As the Cleveland Browns look to recover from a second straight loss in order to get ready for a home game against the Texans before the bye week arrives, the team still has its sights set on postseason play despite falling to a 5-4 record.

However, things aren’t looking quite as peachy as they were just a couple of weeks ago, and it’s never too early for the team to start thinking about upgrades for the upcoming offseason.

Here are four difficult roster decisions the Browns will have to face before next season comes around, despite the fact that Cleveland still has eight more games to play this year:

Offensive line

Based on what we’ve seen through the first half of the season, it’s starting to look like the front office whiffed on the Tytus Howard trade. 

Listen, a full offensive line swap was never an easy proposition. Rookies Fano and Austin Barber have struggled at times, but both have been good additions overall. Zion Johnson is steadily improving, and Elgton Jenkins is the team’s best pass-blocker. 

Howard, on the other hand, has been a liability because of penalties and play. He’s signed through 2028, with cap hits of $10 million for next year and almost $17 million for the year after that. Cutting him loose during the next offseason won’t be cheap because there are also four void years attached to the end of his deal.

Howard would carry a dead cap hit of around $28.5 million for next year, while the team would lose an additional $18.4 million in cap space if he gets cut after this season. Designating him as a post-June 1st cut would translate into a $17.2 million dead cap hit and an additional $7.2 million in cap space lost for 2027, plus an $11.2 million dead cap charge for 2028. 

The Browns could choose to experiment with a tackle swap to the left side, with Fano going right, or kick him inside to right guard, with Barber taking the right tackle spot. They could also give Dawand Jones a shot at right tackle, and leave Howard as the --pretty expensive-- swing tackle option. Or they could stick it out with Howard and wait for some improvement. 

In any case, Howard hasn’t lived up to the expectations so far.

Jerry Jeudy

Jeudy went from being WR1 to WR3 on the Browns’ roster in a hurry. Buried on the depth chart behind rookies Denzel Boston and KC Concepcion, he’s currently on pace for 34 catches and less than 400 receiving yards. He’s also yet to find the end zone. The Browns really don’t need to pay that much for this kind of production.

Should the Browns decide not to trade Jeudy before this year’s deadline, then cutting him after the season would certainly seem the way to go.

Because cutting him outright would trigger a $25.4 million dead cap charge and an additional loss of around $12 million in cap space, designating him as a post-June cut makes sense, as the team would then take on an $8.8 million cap hit in 2027 along with cap savings of $4.6 million, along with a 2028 cap hit of $16.6 million. 

Quinshon Judkins

The team likes a lot of things about its No. 1 running back. But after a season and a half averaging just 3.5 yards a pop, the Browns need to be honest in asking themselves if he truly is a franchise back. 

The rest of the season should serve as an audition to see whether Dylan Sampson and/or Jaleel McLaughlin can handle a bigger share of the workload--Sampson has already started to eat away at Judkins' snaps.

If the answer is no, and Judkins doesn’t show a sizeable improvement either, then the team will most likely have to go hunting for a running back in the draft, where, luckily for the Browns, it doesn’t always cost a fortune in resources to find a stud.

Quarterback

As things stand, Cleveland will want to split Deshaun Watson’s accelerated void year cap charge of $86 million in two, with $34.7 million affecting the 2027 cap and $51.5 million on standby for the 2028 cap. They will need to process him as a post-June cut for this to work. 

After that, the team will have to make a call on Shedeur Sanders and Dillon Gabriel, and see if any one of those passers could drum up a little interest in the trade market. 

Then, of course, the Browns will be faced --once again-- with one colossal decision: Who will be the team’s next quarterback?

Could Cleveland sniff around other teams for a potential trade? Will free agency be an option? Or will the franchise wait and see what comes out of a once-promising draft class at the quarterback position?

All this, provided that the Browns don’t actually extend Watson beyond this season in the NFL’s worst example of the sunk cost fallacy ever.