The Dallas Cowboys may not win championships anymore, but they sure know how to steal headlines. Jerry Jones did it again recently when he came out of nowhere with the Micah Parsons trade to the Green Bay Packers, a move that nobody really saw coming despite the deterioriation in contract talks this summer.
Maybe we should have, though. After all, the Parsons blockbuster is far from the only shocking trade we’ve seen in Cowboys history. But just which was the most egregious? Let’s rank a few of them and see how each stacks up.
4. Roy Williams to Dallas from Detroit (2008)
The less said about this one for Cowboys fans, the better. In a shocking move, Dallas gave up a first-, third- and sixth-round pick to acquire Williams from Detroit. The Cowboys were looking for answers at wideout after the Terrell Owens experiment had just about run its course in Big D. Jones tried to bet on a talented player who had been trapped in a dire situation, but he ultimately came to regret it: Williams never caught more than 38 passes in any of his three full seasons in Dallas.
3. Charles Haley to Dallas from San Francisco (1992)
While the Herschel Walker trade may have been the first building block for what would become a dynasty, the Charles Haley deal is what put Dallas over the top and on the path to a Super Bowl (or three). Dallas acquired the Pro Bowl defensive end for a second- and third-round pick. Haley was already an All-Pro at this point, and the Cowboys got the final piece to their championship puzzle for next to nothing.
Haley had become a thorn in the side of the 49ers and the feeling was certainly mutual. San Francisco wanted him gone and wound up trading Haley to the team that would quickly become their biggest rival. The implications of this trade would last through the Cowboys’ title run, winning three out of four Super Bowls.
2. Micah Parsons to Green Bay (2025)
This one truly came as a surprise to most. And seeing how it just happened, most fans, especially those that root for the Cowboys, are still in shock. The contract dispute that dragged out through the summer and looked like it would continue into the first weekend of the regular season abruptly came to an end earlier this week.
Jerry Jones stunned the football world when he traded away only the second player in NFL history to begin a career with at least 12 sacks in each of his first four seasons. Nobody thought the Parsons contract situation would come to this, and especially not days before the start of the regular season. While the Cowboys received two first-round picks and a Pro Bowl defensive tackle Kenny Clark, Parsons has proven to be a generational talent. Fans in Dallas are beside themselves and fed up with Jerry’s ego.
1. Herschel Walker trade to Minnesota (1989)
Talk about something that came out of nowhere: That’s what we’re talking about with this Cowboys trade. Regardless of what’s transpired since, this is still the most shocking trade in team history. We have to remember this was on the heels of Jones buying the team less than two years earlier and immediately firing the only head coach the franchise had ever known in Tom Landry.
Not to mention that Walker had rushed for 1,514 yards the previous season but that didn’t stop Jerry: Jones gave the OK, and head coach Jimmy Johnson was able to put this trade together with the Vikings, receiving the motherlode of all compensation in return. The multitude of draft picks and players the Cowboys got back for Walker are what helped begin to build the dynasty that followed.
In return, the Cowboys got linebackers Jesse Solomon and David Howard, cornerback Issiac Holt and defensive end Alex Stewart. But that was just the beginning: Dallas also received Minnesota’s first-, second- and sixth-round pick in 1990; their first- and second-round pick in 1991; and their first-, second- and third-round pick in 1992. In all, when factoring in all those packs, the trade involved 18 players.