In Dallas, guaranteed money dictates roster spots. That financial reality now stands as a major roadblock for Joe Milton III, whom Dallas acquired from the Patriots in 2025 following Cooper Rush’s exit. After Milton’s inconsistent performance last season, the front office brought in Sam Howell this year, leveraging his 18 games of starting experience in Washington. Crucially, Howell secured $2 million guaranteed and a $500,000 signing bonus, a financial cushion Milton simply doesn’t have. While the battle is still on between the two, Cowboys insider Todd Archer predicts Milton’s exit.

“Considered going with Joe Milton III and making it three but opted against it,” ESPN’s Todd Archer wrote. “The Cowboys guaranteed Howell $2 million in free agency and don’t make it a habit of letting that financial commitment walk. Milton is still young enough to see how he develops and could be a practice squad guy. Howell has more experience and command.”

Howell’s edge is built on a massive foundation of live reps. Going back to his college days at North Carolina, where he had 37 starts, He was thrown straight into the fire upon entering the league. In 2023, Howell started all 17 games as the Washington Commanders’ primary starter, putting together 3946 passing yards in a single year. That sole season gave him a career’s worth of film and game maturity. It is precisely that trial by fire that has Cowboys head coach Brian Schottenheimer raving, even as he assures that camp reps will remain split. 

“Sam Howell has more starts than Cooper Rush,” Schottenheimer pointed out. “He’s been exposed to a lot, been in a lot of different systems, which I think is great for all of us.” 

On the contrary, Joe Milton’s III’s developmental timeline tells a very different story. Milton didn’t claim a full-time starting role in college until his sixth-year senior season in 2023. Entering the league in 2024, scouts flagged him as a rigid, robotic pocket passer who struggled to process beyond his first read or consistently re-establish his throwing platform. These flaws were laid bare in a 2025 preseason loss to the Ravens.

Milton gave Dallas a glimpse of his raw upside when he launched a stunning 49-yard bomb down the right sideline to Jonathan Mingo. But outside of that singular highlight, his night was a painful showcase of slow processing. He finished 9-of-18 for 122 yards, threw an interception, and was sacked twice, one in his own end zone. 

There’s no doubt that Howell’s battle-tested reliability heavily outweighs Milton’s unrefined ceiling for a team built to win right now. But on-field maturity is only half the story. To understand why Milton’s spot on the 53-man roster is truly in jeopardy, you have to follow the paper trail and examine how Jerry Jones structured both of their contracts.

When Milton originally signed his four-year, $4.2 million rookie contract as a sixth-round pick (No. 193 overall), NFL collective bargaining rules dictated that only $183,316, his signing bonus, was fully guaranteed. When Dallas traded for Milton in April 2025, they inherited that exact deal without renegotiating a single dollar. Because New England had already paid out his signing bonus before the trade, the Cowboys took on a contract with literally $0 remaining guaranteed money.

If Dallas decided to cut Milton during final roster times, it carries zero financial penalty and zero dead cap space. This gives Sam Howell the extra edge towards being Dak Prescott’s backup. But the flip side of that equation is where Jerry Jones’ hands truly get tied.

If the Cowboys were to release Howell, his fully guaranteed $2 million base salary and $500,000 signing bonus wouldn’t just vanish; it would immediately accelerate into “dead money” against Dallas’ salary cap. Front offices traditionally avoid swallowing guaranteed money unless a situation becomes toxic or entirely unavoidable.

While extreme anomalies do happen, like the Denver Broncos absorbing a historic $85 million in dead cap just to cut ties with Russell Wilson. But that is an absolute rarity in modern roster construction. For a backup QB competition, Jerry Jones simply isn’t going to light $2 million on fire just to keep a raw developmental prospect over a proven starter.

For now, the backup for Prescott’s position is up for grabs. But while Milton and Howell battle it out for the 2026 season, the Cowboys may have been looking for a plan beyond that; if not, they did once.

Dallas Cowboys reportedly had eyes on another young QB

Franchise quarterback Dak Prescott‘s contract with the Dallas Cowboys will run through the 2028 season. So, to develop another young, promising signal-caller as the backup to Prescott, the franchise had been making attempts. Joe Milton III (in 2025) and Sam Howell (in 2026) stand as prime examples of it. However, Howell wasn’t the only quarterback the Jerry Jones-owned franchise was interested in.

“When Texas Tech quarterback Brendan Sorsby put his name in the supplemental draft, multiple sources said the Cowboys had high interest even with the gambling issues that surrounded Sorsby. Prescott is signed through 2028, so an attempt to potentially find his successor at what could have been a lower-than-expected price would have made sense even if it drew added attention to the Cowboys’ quarterback room.” ESPN’s Todd Archer wrote.

Brendan Sorsby came out as an interesting prospect to many NFL teams when he submitted a petition to enter the Supplemental Draft. Sorsby was coming off a controversial legal clash with the NCAA as well. Considering that, a few NFL teams even steered cleared off the 22-year-old Texas-born quarterback. But that wasn’t the case for Jerry Jones.

“I do like the Supplemental Draft. Especially where we are,” Jones said to Yahoo Sports’ Jori Epstein. “The sooner to today that we can get as many good ones on the field, that’s a plus for us. Cause I’m in that mood.”

However, the NFL canceled the 2026 supplemental draft because Sorsby was the only applicant, and the league stated that it lacked time to properly review his college gambling violations before the strict deadline. Thus, his potential addition to the Cowboys also went away. That said, Sorsby will now spend a year in training before entering the 2027 NFL Draft, where it will be interesting to see if Dallas makes a formal move for the 22-year-old QB.