
The Chicago Bears, who drafted Grossman late in the first round of the 2003 NFL Draft, might’ve advanced to the Super Bowl in 2006 with Grossman as their starting quarterback, but any Bears fan will readily tell you that they advanced to the Super Bowl in spite of Grossman being their quarterback.
Grossman went 2-6 over the next two seasons as the starting quarterback for the Bears, leading them to eventually trade two first round picks to acquire Jay Cutler (after getting rid of Grossman, of course).