For anyone in Steel City hoping to watch Kenny Pickett line up against his old squad this year, that wish just died. The Cleveland Browns shipped off the 2022 first-rounder to the Las Vegas Raiders in return for a fifth-round pick. That move also means Pickett has now been dealt three times in just 17 months, one transaction away from tying an NFL record.

Meanwhile, the journey itself is wild. After Pittsburgh signed Russell Wilson last spring, Pickett asked out when told QB1 wasn’t in his hands. The Steelers quickly flipped him to the Philadelphia Eagles and then used the 2024 third-round pick they got in return to draft linebacker Payton Wilson. But the Eagles didn’t hold on to him for long either, sending Pickett to the Browns this March. That set up one of the NFL’s messiest quarterback rooms, where he battled Joe Flacco, Dillon Gabriel, and Shedeur Sanders. And now, in another twist, he is Sin City bound to play behind Geno Smith in silver and black.

But here’s where the Browns’ front office faces heat. YouTuber analyst Quincy Carrier broke down the math on the trade chips and didn’t sound impressed. He pointed out that with this Pickett deal, Cleveland enters next year’s draft loaded — their own first, Jacksonville’s first, their own second, third, and fourth, plus two-fifths, two-sixths, and a seventh. Yet, as Carrier questioned, what’s the actual plan for using that pile of picks? His tone suggested concern more than confidence.

Furthermore, Carrier doubled down with a sharp reminder. “And if you’re looking at me and you’re saying, Hey man, what are those six round picks really going to bring you? I don’t know.” He explained that the Browns already burned two-sixths last year trading up for Shedeur Sanders, who had slid down the boards. His fear is simple — history might just repeat itself if Berry leans on the same gamble again.

However, there’s another angle that flips this story. Pickett’s exit clears the runway for Sanders. His tumble from a projected first-rounder to a late-round flier shocked scouts, but flashes in preseason made noise. With Pickett gone, he not only survives cutdowns but can also build his future behind Flacco. And if you feel it’s just a coincidence, it is not. It’s actually the other way around.

The Browns Played a Long Game With Kenny Pickett

The Browns might have been thinking way ahead all along. By stacking up another draft pick, the Dawg Pound’s front office looks like it’s targeting the quarterback-heavy 2026 draft. For weeks, they hinted that Kenny Pickett would be part of the plan, but that was just smoke. His Grade 2 hamstring pull on July 26 didn’t do him any favors, though it wouldn’t have changed much. Joe Flacco was never really going to hand over the starting role to a QB still trying to prove he belonged.

But the idea that Cleveland was serious about Pickett was quickly challenged. As host Jake Vulinec admitted on 92.3 The Fan, “For weeks on weeks, the Browns have been trying to convince us, ‘We are going to move forward with Kenny Pickett.’…..I don’t know how many people were buying it,” Vulinec said on August 25. “It never really felt like I did the only thing that was creeping in was fear that they were actually going to make the wrong decision and just keep four quarterbacks.” And truth be told, the way Pickett’s summer unfolded made that fear real for some.

Meanwhile, the hamstring setback shoved him further down the ladder in a four-man competition. By the time the Browns circled September 7 as their opener, Kevin Stefanski had already gone with the safe call. Flacco got the nod, and Pickett was left behind two rookies who were already pressing hard for snaps.

However, there could be one more card to play. ESPN Cleveland’s Tony Grossi pointed out, “I would not be surprised if they bring back Tyler Huntley to be QB3. Which is what I proposed in my TLOD column this morning.” His take makes sense because Huntley had already filled in during camp when Pickett was sidelined, before being cut. Now with Pickett gone, he’s the only one available with a Pro Bowl on his résumé. So what’s Brown’s next move? To know that, stay tuned!