Jerry Jones seemingly loves to play the long game, but his latest move might’ve backfired worse than a trick play in the Super Bowl. The Dallas Cowboys owner’s patience with quarterback Dak Prescott has turned into a financial Hail Mary. As the NFL’s salary cap keeps rising, Prescott’s price tag is soaring into the stratosphere.

Tim Cowlishaw, ESPN panelist, and Dallas Morning News columnist, didn’t pull any punches. He told Rich Eisen that Jones has “let the market run over” the Cowboys. That’s gotta sting more than a blindside sack. Cowlishaw added, “They weren’t in this position of always being late to the trough so to speak that they have gotten into in the last three or four years.”

Jones’ infamous quip back in April about wanting to “see more leaves fall” before inking Prescott to a new deal has aged like a linebacker’s knees. Since then, the quarterback market has exploded. Trevor Lawrence just scored a whopping $275 million contract with the Jaguars. Even Jared Goff, once considered a potential bust, landed a $212 million payday with the Lions.

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This isn’t Jones’ first rodeo when it comes to contract chicken. In 2021, the Cowboys’ hesitation cost them big time. They ended up forking over $160 million over four years, plus giving Dak both no-trade and no-tag clauses. That’s like paying top dollar for a Hail Mary pass and watching it fall incomplete.

Now, it’s déjà vu all over again. Prescott holds all the leverage as he enters his contract year. With no franchise tag option, the Cowboys risk losing their star quarterback to free agency if they can’t reach a deal. It’s fourth and long, and the two-minute warning just sounded for Jones and Prescott.

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While Prescott’s regular-season stats shine brighter than the star on his helmet, his playoff record is shakier than a rookie’s hands-on opening day. A 2-5 postseason mark has critics questioning if he’s worth breaking the bank.

Cowlishaw drew an interesting parallel between Prescott and his predecessor, Tony Romo. “He’s reached the point where his career is now oddly not that different from Tony Romo,” Cowlishaw noted. Both quarterbacks lit up the regular season but stumbled in the playoffs. It’s like watching a rerun for Cowboys fans, only with a bigger price tag.

ESPN’s Stephen A. Smith didn’t mince words about Prescott’s postseason performance. “Oh, he’s phenomenal from September through December, without question,” Smith admitted last week, “But as the playoffs loom, that brother folds like a cheap tent.”

The $60 million question is whether Prescott can finally lead Dallas to the promised land. Cowlishaw laid it out plain: “At some point you got to beat San Francisco or you got to beat another West Coast offense team… otherwise it’s his dak’s career won’t be viewed uh really any differently from Romos.”

Despite the playoff struggles, Cowlishaw believes Prescott will get paid. The market demands it. “Dak’s not gonna certainly not gonna take less than Trevor Lawrence is getting,” he stated. But with CeeDee Lamb and Micah Parsons also due for big paydays, the Cowboys might be facing a salary cap crunch tighter than a goal-line stand on fourth down.

Jones’ patience has turned into a Hail Mary pass. As the clock winds down, Cowboys fans are holding their breath, hoping this gamble pays off instead of ending up as another costly turnover in Jerry’s World.