4. Hershel Walker (The Best)
The only trade that could top Charles Haley is "The Trade". Jerry Jones dealt the team's best player Hershel Walker to the Vikings in 1989 for a bunch of random players and future draft picks. Dallas might have gone 1-15, but great changes were coming.
In exchange for Walker, the Cowboys received Jesse Solomon, David Howard, Issaic Holt, and Alex Stewart along with a first second and sixth round pick. Dallas cut all five players also giving them conditional draft picks for the 1991 and 1992 drafts. With a boatload of draft picks, the Cowboys could now build a new team around Troy Aikman and Michael Irvin.
Emmitt Smith, Darren Woodson, and Russell Maryland are just a few of the players Dallas acquired over the next few seasons that helped turn the franchise around. To this day, it remains one of the biggest and arguably most notable trades in NFL history. Trading one player who ultimately helped a team rebuild and win three championships is an unbelievable story.
The Hershel Walker trade was undoubtably Jerry Jones' best trade that helped the Cowboys become who they are today, but often Jones would get the short end of the bargain. The early 2000s saw some trades that set the franchise back a few years. The worst coincidentally both involved trading for receivers.