The Dallas Cowboys have pulled off some solid trades in their history but have also made their share of blunders, here we look at their three worst trades of all-time
Back in the early 1990s, the Dallas Cowboys were able to build one of the more impressive dynasties the NFL has ever seen thanks to a huge trade. They sent Herschel Walker to the Minnesota Vikings and were able to use the assets gained to build a dominant roster.
As good as that trade was, they have also had their share of failed moves. Here, we look at the not-so-pleasant trades that the Cowboys front office has pulled off.
Dallas Cowboys worst trades of all-time
Cowboys worst trade No. 3: Joey Galloway, 2000
After losing Michael Irvin to a neck injury, the Cowboys got a little desperate for a new No. 1 wide receiver which led to them sending two first-round picks to the Seattle Seahawks in exchange for speedster Joey Galloway.
Once Galloway was in Dallas, Jerry Jones forked out a boatload of cash despite the wideout playing just eight games the prior season while holding out for a new contract. Galloway then played in just one game for Dallas, tearing his ACL in Week 1.
He wound up playing another three seasons for the Cowboys but never crossed the 1,000-yard plateau and never scored more than six receiving touchdowns in a season.
In 2004, Galloway was traded to the Tampa Bay Buccaneers for Keyshawn Johnson who had 141 receptions for 1,820 yards, and 12 touchdowns in two seasons for them. He wasn’t elite but it was actually a much better move than when they traded for Galloway.
Cowboys worst trade No. 2: Amari Cooper, 2022
One of the better trades the Cowboys have made in recent years was when they sent a first-round pick to the Oakland Raiders for Amari Cooper. Before landing Cooper, Dak Prescott was struggling to find open receivers and the team was a mess overall
They knew they needed someone who can threaten the opposing secondary, which prompted this big trade. Of course, no one at the time thought the move was wise by Dallas and many didn’t hold back in their criticism.
A first-rounder for Amari Cooper.
— Adam Rank (@adamrank) October 22, 2018
The Cowboys are your friend who pays $179 for a T-shirt that they could have bought at Target for $12.
It didn’t take long to see Dallas won this trade. Cooper instantly revitalized the receiving corps and the Raiders used the pick they obtained on safety Johnathan Abram who isn’t a bad player, but he also didn’t have near the impact on his team that Cooper did in Dallas.
In three and a half years, Cooper ended up with 292 receptions for 3,893 yards and scored 27 touchdowns. Then ahead of the 2022 season, the Cowboys traded him to the Cleveland Browns for practically nothing.
The most frustrating part of this trade is that it didn’t have to happen. Dallas should have had the money to spend on Cooper, but they made some seriously poor decisions when it came to handing out extensions that hurt them in the end.
One of those was the freakishly long extension they gave to Ezekiel Elliott — because overpaying a running back isn’t enough, you also have to make sure you pay them beyond their prime. Another was the contract they signed with Jaylon Smith, who is costing them nearly $7 million against the cap this year after being released in 2021.
It’s a passing league and the Cowboys had one of the best aerial attacks in the NFL. Unfortunately, their desire to pay for players that can be replaced led to them seriously weakening their receiving corps while gaining a day three pick in return — and still having to eat $6 million in dead money to not have Cooper.
Cowboys worst trade No. 1: Roy Williams, 2008
Wide receivers have been the Achilles heel for the Cowboys — even though Jerry Jones still refuses to admit it’s a passing league and paid a running back. The Joey Galloway trade was bad, and while they looked brilliant for the Amari Cooper trade when they landed him, they messed that up by trading him for a fifth-rounder.
Having said all of that, there was still a much worse move made by Dallas involving a wideout, which happened in the middle of the 2008 season.
Looking to pair a younger wide receiver with Terrell Owens as they hoped to have an elite duo, with a player to take the reins when T.O. did leave, the Cowboys sent the Detroit Lions a first, third, and sixth-round pick for former Texas star receiver Roy Williams.
Jones had been reportedly trying to trade for Williams for a couple of seasons before making this move, and he didn’t hesitate to give him a six-year extension upon his arrival.
From day one, this looked like a bad move as Williams had just 19 receptions for 198 yards and a touchdown in his first 10 games with Dallas. He hardly improved from there, never even totaling 600 yards or 40 receptions in a single year for the Cowboys.
In all, he gave them 40 games and had 94 receptions for 1,324 yards and 13 touchdowns. For what was given up to acquire him, those numbers should have been from one year. Not three.