Kenny Pickett finds himself in a pivotal moment of his NFL career after being traded to the Cleveland Browns following a Super Bowl-winning season as a backup with the Philadelphia Eagles. Now with the Browns, Pickett joins a crowded quarterback room currently holding five players — a number that will likely shrink with Deshaun Watson sidelined and roster cuts looming.
Despite the competition, Pickett could be in a favorable position. If he performs well in OTAs, minicamp, and training camp, there’s a real chance he could secure a spot — and potentially the starting job. With uncertainty surrounding rookies like Dillon Gabriel and Shedeur Sanders, Pickett or Joe Flacco could emerge as early favorites to lead the offense in Week 1.
Pickett is entering the final year of his rookie contract, making him an affordable option with something to prove. If he’s able to lock down the starting role and deliver a strong season, he could find himself in a prime position heading into free agency — similar to how other quarterbacks have leveraged late success into lucrative deals.
His experience in Philadelphia, learning under coaches like Kellen Moore and Nick Sirianni while observing Jalen Hurts, may have contributed to his development after an up-and-down tenure in Pittsburgh. There, he was thrust into a veteran-heavy environment with high expectations, which didn’t allow much room for gradual growth.
Now entering his fourth year, Pickett has a chance to reset. The Browns are unlikely to carry four quarterbacks on the final 53-man roster, so the competition will be fierce. But for Pickett, this offseason offers a rare second chance — and perhaps, a long-term opportunity — to establish himself as a starter in the NFL.
Cleveland’s quarterback situation remains wide open, and whoever takes the field first could have the best shot at keeping the job. For Pickett, it’s all on the table — roster spot, starting job, and a career resurgence.
