Mandatory Credit: Imagn Images

Browns Trade Kenny Pickett to the Raiders – Who Has This Trade Worked Out for the Most?

Kenny Pickett heads to his fourth team in as many years in the NFL

Mandatory Credit: Imagn Images

The quarterback carousel just ahead of the 53-man deadline for the season continues as the Las Vegas Raiders land Kenny Pickett via a trade with the Cleveland Browns. In exchange for Pickett, the Browns have received Vegas’ fifth-round pick in the 2026 NFL draft.

Incidentally, following the trade, Pickett became only the second player in the history of the NFL to be traded three times in his first four seasons, with Sam Howell becoming the first player just a few days ago.

Still playing on his rookie contract, Pickett’s journey in the league has gone from Pittsburgh to Philadelphia to Cleveland and now to Las Vegas. But why did the Raiders trade for Pickett, and who is the benefactor of this trade?

Kenny Pickett has now been traded from Pittsburgh to Philadelphia, from Philadelphia to Cleveland, and from Cleveland to Las Vegas. https://t.co/F2Wv29X3rS
— Adam Schefter (@AdamSchefter) August 26, 2025

How Do the Raiders Benefit from Kenny Pickett?

The Raiders were carrying three quarterbacks on their roster, but a wrist fracture injury to backup signal caller Aidan O’Connell was a big blow to their plans going forward. O’Connell suffered the injury during the final game of the preseason and is expected to miss 6-8 weeks of the season.

Raiders QB Aidan O'Connell suffered fractured wrist in preseason finale, expected to be out 6-8 weekshttps://t.co/KhPR6O1tRv pic.twitter.com/C89aCHqBfa
— Around The NFL (@AroundTheNFL) August 24, 2025

With O’Connell set to miss a significant portion of the season, Vegas was left with just rookie Cam Miller as the backup to Geno Smith. Picked in the sixth round of this year’s draft, Vegas needed to add another signal caller to the team on an immediate basis.

Following O’Connell’s injury, head coach Pete Carroll confirmed to the media that they would be in the market for a quarterback, but he would prefer one with experience under center. Pickett can provide exactly what Carroll is looking for.

The former first-round pick is now entering his fourth season in the league. He has also started 24 games over two seasons for the Steelers, and although Pickett is not seen as a starting-caliber QB, he can still make a worthy backup for the Raiders.

How Does Shedeur Sanders Benefit from the Pickett Trade?

As for Cleveland, they first traded for Pickett in March and followed that up by bringing back Joe Flacco, who did a commendable job for them in 2023. During the draft, they selected Dillon Gabriel in the third round and Shedeur Sanders in the fifth round.

The Browns also signed free agent Tyler Huntley at the beginning of the month, and at one point, they had 5 quarterbacks all competing for what was thought to be the starting role. In any case, Huntley was waived just a couple of days ago, and now, with Pickett traded to Vegas, that has opened the doors for Shedeur Sanders to fight for the backup spot.

And then there were three: pic.twitter.com/gtAIsyQmff
— Adam Schefter (@AdamSchefter) August 26, 2025

As things stand at the moment, Flacco has already been named the starter by head coach Kevin Stefanski. However, there is no word on who the backup will be, but recent preseason performances indicate that Gabriel has the upper hand over Sanders.

Whatever the case may be, the competition, which was a fierce battle among five players, has now been reduced to just three quarterbacks, of which two are rookies. The Browns have been widely accused of trying to sabotage Sanders’ career with the way they have treated him at training camp and preseason, but the latest development seems to suggest otherwise.

The question now remains, which of the two rookies will receive the backup spot and which of them will challenge Flacco for the right to start under center as the season progresses.

Mandatory Credit: Imagn Images

Cleveland Browns

Kenny Pickett

Las vegas Raiders

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Devavrat Kulkarni

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I am a content writer for the NFL team, and joined The Playoffs after working with Sportskeeda and NFL Analysis as an NFL writer. After starting my professional career as a French-to-English translator, working as a content writer is a new adventure for me. I started out in the sports media field for two main reasons: my love for sports in general, especially the NFL, NBA, and Tennis, as well as my passion for writing. The best part of this job is that I get to write a variety of pieces with the freedom to explore content from various angles. It also enables me to stay up to date with the sporting world, which otherwise can be difficult to do in the day-to-day grind. In a world full of chaos, sports unite and entertain like nothing else!