The Cowboys have a quarterback problem that goes beyond the depth chart.
Monday’s release of Joe Milton III put that front and center again, because Dallas has now gone through another swing at developing a passer and come up short. Milton is still with the organization on the practice squad, but that doesn’t change the bigger picture: this was not the payoff the Cowboys were hoping for when they brought him in.
Dallas sent a fifth-round pick to the New England Patriots in April 2025 to get Milton and a seventh-round pick back. One year in the system apparently wasn’t enough to lock down trust, and the team’s decision to sign Sam Howell last spring made that even clearer.
The Cowboys gave Howell $2.5 million in guaranteed money, which in NFL terms was a loud message about where he stood. It was also not a great sign for Milton’s standing entering the offseason.
Milton did have moments this summer. He turned heads in the second preseason game and was solid otherwise.
Still, that wasn’t enough to keep him from landing in a roster fight that apparently extended beyond what he did on the field. There were also reports that coaches wanted more from him in areas outside the actual game action.
So after two training camps and one season in their system, Dallas was willing to expose a quarterback it had traded for to the rest of the league. The Cowboys were comfortable enough with that risk that they had already prepared for it with the Howell signing. That’s not exactly a ringing endorsement of the process.
And this isn’t the first time.
The Trey Lance situation followed a very similar path. In August 2023, Dallas sent a fourth-round pick to the 49ers for Lance, the former No. 3 overall pick in 2021.
The athletic gifts were obvious. The pedigree was obvious.
The results in Dallas never followed.
Lance spent two years as the third quarterback behind Cooper Rush, and the Cowboys did not bring him back in the 2025 offseason. He and Rush both moved on that spring, and Dallas made the Milton trade soon after. In fact, Lance signed with the Chargers the day after the Milton deal was announced.
Lance is now QB2 in Los Angeles behind Justin Herbert. John Harbaugh has led the Chargers to the playoffs twice since his arrival, so keeping Lance as the primary backup there is no throwaway role.
That’s why the Cowboys can’t keep pretending this is just bad luck. The “one man’s trash” approach hasn’t produced much at quarterback lately.
Dallas spent time with Lance, then moved on. It spent over a year with Milton, and now he’s one step from being available elsewhere again.
The same people keep showing up in these stories: the front office, Will McClary’s scouting group, and Brian Schottenheimer to a degree. Schottenheimer only became head coach in 2025, which means he was the offensive coordinator during Lance’s two seasons and was also around for Milton’s first year.
That leaves the obvious questions. Is the issue happening before the players even arrive?
Is the appeal of making a trade part of the problem, especially in the Lance case? Is it the quarterback coaching, whether that was Scott Tolzien in 2023-2024 or Steve Shimko now in 2024-2025?
Some have pointed the finger at Mike McCarthy for how the Trey Lance situation played out, with reports that the Joneses pushed Lance on him. Even if that were true, it doesn’t explain Milton.
What it does underline is the urgency around Dak Prescott. He turns 34 next July and will be entering his 11th NFL season.
Whether the Cowboys think about replacing him soon or not, they need to keep planning ahead. And even if the starter isn’t changing anytime soon, having a reliable backup should be a year-round priority.
Maybe Howell ends up being the piece that makes Dallas feel better about how it identifies and develops quarterbacks. For now, though, the Cowboys are still looking for proof.
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