Deshaun Watson’s contract with the Cleveland Browns has officially entered “worst transaction in NFL history” territory, at least according to NFL analyst Mike Florio. Back in 2022, the Browns handed Watson a five-year, fully guaranteed contract for $230 million, the richest in league history at the time.
Since then, it’s been nothing but disappointment. While discussing the future of Carson Wentz on his show, Florio said:
"If the Panthers had taken him (Wentz) at a time when they had Sam Darnold, Pickett shows up for the first day of his workouts, and Darnold’s there, and they both throw the ball, and there's no comparing the two. So I think that Wentz would beat him out. I think Pickett was just a cheap insurance policy.

"But I think Carson Wentz will be the one that they bring in to ultimately win the job at a time when they need cheap quarterbacks because they've got so much money and cap space still tied up in that albatross of a Deshaun Watson contract—the single worst transaction in NFL history. And that is not an exaggeration." (10:18)
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Watson didn't just cost money. Cleveland traded three first-round picks, a third-rounder, and two fourth-round picks to acquire the signal-caller from the Texans in 2022.
How has Deshaun Watson fared at the Cleveland Browns?
Watson’s Cleveland tenure started with an 11-game suspension in 2022. When he did return, he looked nothing like the Pro Bowl QB from his Houston days. He posted a 79.1 passer rating and completed just 58.2% of his passes. In 2023, he played only six games before a season-ending shoulder injury.
The 2024 season was even worse. The QB managed just seven games before tearing his Achilles. A setback in early 2025 has now thrown his future into serious doubt, yet the Browns remain financially trapped. He has a $46 million base salary and a cap hit nearing $73 million in 2025.
It will be interesting to see whether the Browns give Watson a chance to redeem themselves or draft a rookie QB like Shedeur Sanders.
Also read: Deshaun Watson’s fiancée Jilly Anais sends 4-word message as QB teases comeback with Browns
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