1. Deshaun Watson, Cleveland Browns — 5 years, $230 million, fully guaranteed
To be fair, there are a lot of reactionary takes floating around regarding Watson, and we still need to allow for more time before making a judgment. Watson didn't play for an entire season, joined a new team, was suspended for 11 games, and has been dealing with a rotator cuff injury this year, missing almost four full games.
With all that said, it's impossible to argue that the Browns have gotten anything close to their money's worth, nearly 600 days after giving up the largest trade package in NFL history and then subsequently giving Watson the most guaranteed money in NFL history.
Watson was flat-out bad in his six games in 2022, and aside from one game in 2023, has been even worse. He looks like a shell of his former Pro Bowl self, and his issues seem to be as much mental as they are physical. In 10 games as a Brown, He's completed 59.6 percent of his passes for 1,785 yards, 11 touchdowns, and eight interceptions. His yards per attempt has fallen 1.9 yards, and his air yards per attempt down 2.7 yards.
Perhaps Watson regains form, but the Browns are completely linked to him long-term. There are essentially no outs in his deal, and while his cap hit is a modest $19 million this season, it skyrockets to nearly $64 million in 2024, and he will lead the league in salary in both 2024 and 2025, and is currently slated to be second behind only Lamar Jackson in 2026.
There is no way to move on from Watson without Cleveland absolutely destroying their cap, and unless something legal happens that allows the team to get out of the contract, Watson will be a Brown through the 2026 campaign, before he becomes a free agent in 2027 with a void year cap hit of just $8.9 million.
If Watson starts to look like the player he used to be, the Browns will look like geniuses for the way they handled this situation. But for now, it's looking like they got too smart and got majorly burned.