Joe vs. Dillon vs. Kenny vs. Shedeur vs. Deshaun, oh my! Cracking Cleveland’s Complicated Quarterback Conundrum

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Save for the periodic intermural push-and-shove, NFL training camps are a snoozefest.
Unless there’s a juicy quarterback battle.
That said, preseason fights for the right to start behind center are, generally speaking, non-fights. Sure, once in a while, a lowly-drafted QB—say, Russell Wilson—will steal the gig from a highly-paid vet—say, Matt Flynn—but the majority of the time, the starter coming into camp is the starter coming out of camp.
Things are going to be different, however, at the CrossCountry Mortgage Campus in Berea, Ohio, the preseason home of the Cleveland Browns, where we’re going to see a cross-generational quarterback battle for the ages.
So Many Signal Callers, So Little Time
Shedeur Sanders breaks down the @Browns QB room.
— Kay Adams (@heykayadams) May 21, 2025
Loves Flacco.@PaniniAmerica @ShedeurSanders pic.twitter.com/lkIvKDyNd6
The Browns head to Berea with five, count ‘em, five potential starting field generals in tow, each of whom comes with a very particular set of skills, but each of whom also comes with a very particular set of baggage—and each of whom comes from a notable age bracket.
Here, in alphabetical order, is Cleveland’s five-headed quarterback monster, age signifiers and fantasy football potential included:
Joe Flacco
Joe Flacco needs to be the QB leading the Browns through the BRUTAL start to their schedule.
— Honor The Land (@honortheland) May 16, 2025
"It's the true test to see where this team stands and what they're capable of... he gives you the best opportunity to go out there and win."
- @chefzae23 | #DawgPound pic.twitter.com/uq4XBnx3SU
Birthdate: January 16, 1985
Age: 40
Notable Birth Year Pop Culture Highlight: Live Aid raises $125 million for famine relief in Ethiopia
Fantasy Football Outlook: Unless you’re a Cleveland resident or a Flacco fantasy truther, you might not recall that in his five starts in with the Browns in 2023, January Joe lit it up the tune of 20.3 fantasy points per game, as per Fantasy Data, which, spread out over an entire season, would’ve led the league.
Last season, Flacco wasn’t nearly as effective in Indy, posting a 12.4 fantasy points average, but the Colts’ offense, for the most part, was reliant on running back Jonathan Taylor, so he can be forgiven.
Flacco has an eminently average batch of receivers—it’s Jerry Jeudy and a cast of thousands—and he can’t run—he was born around Live Aid, f’r cryin’ out loud—so he’s a dart-throw streamer. At best.
Reality Football Outlook: Flacco’s not super-mobile, but he knows the game and he’s likely the most accurate thrower on the roster. It wouldn’t be at all shocking if he lands the starting gig.
Dillon Gabriel
Cleeeeeevveeeelannddddddd…. It’s love pic.twitter.com/WMRmoyjAbq
— Dillon Gabriel (@_dillongabriel_) May 16, 2025
Birthdate: December 28, 2000
Age: 24
Notable Birth Year Pop Culture Highlight: Um, Y2K?
Fantasy Football Outlook: Gabriel’s comps run the gamut from Tua Tagovailoa to Jaren Hall, but considering scouts pegged him as a third-rounder, we’ll lean towards Jaren.
That said, he has wheels—his 40-yard-dash has been clocked at 4.46, which would’ve led all quarterbacks at the 2025 NFL Combine—so if he scoops up the starting spot, his rushing prowess would make him a more appealing fantasy option than Flacco.
Reality Football Outlook: To reiterate: Third-rounder. Then again, the aforementioned Russell Wilson was a third-rounder, so…
Kenny Pickett
Kenny Pickett and Dillon Gabriel will take the No. 1 and No. 2 reps for the Browns when OTAs open, per @MaryKayCabot pic.twitter.com/99hhp8ZPJo
— SleeperNFL (@SleeperNFL) May 20, 2025
Birthdate: June 6, 1998
Age: 26
Notable Birth Year Pop Culture Highlight: James Cameron’s epic film Titanic wins 11 Academy Awards.
Fantasy Football Outlook: In his 2022 rookie season in Pittsburgh, Pickett was a reasonable fantasy option, averaging 14.6 points per game, 24th in the league, ahead of an aging Matt Ryan and still-trying-to-find-himself Baker Mayfield.
Last season, to his credit, in his Week 18 start, Pickett dropped 16 fantasy points—admittedly, it was against the Dallas Cowboys second stringers, but still.
Reality Football Outlook: The Browns threw a boatload of free agent money at Pickett—four years for $14 million, with a $7 million signing bonus—so heading into camp, he’s probably the favorite to start. But if he poops the preseason bed, there are plenty of other options. Plenty.
Shedeur Sanders
Shedeur Sanders reportedly had Browns coaches “shocked” at his precision and accuracy with the short time they had with him at rookie minicamp.
— NFL Rookie Watch (@NFLRookieWatxh) May 19, 2025
Sanders reportedly was throwing the ball with the “touch” of a 10-year NFL veteran.
Sanders reportedly has “goals” of winning the QB1… pic.twitter.com/DTo3kUCKMY
Birthdate: February 7, 2002
Age: 23
Notable Birth Year Pop Culture Highlight: Beyonce and Justin Timberlake both launch their solo careers.
Fantasy Football Outlook: Up until the 2025 NFL Draft, I thought Sanders would be a solid, periodically spectacular professional quarterback. Once every scout in the league passed on him on multiple occasions, though, it dawned on me that I was probably wrong.
Sanders might be worth snatching up at the tail end of your dynasty league draft. But probably not.
Reality Football Outlook: I mean, it’s possible he crushes it at training camp. But there are only so many snaps to go around, and most of them won’t go to a fifth-rounder.
Deshaun Watson
Birthdate: September 14, 1995
Age: 29
Notable Birth Year Pop Culture Highlight: Sony drops the first PlayStation.
Fantasy Football Outlook: There was a point in his career when Watson was a fantasy football beast—but then, um, stuff happened, and he wasn’t. In the last four games he started in 2024, his fantasy points average was a gnarly 11.05.
Watson might be washed, so even if he somehow wins the starting spot, he can be avoided.
Reality Football Outlook: Watson’s 2025 cap hit is just south of $36 million, so Browns head coach Kevin Stefanski will likely give him plenty of rope—even though he probably doesn’t deserve it.
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Alan Goldsher has written about sports for Sports Illustrated, ESPN, Apple, Playboy, NFL.com, and NBA.com, and he’s the creator of the Chicago Sports Stuff Substack. He’s the bestselling author of 15 books, and the founder/CEO of Gold Note Records. Alan lives in Chicago, where he writes, makes music, and consumes and creates way too much Bears content. You can visit him at http://www.AlanGoldsher.com and http://x.com/AlanGoldsher.