Biggest dead money cap hits illustrate Cowboys’ decision-making mistakes

The Cowboys have repeatedly gambled and lost when signing sub-superstar talent on speculative deals

Contrary to popular belief, signing superstar players to big deals rarely gets an NFL team in trouble. No matter what the Cowboys front office tries to say, there’s always room for talent under the salary cap.

Good players who meet or exceed the expectations of their contract are value-added, pure and simple. They take on a bigger proportion of the cap, but they also often take heavier snap counts and make bigger contributions. Teams can save money in rotations and at other positions if highly paid players simply live up to their billing.

Best of all, superstars are usually no brainers. Dak Prescott was an obvious re-signing this past summer. CeeDee Lamb was also an obvious re-signing this past summer. Micah Parsons and Tyler Smith will be obvious re-signings in the near future, while DaRon Bland and DeMarvion Overshown are trending to be obvious re-signings soon after. Health permitting, they will all be well worth the price of doing business.

Where teams get themselves into trouble is by signing players who underachieve and don’t live up to the expectations of their contracts. That’s what really kills the salary cap. Many of these bad contracts are speculative in nature. They involve middleclass players who have shown enough to indicate they could be great but just haven’t done so consistently enough to make it a sure thing. They are calculated gambles by the front office. It’s here where the Cowboys have struggled.

In recent seasons the Cowboys gambled on players like Michael Gallup and Terence Steele. Both offered inconsistent performances throughout their careers, and both were coming off major injury. They represented significant speculation from the Cowboys front office when they were re-signed and now stand as cautionary tales moving forward.

Looking at things today, the biggest dead money cap hit the Cowboys face is from Gallup. Signed to a five-year, $57,500,000 contract in 2022, Gallup fell well short of the expectations implied in the deal. After contributing just 73 receptions for 842 yards, Gallup was released two years into the deal. The contract was a gamble from the start since Gallup had only once posted a thousand-yard season and he was now coming off a significant knee injury. He represents $4,350,000 in dead money this season and a team-leading $8,700,000 in 2025.

Steele is another player the Cowboys seemingly gambled on and lost. After suffering a major knee injury late in 2022, the Cowboys signed him to a five-year, $87,500,000 extension to be their cornerstone at right tackle. Like Gallup, Steele was gamble from the start. His last ten games of 2022 he showed he was a dominant force in the running game but his game play in the years leading up to that were far more pedestrian. In fact, his pass protection was some of the worst in the NFL.

Steele now potentially faces the axe in 2025. At a cap charge of over $18 million next season, Steele is one of the highest paid players on the Cowboys roster. He has an out in his contract in 2025, but it would come with an immediate cap charge of $13,500,000 in dead money. The Cowboys could designate him a post June 1 cut but that would only push more dead money into future years.

The lesson to be learned is sub-superstar contracts that involve speculation are far riskier than max-level contracts that simply demand health and a continued level of play. The Cowboys have a poor track record when it comes to speculating the future of their own midlevel performers and it’s come back to bite them over and over again.

Does this mean the death of midlevel contracts going forward?

Possibly. With so many star players set to make star money, the Cowboys may just round out their roster with rookie contracts and bargain bin pickups. It could mean non-superstar players like Osa Odighizuwa, Chauncey Golston and Rico Dowdle (all pending free agents in 2025) are too expensive and/or risky to bring back.

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