Teams aren’t known to carry four quarterbacks on the roster during the season, but not so long ago, the Dallas Cowboys were. With Dak Prescott firmly established as the starter, Dallas spent much of last season juggling depth behind him, as the front office evaluated who might stick long term. That situation had already set up the possibility of a crowded competition once the offseason program and training camp began. But now, with free agency underway, an unexpected shake-up has quietly taken place within the quarterback room in Dallas. 

As the Dallas Cowboys prepared to make aggressive moves this offseason, owner and general manager Jerry Jones reshaped the team’s financial outlook by restructuring multiple contracts to free up salary-cap space. Part of that flexibility went toward adding former Philadelphia Eagles quarterback Sam Howell, a move that immediately altered the depth chart behind Prescott. The signing briefly pushed Dallas’ quarterback count to four, Prescott, Howell, Joe Milton III, and Will Grier, an uncommon setup for an NFL roster. And rather than waiting until training camp to sort through the logjam, Dallas took another decision that clarified how the competition would take shape.

“The Cowboys released QB Will Grier. It’ll be Sam Howell vs. Joe Milton for the backup spot in Oxnard,” Cowboys reporter Joseph Hoyt reported via X on March 12.

Will Grier, who had spent two separate stints with the team, was best known for setting the national high school record for passing yards (837) in a single game as a senior at Davidson Day School. He later built an impressive college résumé while playing for Florida and West Virginia. During his collegiate career, Grier threw for 8,558 yards and 81 touchdowns, while adding 148 yards and 7 touchdowns on the ground. 

Those numbers helped establish Grier as one of the top dual-threat quarterbacks entering the 2019 NFL Draft. The Carolina Panthers then drafted Grier 100th overall in the third round of that draft. He then spent two seasons in Carolina and started two games as a rookie. In those appearances, Grier completed 53.8% of his passes for 228 yards with no touchdowns and four interceptions while the Panthers lost both games. 

Then, after Carolina acquired QB Sam Darnold via trade in 2021, the team released Grier. Jerry Jones later brought Grier to Dallas to replace Ben DiNucci as the Cowboys’ third-string quarterback for two seasons. In the 2023 preseason finale, Grier delivered a standout 300-yard passing performance that seemed like a strong audition for a larger role in Dallas. But the Cowboys waived him shortly afterward.

From there, Grier bounced around the league and spent time with the Cincinnati Bengals, Los Angeles Chargers, Philadelphia Eagles, and New England Patriots, mostly working as a backup QB or practice squad option. He then returned to Dallas in 2024 and spent most of his time on the practice squad. And at one point last season, Bleacher Report’s Mo Moton even predicted that the Cowboys might trade Grier.

“In April, the Dallas Cowboys acquired big-armed Joe Milton III from the New England Patriots, which means Will Grier could fall to third on their quarterback depth chart,” Moton wrote in an article last year. “Grier has put together solid preseason outings in recent years. Now, he can showcase himself to draw interest from other teams that see him as a No. 2 quarterback.”

Dallas still kept him around, and after the 2025 season, the team signed Grier to a reserve/future contract. 

Does releasing Will Grier complicate the Cowboys’ backup QB choice?

Dak Prescott remains firmly locked in as the Cowboys’ starting quarterback after he delivered one of the most productive seasons of his NFL career in 2025, throwing for 4,552 yards, 30 TDs, and 10 INTs. However, Will Grier’s release leaves Sam Howell and Joe Milton III competing directly for the team’s backup QB job during training camp.

Sam Howell arrives with some valuable experience in the NFC East. He has played for both the Washington Commanders and the Philadelphia Eagles, meaning he already understands many of the defensive schemes Jerry Jones’ team faces twice a year. Washington selected Howell in the fifth round of the 2022 NFL Draft, and his first NFL start came during his rookie year in the season finale against the Cowboys. In that game, Howell threw for 169 yards with 1 TD and 1 INT along with 35 yards and another TD on the ground, helping the Commanders secure a 26-6 victory over the Cowboys.

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The Commanders later named Howell their starter for the 2023 season, and he started all 17 games to throw for 3,946 yards with 21 TDs and 21 INTs. Howell also led the league in passing yards at one point during the season. But behind an inconsistent offensive line, Howell also took a league-high 65 sacks that season.

After that, Howell appeared in only two games for the Seattle Seahawks in 2024. He recorded 24 passing yards and one INT. Howell then started the 2025 season with the Eagles as Jalen Hurts’ backup after Tanner McKee suffered an injury in training camp. But once McKee was healthy, Howell slid down the depth chart. 

Meanwhile, Joe Milton III was drafted 193rd overall in the sixth round of the 2024 NFL Draft by the New England Patriots. He then started his rookie season as the QB3 behind Jacoby Brissett and Drake Maye. Milton eventually made his NFL debut in the 2024 season finale against the Buffalo Bills after Maye left the game. In that outing, Milton completed 22 of 29 passes for 241 yards and 2 TDs and helped the Patriots secure a 23–16 win over the Bills.

Last year, Dallas acquired Milton along with a seventh-round pick in the 2025 NFL Draft, sending a fifth-round selection in the same draft to New England. Milton later served as the Cowboys’ primary backup and played four games last season, recording 183 passing yards, 1 TD, and 2 INTs.

While Howell’s experience as a 17-game starter gives him a clear edge on paper, the Cowboys’ investment in Milton via trade suggests this will be a genuine training camp battle to watch. For a team with Super Bowl aspirations, the decision on who will stand behind Dak Prescott is more critical than ever.