

Another day, another Kenny Pickett relocation. Days after suggesting they were prepared to carry four quarterbacks into the 2025 NFL season, the Cleveland Browns have already said goodbye to two, releasing Tyler Huntley and then, on Monday night, trading Kenny Pickett to the Las Vegas Raiders for a 2026 fifth-round draft pick.
Pickett's abrupt exit marks the second time he's been traded since the end of the 2024 season, and the third time in the last two years alone. He was the first quarterback added by the Browns this offseason, acquired not long after he took the final snaps of Super Bowl LIX as the backup to the Philadelphia Eagles' Jalen Hurts. A hamstring injury sidelined Pickett for the thick of the Browns' quarterback competition, however, leaving rookies Dillon Gabriel and Shedeur Sanders to back up Joe Flacco.
What can we learn from Pickett's bounce around the NFL? Here's what each of his three trades can tell us about his current and previous teams, as well as what the future holds for the former first-round draft pick's career:
Trade No. 1: Steelers to Eagles (2024)
Pickett's first move came in just his third offseason as a pro, and just two years after Pittsburgh selected him 22nd overall in the 2022 NFL Draft. And this one is perhaps the most complicated of his three trades. That's because Pickett was a reported catalyst for the change of scenery, requesting a fresh start after feeling the Steelers misled him about the chance to compete for a starting opportunity with free agent addition Russell Wilson.
Plenty argued Pickett should've stood pat and simply proven to Steelers brass he could beat out an aging Wilson. Others saw Pickett as justified in his frustrations, watching as the Steelers saddled their face of the franchise with poor protection, middling weapons and a much-maligned play-caller in Matt Canada. One thing's indisputable after the fact: The Steelers quickly granting Pickett's request told us they were no longer interested in waiting around for a difference-maker to develop under center. They ended up trading for Justin Fields less than a month later, then let both Fields and Wilson walk for an even more immediate gamble at the position: 41-year-old current starter Aaron Rodgers.
Trade No. 2: Eagles to Browns (2025)
Perhaps no NFL team embraces quarterback projects like the Eagles, who only unearthed Jalen Hurts by risking alienation of predecessor Carson Wentz, and of course only won their first Super Bowl by leaning upon a backup in Nick Foles. Pickett represented a low-risk swing at cheap but experienced depth behind Hurts in 2024, and for the most part, Pickett did his job well in green, winning his lone official start in place of Hurts while nearly guiding a shootout victory in another game. So why, then, did the Eagles feel the need to ship him off to Cleveland just a month after he took the field in relief of Hurts to close the Super Bowl?
Because he was always set up to be an asset-flip in Philly. Unless Hurts had suffered a catastrophic injury and he'd taken over with gusto, Pickett's path in the City of Brotherly Love was destined to be one of reclamation -- figuratively, for his career, but also literally, in terms of the Eagles recouping draft picks in an inevitable trade to a needier team. Pickett left the Steelers because he wanted to start, remember, so even he behind closed doors assuredly welcomed a chance to reclaim a top gig elsewhere. Even more than this, his quick move to Cleveland was evidence of the Eagles' faith in current No. 2 Tanner McKee, who displayed pristine poise and precision as a pure pocket passer in limited action from 2023-2024.
Trade No. 3: Browns to Raiders (2025)
The latest Pickett trade is quite easily the most damning in terms of what the NFL at large thinks of his capacity for earning, let alone maintaining, a starting job. It's one thing to get caught in a numbers game. It's another thing to fail to separate from a 40-year-old Joe Flacco and two rookies, including one fifth-round flyer, in an open competition for arguably the most quarterback-desperate franchise in the league. Pickett's summer hamstring injury deserves a chunk of the blame; it wiped out his preseason availability. But the fact he couldn't do enough prior to the injury to even justify the Browns retaining him as a short- or long-term option speaks to how quickly he's become something of an afterthought journeyman.
Sure, the Raiders were suddenly very needy under center, with backup Aidan O'Connell banged up and Geno Smith left with only rookie Cam Miller to back him up. But the Browns could've easily kept four quarterbacks -- make it five or six -- if they believed each of them had even a morsel of franchise-caliber juice. They needed just five months and zero games to determine Pickett didn't belong. And we can't really argue coach Kevin Stefanski doesn't know ball after he squeezed a playoff bid from Flacco a few years back. The rookies also deserve some credit here, because if Dillon Gabriel hadn't ended the preseason with decisive pocket passing and Shedeur Sanders hadn't opened it with composure, maybe Pickett would've stuck around by default. Now Cleveland is free to see what it has in its younger developmental talent if/when Flacco can't hold up.
What's next for Kenny Pickett?
Well, things are pretty darn bleak at the moment. It's hard to spin it otherwise when you've been dumped by three different teams, including two with clear quarterback needs, in two years. It's fairly safe to say at this juncture that Pickett, while scrappy in some clutch moments to open his short-lived Steelers tenure, is squarely backup material. And plenty of folks arrived at that conclusion years ago. As for whether redemption is possible in Las Vegas, well, it is. That's chiefly because Geno Smith isn't a spring chicken at 34. And coach Pete Carroll wants to compete right now. If Smith goes down at any point, Pickett might even have a clearer path to an extended starting gig than he would've in Cleveland, with two rookies breathing down his neck.
He's also better set up for success in Las Vegas. Whereas the Browns are in clear rebuild mode, featuring outcasts like Diontae Johnson as starting weapons, the Raiders have their eyes on at least a wild-card bid under their new staff. And their offensive lineup is now outfitted with two potential young cornerstones in Ashton Jeanty and Brock Bowers. Does it mean Pickett has what it takes to elevate the group? That'd be quite a revelation for the maligned quarterback, based on what we've seen so far. But the carousel has to stop somewhere. Maybe, just maybe, it'll be with the silver and black.
Grading the trade
Browns: B+
It might've been nice to actually see Pickett in a game before dumping him completely. But they literally drafted two quarterbacks after acquiring him this offseason. And both rookies showed promise at different points this preseason. Why not get a head start on clearing the runway for their respective debuts? Getting anything for Pickett after his injury-riddled summer is also a mild victory.
Raiders: B
Look, they're not giving up much. And they're not asking Pickett to start. So it's really a low-risk move for a guy with a solid handful of starts at the NFL level. Is Pickett trustworthy for the long haul? We don't know that. But is he equally as reliable as, say, Aidan O'Connell when the latter is healthy? Probably. It's a very fine swing for the Raiders to take to address a sudden hole.