The Cleveland Browns' decision to name Joe Flacco as their starting quarterback seemed straightforward. However, as the roster deadline approaches, their quarterback situation is becoming increasingly complex.

On August 26, the team must trim their roster from 90 players down to 53, raising the crucial question: Should they dedicate a valuable roster spot to a fourth quarterback?

While conventional wisdom suggests the Browns may lean towards keeping four quarterbacks, recent remarks from head coach Kevin Stefanski indicate that this won't be an easy choice. When questioned about the possibility, Stefanski acknowledged the ongoing discussions but noted the difficulty of the decisions ahead.

Stefanski responded, “We’ll let it play out as we get closer to the cut down. Those are all conversations that we are always having, but those are tough decisions. I’d like to keep everybody, but that’s not realistic.”

If ‘everybody’ includes Flacco, Kenny Pickett, Dillon Gabriel, Shedeur Sanders, Tyler Huntley, and Deshaun Watson, that's a tall order. Opting to keep four quarterbacks means risking losing valuable talent elsewhere.

One strategy could involve placing a quarterback on injured reserve, allowing the Browns more time to evaluate their options. Alternatively, they might consider trading one of their QBs.

Kenny Pickett appears to be the most likely candidate to be released. With Flacco firmly in place as the starter and the promising rookie backups, Pickett’s future looks bleak. Given the dissatisfaction with many teams’ QB2s, a trade could be beneficial for both parties.

It’s worth noting that Pickett's guaranteed salary of $2.623 million in 2025 could be a factor in the decision-making process. The Browns previously made a move to acquire him by sending Dorian Thompson-Robinson and a fifth-round pick to the Eagles, which seemed like a cautious backup plan.

With the arrival of Flacco and two exciting rookies, the likelihood of Pickett staying with the team diminishes. If a deal can be struck that recoups their draft pick and clears his salary, the Browns might see it as a win, especially with the tough season ahead.

As the clock ticks down, the Browns must make a definitive choice on how many quarterbacks will fill their active roster. As it stands, it’s unclear if they’re truly committed to maintaining four quarterback spots.