The Cleveland Browns' five biggest "What if?" moments of 2025

As the Cleveland Browns face an uncertain future, with a coaching staff in flux and no obvious answer at quarterback, it’s tempting to look back at the crucial moments that shaped the last 12 months.

Hindsight is always 20/20, but the only way of not repeating history is learning from it.

Here are the five biggest “What if?” moments for the 2025 Cleveland Browns:

What if the Browns never bring Kenny Pickett aboard?

This might seem minute in the big picture because Pickett never actually played for the Browns. Cleveland traded for him last March, paying a 2025 fifth-rounder and quarterback Dorian Thompson-Robinson to Philadelphia. After spending the summer in Berea, Pickett was shipped off to Las Vegas for a 2026 fifth-rounder.

Pickett was competing with Joe Flacco for the starting gig, eating up a share of first-team reps that were taken away from eventual starters Dillon Gabriel and Shedeur Sanders. Having Gabriel and Sanders split those reps likely would’ve pointed the Browns in a different direction regarding the rookie quarterback pecking order.

What if the Browns never make the trade with the Jaguars?

This deal was critical for Cleveland’s successful rookie class, but had quarterback Cam Ward not been selected first overall by Tennessee, he’d be in a Browns’ uniform and the team wouldn’t have Mason Graham, Quinshon Judkins or an extra 2026 first-rounder.

The team most likely wouldn’t have picked up Gabriel or Sanders either, settling instead for a depth chart consisting of Flacco, Ward and Bailey Zappe.

Knowing what we know now, would you give up Graham, Judkins, Gabriel, Sanders and this year’s second first-rounder for Ward?

What if the Browns don’t draft Shedeur Sanders in the fifth round?

Sanders’ shocking fall all the way to the fifth round was the storyline of last year’s draft. Even Browns’ principal owner Jimmy Haslam was surprised when Cleveland picked Sanders 144th overall.

Before that, Sanders had a chance to join Baltimore, as the Ravens were planning on taking him 141th after seeing him still available. However, Sanders declined not wanting to become Lamar Jackson’s backup and the rest is history.

Without Sanders on the roster, maybe the team keeps Flacco after demoting him in favor of Gabriel. Or, maybe Zappe gets to play a couple of games after Gabriel’s concussion, before coming back to the rookie for the last few games of the season.

Filling in for an injured Gabriel, Sanders took control of the starting position and never let go. Is he the long-term answer? The jury's still out on that one.

What if Dillon Gabriel never suffers his concussion?

Former head coach Kevin Stefanski’s behavior towards Gabriel and Sanders always seemed vastly different. The Browns managed to create some first-team reps for Gabriel before the season started and he was always instantly confirmed as the starter, no matter how bad he looked or how much he regressed on a weekly basis.

On the other hand, Stefanski always waited until the last minute to announce any status on Sanders, even refusing to name him backup when Gabriel became starter.

But Gabriel’s play fell off so dramatically after his first two games, that it became increasingly hard to justify keeping him in the lineup. Had Gabriel not suffered that concussion against the Ravens in mid-November, Sanders probably would have ended up starting just three or four games instead of seven during his debut season.

What if the Browns don’t win out their final two games of the season?

Sanders never really took off, but at least he did show progress as the season went on, and his regressions were not nearly as dramatic as Gabriel’s. During Cleveland’s next to last game of the season, a shocking win over the Steelers, he offered his best performance to date throwing guys open and anticipating routes. For the final game, though, Sanders was mostly ineffective against the Bengals save for a final game-winning drive that secured the Browns’ fifth win of the season.

Had Cleveland lost those last two games, they’d be holding the first overall pick in next April’s draft, in addition to the Jaguars’ first rounder, as discussed above. That would point to a discussion around Indiana’s Fernando Mendoza/Oregon's Dante Moore as the potential top pick, a debate that seems moot now with Cleveland picking sixth, after the Raiders, Jets and Cardinals.

Another thing to consider: would Stefanski have been fired from Cleveland given the opportunity to draft and develop this year’s top quarterback prospect? We might never know.