The Dallas Cowboys enter yet another offseason where fans are clamoring for a massive spending spree. From the looming extension of George Pickens to shore up a top-notch receiving corps, to a potential blockbuster trade for Maxx Crosby to bolster the pass rush, as well as the never-ending desire for them to finally be aggressive in free agency, the idea of throwing down some serious cash is at an all-time high.
Advocates of this approach often point to restructuring current contracts as the simple solution to afford these stars, viewing the salary cap as a mere suggestion that can be manipulated at will. However, the reality of NFL front office management is far more complex than simply moving numbers from one column to another to free up space for that missing player who will take their team to the promised land.
This offseason, the Cowboys find themselves in a unique position of having the highest restructure potential in the league. They can clear up to $131 million in cap space through simple adjustments. Despite being roughly $29 million over the projected $304 million cap, they possess the tools to open the floodgates of spending simply by pushing base salaries into future years by converting them to bonus money.
While all those extra cap dollars make our eyes widen as we ponder the possibilities, flipping the switch to trigger maximum level restructures is a risky endeavor. That’s because today’s savings are tomorrow’s shackles.
One of the primary pitfalls of aggressive restructuring is roster rigidity. When a team converts base salary into a signing bonus, they are essentially making a serious commitment towards that player because the remaining bonus money accelerates if the player is cut or traded. This creates a situation where a team is all but forced to retain a potential declining veteran because it would cost more in cap space to move on than to keep them on the roster. The New Orleans Saints have famously struggled with this for years, often unable to refresh their depth because their books are tied to the ghosts of past production. It’s like staying in a bad marriage because you can’t afford the financial repercussions of a costly divorce.
Future flexibility is another casualty of the win-now mentality. Every dollar pushed into future seasons is a dollar that cannot be used to sign a future commodity or retain a homegrown talent. Teams that overextend themselves find they have no room to breathe when a new need arises at a critical position. The San Francisco 49ers faced a similar squeeze recently, having to be extremely careful with how they allocated funds to avoid losing their core nucleus. If you keep spending your lunch money on an extra chocolate milk, you could find yourself going hungry at the end of the week.
Finally, there is the looming certainty of massive dead money hits. This is the bill that eventually comes due once a player finally leaves the team, leaving behind a cap charge for money already paid but not yet accounted for. In 2025, three teams carried over $100 million in dead money (Saints, 49ers, and Jets), which is more than a third of the total salary cap going toward players who are not even on the active roster. Paying a hundred million dollars for players to sit on their couch is certainly not a good business strategy.
Many will quickly point out that the salary cap is always increasing. Everyone knows this, and it’s why teams are okay about restructuring in the first place. But when you’re reallocating funds at a much higher rate than how the cap increases, that’s when you run into problems.
Successful organizations typically favor selective restructuring as a more sustainable path to victory. These teams understand that the cap increases each year, and by only restructuring when absolutely necessary, they can use that growth to make improvements rather than just paying off old debts. Managing the cap this way is like being the person who does their best to keep their credit card balance low. It is less exciting in the moment, but the rewards are significantly better in the long run, especially when something comes along that they really need to buy.
Ultimately, the Cowboys must continue to walk a fine line between being aggressive and being reckless. While the potential to create over $100 million in space is a powerful tool, the front office should use it wisely to ensure they do not become the next cautionary tale of cap mismanagement. Maintaining a healthy balance allows the team to remain competitive every season rather than rolling the dice for one year of glory while risking crapping out and becoming a basement dweller.
The Cowboys’ front office believes they are doing enough when it comes to roster building. Most fans don’t see it that way, but to them, the groceries are good enough to prepare a great meal. Yes, they may need to add some ingredients here and there, but ultimately, the rest falls on the coaching staff to do a better job cooking.