The Dallas Cowboys made their most surprising roster move of the 2026 cutdown period on Monday, waiving quarterback Joe Milton after claiming running back Emari Demercado off waivers from the Kansas City Chiefs.

Milton had made the Cowboys’ initial 53-man roster on Sunday, and the move sent shockwaves through a fan base that assumed the former Tennessee quarterback had locked down the QB2 job behind Dak Prescott.

The surprise is understandable. Milton balled out in two of three preseason games, and for the majority of August, he looked like the better quarterback between himself and Sam Howell, the other backup competing for a roster spot. The prevailing question among fans and media wasn’t whether Milton would make the team. It was whether Howell did enough in the preseason finale to force Dallas into carrying three quarterbacks on its 53.

And so the Cowboys did carry three, briefly. Everyone felt like their hypotheses were confirmed. Then came the plot twist. As we try to navigate the shock, let me give you the likeliest explanation for the cut.

Sam Howell bookended a strong preseason

The short version is: The Cowboys liked Howell better all along. Allow me to ellaborate.

Howell closed the preseason in style. He completed 11 of 13 pass attempts in the finale, looked comfortable in the pocket, threw the ball deep, created plays, and did a little bit of everything. His final impression on the coaching staff was a strong one. And it mirrored what he showed in the preseason opener and in training camp, too.

The key detail about that opener is that Dallas started Howell. Cowboys head coach Brian Schottenheimer confirmed that Howell was ahead in the quarterback competition entering the preseason based on what he’d done during training camp in Oxnard, California.

So consider the full picture. The Cowboys liked Howell better than Milton entering the preseason, and the preseason ended with Howell looking vastly better than Milton in the finale.

Milton’s old habits resurfaced at the worst time

The problem wasn’t just that Howell outplayed Milton. The problem was that many of Milton’s flaws from 2025 showed up again in the 2026 preseason finale against the New Orleans Saints. He bailed from the pocket early. He held the football too long. He misfired on throws. The bad habits that had seemingly vanished during his first two preseason outings, when he looked like a completely different quarterback, were suddenly back in full view.

That may have been enough for Schottenheimer to confirm his initial evaluation heading into camp and make the decision that Howell is the better option.

So, why did Milton make the roster on Sunday?

If the Cowboys were going to cut Milton anyway, why include him on the initial 53? The most logical explanation is that Dallas tried to find a trade partner over the last 48 hours. Milton put good film on tape for two games. It would make sense for the Cowboys to shop him to quarterback-needy teams like the Arizona Cardinals, the Pittsburgh Steelers, or the Minnesota Vikings, whether for starting or backup help.

To be clear, I am not reporting that trade conversations happened. I’m speculating. But I don’t think the Cowboys just waived Milton for no reason. I think they explored the market, didn’t find a willing suitor, and moved on.

What happens next for Joe Milton?

Milton will head to waivers. If he clears them, I would not be surprised by the Cowboys trying to bring him back on the practice squad. But I would be surprised if he actually clears. Milton feels like a player worth a flyer for at least one team around the NFL that maybe didn’t want to give up trade assets but would happily claim him for free.

We’ll see if it happens.