Dak Prescott has been the Cowboys’ franchise quarterback for the last decade, but the franchise does not want to put all the pressure on him. Overcoming the injuries in 2024, Prescott started all 17 games in the last season. The quarterback is already 32, and it could be the time for the Cowboys to take proper measures to strengthen the QB lineup, since an injury to Prescott will open a massive gap in their offense.

“Prescott is the sure-first starting quarterback for the Cowboys,” Tommy Yarrish wrote on his blog, via DallasCowboys.com. “As things stand right now, Joe Milton is the only other quarterback on the roster, as Will Grier was not signed to a reserve/futures deal.”

He further added, “That doesn’t mean Grier can’t return, just that he hasn’t yet. For now, Milton will remain Prescott’s backup, and it appears to be trending that way for a second season.”

Unlike Prescott, who just played his 10th season, Milton just finished his second. Initially, the New England Patriots drafted him during the 2024 NFL Draft, but the franchise traded him and a seventh-round pick for a fifth-round pick to the Cowboys before the 2025 season. If the Cowboys are to compete for the Super Bowl, they require a top-tier backup quarterback who could lead the offense in the absence of the primary quarterback. And with proper training, Milton could take that role, since he definitely has the knack for it. In four games, he completed 15 of his 24 passes for 183 yards, a touchdown, and two interceptions.

A QB3 is also necessary for the franchise. Will they go for Will Grier again or use free agency to their benefit? It remains uncertain. Be it on the main roster or the practice squad, Jerry Jones will be hoping to bring another quarterback ahead of the 2026 season. The Kansas City Chiefs were a good example of how three QBs are better for a franchise, especially after they lost both QB1 and QB2 because of injuries.

The Cowboys’ divisional rivals, the New York Giants, signed veteran Russell Wilson as their QB3 for the 2025 season. Jones can also walk that path of bringing a veteran quarterback. Dak Prescott will be the starter QB for sure, but whether he will have the proper backup quarterback is the question. Unfortunately, signing new quarterbacks is not the only problem the Cowboys have to deal with. Prescott’s contract has enough knots to give Jerry Jones a headache.

Dak Prescott’s cap hit could pose a problem for Jerry Jones

Dak Prescott’s current contract runs till the 2028 season, with his current base salary being $40 million. With the 2026 season hitting soon, the franchise’s cap space is estimated to be between $295 and $305 million, as per the league’s projection. It’s a huge number, but the Cowboys have exceeded that limit by almost $30 million. They need to clear out that amount to stay legal. However, it will be challenging if they resign WR George Pickens.

By reshaping the deals of star players such as Prescott, CeeDee Lamb, Tyler Smith, and a few more, the franchise will open up almost $100 million. Things will become more complicated unless Jones deals with his star quarterback. A full restructure would push nearly $8 million into future seasons from 2027 through 2031.

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That is not the end. As things stand, the four-time Pro Bowler’s combined cap hit for 2027 and 2028 is $160 million ($75 million and $85 million). Perhaps, it will be beneficial for Jones to stop fully converting his $40 million base salary over the years, especially since it will not only empty his pockets faster but also put the franchise at risk.

It will be interesting to see how Jerry Jones handles the quarterback situation and Prescott‘s contract, with free agency approaching.