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At what point could the Deshaun Watson trade be dubbed a disaster for the Browns?
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For Watson to be worth the trade capital and salary cap investment, he would need to be a top-3 QB in the league every year and be a major player in the Browns winning at least one SB.
Even if Watson was good and the Browns don't go to the playoffs that's already a disaster. If he plays at his current level for the next few years, it's one of the worst trades in NFL history because the Browns will likely have to shelf what is one of the better all-around teams in football because they have a QB who cannot be traded or cut without destroying their salary cap, and by the time he can walk many of these players will be over the hill or retired entirely.
I think they get forgiven a ton if they win a sb, even if he never scratches the top ten mark. It'll be looked at as a dumb deal, but ultimately that Lombardi in Cleveland would erase any other thoughts.