The 7 best Cowboys trades in the Jerry Jones Era
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The Dallas Cowboys finally made a splashy move that their fans had been waiting for at the wide receiver position. On Wednesday, they agreed to a trade with the Pittsburgh Steelers for George Pickens. As part of the deal, Dallas will send Pittsburgh a 2026 third-round pick and a 2027 fifth-round pick, while the Cowboys will receive a 2027 fifth-round pick.
On its surface, the move might seem like good value for the Cowboys. They landed a 24-year-old wide receiver who has recorded at least 800 receiving yards in each of his first three seasons in the league, putting up strong numbers even as the Steelers have had less-than-stellar play at quarterback. It also gives quarterback Dak Prescott another playmaker in the passing game. The Cowboys haven’t had much production at wide receiver beyond CeeDee Lamb over the last couple of seasons.
Of course, we’ll still need to see how good Pickens is with the Cowboys before determining if this deal worked out. Pickens is entering the last year of his rookie contract, meaning he could end up as a one-year rental.
If Pickens does prove to be a success in Dallas, the trade will join a list of other solid deals Jerry Jones has conducted since becoming the team’s owner in 1989. Let’s take a look at the best trades the Cowboys have made in the Jones Era.
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Sure, swinging a trade with the Eagles gave the Cowboys’ divisional rival a chance to draft DeVonta Smith, a receiver who helped Philadelphia win a Super Bowl title. However, it’s tough to argue that Smith has been a better player than Parsons through the first four seasons of their careers.
Parsons has turned into a perennial Defensive Player of the Year candidate. The linebacker has been named a first-team All-Pro twice and a Pro Bowler in each of his first four years in the league. It’s also hard to make the case that the Cowboys would be hoisting the Lombardi Trophy with Smith instead of Parsons on the roster, especially this past season when Dallas struggled defensively.
As part of the deal, Dallas landed a third-round pick that turned into defensive end Chauncey Golston, too. Golston recorded 5.5 sacks for the Cowboys in 2024 before signing with the New York Giants in free agency.
Dallas secured Lawrence in a draft-day swap in 2014, trading the 47th and 78th overall picks to Washington for the 34th overall pick. The two picks Dallas gave up became defensive end Trent Murphy (26 career sacks) and center Spencer Long (44 career starts).
Meanwhile, Lawrence is entering his 12th season in the league and is, statistically, one of the game’s top active pass-rushers. The four-time Pro Bowler has racked up 61.5 career sacks, with that number ranking 15th among players currently on a roster. He also had two seasons in which he recorded four forced fumbles, an impressive amount for a player at his position.
Lawrence – who signed with the Seattle Seahawks in free agency – and Parsons got into a social media spat earlier in the offseason over the Cowboys’ shortcomings during their time together in Dallas. But giving up two replacement-level players for a decade-long mainstay was well worth it for the Cowboys.
Trading up for Dez Bryant (2010)
The Cowboys acquired one of their best wide receivers in franchise history on draft night in 2010. As Bryant surprisingly slipped toward the bottom of the first round, the Cowboys made a deal with the New England Patriots to move up three spots to the 24th overall pick to select Bryant.
With the Cowboys, Bryant formed one of the top quarterback-wide receiver duos in the league with Tony Romo, before having brief success with Prescott. A three-time Pro Bowler, Bryant recorded at least 700 receiving yards in six of his eight seasons in Dallas. He led the league in receiving touchdowns in 2014 with 16, nearly helping the Cowboys reach the NFC Championship Game for the first time since their last Super Bowl win in the 1995 season. However, a pivotal would-be catch in the NFC divisional-round loss to the Green Bay Packers was overturned.
Even if Bryant was on the wrong side of an infamous play, he ended his career in Dallas fifth in team history in receiving yards (7,459), while his 73 receiving touchdowns are the most ever for a Cowboys player.
The Patriots moved down to pick No. 27 after the trade and used the selection on defensive back Devin McCourty, who was an integral piece to three of the Patriots’ Super Bowl wins. But getting Bryant more than made up for that.
George Pickens makes Cowboys ‘one of, if not, the most balanced offense in football’
Charles Haley trade (1992)
Just days ahead of the 1992 season, the Cowboys took a chance on Haley after the San Francisco 49ers decided they were finished dealing with his attitude. Dallas offered a second- and third-round pick for the then-three-time Pro Bowler.
The risk paid off for the Cowboys as it turned out that Haley was the missing piece for their dynasty run. He led Dallas’ league-best defense during the 1992 season, which ended with the Cowboys as Super Bowl champs. He was named a Pro Bowler two more times in Dallas, recording 22.5 sacks between the 1994 and 1995 seasons. He also won two more titles after the 1992 season, giving him five Super Bowl wins, which was the most for a player in NFL history until Tom Brady came along.
The trade also temporarily hamstrung the 49ers, who lost to Haley and the Cowboys in the 1992 NFC Championship Game.
George Pickens traded to the Cowboys
Getting the pick that became Darren Woodson (1992)
After trading up to the 36th overall pick to draft wide receiver Jimmy Smith, the Cowboys made back-to-back selections early in the second round in 1992. Thanks to a first-round pick they received from the Herschel Walker trade, the Cowboys moved down from one of that selection to get another first-rounder and the 37th overall pick from the New England Patriots in the 1992 NFL Draft. Dallas used the 37th overall pick to take Woodson, who became a five-time Pro Bowler and a major contributor at safety for three of the Cowboys’ Super Bowl-winning teams.
The two picks that the Cowboys gave up in the trade were offensive tackle Eugene Chung and fullback Kevin Turner, who each only spent three years in New England. The Cowboys missed on their trade up of Smith, though, cutting him after two seasons before watching him become one of the NFL’s best wide receivers with the Jacksonville Jaguars.
Trading up for Emmitt Smith (1990)
A couple of years before trading for Haley, the Cowboys nabbed another future Hall of Famer who was a core member of their dynasty in the 1990s. Armed with picks from another deal on this list, the Cowboys decided to cash a couple of those chips to trade up from No. 21 to No. 17 in the 1990 draft.
The player they selected wound up becoming the NFL’s all-time leading rusher. Smith’s records for rushing yards (18,355) and rushing touchdowns (164) still stand today.
The Cowboys surrendered picks that the Steelers turned into tight end Eric Green and defensive tackle Craig Veasey. Green was a two-time Pro Bowler, but giving up a two-time Pro Bowler for arguably the greatest running back of all time is a trade that everyone would make 100 times out of 100.
Herschel Walker trade (1989)
We didn’t rank the trades on this list, but if we did, this deal would certainly be No. 1 as it’s considered the biggest heist in NFL history. In the midst of Jerry Jones’ and Jimmy Johnson’s first-season struggles in Dallas, the team opted to move on from Walker, its star running back. In an exchange with the Vikings for Walker, the Cowboys received linebacker Jesse Solomon, linebacker David Howard, cornerback Issiac Holt and defensive end Alex Stewart. They wound up cutting those players and trading Darrin Nelson to finish with a total of eight draft picks in the deal.
Dallas turned those picks into Emmitt Smith, Russell Maryland, Kevin Smith, Clayton Holmes and Darren Woodson, with each playing a key role in the Cowboys’ three Super Bowl wins in the 1990s. As for Minnesota, Walker helped the Vikings reach the playoffs in 1989, but his tenure there was largely a disappointment. The deal quickly became known as one of the most lopsided in sports history.
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