NBC’s Mike Florio called the Cleveland Browns’ Deshaun Watson’s trade “one of the worst transactions in NFL history.” In the past four years, the quarterback’s reputation has taken a massive hit. The upcoming 17 games will decide if he can secure a better future in the NFL, and it is a challenge like no other in the Browns’ history. 

“What would Deshaun Watson have to do to convince the Browns to re-sign him after this year?” ESPN insider Dan Graziano asked in an episode of Get Up. “Inconceivable. 17-0 and the Super Bowl, and then we can talk about it.” 

Graziano has made a difficult ask of Watson, who is 30, past his prime and just recovered from an injury that set back his career. If, however, Watson does deliver, it would make for one of the greatest comeback stories in the NFL. 

On July 27, the ESPN Get Up panel was discussing how pivotal the 2026 season is for Watson. It is the final year of his five-year contract, and one of two things could happen. 

The Browns either welcome him back with open arms or he starts afresh on another team. But both these outcomes depend on one thing: an undisputed winning season, which in itself is a task. 

Watson’s fall from grace has cost the Browns a Super Bowl window. In 2020, he was the NFL’s lead passer with 4,823 passing yards, and despite an 11-game suspension in the following season, he landed a massive contract. 

The Browns offered him a now-infamous $230 million, five-year guaranteed contract. This investment would haunt them later on.

In the past four years, Watson has played in just 19 games and combined for 3,365 passing yards. On top of that, Watson’s 2024 season ended in October when he ruptured his left Achilles.

He sat out the 2025 season entirely when he sustained another injury to that same spot. Franchise owner Jimmy Haslam publicly called Watson’s costly trade a “swing and a miss.”

Yet, the Browns have given him a chance to fight for this season’s QB1 role against Shedeur Sanders. Under new head coach Todd Monken, both have a chance, but Watson’s future is uncertain. 

The Sanders factor: why Dan Orlovsky believes Watson's window is closing

As the 2026 training camp approaches, the tension between Deshaun Watson and Shedeur Sanders to win the QB1 race is all everyone can talk about. Former QB and now an analyst, Dan Orlovsky has made his point clear. 

On the ESPN Get Up panel, he opined that the Browns should stick to Sanders. 

“You have two first-round picks next year,” Dan Orlovsky said. “At some point, you have to look at that young player, see if he even has the potential to be your future, because what are you going to do? Deshaun? If he plays well, then you're going to pay him again? Shedeur Sanders should be the starting quarterback of the Cleveland Browns.” 

Orlovsky has warned the Browns against Watson. He opines the 24-year-old Sanders is their future. Will Watson pull a comeback no one deemed him capable of? 

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Written by

Akanksha Biradar