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The Dallas Cowboys haven't won a Super Bowl in 30 years, but they definitely are the best in the NFL at least one thing: creating contract drama with their star players. Last year, it was CeeDee Lamb and Dak Prescott. This year, it's Micah Parsons, who is so fed up with the organization that he has now requested a trade

With Lamb and Prescott, the Cowboys essentially waited until the last second to get a deal done, and in Prescott's case, it really was the last second: The Cowboys quarterback was given a record-setting four-year, $240 million extension just HOURS before the team's regular-season opener in September 2024. 

The problem for the Cowboys is that the longer they wait to get a deal done, the more money they're throwing away. As a matter of fact, the next time Jerry Jones needs to get a big contract done, he might want to call JJ Watt for advice. After Parsons' trade request came out Friday, the three-time NFL Defensive Player of the Year and current game analyst for 'The NFL on CBS' offered some simple advice to the Cowboys (and the rest of the NFL). 

"Take care of your best players early," Watt wrote. "Saves money. Saves headaches. The longer you wait, the higher the price."

If the Cowboys had followed that advice, they could have saved some serious money with Lamb and Parsons. Let's take a look at how much they could have saved. 

CeeDee Lamb
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  • Contract he got from the Cowboys: The receiver signed a four-year, $136 million extension in August 2024 that pays out an average of $34 million per year. Lamb became the second-highest-paid receiver, trailing only Justin Jefferson, who had signed a deal in June 2024 worth $35 million per year
  • What the Cowboys could have done: When the 2024 offseason started, Tyreek Hill was the highest-paid receiver in the NFL at $30 million per year, but that price went up in April 2024 after A.J. Brown signed an extension for $32 million per year. It went up again in June 2024 after Jefferson signed his extension. If the Cowboys had gotten a deal done with Lamb at any point between January and March 2024, they likely could have gotten him under contract for $30 million or $31 million per year. At $31 million per year, Lamb would have become the highest-paid receiver in NFL history, so it's hard to imagine that he would have turned that kind of offer down. 
  • Savings: At $31 million per year over four years, the Cowboys would have saved $12 million over what they ended up paying him. 
  • Contract he might get from the Cowboys: Parsons is expected to become the highest-paid non-quarterback in NFL history, so if he does rescind his trade request and sign a new deal, it's a near certainty the contract will pay him at least $42 million per year (TJ Watt is currently the highest-paid non-QB at $41 million per year). 
  • What the Cowboys should have done: Parsons has been eligible for an extension since the end of the 2023 season. From January 2024 through January 2025, the numbers didn't really change on what an offer might have looked like. During most of that span, the highest-paid non-quarterback was Nick Bosa, who was making an average of $34 million per year. Justin Jefferson then topped it in June 2024 with a deal worth $35 million per year. That's the number the Cowboys needed to beat. Maxx Crosby topped that number in early March 2025 with a three-year extension that's worth an average of $35.5 million per year. If the Cowboys had gotten a deal done between January 2024 and March 4, 2025, they probably could have gotten Parsons under contract for $36 million or $37 million per year. That would have put him comfortably above Bosa as the highest-paid pass-rusher and above Jefferson as the highest-paid non-QB. 
  • Savings: If Parsons ends up getting a four-year, $172 million deal (worth $42 million per year) from the Cowboys, that will sting. At $37 million per year over four years, the Cowboys would have saved $20 million if they had gotten the deal done earlier. If Parsons gets a deal worth MORE than $42 million per year, that's just more savings out the window for a franchise that apparently loves to burn money. 

TOTAL SAVINGS ON JUST THOSE TWO CONTRACTS: $32 million

2025 NFL contract dispute tracker: Predicting deals or trades for Cowboys' Micah Parsons, Bills' James Cook
Cody Benjamin
2025 NFL contract dispute tracker: Predicting deals or trades for Cowboys' Micah Parsons, Bills' James Cook

You could also throw Prescott's deal into the mix, but that's a little more complicated, because he had a no-tag and no-trade clause, which means he had a lot of leverage in 2024 that Lamb didn't have and Parsons doesn't have. The Prescott drama started in 2020 when he was hit with the franchise tag for the first time, and the Cowboys have been essentially been dragging their feet in every negotiation they've had with him since then. 

The bottom line is that if the Cowboys had followed Watt's advice of getting a deal done as early as possible, they could have saved millions, which is a big deal in a league where every team is limited by a hard salary cap.