The Dallas Cowboys enter the 2025 season with a first-time head coach, Brian Schottenheimer, and the highest-paid quarterback annually in the NFL, Dak Prescott. Nobody can predict how this pairing will go, but either way you slice it or dice it, this is Dak Prescott’s last chance.

The Cowboys had three consecutive 12-win seasons before an unfortunate 7-10 season in 2024 ended Mike McCarthy’s tenure as the head coach of the organization. With high expectations coming into 2024, injuries and a lack of free agency set the Cowboys up for failure and fans are not happy. Not even a new head coaching hire could satisfy a critical Cowboys Nation.

Schottenheimer gets his first crack at being one of the 32 head coaches in the NFL and his contract runs through the 2028 season. Traditionally, Jerry Jones allows coaches to stay for the duration of their contract. So barring anything drastic, expect Schottenheimer to be in Dallas for the next four seasons.

Who else is under contract until 2028? Franchise quarterback Dak Prescott.

All the time in the NFL, teams pair head coaches and quarterbacks. In most cases, those are the two most important people on your coaching staff and on the field. Getting the coach and quarterback in sync is vital to an organization’s success. Prescott has been supportive publicly in regard to Schottenheimer’s promotion. Schottenheimer knows Prescott thrives in a balanced run-pass system to open up play-action opportunities. If there’s anyone who can put Prescott in position for instant success in a comeback year from injury, it might be Schottenheimer.

But what if this marriage doesn’t work out? The Eagles just won a Super Bowl, the Commanders likely found their quarterback in Jayden Daniels, and the New York Giants are picking high in the draft. Anything less than division dominance and chasing Super Bowls will be infuriating.

At the end of Schottenheimer’s contract, he’s young enough where his record, playoff success, and locker room control will dictate whether he gets a new contract with the Cowboys or not. For Prescott, he’ll be 36 when the 2029 season begins. In today’s NFL, only one starting quarterback (Matthew Stafford for the Rams) is 36 or older.

It’s very likely Dak Prescott’s 4-year, $240 million (60 million per year) contract is the final deal he’ll sign with the Dallas Cowboys, at least the biggest. Perhaps Prescott would sign a smaller one or two-year deal if the team is competing and he stays at a high level, but it’s more than likely Prescott is in the final four years of his playing window.

The question remains: is Dak Prescott’s championship window also four years long? That will depend on a lot of determining factors outside of Dak Prescott’s control and on-field production, but the Cowboys must maximize Prescott while they have him and surround him with the best opportunity to bring the franchise its sixth Super Bowl, or at the very least, end the NFC Championship Game drought.