Cowboys’ most agonizing roster decision looming on 2026 cutdown day

Dallas has spent the summer constructing a new defensive identity. Now, though, its most painful roster decision could come at the position that gets the least amount of playing time. Behind Dak Prescott, the Cowboys have two fundamentally different answers in Joe Milton III and Sam Howell. Both have made compelling cases to remain in the building. The problem is that Dallas cannot simply keep everyone. Every quarterback spot consumes a valuable place elsewhere on the 53-man roster. That could force Brian Schottenheimer and the front office to choose between protecting a developmental asset and preserving depth.

New defensive identity

The Dallas Cowboys’ 2026 preseason has been defined by the fast-tracked installation of defensive coordinator Christian Parker’s new 3-4 scheme. The preseason exhibition slate provided a proving ground for the revamped interior offensive line and defensive front. It also put the backup quarterback clash between Milton and Howell squarely under the microscope. Standout defensive integration highlighted an aggressive, turnover-minded identity. Meanwhile, the offense focused on building early timing and sorting out rotational depth behind Prescott, CeeDee Lamb, and George Pickens. That evaluation process has left Dallas with fewer easy decisions than it might have hoped.

High-stakes dilemma

Milton and Howell represent almost opposite philosophies for the Cowboys. Milton is the swing-for-the-fences option. His arm talent is eye-catching, and his athleticism gives him an additional dimension. During the preseason, those traits have periodically come alive in spectacular fashion. When pressure closes in, Milton can escape. When a defense appears to have the play contained, he can create something outside structure. Milton also possesses the arm strength to punish a defense from deep.

On the other side, Howell offers something Milton cannot simply replicate through athletic ability: experience. Howell has already dealt with the speed, pressure and complexity of regular-season NFL football. He has started games and operated under difficult circumstances. He has also experienced what it takes to prepare for an opponent as an NFL quarterback. If Prescott were forced to miss time, Howell could theoretically step into the huddle with considerably less uncertainty.

It really comes down to choosing between upside and insurance.

Dangerous calculus

The cleanest solution would be keeping both. Of course, the problem is that Dallas would then have three quarterbacks on the active 53-man roster. That third spot has to come from somewhere.

Now, quarterback is particularly unforgiving because only one player can take the majority of offensive snaps. A third quarterback can sit inactive for much of the season while a defensive lineman, special teams contributor, or reserve defensive back might be asked to contribute every Sunday. That is the price of protection.

Keeping three quarterbacks would prevent Dallas from losing either Milton or Howell. However, it could force a difficult sacrifice elsewhere. A rotational defender could miss the roster, or a special teams contributor could become expendable. A promising receiver could be exposed to waivers.

The Cowboys would essentially be spending a roster spot today to protect against two different risks tomorrow.

The first is losing Milton. Trying to move him through waivers in the hope of placing him on the practice squad would be an enormous gamble. Quarterbacks with his physical profile are precisely the type of players another franchise could claim and develop for itself.

The second risk is losing Howell. If Dallas releases an experienced backup and Prescott suffers an injury, the Cowboys could suddenly find themselves relying on a far less proven option during a season in which expectations are high once again.

Creating new problems

The quarterback dilemma becomes even more painful when viewed through the rest of the roster. The defensive line is an obvious consideration for losing depth because Parker’s new system demands versatility and rotation. The secondary could also use as much depth as possible, particularly with players such as Downs expected to have multifaceted responsibilities.

Then there is the edge-rushing group. A rotational defender such as Sam Williams or James Houston could find himself caught in the numbers game. The same applies to wide receiver, where the final roster spots can determine how much offensive flexibility Dallas possesses throughout the season.

Upside or stability?

The argument for Milton is straightforward. Dallas could potentially have an inexpensive, high-ceiling quarterback developing behind Prescott.

The argument for Howell is just as compelling. If Prescott goes down, the Cowboys need someone capable of taking command immediately.

And the argument for keeping only two quarterbacks is perhaps the simplest of all: roster spots are precious.

If Dallas believes Milton can clear waivers, or if the organization determines that Howell’s experience is replaceable, the extra spot could strengthen a position group that is more likely to require weekly contributions.

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