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Dallas Cowboys contract mistakes with Parsons, Prescott, Lamb

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Riddick: Jerry Jones conducting business like it's 1993 (0:56)

Louis Riddick explains why Jerry Jones' championship window with the Cowboys is closing and why his approach to Micah Parsons' contract is outdated. (0:56)

In an era in which "player empowerment" is a buzzy phrase and NFL teams pour the GDP of small nations into finding and retaining superstar players, one franchise has chosen to proudly install itself as the test case for what a team could do if it didn't care about making its best players happy. While most franchises coddle their young stars publicly and privately, sign them to contracts as quickly as allowed and position them as core pieces for their Super Bowl runs, the Dallas Cowboys have posited an entirely different argument: What if we just make them mad with no real benefit in return?

And so, in a league in which lesser quarterbacks have been happily paid tens of millions of dollars and have been given glowing reports by the coaches and general managers whose job security is tied to their success, the Cowboys discussed how paying a quarterback too much money hurts a team's chances of winning a Super Bowl before eventually paying Dak Prescott. They suggested they wouldn't redo star guard Zack Martin's contract because they had to pay pass rusher Micah Parsons, before then redoing Martin's contract.

Here, in 2025, the Cowboys might have taken things just a tiny bit too far. With Parsons entering the final year of his rookie deal on a fifth-year option, they and their star edge rusher spent the spring publicly throwing out vaguely positive ideas about an extension. Although most teams would have already done an extension with such a talented player after his third season in the league, 31 other franchises would have avoided saying what Dallas team owner Jerry Jones said, noting that Parsons missed six games with an injury last season. (It was four.) Parsons responded days later by publicly requesting a trade, citing both the public comments and an attempt by the Cowboys to negotiate a deal while excluding his agent, a move Jones didn't seem to deny.

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Now, I'll be clear: Just as Myles Garrett requested a trade out of Cleveland before signing a market-resetting contract to stay with the Browns, I don't think Parsons is heading anywhere. Dallas fans have every right to be terrified of their local team trading away a star player after the Luka Doncic fiasco, but this is hardly the first time the Cowboys have pushed a negotiation to its breaking point before getting a contract done with a star player. In fact, it seems difficult for them to conduct their business in any other way in terms of recent negotiations.

Instead, what has been missing from this conversation is one very important and impossibly frustrating fact. It would be one thing if the Cowboys were toeing an incredibly hard line on contract negotiations and getting players to take team-friendly compromises on contracts in the process. Bill Belichick's Patriots teams were known for their aggressive stances on contracts, in terms of both forcing stars such as Corey Dillon and Randy Moss to take pay cuts to get their foot in the door and then moving on from stalwarts such as Moss, Logan Mankins and Lawyer Milloy when their contracts outstripped their level of play, but Belichick was able to extract meaningful concessions and build better rosters as part of those negotiating tactics.

The Cowboys aren't saving any money with their negotiating process. In fact, the delays and inability to get these deals done on time have cost them millions of dollars, significant negotiating leverage and untold amounts of goodwill with both their players and fans. Success, as the Patriots dynasty showed, can overshadow a lot of sudden breakups, tough negotiations and fan favorites leaving town. The Cowboys haven't been able to fall back on their on-field performance as proof they're making the right decisions.

Let's look at Dallas' three biggest stars and what the organization's negotiating philosophy has accomplished. How much has the organization cost itself by being too slow or too reticent to get contracts done with Prescott, Parsons and CeeDee Lamb? What has that meant for the franchise? And what could have happened if the Cowboys had been more like the Eagles in getting contracts done before absolutely necessary?

Let's start at quarterback, where the Cowboys spent a half-decade hemming and hawing before paying Prescott more money than any other quarterback. What has gone down with Prescott, and what could have happened if they had been smarter about how they approached the situation?

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?

Dak Prescott

What actually happened: Let's start in 2019, when Prescott was entering the final year of his rookie deal, which had been one of the league's biggest bargains. 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 on a deal. At a position at which most every team would get a contract done earlier rather than later, they let him play out the final year of his deal.

In 2020, the Cowboys used the franchise tag to retain Prescott, who made $31.4 million. The organization reportedly offered him a deal worth $33 million per season with over $100 million in guarantees, but it's unclear how much of that money was fully guaranteed at signing as opposed to being partially guaranteed for injury. With Prescott in position to make $37.7 million on a second franchise tag in 2021 before hitting unrestricted free agency the following year as a 29-year-old, he had more leverage than the organization.

He showed that 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 larger contract from the Cowboys to avoid losing him for nothing in free agency the following season. Prescott signed a four-year, $160 million deal, averaging $40 million per year. And crucially, with all of his leverage, he was able to get the Cowboys to add both no-trade and no-tag clauses to his deal, which gave him the ability to hit unrestricted free agency at the end of his extension.

With one year left on his deal 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 pact. Inking 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 good measure, Dallas gave him no-tag and no-trade clauses for the second consecutive deal.

This is such a player-friendly deal that other quarterbacks simply haven't been able to approach it in their own negotiations. Brock Purdy, who in many ways became the successor to Prescott 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 deal with the Bills was essentially a new contract after wiping away what was left on his old deal, but even that came in at $55 million per season. Teams appear to see the Prescott deal as an outlier and have convinced agents and players accordingly.

What could have happened: Let's go back to 2019 again. Prescott was set to make just over $2 million. That summer saw former first-round picks Carson Wentz and Jared Goff sign deals within days of each other in June. Wentz's deal came in at four years and $128 million, for an average of $32 million per season. Goff narrowly topped him at four years and $134 million, for $33.5 million per season.

If the Cowboys had been aggressive, they could have gotten the Prescott deal done before either of those contracts had been put to paper. With his asking price north of $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 the Eagles eventually gave Wentz? At $32 million per year, that would have been a fair deal for both parties.

We don't know what the structure of that deal would have looked like, but let's plug in a $53 million signing bonus, which roughly matches the percentage of Prescott's actual deal the following year that was paid out up front. (The Eagles structure their deals differently than the Cowboys, who prefer to give out a large signing bonus up front, whereas the Eagles opt for bonuses throughout the early years of the deal.) The Cowboys would have him signed for five years and just over $130 million, for an average of $26 million per season. Over the first four years of the contract -- between 2019 and 2022 -- they would have saved more than $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 move 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 been offered one.

If they had done the deal in 2019, the Cowboys wouldn't have needed to use either of the franchise tags on Prescott in the first place, which would have provided the franchise some negotiating leverage in building his subsequent deal. Prescott also wouldn't 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's unclear how valuable the no-tag clause is, but it's also clear the right price isn't zero dollars, either. There's a reason the Bears said no when Caleb Williams reportedly asked for the same no-tag clause at the end of his rookie deal. Williams, years away from free agency, didn't have the leverage to back his new franchise into a corner.

Entering the final year of that extension in 2023, the Cowboys would again be faced with a tough decision. Prescott was coming off a season with a league-high 15 interceptions, but he had been the quarterback of a team that won 12 games and blew out Tom Brady and the Bucs in Tampa to win a playoff game. He had missed five games with a thumb injury, and there had been some brief chatter that backup Cooper Rush was a viable alternative, but Dallas was always going to do an extension with him.

Again, what would have been a realistic deal if the Cowboys had been relatively aggressive? Jalen Hurts signed a five-year, $255 million extension that April, and Aaron Rodgers had become the first quarterback to top $50 million per year on a deal the prior March, albeit on a shorter-term pact. Deshaun Watson had inked a five-year, fully guaranteed deal worth $46 million per season as part of his trade to the Browns, although those were unique circumstances relative to what Prescott would have been facing.

There's another round number here that seems realistic: $50 million. Maybe a four-year, $200 million pact wouldn't have gotten things done, but with the franchise tags available for leverage, a disappointing season in Prescott's rearview mirror and a smaller contract to work off, $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 pushed the average annual salary sweepstakes forward, giving Prescott a path to get $60 million per year.

With one year and $18.8 million remaining on his prior deal 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 hand out $66 million at the top of the contract, meaning he would make more than $84 million in Year 1. Between 2023 and 2027, which is where the practical guarantees for full base salaries end on his real contract, the Cowboys would have saved another $32.7 million by getting the deals done a year earlier, bringing the combined savings up to $49.9 million:

This doesn't include 2028, when Prescott has a $55 million base salary on his deal, $17 million of which guarantees in 2027. While that could turn out to be a bargain and provide some value by the time we get to that ballpark, it's tough to believe the surplus value of that one year will be worth all the money the Cowboys could have saved by virtue of getting Prescott's two massive contracts done earlier. The 2027 season in his theoretical deal also likely wouldn't have been guaranteed, giving them some more flexibility at a time when their quarterback is likely to be on the decline.

And again, if $49.9 million over nine years doesn't sound like much, consider the value of the two no-tag clauses. Would Prescott and his representation have been willing to take those clauses out of the agreement if the Cowboys had offered $5 million more per season over those two contracts? If so, that's another $45 million in savings. Dallas would have had the ability to use the franchise tag on somebody else in 2020, which would have helped it in negotiations with Amari Cooper, who ended up signing a five-year, $100 million deal. Would the franchise have saved money on the Cooper contract?

Realistically, we're looking at about $50 million and some meaningful, incalculable amount more lost by the Cowboys by waiting to get Prescott's deal done twice. Waiting did not save them any money or prove anything beyond the fact that the organization failed to get the negotiations over the line until it had forfeited virtually all of its leverage, allowing him to sign two of the league's most player-friendly deals over the past decade.


CeeDee Lamb

What actually happened: The math with the Lamb contract is a little simpler and revolves mostly 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 racked up 1,359 yards and nine touchdowns, firmly establishing himself as Prescott's top wideout. 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 wideouts in the NFL.

Spring 2023 would have been a great time for the Cowboys to sign Lamb to an extension. Although veterans such as Tyreek Hill, Davante Adams and Cooper Kupp had reset the wideout market in 2022, there was another reckoning coming for players near the end of their rookie deals. 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 get paid more than them. But some of these wideouts were going to raise the bar for compensation, and it was always going to be better for teams to get out in front of those contracts.

Instead, contracts stagnated. The biggest contract signed by any wideout in 2023 was the four-year, $44 million deal Allen Lazard inked with the Jets in free agency. Jefferson, Aiyuk and the rest of the 2020 draft class all played out the fourth year of their rookie deals. Maybe there was never a scenario where the Cowboys agreed on 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 1,749-yard season and a first-team All-Pro appearance in 2023, there was no debating Lamb's importance. Furthermore, he was now one 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 franchise-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 wideout after seeing how it went with Prescott.

If 2023 would have been the best time to sign Lamb, the second-best time would have been spring 2024, before so many of the aforementioned wideouts signed their own extensions. It's no surprise that the Eagles got their work done quickly, extending Smith on a deal worth $25 million per year in March. In April, Lamb's closest comp 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 per year. In May, Collins signed for $24.3 million per year, which has proved to be one of the biggest bargains of any veteran deal. Waddle's extension came in two days later at $28.3 million per season.

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Why Stephen A. doubts the Cowboys will make the NFC Championship

Stephen A. doesn't believe Dak Prescott's claim that the Cowboys will make the NFC Championship, having heard it year after year.

The following week, the biggest domino fell. Jefferson signed a four-year, $35 million per season deal with the Vikings. Hill's and Adams' deals had contained meaningful amounts of fake money at the end of their contacts to raise the per-year value, but Jefferson's deal was much closer to a true value of $35 million, per OverTheCap.com.

Although the Cowboys were lucky to have the Bengals hold Chase's deal off until 2025, they waited until the end of August to sign Lamb to his extension. Lamb didn't quite match Jefferson's average salary, but his four-year deal netted him $34 million per season with favorable cash flow. His $93 million in cash earned over the first three seasons was second behind Jefferson and more than $14 million ahead of anybody else besides Hill.

Lamb was never signing for the $25 million-per-year mark that Smith hit in March 2024, but the Jefferson deal undoubtedly propelled his asking price upward, as it should have. The $82.1 million in new practical guarantees was a new high at the position.

What could have happened: Deals don't happen in a vacuum. Agents are paid for their abilities to both get their players paid and anticipate when other players are going to get their money. Lamb was undoubtedly waiting to see what Jefferson and Chase would make -- and vice versa. One of those guys had to get his deal done first, and maybe it was always going to be Jefferson.

In 2023, though, the Cowboys could have gone to Lamb with a tantalizing question: Do you want to be the highest-paid wide receiver in football right now? Hill's four-year, $120 million deal with the Dolphins was the highest at the time, and despite a massive amount of agent inflation hiding the true value of the contract, deals were bound to reach $30 million per season when the young stars signed.

That would have been a difficult proposal to turn down, especially with Lamb set to make $2.5 million in the fourth year of his rookie deal in 2023. A four-year, $122 million contract would have been an aggressive move for a player who hadn't put together his All-Pro season, but it would have anticipated other wideout deals. It also would have likely 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 at the time of signing.

In both cases, Lamb would have been paid his fourth-year base salary ($2.5 million) and his fifth-year option ($18 million). But the Cowboys likely spent $14 million more on Lamb's deal in 2024 than they could have negotiated for in 2023. That takes our total to $63.9 million in extra money paid by the Cowboys because of their negotiating tactics.


Micah Parsons

What actually happened: Nothing, so far. Parsons was eligible for an extension before the 2024 season, when the Cowboys were busy negotiating with Prescott and Lamb. Instead, they paid their star edge rusher his $3 million base salary in 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 comes in at just over $24 million.

In spring 2024, 49ers' Nick Bosa had propelled the edge rusher position forward with a five-year, $170 million extension the year before. His $34 million average annual salary was nearly $6 million ahead of the Steelers' T.J. Watt, the prior leader via a rookie deal extension in 2021. By cap percentage, the two deals were virtually identical: Bosa's average salary was 15.1% of the 2023 cap and Watt's deal was 15.3% of the cap in 2021.

Nobody, not even the Cowboys, can pretend to construct a scenario where Parsons was anything less than the highest-paid edge rusher in league history. The only question was whether Parsons would be topping Bosa's deal or moving past somebody else's. When the Cowboys neglected to get Parsons's deal finished in 2024, other teams made deals that left the Cowboys behind.

Again, even after failing to get the Parsons deal done early, the Cowboys could have been aggressive to act in spring 2025. Instead, they watched a series of star edge rushers secure increasingly more valuable contracts. Maxx Crosby signed an extension with the Raiders for $35.5 million per season. The Browns gave Garrett $40 million per year to change his mind and stay in Cleveland. And after a few months of half-hearted chatter about potentially going elsewhere, Watt agreed on a three-year, $123 million extension with the Steelers, which comes out to $41 million per season.

When Parsons signs his deal, whether that comes with the Cowboys or somebody else, it'll top Watt's average salary -- and not by a few pennies. The most likely contract is a four-year deal for $172 million, with a record average salary of $43 million per season. With Parsons' $24 million salary for 2025 already guaranteed, that would come out to five years and $196 million, for an average of just over $39 million per year.

If Parsons really decides to play hardball, he could play out the fifth-year option and force the Cowboys to play the franchise tag game like they did with Prescott. Parsons would earn a projected $27.7 million in 2026 and $33.3 million in 2027 before hitting free agency in 2028 as a 29-year-old. That's not the best-case scenario for Parsons given the injury risks for edge rushers, which is why a deal with the Cowboys makes sense for him, too.

What could have happened: With Parsons and Watt approaching the end of their respective deals, the Cowboys shouldn't have been taken aback by rising edge rusher valuation. Retaining Parsons was never going to be a bargain, but he essentially spent 2024 on the contractual back burner as the Cowboys dealt with Lamb and Prescott, who were closer to free agency and higher priorities.

Instead, with Lamb and Prescott taken care of during spring 2023 in this alternate scenario, Parsons would have been the focus of Dallas' 2024 budget. With two years of runway left on his existing contract, the Cowboys could have had plenty of leverage while negotiating a deal, and Jones can't even overstate the impact of a potential injury impacting the talks, as Parsons is coming off a healthy 2023 campaign.

To top Bosa's deal, the Cowboys would roughly match that 15% AAV figure on the 2024 cap with a four-year, $152 million extension ($38 million per year) for Parsons. Dallas would also still pay Parsons his $3 million base salary in 2024 and $24 million fifth-year option for 2025, making this a six-year deal for $179 million, averaging $29.8 million per campaign.

If Parsons' deal does come in at $43 million per year, waiting to do the deal late in the 2025 offseason would have cost the Cowboys an additional $5 million per year. That would add a total of $20 million to the cost of this negotiating philosophy.

In all, waiting to pay Parsons, Lamb and Prescott will likely cost the Cowboys nearly $84 million. That figure doesn't include the value of the no-tag clauses afforded to Prescott, which helped push his second contract to a level that the rest of the league hasn't matched with their own quarterbacks. So, it's not out of line to suggest the Cowboys' negotiating tactics will have cost them approximately $100 million.

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Stephen A. calls Jerry Jones' dealings with Micah Parsons 'egregious'

Stephen A. Smith vents his frustrations about Jerry Jones' latest comments on Micah Parsons' contract feud with the Cowboys.

A hundred million dollars over nearly a decade isn't going to make or break the franchise. The Cowboys are especially secure, as they were valued at a league-high $10.32 billion by Sportico last year. A hundred million dollars certainly would have landed the Cowboys a few more talented players over that decade, though. Could they have added another pass rusher or receiver who might have made the difference in those narrow playoff losses to the 49ers? Would there have been more budget space cleared up to keep useful players such as Amari Cooper, Tyler Biadasz and Dorance Armstrong with the organization? Would the extra budget space have allowed the Cowboys to avoid ill-fated moves for the likes of Brandin Cooks and Eric Kendricks?

It's impossible to say how the Cowboys would have changed if they had been more aggressive with their extensions, but there's one thing that's clear: For the $84 million (or more) extra they spent, the Joneses got absolutely nothing in return. They were forced to hand Prescott two of the most player-friendly contracts in the league and apparently upset Parsons enough to inspire a public trade request. Some teams are willing to overpay a bit to ensure good vibes in the locker room. The Cowboys paid nearly nine figures for bad vibes instead.


Why are the Cowboys operating this way?

It hasn't always been like this for Jones and the Cowboys, who have had some successes by acting more aggressively in years past. Tyron Smith, one of the team's best players of the past quarter-century, signed an eight-year, $64 million deal the summer after his third season. It turned out to be a bargain as offensive tackle contracts continued to increase; while Smith dealt with injuries later in his career, he routinely made between $10 million and $12 million a year in an era in which top tackles eventually approached and topped $20 million per season. Fellow first-round offensive lineman Travis Frederick also signed his deal after three years, although his career was altered by a bout with Guillain-Barre syndrome.

Not every deal played out as well as Smith's, to be fair, even if they came with varying levels of drama. Running back Ezekiel Elliott briefly held out in Mexico after his third season before signing a six-year, $90 million extension. Linebackers Sean Lee and Jaylon Smith, who were both second-round picks, signed their deals after three years. Edge rushers DeMarcus Lawrence and Anthony Spencer each hit the franchise tag, with Lawrence signing an extension, while Spencer played out two tags. And Martin, the team's star guard, signed an extension after his fourth season making him the highest-paid guard.

Getting a deal done early is no guarantee things will work out. Elliott declined throughout his second contract. The Cowboys made a significant bet on Smith that went terribly. I've made comparisons above to the Eagles and how aggressive they are with contracts, but they don't have a 100% hit rate, either; the Wentz contract they signed after three years turned out to be a mess, as the once-quarterback of the future was traded away after his fifth season.

I've seen a range of arguments for why the Cowboys appear to be approaching their most important contracts this way. Let's evaluate them and see if they make sense.

The Cowboys want the attention!

No team owner finds his way in front of microphones and cameras more than Jerry Jones. In an era in which the Cowboys haven't had championship-winning success, one way to keep attention on the sport's most popular team is to stretch out every contract negotiation until the last possible moment, creating headlines and stories along the way.

I'm not so sure. You could spin the Prescott contract getting done on the first Sunday of Week 1 both ways. Yes, the Cowboys spent the entire offseason getting every debate show and columnist to speculate about his future and whether it was a good deal to pay him a massive amount of money. At the same time, Jones & Co. didn't exactly get to take a victory lap for their troubles, given that the Prescott news was quickly buried by actual football hours after the deal was done.

At the same time, the Cowboys continue to garner the attention of those same shows and columnists, even when they aren't in the middle of negotiating contracts. There are much less expensive ways of attracting attention from the national media than waiting to sign contracts until cost has increased and leverage has dried up. They make headlines by winning, losing or merely by existing in relation to more successful teams. And frankly, if they had been better about getting these deals done, they could have used that money to make more significant additions to their roster, which would have kept attention on them throughout the offseason.

It's a sound move for financial/cap reasons.

While I suppose the Cowboys saved some cash by waiting to pay Prescott twice and could have earned interest or additional cash by investing that money, I can't imagine an NFL team with Dallas' budget being so penurious and focused on the amount of cash it could earn by waiting until the last second to pay star players.

It's true that the Cowboys waiting until the end of these respective deals to pay Prescott, Lamb and Parsons keeps their cap numbers low earlier in their contracts, which aligns with a reality in which the cap often (but doesn't always) go up year on year. By waiting to sign their big stars, though, they lose the benefits of folding those bargain years at the end of rookie deals into a new deal, which allows for smoother cash and cap figures.

As a result, the Cowboys have often been a team playing the restructure game, where they'll pay a large signing bonus up front, then annually convert their top players' base salary to a bonus, guaranteeing the money and spreading the accounting over five years for cap purposes. That's fine when they're healthy and productive, but if things go awry, it can lead to messy dead cap situations. When Prescott took over for an injured Tony Romo and kept the starting job, the Cowboys were left with little choice but to cut their former starter. They paid $19.6 million in dead money over the next two seasons, which would be the equivalent of nearly $32 million today.

Instead, the large bonuses have led to significant one-year cash payouts. Prescott took home $75 million in 2021 and a whopping $86.2 million in 2024, with the latter still standing as the largest amount of cash earned by any player in any season in NFL history. Lamb's $39.2 million take-home pay in 2024 is the largest for any wideout in any season in league history, coming one year after he took home $2.5 million. The Cowboys aren't saving money, as I covered above. They're paying a lot less early and a lot more immediately afterward.

Those figures also lead me to be skeptical over concerns that Dallas' ownership group doesn't have the liquid cash to get these deals done. It's true that the organization has spent less cash than the vast majority of other franchises at times over the past 15 years, but over the past three seasons, the Cowboys have ranked 11th, 16th and now 12th in cash spending.

The Cowboys have traditionally been a draft-and-develop team that doesn't spend a ton in free agency, and that's going to lead to stretches where they don't have a ton of cash being spent. For what it's worth, while the Eagles were third in cash spent last season, the other five teams in the top six -- the Browns, 49ers, Falcons, Dolphins and Jaguars -- all posted losing records. It's tempting to assume the Cowboys are being cheap by not matching the cash spend of other teams, and it's certainly at odds with any idea that the organization is selling out to try and win in any given season.

But when the Cowboys have needed to get the big deals done for their homegrown players in recent years, they've managed to do so. Again, had they done the contracts earlier, they would have saved cash that could have gone to other players, either within or outside of the organization. If they are really keeping cash spending low, it hasn't been on the Prescott's and Lamb's of the world; it has been on guys like Biadasz, Armstrong and cornerback Chidobe Awuzie, all of whom have walked out the door without breaking the bank.

And now, with the league allowing teams to take on private equity investments for minority shares of franchises, the Cowboys could have more money than they would ever need to sign players if the Jones family was really cash-poor and wanted to sell a small portion of the team to outside investors. I suspect Jones would have had no trouble raising cash in the past if needed. You can certainly take issue with how this team manages its budget, but that hasn't precluded it from getting these deals done. If anything, it has cost it more money.

Jones is past his prime/out of touch/something worse.

While every owner has a meaningful role behind the scenes in making decisions, Jones is rightfully regarded as arguably the league's most hands-on owner. He's the de-facto general manager and has been so for most of his tenure in Dallas. Combining the decision-making I've broken down with public commentary that has ranged from awkwardly antagonistic to statements that are out of touch with reality, it's understandable to see concerns that the 82-year-old is no longer up to the task of being his team's lead executive.

Well, that might be true, but I'm also not so sure Jones is the one making all the decisions on a day-to-day basis these days. As I mentioned in my piece on the Jonathan Mingo trade this past season, the Cowboys do a lot of things that don't align with what Jones has said or done in the past. They have one of the largest analytics groups in the league. They've stopped paying running backs, almost to a comical degree. They've pursued a "second-draft" philosophy for young talent to try to find diamonds in the rough. They've repeatedly invested first-round picks in offensive linemen, trying to build through the line of scrimmage. If anything, in many ways, the team the Cowboys appear to be emulating are the pre-2024 Eagles.

It's fair to wonder how much of a role Jerry's son, Stephen Jones, has on day-to-day decision-making for the organization. While I'm sure Jerry Jones still has plenty of power and might be insistent on the Cowboys being difficult in negotiations with their biggest stars, it's also realistic to point out there's a consistent and meaningful disconnect between what he has said publicly over the past few years and what the Cowboys are actually doing with their decisions. That could be the product of an owner who isn't careful with his words, but it could also be because he simply isn't doing as much as he used to.

The Cowboys feel like they've been burned by injuries when players have signed extensions.

The elder Jones went out and told us one of the reasons he hasn't been enjoying signing his top players to extensions: injuries. As covered earlier, Jones criticized Parsons for missing six games this past season, then discussed how he had made Prescott the highest-paid player at his position, only for his quarterback to then miss two-thirds of the season.

Again, it's fair to raise credibility concerns with Jones: Parsons missed four games, and if Jones is referring to Prescott's 2024 season, he played eight of 17 games. If he's instead referring to the 2020 campaign, when Prescott only played five games before injuring his right ankle, that came when Prescott was on the franchise tag and before he signed that massive first extension.

Other players have had issues after signing their deals, too. Cornerback Trevon Diggs, who tore his left ACL after signing an extension in 2023, hasn't been the same player since returning from his injury. Lee missed all of 2014 with a torn left ACL. Lawrence missed half the year in 2021. Tyron Smith played two full seasons after signing his extension and then never topped 13 games again. And Romo missed significant time in 2010, 2015 and 2016 during his pair of extensions.

Of course, if you made a list of any team's players who were signed to extensions, you would be able to find years where their best players missed time. This is football and players get hurt. The Cowboys might have been hit by relatively bad luck with some of their injuries, but if you're only going to count permanently healthy players as successful contracts in the NFL, you're not going to do many good deals.

Jones' argument really falls apart considering what has happened to many of these players before they signed extensions with the team. If the Cowboys were really worried about players getting injured after signing big-money deals, they would shy away from handing out contracts to players with recent injuries or meaningful injury histories.

Instead, Prescott had a traumatic ankle injury, and the Cowboys signed him to a $160 million extension after the season anyway. They signed Lee to a significant deal after he missed 15 games between 2012 and 2013 with toe, hamstring and neck injuries. They signed wide receiver Michael Gallup to a five-year, $57.5 million deal in the months after he tore his left ACL. Jaylon Smith had a traumatic knee injury in college, and while he stayed healthy early in his NFL career, the Cowboys signed him to a six-year, $68.4 million extension, only for his performance to quickly decline.

Do the Cowboys have buyer's remorse on some of their deals because of injuries? Of course. Is that a fair reason to not pay Parsons? Absolutely not. The 49ers didn't raise those concerns with Bosa, who missed most of his second season with a torn ACL. The Browns didn't criticize Garrett for struggling with an ankle injury earlier in his career or playing through a shoulder issue that sapped his production late in the 2023 campaign. There's no reason for them to publicly scrutinize Parsons' health or use that as an argument against paying him. There's also scant evidence that they'll use that as a meaningful part of their decision-making process.

My belief is there's some element of organizational inertia driven by ownership and an unwillingness to be the first team over existing salary expectations until it's absolutely necessary preventing the Cowboys from getting these deals done in time, compounded by unnecessary self-flagellating commentary in public and Jones' reported attempts to negotiate with players away from their agents.

There were also factors influencing each deal in a unique way. These are the same Cowboys who wanted to draft Connor Cook and Paxton Lynch before settling for Prescott in 2016. I'm not sure they were ever really committed to Prescott until they had no choice. Lamb was in a position where elite wideouts were all waiting for each other to sign a deal. And Parsons was put on the backburner as Dallas tried to resolve both of those issues.

What's so frustrating for Cowboys fans is that things don't have to be this way. These are unforced errors, mistakes that look even worse when the team's divisional rivals in Philadelphia approach things from the opposite perspective and have made it to four Super Bowls over the past two decades. Whether it's $84 million or something more, the Cowboys continue to unnecessarily burn money and antagonize some of the most important people inside and outside their building with no real benefits in return.