The Cowboys and the Chaos Strategy: Success or Own Goal?
In today’s NFL, where “player empowerment” is the norm and teams invest astronomical sums to secure their stars, the Dallas Cowboys have opted for a peculiar approach: What if we simply frustrated our best players? While most franchises pamper their young talents, offering them lucrative contracts and positioning them as cornerstones to aspire to the Super Bowl, the Cowboys seem to be following a different path. This strategy, which has generated controversy, focuses on a handling of contractual negotiations that has led to tensions and, at times, questionable results. This 2025 season, the Cowboys may have taken things too far. With Micah Parsons about to finish his rookie contract and with a fifth-year option, negotiations for an extension have become public, with team owner Jerry Jones making comments that have not been well received by the player. The situation reached a point where Parsons requested a trade, citing both public comments and an attempt by the Cowboys to negotiate a deal without his agent present, something Jones did not deny.Listen to “The Bill Barnwell Show”
Although it’s common for players to seek better contracts, the way the Cowboys approach negotiations has raised doubts. It’s not about saving money, but an apparent inability to close deals on time, which has cost them millions of dollars, influence in negotiations, and goodwill with players and fans. Success, as the Patriots dynasty demonstrated, can hide many sudden ruptures and difficult negotiations. But the Cowboys have not been able to back up their decisions with on-field performance that justifies their approach. Let’s analyze Dallas’ three most important stars and what the organization’s negotiation philosophy has achieved. How much has it cost the organization to be too slow or reluctant to close deals with Dak Prescott, Micah Parsons, and CeeDee Lamb? What has that meant for the franchise? Let’s start with the quarterback, where the Cowboys hesitated for half a decade before paying Prescott more money than any other quarterback. What has happened with Prescott and what could have happened if they had been smarter in their approach?How Dallas ruined negotiations with PrescottCeeDee LambWhat really happened: Let’s start in 2019, when Prescott was entering the final year of his rookie contract, which had been one of the biggest bargains in the league. The fourth-year pro reportedly wanted a deal worth more than $30 million per season, but he and the Cowboys didn’t find common ground. In a position where almost every team would close a deal before, they let him play the final year of his contract. In 2020, the Cowboys used the franchise tag to retain Prescott, who earned $31.4 million. According to reports, the organization offered him a deal worth $33 million per season with over $100 million in guarantees, but it’s not clear how much of that money was fully guaranteed at the time of signing instead of being partially guaranteed for injuries. With Prescott in line to earn $37.7 million with a second franchise tag in 2021 before becoming an unrestricted free agent the following year at age 29, he had more leverage than the organization. He proved it the following year. Even after Prescott’s 2020 season was ruined by a season-ending ankle injury, he was still able to extract an even bigger contract from the Cowboys to avoid losing him for nothing in free agency the following season. Prescott signed a four-year, $160 million contract, averaging $40 million per year. And, crucially, with all his influence, he was able to get the Cowboys to add no-trade and no-tag clauses to his deal, giving him the ability to reach unrestricted free agency at the end of his extension. With one year remaining on his contract again in 2024, the Cowboys had no choice but to give Prescott the most team-friendly deal in football. His four-year, $240 million extension made him the first player in league history to average $60 million per season on a new deal. Upon signing the deal on the first Sunday of the regular season, he got $129 million of the contract guaranteed at signing and $231 million in injury guarantees. And, of course, for added security, Dallas gave him no-tag and no-trade clauses for a second straight deal. This is such a favorable deal for the player that other quarterbacks simply haven’t been able to come close to in their own negotiations. Brock Purdy, who in many ways became Prescott’s successor as a quarterback whose Day 3 rookie contract was a massive bargain, signed a deal this year worth $53 million per season with the 49ers, even with the salary cap having increased between 2024 and 2025. Josh Allen’s six-year contract with the Bills was essentially a new contract after eliminating what remained of his old contract, but even that reached $55 million per season. Teams seem to view Prescott’s deal as an exception and have convinced agents and players accordingly.What could have happened? Let’s go back to 2019. Prescott was about to earn just over 2 million dollars. That summer, former first-round picks Carson Wentz and Jared Goff signed deals within days of each other in June. Wentz’s deal came in at four years and 128 million dollars, averaging 32 million dollars per season. Goff narrowly surpassed him, with four years and 134 million dollars, averaging 33.5 million dollars per season.If the Cowboys had been aggressive, they could have closed Prescott’s deal before any of those contracts were put in writing. With his asking price exceeding $30 million, what if they had been the ones to start the quarterback carousel that offseason and paid him the same four-year, $128 million deal that the Eagles ultimately gave Wentz? At $32 million per year, that would have been a fair deal for both sides.
We don’t know what the structure of that deal would have looked like, but let’s add a $53 million signing bonus, which roughly matches the percentage of Prescott’s actual deal the following year that was paid upfront. (The Eagles structure their deals differently than the Cowboys, who prefer to give a large signing bonus upfront, while the Eagles opt for bonuses throughout the first few years of the deal.) The Cowboys would have signed him for five years and just over $130 million, averaging $26 million per season. During the first four years of the contract, from 2019 to 2022, they would have saved over $17 million by paying him early: That figure also doesn’t include the value of the no-tag and no-trade clauses. The Cowboys were forced to use the first franchise tag on Prescott in 2020 and then a second franchise tag as a procedural measure as part of the negotiations in 2021, meaning that any future tag for him would be the third franchise tag, a deal so punitive that no player in the franchise tag era has ever received one.If they had made the deal in 2019, the Cowboys would not have needed to use any of the franchise tags on Prescott in the first place, which would have provided the franchise with some leverage in the negotiations to build their subsequent agreement. Prescott also would not have had the leverage to insist on a no-tag clause in 2019, given that he was three years away from free agency at the time. It is not clear how valuable the no-tag clause is, but it is also clear that the right price is not zero dollars either. There is a reason why the Bears said no when Caleb Williams, according to reports, requested the same thing, the no-tag clause at the end of his rookie contract. Williams, years away from free agency, did not have the leverage to corner his new franchise.
Entering the final year of that extension in 2023, the Cowboys would face a difficult decision again. Prescott was coming off a season with the most interceptions in the league, 15, but he had been the quarterback of a team that won 12 games and defeated Tom Brady and the Bucs in Tampa to win a playoff game. He had missed five games with a thumb injury and there were some brief conversations that backup Cooper Rush was a viable alternative, but Dallas was always going to do an extension with him. Once again, what would have been a realistic deal if the Cowboys had been relatively aggressive? Jalen Hurts signed a five-year, $255 million extension in April, and Aaron Rodgers had become the first quarterback to surpass $50 million per year in a deal last March, albeit on a short-term pact. Deshaun Watson had signed a five-year, fully guaranteed deal worth $46 million per season as part of his move to the Browns, although those were unique circumstances in relation to what Prescott would have faced.There’s another round number here that seems realistic: $50 million. Perhaps a four-year, $200 million pact wouldn’t have gotten things done, but with franchise tags available to gain leverage, a disappointing season in Prescott’s rearview mirror, and a smaller contract to work with, $50 million seems like a reasonable compromise. By the time he actually signed his real contract in 2024, Goff ($53 million per year), Tua Tagovailoa ($53.1 million), Trevor Lawrence ($55 million), and Jordan Love ($55 million) had driven up the average annual salary draw, giving Prescott a path to $60 million per year.
With one year and $18.8 million remaining on his previous contract in this hypothetical scenario, Prescott would be under contract for five years and $218.8 million, an average of $43.8 million per season. While we would have to guess the specific cash flow of that contract, let’s use the 33% signing bonus figure and deliver $66 million at the start of the contract, meaning he would earn more than $84 million in year 1. Between 2023 and 2027, which is where the practical guarantees for full base salaries end in his actual contract, the Cowboys would have saved another $32.7 million by closing the deals a year earlier, bringing the combined savings to $49.9 million: This doesn’t include 2028, when Prescott has a base salary of $55 million in his contract, $17 million of which is guaranteed in 2027. While that could prove to be a bargain and provide some value when we get to that ground, it’s hard to believe that the surplus value of that single year will be worth all the money the Cowboys could have saved by making Prescott’s two massive contracts earlier. The 2027 season in his theoretical agreement would also likely not have been guaranteed, which would give them some more flexibility at a time when their quarterback is likely to be in decline.And, again, if $49.9 million in nine years doesn’t seem like much, consider the value of the two no-tag clauses. Would Prescott and his representation be willing to remove those clauses from the deal if the Cowboys had offered $5 million more per season on those two contracts? If so, that’s an additional savings of $45 million. Dallas would have had the ability to use the franchise tag on someone else in 2020, which would have helped them in negotiations with Amari Cooper, who ended up signing a five-year, $100 million contract. Would the franchise have saved money on Cooper’s contract?
Really, we’re talking about some $50 million and a significant and incalculable amount more lost by the Cowboys by waiting to close Prescott’s deal twice. Waiting didn’t save them money nor did it prove anything beyond the fact that the organization failed to close negotiations until it had practically lost all its leverage, allowing it to sign two of the most player-friendly deals in the league in the last decade.CeeDee LambWhat really happened: The math with Lamb’s contract is a bit more simple and mainly revolves around the Cowboys not recognizing or being unwilling to believe how contract valuations would increase. In Lamb’s third season, the former first-round pick amassed 1359 yards and nine touchdowns, firmly establishing him as Prescott’s primary wide receiver. While he would have an even better season in year 4, Lamb was now eligible for an extension, one that would make the then 23-year-old one of the highest-paid wide receivers in the NFL. The spring of 2023 would have been a great time for the Cowboys to sign Lamb to an extension. Although veterans like Tyreek Hill, Davante Adams, and Cooper Kupp had reset the wide receiver market in 2022, another reckoning was looming for players near the end of their rookie contracts. Lamb’s 2020 draft class included Justin Jefferson, Michael Pittman Jr., Tee Higgins, and Brandon Aiyuk, all of whom were about to get paid. The 2021 class, eligible for an extension the following spring, would send Ja’Marr Chase, Jaylen Waddle, DeVonta Smith, Nico Collins, and Amon-Ra St. Brown to the pay window for deserved raises. Lamb was better than some of these guys, so he was always going to command more than them. But some of these wide receivers were going to raise the bar for compensation, and it was always going to be better for teams to get ahead of those contracts. Instead, contracts stalled. The largest contract signed by any wide receiver in 2023 was the four-year, $44 million deal Allen Lazard signed with the Jets in free agency. Jefferson, Aiyuk, and the rest of the 2020 draft class played out the four years of their rookie contracts. Perhaps there was never a scenario where the Cowboys would agree to a deal with Lamb in 2023. I’d like to think a more enterprising organization could have completed a deal, but we’ll get to that in a minute. After a 1749-yard season and a first-team All-Pro appearance in 2023, there was no debate about Lamb’s importance. Furthermore, he was now a year closer to potential unrestricted free agency. The Cowboys had him on a fifth-year option for $17.9 million in 2024, but they would have to tag Lamb in 2025 and 2026 without a new deal. Although they weren’t in real danger of losing Lamb, the Cowboys obviously didn’t want to play the franchise tag game with their star wide receiver after seeing how it went for Prescott.If 2023 had been the best time to sign Lamb, the second-best time would have been the spring of 2024, before so many of the aforementioned wide receivers signed their own extensions. It’s no surprise that the Eagles did their work quickly, extending Smith with a contract worth $25 million per year in March. In April, Lamb’s closest comparison as a star wide receiver, St. Brown, signed for $30 million per season. The Eagles extended A.J. Brown the same month with a new deal for $32 million per year. In May, Collins signed for $24.3 million per year, which has proven to be one of the biggest bargains of any veteran deal. Waddle’s extension came two days later with $28.3 million per season.
