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What’s the end game for Dak Prescott and the Cowboys?

The Cowboys have a lingering contract mess with quarterback Dak Prescott. And they only have themselves to blame.

They started this mess by failing to extend Dak’s contract after his third season, forcing him to play out the final year of a slotted rookie deal. Then, they forced him to play under the franchise tag. Then, when they finally realized they were a year away from Dak making a Kirk Cousins-style exit, they gave him a four-year, $160 million contract that was designed to force the team back to the table after three seasons.

The Cowboys are back at the table, but nothing is happening. As it stands, Dak has a $55.4 million cap charge in 2024, plus another $54 million in dead money that will hit the cap in 2025.

The Cowboys need to re-do the deal and drop the cap number, so that they can extend receiver CeeDee Lamb and/or linebacker Micah Parsons. Dak knows that. It’s part of his leverage. And he made it clear on Wednesday that business is business.

That’s why they haven’t resolved the contract. He wants more than the Cowboys are willing to offer. And that likely will continue, perhaps into the season. Perhaps beyond.

The Cowboys might think Prescott wants more than anyone else would pay him. The Cowboys and Prescott might need to test that theory.

That feels like the current end game. After the season, other interested teams make overtures to Prescott’s agents. They’ll find out what’s behind Door No. 2 (or No. 3). Then, Prescott will decide whether to take the best offer from the Cowboys or change teams.

My own guess (and it’s just a guess) is that the Cowboys will sweeten their offer once they see what other teams will pill, and that Prescott will take less to stay in Dallas than he could get elsewhere.

There’s one specific caveat to this approach. Prescott’s agents will have to find out what else is out there well before the annual 52-hour negotiating window. His contract voids before the franchise-tag deadline. Which will saddle that Cowboys with the massive 2025 cap hit. If the Cowboys extend him before that, the damage for the 2025 cap could be minimized.

Of course, there’s a chance the Cowboys cave. There’s a chance they give Prescott what he wants. There’s a chance Dak bends a little now, even with maximum leverage.

As it stands, the two sides are on pace for a high-stakes game of contract chicken that will start to play out the minute the Cowboys’ 2024 season ends. Until the deal is done, there’s a chance Prescott will end up with another team.