Cowboys Land Multiple Spots in Ranking of NFL's Biggest Trades Ever

Jerry Jones orchestrated two of the biggest trades in NFL history.

Dallas Cowboys running back Herschel Walker runs with the ball against the Pittsburgh Steelers at Three River Stadium. | Malcolm Emmons-Imagn Images

Jerry Jones is considered a gambler for a reason. After purchasing the Dallas Cowboys in 1989, he and Jimmy Johnson pulled off a massive trade, which sent Herschel Walker to the Minnesota Vikings, helping the Cowboys build their 1990s dynasty.

In 2025, Jones again pulled off a shocking trade, sending Micah Parsons to the Green Bay Packers. They used the draft capital in that deal to rebuild their defense, and while we have yet to see if it works out, it's still considered a massive trade since it involved one of the league's premier pass rushers in Parsons.

Those trades were so significant that each of them were named by Bleacher Report's Kristopher Knox in his recent ranking of the top 10 biggest trades in league history.

Micah Parsons to Packers comes in at No. 6

Green Bay Packers defensive end Micah Parsons looks to rush the line during the game against the Dallas Cowboys. | Jerome Miron-Imagn Images

Parsons was sent to the Packers ahead of the 2025 season after contract negotiations broke down. Dallas received defensive tackle Kenny Clark and two first-round picks. The Cowboys used one of those picks, as well as their own second-rounder in 2026, to bring in Quinnen Williams.

This year, they traded back with the pick from Green Bay, which resulted in the Cowboys selecting EDGE Malachi Lawrence, cornerback Devin Moore, and defensive end LT Overton. Knox also says the end result has yet to be known, but believes this deal would have been the biggest involving a pass rusher if not for the recent Myles Garrett trade to the Cleveland Browns.

"If not for the Garrett trade, the Micah Parsons deal from 2025 might stand as the biggest blockbuster involving a pass rusher in NFL history," Knox wrote.

Herschel Walker to Vikings still ranks No. 1 all-time

Minnesota Vikings running back Herschel Walker in action against the Atlanta Falcons during the 1991 season. | Manny Rubio-Imagn Images

Coming in at No. 1 on the list was the Herschel Walker trade, which is hard to dispute. Walker was one of the best players in the league, but he only played 42 games in Minnesota and never turned them into true contenders.

Knox went as far as to call it a bust for Minnesota, while jump-starting the Dallas dynasty. There were multiple players added, including the NFL's all-time rushing leader, Emmitt Smith.

"The end result was a bevy of high draft picks that became stars like running back Emmitt Smith, cornerback Kevin Smith and safety Darren Woodson," Knox wrote.

This trade was so good for Dallas that hardly anyone would be able to argue there should be another No. 1. It's also impossible to see such a deal happening again.

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