It probably didn’t take the latest poor preseason performance by Deshaun Watson to convince anyone that his tenure as Cleveland Browns quarterback has been a failure. But seeing as he is still in contention to become their starting quarterback this season after such an awful outing probably doesn’t help matters.
The March 2022 trade with the Houston Texans that brought Watson to Cleveland was a controversy right away. He was facing sexual assault allegations that caused the Texans to sit him out for the entire 2021 season, but not only did the Browns give Houston three first-round picks, plus three later-round selections, they also signed Watson to a record-breaking fully guaranteed $230 million contract, and he has played in just 19 out of 68 possible games.
All of that set the Cleveland franchise back, and it will still be carrying a salary cap burden once the contract expires. It also convinced NFL owners to stay away from any such similar deals.
With all of that, and more, in mind, podcast host Bill Simmons is giving the Browns an unwanted NFL recognition, sarcastically saying that they should be proud that they made the worst trade of all time.
“I would urge the Browns fans to go glass-half-full here. You haven’t won a title since ’64. But you can now claim making the worst NFL trade of all time. People think Herschel Walker. No. People think the Colts trading the rights to John Elway. No. You have it. This was the worst one ever, so you won. That’s a positive. They changed the league. I think they set a good example for what not to do,” Simmons said.
“You have it. This is the worst one ever.”@BillSimmons and @HousefromDC on the worst NFL trade of all time: the Browns' trade for Deshaun Watson. pic.twitter.com/j9mcnURZ77
— The Ringer (@ringer) August 24, 2026
In October 1989, the Dallas Cowboys traded running back Herschel Walker to the Minnesota Vikings and got back three first-round picks, three second-round picks, and two later picks. Those laid the foundation for the Cowboys’ dynasty of the 1990s, while the Vikings have not been back to the Super Bowl since, though they did make the NFC Championship Game four times.
In May 1983, coming out of that year’s NFL Draft, Elway refused to play for the Baltimore Colts, who selected him No. 1 overall, and threatened to play minor league baseball instead. The Colts then traded him to the Denver Broncos for offensive tackle Chris Hinton, who was the No. 4 overall pick, backup QB Mark Hermann, and a first-round pick in the 1984 draft. Elway went on to win the Super Bowl twice with the Broncos, while the Colts had to wait for Peyton Manning to arrive to get another title.
Fast forward to today, and the Browns are still searching for a franchise QB. Meanwhile, the Texans have been to the playoffs for three straight years and could be a Super Bowl contender in the AFC this season.
Browns owner Jimmy Haslam has said that the Watson trade was a “big swing and miss,” but Simmons believes it deserves much more disdain than that.
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