Barnwell: Jerry Jones’ Contract Bungles Cost Cowboys $100M

In a period marked by heightened athlete agency and substantial investments by NFL franchises in acquiring and maintaining elite talent, a particular team has emerged as an exemplar of what might transpire if a franchise demonstrates disregard for the contentment of its top-tier players. While many teams prioritize public and private displays of support for their rising stars, swiftly securing them with contracts and positioning them as vital assets for their championship aspirations, the Dallas Cowboys have presented a divergent viewpoint: what if, without any tangible upside, we simply provoked their dissatisfaction?

Thus, in a league where less accomplished quarterbacks have received lucrative contracts accompanied by glowing endorsements from coaches and general managers whose livelihoods hinge on their success, the Cowboys deliberated on the potential detriment of overpaying a quarterback to a team’s Super Bowl ambitions, before ultimately extending Dak Prescott’s contract. They initially signaled reluctance to revise star guard Zack Martin’s deal, citing the necessity to compensate pass rusher Micah Parsons, only to later renegotiate Martin’s contract.

Now, in 2025, the Cowboys might have pushed the envelope a tad too far. As Parsons neared the culmination of his rookie contract, inclusive of a fifth-year option, both he and the organization engaged in public pronouncements expressing nebulously optimistic sentiments regarding a contract extension. Although the standard practice involves securing extensions for exceptionally gifted players following their third season, the Cowboys’ owner, Jerry Jones, articulated a perspective that 31 other teams would have refrained from uttering, emphasizing Parsons’ absence from six games last season due to injury. (The actual count was four.) Parsons countered these remarks days later with a public trade request, pointing to both the aforementioned comments and an alleged attempt by the Cowboys to negotiate a deal excluding his agent, an assertion that Jones appeared to acknowledge.

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Let me clarify: much like Myles Garrett’s previous trade request from Cleveland before ultimately agreeing to a market-leading contract with the Browns, I doubt Parsons will depart from Dallas. While Cowboys supporters are legitimately anxious about the prospect of the team trading a premier player following the Luka Doncic debacle, it is hardly unprecedented for the Cowboys to extend negotiations to their limits before finalizing agreements with key players. Indeed, this approach has become almost habitual in their recent contract dealings.

What has been notably absent from the discourse is a significant and disconcerting factor. The Cowboys’ steadfast approach to contract negotiations would be justifiable if it resulted in securing team-friendly deals from players. Bill Belichick’s Patriots were renowned for their tough stance on contracts, compelling stars like Corey Dillon and Randy Moss to accept pay reductions for the chance to join the team, and releasing mainstays such as Moss, Logan Mankins, and Lawyer Milloy when their compensation surpassed their performance level. However, Belichick successfully extracted substantial concessions and constructed superior rosters through these negotiating strategies.

Conversely, the Cowboys gain no financial advantage from their negotiation tactics. In reality, the delays and failures to finalize agreements in a timely fashion have cost them considerable sums, diminished their negotiating power, and fostered discontent among both players and fans. As the Patriots dynasty demonstrated, achievement can compensate for controversial departures, difficult negotiations, and the exit of beloved figures. The Cowboys, however, cannot rely on on-field results to validate their decisions.

Let’s examine Dallas’s three most prominent players and the ramifications of the organization’s negotiation strategy. How much has the team lost by being slow or hesitant to finalize deals with Prescott, Parsons, and CeeDee Lamb? What implications has this had for the franchise? And what might have transpired had the Cowboys mirrored the Eagles’ proactive approach to contract extensions?

Beginning with the quarterback position, the Cowboys deliberated for half a decade before compensating Prescott more handsomely than any other quarterback. Let’s delve into the details of the Prescott situation and explore how a more strategic approach might have altered the outcome.

Jump to a section:
How Dallas bungled the Prescott negotiations
How waiting to sign Lamb cost the franchise
How Jerry Jones & Co. have made Parsons mad
Why are the Cowboys operating this way?

What transpired: Beginning in 2019, Prescott entered the concluding year of his rookie contract, which had been exceptionally favorable for the team. The fourth-year player reportedly sought a deal surpassing $30 million annually, but an agreement eluded both parties. In contrast to most teams, which expedite contract extensions at this pivotal juncture, they permitted him to fulfill the final year of his existing contract.

In 2020, the Cowboys deployed the franchise tag to retain Prescott, compensating him $31.4 million. The organization reportedly presented him with a proposition valued at $33 million per season, inclusive of over $100 million in guarantees; however, the quantum of fully guaranteed funds at signing versus those partially guaranteed due to injury remains unclear. Given Prescott’s potential earnings of $37.7 million via a second franchise tag in 2021, and the prospect of unrestricted free agency the ensuing year at age 29, he held greater negotiating leverage.

He proved this the following year. Even after an ankle injury prematurely ended Prescott’s 2020 season, he still managed to extract a more significant contract from the Cowboys, thereby preventing his potential departure in free agency. Prescott inked a four-year, $160 million pact, averaging $40 million annually. Critically, leveraging his advantageous position, he persuaded the Cowboys to incorporate both no-trade and no-tag clauses, granting him the capacity to explore unrestricted free agency upon the contract’s expiration.

With one year remaining on his deal once more in 2024, the Cowboys were compelled to extend Prescott the most player-centric contract in the sport. His four-year, $240 million extension established him as the inaugural player in league annals to average $60 million per season on a fresh agreement. Finalizing the deal on the opening Sunday of the regular season, he secured $129 million in guaranteed funds at signing and $231 million in injury guarantees. And, naturally, the team furnished him with no-tag and no-trade clauses for the second consecutive contract.

This arrangement is so skewed in favor of the player that other quarterbacks have struggled to attain similar terms in their respective negotiations. Brock Purdy, who followed in Prescott’s footsteps as a quarterback whose rookie contract proved exceedingly valuable to the team, signed a deal this year valued at $53 million annually with the 49ers, despite the salary cap’s escalation between 2024 and 2025. Josh Allen’s six-year contract with the Bills essentially served as a new deal after negating the remnants of his previous agreement, yet it still amounted to $55 million per season. Teams seemingly perceive the Prescott arrangement as anomalous and have influenced agents and players accordingly.

Alternative outcomes: Let’s rewind to 2019. Prescott was slated to earn slightly over $2 million. That summer witnessed former first-round picks Carson Wentz and Jared Goff agreeing to contracts within days of each other in June. Wentz’s deal amounted to four years and $128 million, equating to $32 million per season. Goff marginally exceeded him with a four-year, $134 million agreement, averaging $33.5 million annually.

Had the Cowboys been more proactive, they could have finalized Prescott’s contract before the execution of either of those aforementioned deals. With his asking price exceeding $30 million, what if they had initiated the quarterback carousel that offseason and compensated him with the same four-year, $128 million package that the Eagles ultimately bestowed upon Wentz? At $32 million per year, such a deal would have been equitable for both sides.

The specifics of the agreement remain unknown, but let’s impute a $53 million signing bonus, mirroring the percentage of Prescott’s eventual deal the subsequent year that was disbursed upfront. (The Eagles adopt a different contract structure than the Cowboys, preferring bonuses throughout the contract’s initial years, whereas the Cowboys favor a substantial signing bonus upfront.) The Cowboys would have secured his services for five years and just over $130 million, averaging $26 million annually. Over the contract’s initial four years—between 2019 and 2022—they would have conserved over $17 million by securing his signature early:

That figure also neglects to account for the value of the no-tag and no-trade clauses. The Cowboys were compelled to utilize the first franchise tag on Prescott in 2020 and then a second one as a procedural measure during the 2021 negotiations, implying that any prospective tag for him would constitute the third, a deal so financially onerous that no player during the franchise tag era has ever been offered such an arrangement.

Had they concluded the deal in 2019, the Cowboys would not have needed to invoke either franchise tag on Prescott, affording the team greater negotiating leverage in structuring his subsequent agreement. Prescott also would have lacked the bargaining power to insist on a no-tag clause in 2019, given his position three years from free agency. While the precise worth of the no-tag clause remains unclear, it undeniably possesses intrinsic value. There exists a legitimate rationale for the Bears’ rejection of Caleb Williams’s request for a similar no-tag provision upon the expiry of his rookie deal. Williams, still years away from free agency, lacked the leverage to pressure his new team.

Entering the ultimate year of that extension in 2023, the Cowboys would again confront a challenging choice. Prescott was coming off a campaign marked by a league-high 15 interceptions, but he had also quarterbacked a squad that amassed 12 wins and convincingly defeated Tom Brady and the Buccaneers in Tampa during a playoff game. Having missed five games due to a thumb injury, and despite brief speculation that backup Cooper Rush presented a viable alternative, Dallas was inevitably poised to extend his contract.

Again, what would constitute a plausible agreement had the Cowboys adopted a relatively aggressive stance? Jalen Hurts signed a five-year, $255 million extension that April, and Aaron Rodgers had previously become the first quarterback to exceed $50 million annually on a deal the prior March, albeit one of shorter duration. Deshaun Watson had inked a five-year, fully guaranteed contract valued at $46 million per season as part of his trade to the Browns, although the circumstances were unique relative to what Prescott would have faced.

Another round number seems plausible: $50 million. A four-year, $200 million arrangement may not have sufficed, but with the franchise tags accessible for leverage, a disappointing season in Prescott’s rearview mirror, and a smaller contract to build upon, $50 million seems like a reasonable compromise. By the time he officially signed his actual contract in 2024, Goff ($53 million per year), Tua Tagovailoa ($53.1 million), Trevor Lawrence ($55 million), and Jordan Love ($55 million) had advanced the average annual salary sweepstakes, providing Prescott with a route to attain $60 million annually.

With one year and $18.8 million outstanding on his prior deal in this hypothetical scenario, Prescott would be under contract for five years and $218.8 million, averaging $43.8 million per season. While we would need to estimate the precise cash flow of that contract, let’s utilize the 33% signing bonus figure and allocate $66 million at the outset, implying he would earn over $84 million in Year 1. Between 2023 and 2027, which is where the practical guarantees for full base salaries terminate on his actual contract, the Cowboys would have saved an additional $32.7 million by finalizing the deals a year earlier, bringing the aggregate savings to $49.9 million:

This excludes 2028, when Prescott is slated to receive a $55 million base salary on his deal, $17 million of which is guaranteed in 2027. While that could evolve into a bargain and deliver some value as time progresses, it is difficult to imagine the surplus value of that solitary year offsetting the funds the Cowboys could have preserved by finalizing Prescott’s two lucrative contracts sooner. Furthermore, the 2027 season in his theoretical deal likely would not have been guaranteed, affording them greater flexibility at a juncture when their quarterback is likely to be declining.

Again, if $49.9 million over nine years seems insignificant, consider the value of the two no-tag clauses. Would Prescott and his representatives have relinquished those clauses had the Cowboys proposed an additional $5 million per season over the course of those two contracts? If so, that constitutes another $45 million in savings. Dallas would have retained the option of deploying the franchise tag on another player in 2020, thereby bolstering its negotiating position with Amari Cooper, who ultimately signed a five-year, $100 million deal. Would the franchise have economized on the Cooper contract?

Realistically, the Cowboys forfeited approximately $50 million, and a meaningfully immeasurable sum beyond that, by postponing Prescott’s deal twice. This delay yielded no savings or compelling revelations, except that the organization neglected to finalize negotiations until it had surrendered virtually all leverage, empowering him to sign two of the league’s most player-friendly contracts in the past decade.

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What transpired: The calculations for the Lamb contract are somewhat simpler, centering primarily on the Cowboys’ inability or unwillingness to anticipate the escalation of contract valuations. During Lamb’s third season, the former first-round pick accumulated 1,359 receiving yards and nine touchdowns, cementing his status as Prescott’s primary receiving threat. While he would experience an even more productive season in Year 4, Lamb became eligible for a contract extension, one that would position the then-23-year-old among the NFL’s highest-compensated wideouts.

The spring of 2023 would have presented an opportune moment for the Cowboys to extend Lamb’s contract. Although veterans such as Tyreek Hill, Davante Adams, and Cooper Kupp had recalibrated the wide receiver market in 2022, another reckoning was forthcoming for players nearing the culmination of their rookie deals. Lamb’s 2020 draft class included Justin Jefferson, Michael Pittman Jr., Tee Higgins, and Brandon Aiyuk, all of whom were poised to secure lucrative contracts. The 2021 class, eligible for extensions the following spring, would usher Ja’Marr Chase, Jaylen Waddle, DeVonta Smith, Nico Collins, and Amon-Ra St. Brown to the bargaining table for well-deserved raises. Lamb surpassed some of these individuals in talent, so he was invariably destined to earn more. However, certain wideouts were destined to elevate the compensation standard, and it was invariably advantageous for teams to finalize deals ahead of those contracts.

Instead, contract negotiations stagnated. The most significant contract signed by any wide receiver in 2023 was the four-year, $44 million pact Allen Lazard inked with the Jets during free agency. Jefferson, Aiyuk, and the remainder of the 2020 draft class all fulfilled the fourth year of their rookie deals. Perhaps there was never a scenario where the Cowboys and Lamb would have reached an agreement in 2023. I remain optimistic that a more resourceful organization could have consummated a deal, but more on that in a moment.

Following a 1,749-yard season and a first-team All-Pro designation in 2023, Lamb’s importance was indisputable. Furthermore, he was now one year closer to potential unrestricted free agency. The Cowboys retained him via a fifth-year option for $17.9 million in 2024, but they would have been compelled to franchise-tag Lamb in 2025 and 2026 without a fresh agreement. While the Cowboys were not in imminent danger of losing Lamb, they were understandably averse to engaging in the franchise tag game with their star wideout, having witnessed the ramifications with Prescott.

If 2023 represented the optimal time to sign Lamb, the second-best window would have been the spring of 2024, before so many of the aforementioned wideouts signed their respective extensions. Unsurprisingly, the Eagles acted swiftly, extending Smith on a deal worth $25 million annually in March. In April, Lamb’s closest parallel as a superstar slot receiver, St. Brown, signed for $30 million per season. The Eagles extended A.J. Brown the same month on a new deal for $32 million annually. In May, Collins signed for $24.3 million per year, proving to be among the most favorable veteran deals. Waddle’s extension followed two days later, amounting to $28.3 million per season.

The ensuing week, the most significant domino fell. Jefferson signed a four-year, $35 million per season deal with the Vikings. While Hill’s and Adams’ contracts incorporated substantial amounts of artificial money at the end to inflate the per-year value, Jefferson’s deal more accurately reflected a true value of $35 million, according to OverTheCap.com.

Although the Cowboys were fortunate that the Bengals deferred Chase’s deal until 2025, they waited until the end of August to extend Lamb’s contract. Lamb did not quite match Jefferson’s average salary, but his four-year deal yielded him $34 million per season with favorable cash flow. His $93 million in cash earned over the first three seasons trailed only Jefferson and exceeded anyone else besides Hill by more than $14 million.

Lamb was never likely to sign for the $25 million-per-year mark that Smith attained in March 2024, but the Jefferson deal undeniably propelled his asking price upward, as anticipated. The $82.1 million in new practical guarantees established a new high at the position.

Alternative outcomes: Deals are not negotiated in isolation. Agents are compensated for their proficiency in securing lucrative contracts for their clients and anticipating when other players are poised to receive their payouts. Lamb was undoubtedly monitoring the developments surrounding Jefferson and Chase—and vice versa. One of those players had to finalize their deal first, and perhaps Jefferson was always destined to be that player.

However, in 2023, the Cowboys could have approached Lamb with an intriguing proposition: Do you aspire to be the highest-paid wide receiver in the sport right now? Hill’s four-year, $120 million agreement with the Dolphins was the highest at the time, and despite significant agent inflation concealing the contract’s true value, deals were poised to reach $30 million per season once the young stars signed.

This would have been a difficult proposal to decline, especially with Lamb slated to earn $2.5 million in the fourth year of his rookie deal in 2023. A four-year, $122 million contract would have constituted an aggressive move for a player who had not yet achieved his All-Pro season, but it would have anticipated other wide receiver deals. It also likely would have split the difference between the gimmicky, backloaded pay structure of the Hill contract from 2022 and the more player-friendly structure of the Lamb contract, where $99 million of the deal is practically guaranteed upon signing.

In both scenarios, Lamb would have received his fourth-year base salary ($2.5 million) and his fifth-year option ($18 million). However, the Cowboys likely expended $14 million more on Lamb’s deal in 2024 than they could have negotiated in 2023. That brings our total to $63.9 million in additional funds expended by the Cowboys as a result of their negotiating tactics.

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What transpired: Nothing, to date. Parsons became eligible for an extension before the 2024 season, a period when the Cowboys were preoccupied with negotiations involving Prescott and Lamb. Instead, they compensated their star edge rusher his $3 million base salary during the fourth and final year of his rookie deal. Parsons is now under contract for 2025 at the cost of his fifth-year option, which amounts to slightly over $24 million.

In the spring of 2024, the 49ers’ Nick Bosa had propelled the edge rusher position forward with a five-year, $170 million extension the previous year. His $34 million average annual salary surpassed that of the Steelers’ T.J. Watt, the prior leader via a rookie deal extension in 2021, by nearly $6 million. Expressed as a percentage of the salary cap, the two deals were virtually indistinguishable: Bosa’s average salary constituted 15.1% of the 2023 cap, while Watt’s deal represented 15.3% of the cap in 2021.

No one, not even the Cowboys, can realistically envision a scenario in which Parsons is compensated less than the highest-paid edge rusher in league history. The sole question revolves around whether Parsons would merely surpass Bosa’s deal or leapfrog someone else’s. When the Cowboys neglected to finalize Parsons’ deal in 2024, other teams executed agreements that left the Cowboys behind.

Again, even after failing to secure the Parsons deal early, the Cowboys could have acted aggressively in the spring of 2025. Instead, they observed a series of star edge rushers secure progressively more lucrative contracts. Maxx Crosby signed an extension with the Raiders for $35.5 million per season. The Browns rewarded Garrett with $40 million annually to incentivize him to remain in Cleveland. And following a period of tepid speculation about potentially seeking opportunities elsewhere, Watt agreed to a three-year, $123 million extension with the Steelers, equating to $41 million per season.

When Parsons signs his deal, whether with the Cowboys or another team, it will eclipse Watt’s average salary—and by a significant margin. The most plausible contract is a four-year deal for $172 million, boasting a record average salary of $43 million per season. With Parsons’ $24 million salary for 2025 already guaranteed, this would culminate in a five-year commitment of $196 million, averaging slightly over $39 million annually.

Should Parsons truly adopt a combative negotiating stance, he could fulfill his fifth-year option and compel the Cowboys to engage in the franchise tag game, as they did with Prescott. Parsons would earn a projected $27.7 million in 2026 and $33.3 million in 2027 before attaining free agency in 2028 as a 29-year-old. Given the inherent injury risks for edge rushers, this does not represent Parsons’ optimal course of action, which is why an agreement with the Cowboys remains sensible for both parties.

Alternative outcomes: With Parsons and Watt nearing the expiry of their respective deals, the Cowboys should not have been surprised by the increasing valuations of edge rushers. Retaining Parsons was never likely to be a bargain, but his contract negotiations essentially took a backseat in 2024, as the Cowboys addressed Lamb and Prescott, who were closer to free agency and deemed higher priorities.

Alternatively, with Lamb and Prescott secured during the spring of 2023 in this alternate scenario, Parsons would have become the focal point of Dallas’s 2024 budget. With two years remaining on his existing contract, the Cowboys could have wielded considerable leverage during negotiations, and Jones cannot overemphasize the potential impact of an injury on negotiations, as Parsons was coming off a healthy 2023 campaign.

To surpass Bosa’s deal, the Cowboys would roughly align with that 15% AAV figure on the 2024 cap by offering Parsons a four-year, $152 million extension ($38 million annually). Dallas would also continue to compensate Parsons his $3 million base salary in 2024 and his $24 million fifth-year option for 2025, culminating in a six-year commitment of $179 million, averaging $29.8 million per campaign.

If Parsons’ deal ultimately reaches $43 million per year, postponing the deal until late in the 2025 offseason would have cost the Cowboys an additional $5 million annually. This would inflate the total cost of this negotiating strategy by $20 million.

In sum, postponing the compensation of Parsons, Lamb, and Prescott will likely cost the Cowboys nearly $84 million. That sum excludes the value of the no-tag clauses granted to Prescott, which elevated his second contract to a level unmatched by other quarterbacks in the league. Thus, it is not unreasonable to posit that the Cowboys’ negotiating tactics will have cost them approximately $100 million.

One hundred million dollars over nearly a decade will not bankrupt the franchise. The Cowboys possess exceptional financial stability, having been valued at a league-high $10.32 billion by Sportico last year. Nevertheless, $100 million could have attracted a few more gifted players over that decade. Could they have augmented their roster with another pass rusher or receiver, potentially