The Pittsburgh Steelers drafted quarterback Kenny Pickett 20th overall in the 2022 NFL Draft, hoping he could be the heir apparent to Ben Roethlisberger. Replacing a franchise legend was always going to be a daunting task, and while Pickett had flashes of brilliance in Pittsburgh, his tenure was short-lived. After just two seasons, Pickett forced his way out, reportedly feeling misled by Mike Tomlin. Once the Steelers brought in Russell Wilson for the 2024 season, Pickett requested a trade, ultimately landing with the Philadelphia Eagles.
Former Steelers quarterback Kenny Pickett and Head Coach Mike Tomlin look on during a home game at Acrisure Stadium.
Pickett was a backup and played little role in his team's Super Bowl run, yet his departure was met with skepticism. Despite this, he ended up as part of the Eagles' championship-winning season in 2024. However, his time in Philadelphia was brief, as he was later sent to the Cleveland Browns, where he now has a legitimate chance to compete for a starting role. The Browns have expressed excitement about acquiring Pickett, but a recent revelation suggests they had their eyes on him long before his arrival.
On Monday, a Browns insider Kelsey Russo revealed that Cleveland had been interested in Pickett dating back to when he was first traded to Philadelphia. In fact, the Browns allegedly had plans to "steal" him from the Steelers, indicating their long-standing belief in his potential. While Pickett's tenure in Pittsburgh ended abruptly, it's clear that at least one division rival has been eager to give him another shot.
"In the meantime, they are rebuilding their quarterback room – which started with the trade for Pickett," Russo said. "[Andrew] Berry said the Browns sought out the trade with the Eagles for Pickett. He was a player they were interested in the 2024 offseason when the Steelers traded him to Philadelphia. When the opportunity surfaced again this offseason, Berry took the chance. Cleveland sent QB Dorian Thompson-Robinson and a 2025 fifth round pick to the Eagles in exchange for Pickett."
Browns Head Coach Kevin Stefanski and the organization had plenty of opportunities to evaluate Pickett firsthand. While he showcased flashes of promise, he also had concerning moments that ultimately led to him spending the 2024 season as a backup after two seasons of trying to establish himself as a starter.

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Browns Head Coach Kevin Stefanski greets Steelers Head Coach Mike Tomlin near midfield after their teams played one another in a professional football game in Cleveland, OH.
Browns General Manager Andrew Berry was already familiar with Pickett long before his time with the Steelers. Cleveland had extensively studied him during the 2022 NFL Draft process, making their long-standing interest in him no real surprise.
"With Kenny, a young player, we spent a good amount of time with him during the pre-draft process when he came out," Berry said. "Feel like he's a good decision maker. He does a really good job of protecting the ball. He's very mobile and we think that his relative strengths are something that fit well with the offense that we're putting into place for this upcoming year. We do think that there's a pretty credible path for him to continue to improve and take a step forward and I think you've seen that with players that they get into maybe new or sometimes maybe better environments for their particular path and their career."
Ex-Steelers QB Kenny Pickett Will Have A Very Real Chance For Revenge
By the time Pickett left the Steelers, he had become a controversial figure. As a Pitt star in his final college season, he always had strong support from the local fan base. However, his time in Pittsburgh was rocky, and while his defenders argue the Steelers mishandled the situation, others believe Pickett didn’t handle things well himself. The truth about who’s truly to blame remains unclear, but what is certain is that Pickett had plenty of opportunities. Ultimately, he didn’t meet the Steelers' expectations, and they decided to move on.
Now, Pickett has the chance to face the Steelers at least twice a year, and if he earns the starting job in Cleveland, those matchups would make for must-watch television. A showdown against the team that gave up on him would add even more fuel to an already heated AFC North rivalry. But it’s worth noting that Pickett also gave up on the Steelers—he could have stayed, competed for the job, and learned from a Super Bowl-winning veteran in Wilson. Instead, he chose to leave.

Lucy Schaly / Post-Gazette
Former Steelers quarterback Kenny Pickett drops back in the pocket and delivers a pass against the Cleveland Browns.
Despite how things unfolded in Pittsburgh, the Browns seem genuinely excited about adding Pickett. Whether he can take advantage of this fresh start remains to be seen, but Cleveland clearly believes he still has untapped potential.