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

Cowboys quarterback Dak Prescott is looking at the NFL's first $60 million-per-year deal, but will he get that contract from Dallas? Photo by Joe Nicholson/USA TODAY Sports

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.

Jump to a topic:
The road that led to this impasse
The no-trade, no-tag clause
The inexplicable quote from Jerry Jones
Can the Cowboys afford their core?
How does Dak compare to other QBs?
What does Lamar have to do with this?
What could Prescott's deal look like?
Who could Dallas target if he walks?
Should the Cowboys actually move on?

How Prescott and the Cowboys got here

Let's go all the way back to spring 2019. Coming off a 10-6 season and the team's first playoff victory in four years, the Cowboys were riding high. After they started the 2018 season 3-5, their trade for Amari Cooper seemed to kick-start the offense. They won seven of their final eight games to claim the NFC East. Their official Twitter account bragged about trading their first-round pick for Cooper when it came up on draft day. To the extent the vibes are ever good in Dallas, things felt like they were heading in the right direction.