16. Cowboys Trade Herschel Walker For 'Chips

Dumbass Move By: Wheelock Whitney, Jr.
Date: 10/12/1989
Initially, this trade may have looked like a lop-sided deal heavily in favor of the Vikings. Looking at it now, things took a huge turn in the Cowboys' favor after they used two of the draft picks given to them on Darren Woodson and Emmitt Smith. One dynasty team later, Dallas has multiple Super Bowl titles to thank for that deal, while Minnesota has two seasons of under 1,000 yards rushing from Herschel Walker.