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Contract extensions can be tricky things. Re-sign or extend too soon, and the player may fall short of expectations, causing regret. Re-sign too late, and things can get ugly in a hurry, leading to increased dollar amount and possibly bad blood. That too, might be something to regret. Even an act of indifference such as letting a deal expire and letting the player walk free and clear is a potentially regretful situation for the Dallas Cowboys to find themselves in.
While contract extensions will always be second-guessed, regardless of the logic and regardless of the circumstance, we will attempt to hammer out some today as we navigate these tricky extension situations facing the team in 2026
The Cowboys have more than a few players up for new deals, but which players demand extensions now, which ones are more wait-and-see and which are too risky to re-up and just something that should ride out?
Williams is locked in through the 2027 season, but the Cowboys' commitment to him is obvious and the intention to extend has been made clear. Instead of waiting until this time next year, it may be more economically responsible to extend him now.
Williams, 28, is slated to count over $21M in 2026 and over $25M in 2027. With the market currently set at $35M/year, getting ahead of this now makes more sense than waiting until the market grows larger and Williams is on the wrong side of 30. An extension with a boost in pay now could soften the blow, ease the tension and commit to a player everyone feels extremely good about.
This is an impossibly difficult situation that has me firmly on the fence. On one hand, Overshown is a game-changing talent with All-Pro ability. On the other hand, he’s a player who had multiple knee injuries and someone who’s missed more games than he’s played.
It comes down to this: Even if Overshown stays healthy and plays brilliantly in 2026, can the Cowboys afford to pay a player with his medical history top of the market prices? That question led me to propose a one-year extension earlier in the offseason. Giving him a megadeal off just one healthy season is too risky but if he can stay healthy for 2026 and 2027, it makes such a committment a little less scary. But deals like that are rare, and for the purposes of this exercise, Overshown is too risky to sign on a high-dollar deal now, or over the next offseason.
The deadline to an extension has already come and gone for Pickens and the Cowboys, so this really just came down to “reassess” or “ride it out” status here. If Pickens repeats his 2025 breakout campaign and posts over 1200 yards and double-digit touchdowns, the market will explode for him. If he falls back to the production levels of previous years and/or raises behavioral concerns, his value will tank. It all makes the Cowboys’ approach to wait-and-see completely logical.
At the end of the day, Pickens’ high is too high to rule out an extension. Even with all the money going to the offense already, a multi-year deal has to be considered if he proves dominant once again. His situation demands open minds and potentially open wallets.
You can follow Reid on X @ReidDHanson and be sure to follow Cowboys Wire on Facebook to join in on the conversation with fellow fans!
This article originally appeared on Cowboys Wire: 3 Cowboys in need of contract extensions, 3 different paths
Continue reading...
While contract extensions will always be second-guessed, regardless of the logic and regardless of the circumstance, we will attempt to hammer out some today as we navigate these tricky extension situations facing the team in 2026
The Cowboys have more than a few players up for new deals, but which players demand extensions now, which ones are more wait-and-see and which are too risky to re-up and just something that should ride out?
Re-sign today: Quinnen Williams
Williams is locked in through the 2027 season, but the Cowboys' commitment to him is obvious and the intention to extend has been made clear. Instead of waiting until this time next year, it may be more economically responsible to extend him now.
Williams, 28, is slated to count over $21M in 2026 and over $25M in 2027. With the market currently set at $35M/year, getting ahead of this now makes more sense than waiting until the market grows larger and Williams is on the wrong side of 30. An extension with a boost in pay now could soften the blow, ease the tension and commit to a player everyone feels extremely good about.
Ride it out: DeMarvion Overshown
This is an impossibly difficult situation that has me firmly on the fence. On one hand, Overshown is a game-changing talent with All-Pro ability. On the other hand, he’s a player who had multiple knee injuries and someone who’s missed more games than he’s played.
It comes down to this: Even if Overshown stays healthy and plays brilliantly in 2026, can the Cowboys afford to pay a player with his medical history top of the market prices? That question led me to propose a one-year extension earlier in the offseason. Giving him a megadeal off just one healthy season is too risky but if he can stay healthy for 2026 and 2027, it makes such a committment a little less scary. But deals like that are rare, and for the purposes of this exercise, Overshown is too risky to sign on a high-dollar deal now, or over the next offseason.
Reassess later: George Pickens
The deadline to an extension has already come and gone for Pickens and the Cowboys, so this really just came down to “reassess” or “ride it out” status here. If Pickens repeats his 2025 breakout campaign and posts over 1200 yards and double-digit touchdowns, the market will explode for him. If he falls back to the production levels of previous years and/or raises behavioral concerns, his value will tank. It all makes the Cowboys’ approach to wait-and-see completely logical.
At the end of the day, Pickens’ high is too high to rule out an extension. Even with all the money going to the offense already, a multi-year deal has to be considered if he proves dominant once again. His situation demands open minds and potentially open wallets.
You can follow Reid on X @ReidDHanson and be sure to follow Cowboys Wire on Facebook to join in on the conversation with fellow fans!
This article originally appeared on Cowboys Wire: 3 Cowboys in need of contract extensions, 3 different paths
Continue reading...
