Dallas Cowboys owner Jerry Jones is no stranger to making deals. While Jones’ reputation for being a wheeler and dealer has subdued a bit lately, it doesn’t erase the history of the great moves he’s made in the past.
Jones has been the author of many impactful moves, including arguably one of the greatest trades in NFL history.
Ranking the Greatest Trades in Dallas Cowboys History
In recent years, Jones and Co. have opted for a homegrown approach to fortifying the roster. They value drafting and developing rather than dealing their assets to acquire other teams’ talent.
However, while Jones isn’t as prone to making big moves as he once was, that doesn’t mean he has stopped doing so altogether. Some moves are more recent than others, and while only some were championship-caliber acquisitions, all were impactful in their own way.
Here’s a closer look at the top five Cowboys trades of all time.
5) Robert Quinn for 2020 Sixth-Round Pick | 2019
Over the last decade, where Jones has been the most impactful on the trade market hasn’t been with blockbuster moves. Rather it’s been through taking late-round picks and flipping them for veterans who can help right away.
Such is the case for Robert Quinn, for whom the Cowboys traded a 2020 sixth-round pick to the Miami Dolphins ahead of the 2019 season. Quinn then signed a new one-year deal worth $9.2 million with Dallas, ensuring that the Cowboys got a formidable pass rusher under contract for a good price.
While his time in Dallas only lasted one season, the Cowboys certainly got their money’s worth with the move. Quinn finished the year with 11.5 sacks and 34 total tackles.
Although it turned out to be a one-year rental, the Cowboys flipped a late-round compensatory pick into a double-digit sack contributor, setting the stage for one of the five best trades in Cowboys history.
4) Brandin Cooks for 2023 Fifth-Round and 2024 Sixth-Round Picks | 2023
In the same vein as Quinn, the Cowboys were able to flip two Day 3 selections to add a playmaker who is still currently under contract. The Cowboys used a 2023 fifth-round pick and a 2024 sixth-rounder to trade for then-Houston Texans WR Brandin Cooks.
Cooks, along with veteran CB Stephon Gilmore, were the team’s big offseason additions in 2023. With Cooks still on the roster and looking to be WR2 this season, the move is working out as the Cowboys had hoped it would.
The veteran WR finished with 657 receiving yards last season, lower than he is accustomed to. However, he also recorded eight touchdowns, good for the second most of his career. With another year in the offense and another year of chemistry with QB Dak Prescott, those in Dallas are expecting a big season for Cooks in 2024.
3) Amari Cooper for 2019 First-Round Pick | 2018
The pass-catching options for the Cowboys in 2018 were lackluster, to say the least. However, all that changed when Jones and Co. identified the problem early in the season and brought Amari Cooper into the fold.
Dallas traded the next season’s first-round selection to acquire Cooper with the hopes that he would be able to turn the offense around. It was a steep price to pay, but it’s tough to argue with the results during his Dallas tenure.
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Cooper spent 3.5 seasons with the Cowboys, scoring at least eight touchdowns and finishing with over 800 receiving yards in every full season with them. He was the Cowboys’ true WR1, and while his time with Dallas wasn’t a lengthy one, it was impactful.
However, on the other hand, when the Cowboys decided to part ways with Cooper, they did so by accepting a fifth-round selection from the Cleveland Browns in return for the wideout — a move that has had many scratching their heads in disgust.
2) Charles Haley for 1993 Second-Round and 1994 Third-Round Picks | 1992
Charles Haley had quite the reputation for being a tough NFL player. He was someone you were glad to have on your team but dreaded playing against. The Cowboys understood that all too well from his time with the San Francisco 49ers and opted to do something about it.
Billed as one of the worst decisions the 49ers have made in their rich history, they decided to trade Haley to the Cowboys in exchange for a 1993 second-round pick and a 1994 third-round selection.
In Haley’s five seasons with Dallas, he amassed 34 sacks and 172 total tackles and was part of three Super Bowl-winning teams. Haley was one of the true bad boys of the NFL in the 90s, and when given the chance to bring him to his side, Jones didn’t hesitate to do so.
1) Herschel Walker Traded for a Haul | 1989
The Cowboys’ trading of RB Herschel Walker to the Minnesota Vikings is considered arguably the greatest trade in NFL history. While Walker was an outstanding talent, the haul the Cowboys received from Minnesota still gets talked about to this day.
In 1989, at the peak of Walker’s career, the Cowboys sent him to the Vikings for five players and six draft picks. The players involved were LB Jesse Solomon, DB Issiac Holt, RB Darrin Nelson, LB David Howard, and DE Alex Stewart.
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But the impressiveness of the trade starts with the draft picks, which turned into players such as Emmitt Smith, Russell Maryland, Kevin Smith, and Darren Woodson. Smith turned out to be the NFL’s all-time leading rusher, and Woodson was a five-time Pro Bowler who may hear his name get called for the Pro Football Hall of Fame soon.
Maryland and the others turned out to be key contributors to the Cowboys’ impressive run in the 1990s, and it all started with their decision to part ways with a talented RB already on the roster, solidifying the greatest trade in franchise history.
