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Cowboys Quietly Raise Joe Milton III Alarm Bells in Middle of Free Agency

Jan 4, 2026; East Rutherford, New Jersey, USA; Dallas Cowboys quarterback Joe Milton III (10) drops back to pass during the third quarter against the New York Giants at MetLife Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Jan 4, 2026; East Rutherford, New Jersey, USA; Dallas Cowboys quarterback Joe Milton III (10) drops back to pass during the third quarter against the New York Giants at MetLife Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

Everything the Dallas Cowboys do is placed under a magnifying glass, and that was the case when they swung a trade for quarterback Joe Milton III. Milton had raised the antennas of rival general managers as Drake Maye’s backup with the New England Patriots and the Cowboys pounced on the opportunity, sending a 2025 fifth-round pick to acquire Milton and a 2025 seventh-round pick last March.

One year later, it appears the Cowboys have admitted their own failure. Dallas added Sam Howell in free agency on March 10, and he signed to compete for the backup role behind Dak Prescott. While the addition doesn’t eliminate Milton from the picture, it should activate everyone’s inner Brian Windhorst and make them wonder if the 26-year-old isn’t long for Dallas.

Joe Milton III Already Playing for a Job After One Year with Cowboys

Milton had the intrigue of Peter Griffin’s mystery box this time a year ago. Gifted with a cannon for an arm, many thought Milton could go higher in the 2024 draft before he fell to the Patriots in the sixth round. Milton was a reserve behind Maye and Jacoby Brissett for the entire season before getting his chance in a Week 18 start, as the Buffalo Bills' backups made him look like Tom Brady, completing 22-of-29 passes for 241 yards and a touchdown.

The performance caught everyone’s attention, and Milton’s desire to start caused New England to trade him to the Cowboys as part of “the process of establishing team culture,” according to ESPN’s Mike Reiss. Greg Bedard of the Boston Sports Journal also added that Milton was “not a good dude,” but it didn’t stop the Cowboys from making the trade.

Milton’s play in the preseason may have given everyone second thoughts. According to Pro Football Focus, he completed just 36-of-65 passes for 397 yards with two touchdowns and two interceptions. In addition, he had more turnover-worthy plays (4) than “big time throws” (3) with an average depth of target of 12.7 yards.

Playing YOLO ball is a quick way to remove yourself from any team’s plans, and Milton played mostly in garbage time during his first season in Dallas, completing 15-of-24 (62.5 percent) of passes for 183 yards, one touchdown, and two interceptions.

With that in mind, it wasn’t a surprise for the Cowboys to sign Howell. Howell had similar turnover issues, including 21 interceptions in 2023, before being traded by the Minnesota Vikings before even playing a regular-season snap for them last summer. His arrival is alarming, considering the potential that many saw in Milton just one year ago.

Milton believes he can play in the NFL, but the Cowboys may not feel the same way after adding Howell to the mix.

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