3 worst trades in Dallas Cowboys history

All NFL teams make mistakes. The Dallas Cowboys are certainly no exception. Teams make draft mistakes. They give out absurd contracts. They make poor hires. And, yes, they make terrible trades.

Jerry Jones has never shied away from trades. Sometimes Jones makes blockbuster trades that pan out and other times he makes highly questionable decisions.

With the offseason upon us, Dallas has a lot of difficult choices to make about the 2022 roster. With 24 players set to hit the free market in March, who will stay, and who will go? What positions will the front office prioritize in the draft? With their current cap space struggles, will Jones choose to make any trades to fill positional needs? All of this remains to be seen. Until then, we can take a look back at these biggest trade blunders in franchise history.

Buckle up. Because one of these trades was so catastrophic that it ended up on Bleacher Report’s seven worst trades in NFL history list. While we don’t want to reminisce on the ugly moments in Cowboys history, it is important to take a look at the past to learn for the future. Right, Jerry?

Here are the 3 worst trades in Dallas Cowboys history

3. Alex Barron, 2010

This story is a sad tale of promising talent that didn’t deliver. These two former first-round picks simply didn’t live up to their expectations. In May of 2010, the Cowboys traded linebacker Bobby Carpenter to the St. Louis Rams in exchange for tackle Alex Barron. Despite the fact that Barron was benched for disciplinary reasons in a loss to the San Francisco 49ers in 2009 and was highly inconsistent, apparently Jones still thought trading for this guy was a good move.

The Florida State product was the 19th overall pick in the 2005 NFL Draft. He played in 74 of 76 games with the Rams. Several false start and holding penalties (sounds like someone on the current roster… **cough cough Connor Williams**) caused frustration in St. Louis. Dallas likely figured that getting rid of a guy who didn’t do enough would mean that the person they were getting in return couldn’t be all that worse… but they were wrong.

Barron’s biggest blunder? He was called for a holding penalty on what would have been a game-winning touchdown vs. the Washington Redskins in his very first game with the Cowboys. The gorgeous pass from Tony Romo to Roy Williams that would have created a come-from-behind win against a divisional rival was erased. That play was his only appearance of the year and his last with the franchise. Dallas got rid of him before the next season, and Barron never played in another NFL game again. Ouch.

2. Joey Galloway, 2000

This trade was bad for so many reasons that it’s hard to know where to even start. But I guess the beginning is apparently the best place. The Cowboys needed help at wide receiver after Michael Irvin sustained a spinal cord injury in 1999 that forced him to retire. Enter Jones with a typical “Jerry Jones splash move.” The GM decided to send two first-round picks to the Seattle Seahawks for the high-powered Joey Galloway.

Jones wasn’t wrong to want Galloway. In four years with Seattle, he averaged more than 1,000 yards per season and had 36 touchdowns. The receiver wanted a contract from Seattle badly enough that he held out the entire first half of the 1999 season. The Seahawks put the franchise tag on him and then traded him to Dallas for money and prime draft selections.

If Galloway played the way he did in Seattle, this might have made sense. But he didn’t. Galloway tore his ACL in his very first game with the Cowboys and never did much for America’s Team after that. Not only was Galloway a bust, but the lack of first-round picks when the team needed to replace QB Troy Aikman made the trade even worse.

An argument in Galloway’s favor is that Aikman was only under center for one of his games in Dallas. The receiver had 64 yards and a touchdown in that contest. So there’s a possibility that he could have been more productive if Aikman had remained QB and stayed healthy. Regardless, he was later traded to the Tampa Bay Buccaneers, where he would sadly have more success. In his mid-30s, Galloway had three 1,000-yard seasons with the Bucs. Thanks for saving it for Tampa, Joey.

But wait! There’s more! Remember those draft picks that Dallas gave up? Those would come back to haunt Dallas, too. One of those picks was Shaun Alexander, a running back selected out of Alabama who would go on to win a league MVP award and set an NFL record for single-season touchdowns. He also obliterated records in Seattle for both yards and touchdowns. Sigh.

1. Roy Williams, 2008

If there’s a trade worse than the Galloway one, it’s this one. But it’s dang close. FOX Sports labeled this trade as the worst ever for the team. And the quote from Jones? That’s an actual sentence he said to the press in 2011. The story goes that Jerry Jones was enamored with Roy Williams long before the team sent three draft picks to the Detroit Lions. In 2008, Jones sent a first, third, and sixth-round pick to Detroit in exchange for Williams. The Cowboys immediately signed the receiver to a $54 million contract.

Jones was trying to take advantage of a 0-16 team, but it was the Cowboys owner who ended up worse off. Williams had fewer than 38 catches in both of his seasons with Dallas. It just wasn’t a good fit. He never broke 600 yards and was one of the few receivers in Cowboys history to struggle with Tony Romo. He caught just 48% of the passes thrown his way in Dallas.

You’d think Jones would learn to be careful about trading for wide receivers and giving up draft picks after these two blunders, but that’s not how this stubborn GM rolls. They did the same with Amari Cooper. They gave up yet another first-round pick for Cooper who unironically had quite a meager 2021 campaign. History repeating itself? I’d say so.

Williams was a Pro Bowl receiver in 2006, but he never played at that level in Dallas. The receiver was supposed to help the team when Romo was in his prime. This was a time when the franchise had a chance to actually win a Super Bowl again. Plus, they not only got little production out of Williams, but they also lost a ton of money after wildly deciding to immediately sign him to a giant extension. They could have used the money and fresh talent to help boost the roster.

You’d think that Jones would have learned from his previous mistakes, but he has proven otherwise. Let’s hope the entire front office makes better decisions for the team in the future.