A financial reckoning is bearing down on Jerry Jones and the Dallas Cowboys, and the most troubling part of their $330 million problem lies within the fine print of Dak Prescott’s future. Before Cowboys Nation can dream about new faces, Dallas has to get under the 2026 salary cap. This could be around a $30 million problem, but the exact number remains a mystery for now. But the silver lining is that by restructuring a few stars’ deals, they could be in the clear, at least for now.

The Cowboys can open up close to $100 million by reshaping deals for Dak Prescott, CeeDee Lamb, Tyler Smith, Osa Odighizuwa, DaRon Bland, and Jake Ferguson. By pushing base salaries down to the minimum, Dallas buys flexibility. In theory, that gives Jerry Jones room to move and room to breathe, acording to ESPN.

The Cowboys are sitting on roughly $330 million in contracts, while league projections float closer to $295 to $305 million. Because of that, Dallas needs to clear at least $30 million just to stay legal. However, securing their unrestricted free agent George Pickens could also cost the franchise nearly $28 million, which hits the books immediately. To make matters worse, the fundamental issue lies with their star quarterback.

There is a real risk involved, especially with Dak Prescott. A full restructure would push nearly $8 million into future seasons from 2027 through 2031. Even worse, Dak’s cap hits in 2027 and 2028 would soar past $75 million and $85 million. Because of that, easing off a full conversion of his $40 million base salary might save pain later.

Ideally, all this work gets done before free agency opens on March 11. From a cap angle, that puts the Cowboys in control. Still, the bigger question remains whether Dallas will actually spend the way fans at AT&T Stadium hope.

“I don’t want to sound [optimistic] by saying, ‘We’re going to be active in free agency,’ then disappoint and say that we weren’t,” Jones revealed recently. “But if we have an opportunity in free agency, and if we have more than one opportunity, we’re going to take advantage of the fact that we’re in better shape today to be active in free agency than we thought we might be. So we’re going to use it.”

Ultimately, Jerry Jones wants one thing above all. He wants a championship-level roster around Prescott, and time is clearly ticking. The management, meanwhile, has already started interviewing candidates for the defensive coordinator role. While soon enough, an update will arrive on that front, Jones still had work to do with regard to his star quarterback.

Jerry Jones is focused on his Super Bowl dream

Jerry Jones, the longtime owner, knows this stretch will shape what comes next for Dak Prescott as the face of the franchise. Earlier this season, the veteran tied Tony Romo’s record of 4 seasons with 30 or more touchdowns. At this rate, Prescott could even surpass the legend. But personal success hasn’t quite translated into playoff success.

After years of coming up short past the divisional round, the pressure around AT&T Stadium feels heavier. Because of that, Jones is tweaking his staff, weighing contract paths, and searching for moves that keep Prescott squarely in the Super Bowl conversation.

Meanwhile, age has not softened Jones’ drive. At 83, his focus stays locked on building a roster that can deliver one more parade.

“I’ve had the most fun in the last 20, 21 years,” Jones said. “Everybody likes to dream. I promise you, high and hard on my dream list, way ahead of making a buck, is to go down as the owner that won the most Super Bowls.”

The Cowboys have not touched the Lombardi Trophy since 1996. So, the next real shot depends on one key question. Can Prescott turn steady regular-season success into playoff wins when it matters most? Stat-wise, Prescott continues to do his part. Last season, he completed 67.3 percent of his throws for 4,552 yards. Just as important, he stayed healthy once again. When asked about how long he wants to play, the 32-year-old had an answer ready.

“Forties would be a good number,” he said. “If I can get to 40 playing at the standard I want, yeah, that would be awesome.”

With several years remaining on Prescott wanting to leave the game, the question now looms over the Cowboys’ plans. The next step is clear: Jones has to build the right squad around his quarterback and give Cowboys Nation a real reason to believe again.