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Dak Prescott has Jerry Jones in contract checkmate — and Jerry knows it

There’s a beautiful irony to the situation in which Cowboys owner and G.M. Jerry Jones finds himself, when it comes to quarterback Dak Prescott’s contract.

Prescott currently has PRECISELY the kind of leverage that Jerry would relish and maximize if he were in Dak’s shoes.

The problem traces to the Cowboys failing and refusing to reward the 2016 fourth-round draft pick after he became eligible for a second contract, following his third season. They retained him in 2019 at a bargain-basement price, before using the franchise tag in 2020.

By 2021, they realized they were over a barrel. If Dak was willing to spend one more year under the tag, he would have become a free agent in 2022 — unless the Cowboys had given him a 44-percent raise over his second tag, which was 20 percent higher than his first one.

Prescott parlayed the predicament into a four-year, $160 million deal with low cap numbers early, and an enormous cap number late. Next year, Dak’s salary-cap number mushrooms from $26.8 million to $59.455 million.

The team’s desperation to shrink that number gives Prescott incredible leverage. He can simply say to the team, “I’ll honor my contract,” allowing cap-number nature to take its course. And if Jones wants Dak to reduce that figure for 2024, Dak can say, for example, “Make me the highest-paid player in the NFL.”

A new deal that pays Dak, for example, $55.1 million per year in new money, would be structured to have low cap numbers now, big cap numbers later. And it’s obvious that, whatever Dak is proposing in order to alleviate next year’s cap mess, Jones doesn’t want to do it.

Appearing Friday on 105.3 The Fan (via Clarence E. Hill, Jr. of the Fort Worth Star-Telegram), Jones complained that, if he were to extend Dak’s contract in 2023, the Cowboys would have to “cut four players” — and that “I want to use those players this year to win now.”

It’s impossible to know whether there’s any truth to that. Jones could muster cap space if he needed to do so. And if he doesn’t do so now, he’ll need to do so next year, when he has to put a team on the field with a quarterback who counts for nearly $60 million.

Regardless of Jones’s desire to “win now,” past efforts to “win now” have contributed to the present mess. At some point, the salary-cap pill needs to be swallowed. And Dak has exactly the same obligation to help Jerry as Jerry had in the many situations during his life in which he had someone else by the balls.

When faced with such occasions, Jerry always had one move. Squeeze as hard as possible.