The Pittsburgh Steelers were searching for a solution at quarterback during the 2022 offseason after Ben Roethlisberger retired, and the organization decided to draft Kenny Pickett in the first round of the 2022 NFL Draft. The quarterback showed some flashes during his time with Pittsburgh, but over his two years with the Steelers, he was far too inconsistent and he struggled with injuries. Many fans wanted Pickett to be the next franchise quarterback in Pittsburgh, but it just didn't work out that way for the two sides.

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Eagles' Kenny Pickett gets ready to throw a football during a preseason game in 2024.
The Steelers parted ways with Pickett during the 2024 offseason, as the organization decided to trade him to the Philadelphia Eagles. The trade worked out for both sides, as the Steelers were able to move on quickly and one of the picks they received resulted in linebacker Payton Wilson. Pittsburgh also has two seventh round selections in the 2025 NFL Draft as a result of the trade.
Philadelphia decided to then deal Pickett to the Cleveland Browns during the 2025 offseason, and he now has a chance to be a starting quarterback again. The former Steeler had his introductory press conference with the Browns on Thursday, and he was asked about being in the same division with Pittsburgh, as well as the other teams he is familiar with in the AFC North.
"I think it's definitely a big advantage," Pickett said. "It's understanding the style of play when you're playing in December and January. What those games kind of look like. It usually comes down to one possession at the end of the game. Teams that protect the ball usually have a good chance to win those games. I have a good understanding of how those games go over the course of the year and season, and at the end of the year when it's really important. I definitely want to use that experience to my advantage."
Pickett spent a season with the Eagles as the backup to Jalen Hurts, and he did get into some games that the Eagles were dominating. He also had to play in relief of a concussed Hurts for a couple of weeks, as he finished one game for Philadelphia and started another. He put good tape out there during those appearances, which made him comfortable with being traded.

Eagles.com
Steelers' former QB Kenny Pickett in his first preseason game with the Philadelphia Eagles after being traded.
The former Pittsburgh quarterback won Super Bowl LIX as a backup, and now he wants to return to being a starter. He will compete for the starting job in Cleveland, and currently, he is the front runner. The Browns can still bring in another veteran, as Russell Wilson is expected to take a visit to Cleveland and could end up signing there too. The franchise also has the second overall pick in the 2025 NFL Draft, which means Pickett could be competing with either Cam Ward or Shedeur Sanders.
Wilson landing in Cleveland would be interesting, as the Steelers signing Wilson in the first place wound up being the reason Pickett requested a trade from Pittsburgh. Now, Pickett can find himself in the same exact position.

Eagles Press Conference
Former Eagles backup quarterback, Kenny Pickett speaks to the Philadelphia media in 2024.
Steelers May Have To Square Off Against Kenny Pickett
There is a very strong possibility that Pickett will be the starting quarterback heading into the 2025 season. The Browns' current quarterback situation isn't much better than Pittsburgh's, and barring another veteran addition, Pickett has a pretty easy path to returning to a starting role. This means he could actually play against his former team for the first time as a starter, and he already knows how those games typically go.
"The games aren't always pretty, but it's a violent style of football," Pickett said. "I'm excited to get back into it, just think it's a great opportunity to go compete again. That's really all you can ask for. That's what I was told coming in here."
Pickett will have the chance to win the starting job, and he may be starting against Pittsburgh twice in 2025. The Steelers have split the season series with Cleveland in each of the last three seasons, so they should be competitive matchups.
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