Dak Prescott’s Cowboys future: New contract or test free agency?

In the real world, patience is a virtue. In Jerry World, patience is expensive. For the second straight contract cycle, team owner Jerry Jones and the Dallas Cowboys find themselves in an inexplicable game of contract chicken with quarterback Dak Prescott. The mistakes made leading up to his four-year, $160 million deal in 2021 have left the franchise in an intensely vulnerable position as the season approaches. With Prescott’s price only rising, the Cowboys run a serious risk of losing him for nothing in 2025.

Would that be a bad thing? What are Dallas’ options if it does move on from Prescott? Are the Cowboys doomed to fail if they re-sign him? I’ll answer those questions and a bunch more in a deep dive into the signal-caller’s future.

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To understand what happens next, though, you have to understand how the Cowboys got here in the first place. They handed Prescott more leverage than any other player in football when they stalled on his last deal. They’re in an even more perilous position this time around.