Jerry Jones is finally ready to open his checkbook for the Dallas Cowboys this offseason, but a grim financial reality check suggests his spending spree may be over before it even begins. Ahead of free agency, Jason Fitzgerald, founder of Over the Cap, shared a sobering update about the Cowboys’ financial outlook.

“The Cowboys creating $66m in cap room with restructures would move them to around $10m in cap room. They have a lot more they would need to do to be active in free agency since $66m more or less will just get them cap compliant,” Jason revealed via X on February 28. 

The Cowboys want to improve on both sides of the ball after another playoff-less campaign. The urgency is clear in Dallas, but it doesn’t erase cap math. The Cowboys currently sit about $56 million over the newly set $301.2 million salary cap for 2026. Yes, Jerry Jones has started making moves with significant contract restructures, but Jason pointed out that it would barely scratch the surface if the Cowboys want to spend big in an effort to sign new players.

Most multi-year veteran deals in the NFL include automatic restructure clauses. So, by converting base salary into signing bonuses and spreading the cap hit over future years, NFL teams can create short-term flexibility, and Jerry Jones plans to use that lever aggressively.

“I look at where we are with Dak, and I look at where he is in his career,” Jones said from the NFL Scouting Combine on February 27. “And I look at some of the pluses that we have on our front and what we think we can do there. And what we can do with (George) Pickens and Lamb, and what we can do with our running back (Javonte Williams) that we just signed. So, all of those things, I want to do everything we possibly can to stop somebody and to basically win some third downs more than we did last year.” 

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“And so I think that would be the area that you would see me bust the budget. Where you would see me do that is what we’re doing defensively,” Jones added. “And I would expect anybody that’s a Cowboy fan or a critic of the Cowboys to say, ‘Duh, that’s not hard to see, Jerry, to do.’ But I guess what I’m doing is saying, yes, I intend to do that if given the opportunity.”

The Cowboys have already begun this financial maneuvering, starting with significant restructures for key offensive players. They’ve cleared a combined $66 million in immediate cap space by reworking the deals of receiver CeeDee Lamb, guard Tyler Smith, and most notably, quarterback Dak Prescott.

As Jason pointed out, those moves are expected to free up about $66 million against the 2026 cap for the Cowboys. That money simply shifts to future years, and while the cap space in the NFL will likely continue to rise, it will soften the blow later for the Cowboys. So, Jerry Jones is still borrowing from tomorrow for his team to survive today.

On top of that, there’s the situation with receiver George Pickens. The Cowboys placed the franchise tag on him on February 27, which locks in a hefty $27.298 million cap hit for the team. That’s a massive jump from Pickens’ $3.65 million cap hit in 2025, and it was already included in Dallas’ cap problem.

Can Jerry Jones and his team still spend big in free agency this year? 

The Cowboys could still restructure additional deals, including those of defensive tackles Kenny Clark, Quinnen Williams, and Osa Odighizuwa, who are set to combine for around $63 million against the cap. The team could also extend Clark and Williams early, potentially lowering their combined cap hits by about $31 million while securing them long-term.

If Jerry Jones pushes for all those contract restructurings, his team could technically create upwards of $120 million in cap room. Meanwhile, a long-term deal with George Pickens before the mid-July deadline would significantly reduce his $27.3 million franchise tag hit for Dallas. The sooner they finalize that deal, the more flexibility the Cowboys gain for the early waves of free agency. Waiting too long could limit their options, but Jones remains publicly committed to making a splash.

“I would bet that we will spend more money in free agency than we have,” Jerry Jones said from the NFL Scouting Combine on February 27. “I want you to know that the only way to push forward is for me to borrow some of my future. Expect me to go borrow some of my future, OK?”

This might be the mindset Cowboys fans have been waiting to hear. The franchise hasn’t reached an NFC Championship Game since 1995, and patience has worn thin in Dallas. Jerry Jones even hinted at “dramatic things” this offseason to end the 30-year Super Bowl drought. But before busting the budget, Jones has to figure out a way to balance the books in Dallas.