Kenny Pickett trade grades for Raiders, Browns

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For the second time this year, Kenny Pickett has been traded, going from the Super Bowl-winning Philadelphia Eagles to the Cleveland Browns, and now to the Las Vegas Raiders in exchange for a 2026 fifth-round pick.

With Aidan O’Connell expected to miss months, not weeks, following a fractured forearm, the Raiders found themselves in dire need of another just in case something happened to Geno Smith, with 2025 sixth-round pick Cam Miller simply unready to take on such a major responsibility right out of the gates.

Fortunately, the Browns famously had more quarterbacks than opportunities for playing time, with a pair of mid-round rookies, Dillion Gabriel and Shedeur Sanders, both flashing enough potential to justify being gameday options behind Joe Flacco.

After a summer where it looked like four quarterbacks might just make the Browns’ roster, the team found a deal for their least likely contributor long-term and helped the Raiders when they needed it most, forming the rare win-win trade that helps all parties involved.

The Raiders lucked out by landing Kenny Pickett

When news broke that O’Connell was going to be out of action for an extended period of time, it wasn’t if the Raiders were going to trade for a veteran quarterback to back up Smith, but who the player was going to be and how much it was going to cost to get a deal done.

While Smith has played a ton of games over the past three seasons, recording more starts from 2022-24 than his previous eight seasons combined, at 34, he’s one of the elder statesmen of the NFL, with a body that simply doesn’t bounce back in the same way as one belonging to someone in their 20s.

Granted, the Raiders likely won’t be running Smith on too many designed runs, especially with Ashton Jeanty drafted early on to serve as the team’s bellcow. But over the course of an NFL game and especially over a 17-game season, quarterbacks are going to get hit, and may ultimately spend time on the bench, as happened to Smith in 2023.

Enter Pickett, who knows how to win games at the NFL level in multiple different situations.

Originally drafted in the first round out of Pittsburgh by the team across town, Pickett’s run with the Steelers was up and down, with the team ultimately trading him to the Eagles in favor of rolling with the dynamic duo of Justin Fields and Russell Wilson, neither of whom is on the team in 2025.

From there, Pickett played a few games for the Eagles, going 1-0 as a starter despite playing through a rib injury and proving that he can be a winning quarterback on a really good roster over a five-game sample size. While the Eagles ultimately chose to roll with Tanner McKee as their QB2 heading into the fall – even if they just traded for their own backup quarterback due to injury in Sam Howell – in the end, the Browns felt comfortable with Pickett as their guy heading into the fall before adding Flacco, Gabriel, or Sanders to their roster.

After missing time over the summer due to injury, Pickett is likely the least experienced quarterback in Kevin Stefanski’s system, which, when coupled with the long-term team control of the rookies, made him the odd man out for the Browns. For the low-low price of a fifth-round pick – the same selection the Browns initially traded – the Raiders get that final year of Pickett’s rookie contract and hope that he will perform up to his Eagles’ standards should his number be called this fall.

Trade grade: B+

The Browns did right by all of their quarterbacks

When the Browns traded for Pickett, they were in a very different place.

They had just re-signed Myles Garrett, were in the middle of quarterback evaluations – when Sanders and Cam Ward looked like they would go No. 1 and No. 2 in some order – and just needed to guarantee a base level of quarterback play under center for Stefanski’s squad, especially after their 2024 season fell apart in such spectacular fashion.

Fast forward to August of 2025, and Pickett was simply unnecessary on the Browns’ roster, with his expected spot on the 53-man roster being deemed a misallocated asset, instead of a luxury for a team that has often been cursed from a quarterback health standpoint.

Will Flacco play at a high level for 17, 20, or even 21 games, leading the Browns to their first Super Bowl since being reformed in 1999? Theoretically, he could, but there isn’t a huge sample size of players doing so at 40, which Flacco turned earlier this year.

No, when Flacco ends up on the bench for one reason or another, few fans are going to want to see the Browns bring out Pickett in the hopes of winning a few more games, presumably including owner Jimmy Haslam, who can’t be particularly happy with how many quarterback jerseys he’s had to print out over the last 26 seasons and counting.

By trading Pickett for the same pick he was acquired for, the Browns effectively get to have a mulligan on that move and can now internally debate who gets the QB2 nod behind the former Ravens quarterback, with Gabriel and Sanders both having flashed why they were premier prospects coming out of college in the preseason. While only time will tell if either or even both quarterbacks are franchise-caliber at the NFL level, no one will find out unless they actually get to take the field against professional talent, which is a much more likely occurrence now that Pickett is out of the way on the depth chart.

Trade grade: A

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