Cowboys will regret cutting Joe Milton before October

The NFL is filled with roster decisions that look perfectly reasonable in August and completely whacked out six weeks later. Dallas waiving Joe Milton feels like one of them – because quarterback insurance hurts most when you suddenly need it and don’t have it. MORE:Previewing all 16 NFC teams & predicting every record in 2026 Dallas chose roster flexibility over upside Aug 16, 2025; Arlington, Texas, USA; Dallas Cowboys quarterback Joe Milton III (10) runs with the ball during the game between the Dallas Cowboys and the Baltimore Ravens at AT&T Stadium. Mandatory Credit: Jerome Miron-Imagn Images The Cowboys waived Milton to make room for running back Emari Demercado, essentially choosing Sam Howell as Dak Prescott’s primary insurance policy. Maybe that works. Like Pat Healy once said… “It’s cute, but I’m not buying it.” Dallas just discarded a quarterback who completed 29 of 43 passes for 378 yards, three touchdowns and zero interceptions this preseason. Milton also ran for another score. That isn’t a developmental quarterback completely lost in an NFL offense. That’s a talented, physically gifted backup who appeared to be getting better. And this wasn’t an obvious cut everyone saw coming. Only days earlier, Brian Schottenheimer publicly expressed confidence in both Howell and Milton as capable backups. Then Milton was gone. Poof.  Jon Machota captured just how unexpected the move was when he reported the release Monday afternoon: Because backup quarterback isn’t a position where I care much about squeezing every last percentage point of roster efficiency. I want someone who can win me a game. MORE:NFL predictions: Previewing all 16 AFC teams & predicting every record in 2026 Milton gave Dallas something Howell doesn’t Milton isn’t perfect. Nobody is arguing otherwise. But the ridiculous arm strength changes what a defense has to respect, and his physical upside gives Dallas a different level of contingency if Prescott misses time. Howell may be steadier, I’ll give you that. But Milton might have been more dangerous. Correction: Milton is more dangerous. For a Cowboys team built to win this season, I’d rather keep the quarterback with legitimate game-changing traits than expose him simply to create room elsewhere on the roster. Maybe Prescott plays all 17 games and none of this matters. But maybe not. And what if? That’s my whole point. My prediction: something happens around Prescott by Halloween, and Cowboys fans are forced to ask the question. Why exactly did we give Joe Milton away? — Enjoy free coverage of the top news & trending stories with The Big Lead Newsletter —