The Dallas Cowboys are at a crossroads, and their recent decision to secure quarterback Dak Prescott with a lucrative long-term contract has sparked intense debate among fans and analysts alike. While Prescott’s value to the team is undeniable—his leadership, poise, and ability to deliver in clutch moments have solidified his role as the franchise cornerstone—the financial implications of his new deal could hamstring the Cowboys’ roster flexibility for years to come. With Joe Milton’s lackluster preseason performance reinforcing Prescott’s importance, the team’s choice to keep their star quarterback off the field during the preseason raises questions about their strategy heading into a pivotal 2025 season.
The hype surrounding Joe Milton as a potential challenger to Prescott’s throne has fizzled out faster than a summer thunderstorm. Many believed the young quarterback could push Prescott for the starting role, but Milton’s underwhelming play in the first two preseason games has only underscored how critical Prescott is to Dallas’ success. His inability to find a rhythm has led to calls for third-stringer Will Grier to take the reins in the preseason finale against the Atlanta Falcons, simply to give the offense a chance to function before the regular season kicks off.
Despite Milton’s need for reps, Cowboys offensive coordinator Brian Schottenheimer confirmed on Monday that Milton will start Friday’s game. This decision, while understandable for a developmental quarterback, has sparked a larger conversation about Prescott’s absence from the preseason entirely. With the Cowboys facing a brutal season opener against the reigning Super Bowl champion Philadelphia Eagles on September 4, 2025, Prescott’s lack of game action since his season-ending hamstring injury last November is a gamble that could backfire.
Prescott’s new contract, reportedly one of the richest in NFL history, locks him in as the Cowboys’ quarterback for the foreseeable future. However, the decision to keep him sidelined for the entire preseason is raising eyebrows. It’s been 10 months since Prescott last took a meaningful snap, and while no one is suggesting he needs to play extensive minutes to prepare, a drive or two could go a long way. Shaking off the rust, syncing with a revamped offensive line featuring new right guard Tyler Booker and temporary starting left tackle Nate Thomas, and building chemistry with new WR2 George Pickens are critical steps for a team with Super Bowl aspirations.
The Cowboys are the only NFL team with a new head coach this offseason—joining the Jets, Jaguars, Bears, Saints, Patriots, and Raiders—that hasn’t given their projected starting quarterback any preseason reps. While Prescott’s experience sets him apart from younger starters like Caleb Williams or Drake Maye, even veteran quarterbacks like Patrick Mahomes, Joe Burrow, Brock Purdy, and C.J. Stroud have seen action in exhibition games. Even Tom Brady, widely regarded as the greatest quarterback of all time, never skipped the preseason entirely during his storied career.
The decision to protect Prescott may stem from his injury history, including last year’s hamstring issue and previous ankle and shoulder concerns. A freak injury in a meaningless game would be catastrophic for a Cowboys team already under pressure. But with a grueling late-season schedule looming, Dallas can ill afford a slow start, and Prescott’s lack of game reps could lead to early-season rust that costs them in a hyper-competitive NFC East.
Prescott’s new deal, while a testament to his value, has plunged the Cowboys into a salary cap quagmire. His massive contract, combined with existing commitments to players like CeeDee Lamb and Micah Parsons, leaves Dallas with limited room to maneuver. Over the next five years, the Cowboys will face tough decisions about retaining key talent, signing free agents, or addressing depth issues—particularly on the offensive line and in the secondary, where injuries have exposed vulnerabilities in recent seasons.
The financial strain is already evident. The Cowboys’ reluctance to play Prescott in the preseason may reflect a broader strategy of risk aversion, prioritizing his long-term health over short-term readiness. However, this approach could backfire if Prescott struggles early in the season, especially against a juggernaut like the Eagles, who are fresh off a Super Bowl victory. With Milton failing to inspire confidence as a backup, the pressure on Prescott to perform immediately is immense—rust or no rust.
The Cowboys’ faith in Prescott is unwavering, and his new contract reflects their commitment to building around him. But the decision to keep him on ice during the preseason, coupled with the salary cap constraints his deal imposes, puts Dallas in a precarious position. If Prescott comes out firing on all cylinders, the Cowboys could silence their critics and make a deep playoff run. But if early-season struggles expose lingering rust or chemistry issues with his new offensive pieces, the narrative around Prescott’s contract and the team’s cautious approach will only grow louder.
As the Cowboys prepare for their season opener, the stakes couldn’t be higher. Prescott’s new deal has locked Dallas into a high-risk, high-reward future. Whether it’s a masterstroke or a miscalculation will depend on how quickly Prescott can shake off the cobwebs and lead a roster constrained by his own massive paycheck. One thing is certain: in Dallas, the spotlight burns brighter than ever, and Prescott will need to deliver to justify the Cowboys’ all-in bet on their franchise quarterback.