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.