There are two things Jerry Jones seemingly loves more than anything else: winning football games and negotiating contracts. The Dallas Cowboys’ three championships in the 1990s helped cultivate Jones’s reputation as an owner who will do anything to succeed—unless, of course, it meant looking like a mark at the negotiation table.
Jones is notorious for playing hardball with his best players. In 1993, Emmitt Smith sat out the first two games of the season after his request for a contract on par with those of the league’s best quarterbacks was denied. Smith wound up dropping the demand after the Cowboys started 0-2, took a more reasonable salary, and went on to earn league MVP honors. Jones came out on top. A few months later, he won again when Troy Aikman signed an unprecedented eight-year, $50 million deal that made him the then-highest-paid player in league history. Aikman and his agent Leigh Steinberg got that all-important title, but when the salary cap era started the following year, the franchise quarterback was essentially locked down at a fixed cost for the remainder of the decade. The 49ers, Dallas’s biggest threat in the NFC, had just given quarterback Steve Young a five-year, $26.75 million deal. But while the annual money of the two contracts was essentially the same, Young and San Francisco could have been right back at the negotiation table a few years later, while Jones still had Aikman at the 1993 price for three more years.
Aikman and Smith, perhaps the two most important players in the team’s dynastic run, were forced to wait … and wait … and wait to get their paydays. Even back in the ’90s, players didn’t typically sign big contracts weeks or, in Aikman’s case, months into the regular season. But Jones was never a typical NFL owner. He was a key member of the team, and that team would go on to win a Super Bowl a few months after Smith and Aikman signed their deals. They’d also win another title two seasons later. It’s easy to see why Jones would think he had this whole salary cap thing figured out and that his negotiation style was the best way to handle the contract demands of star players.
A quarter century later, though, Jones hasn’t made many adjustments. And his tack doesn’t work as well in 2024 as it did in the early ’90s. There are more voices in the room now who are dictating the overall roster-building strategy in Dallas—including Jones’s son and chief operating officer, Stephen Jones, and vice president of player personnel, Will McClay. And there are other impediments to doing things Jerry’s way.
Jones has never been one to just accept the market price for a player. And over recent years, he’s convinced several key players to sign atypical deals to keep the players’ annual cap numbers down, continuing a Dallas tradition that dates back to before he purchased the team. All-Pro left tackle Tyron Smith signed a rare 10-year deal in 2014 that was similar to the one Aikman inked in the ’90s. When Jones gave Ezekiel Elliott an extension in 2019, he back-loaded the deal—a gamble that did not pay off when the running back’s play predictably fell off years later. Dallas tore up La’el Collins’s rookie contract a year early and gave him more guaranteed money to get him signed before the offensive tackle market was set to balloon, and it made a similar deal with linebacker Jaylon Smith, who mentioned the business connections Jones could offer as a reason for re-signing with the team. These moves may have saved the Cowboys a few million against the cap initially, but they didn’t provide the long-term advantages Jones may have hoped.
Now, the Cowboys are facing a rash of contract negotiations all at the same time. Earlier this week, superstar wideout CeeDee Lamb signed a new four-year, $136 million contract with Dallas, but not until after some very public negotiations. It’s important to note that the new deal did not make Lamb the NFL’s highest-paid receiver—that distinction belongs to Justin Jefferson—but he did receive the largest signing bonus ever for the position. Another atypical deal for the Cowboys.
But while that signing was welcome news for Cowboys fans, they can’t get too excited given the players who are still sitting without deals. Dak Prescott is set to enter the final year of his contract and is all but certain to hit free agency next offseason (due to a clause in his contract, the team is unable to use the franchise tag on him next March). All-Pro guard Zack Martin and defensive end DeMarcus Lawrence are also entering contract years, and the team’s best player, superstar pass rusher Micah Parsons, and emerging guard Tyler Smith are eligible for extensions, and both will likely be seeking new deals before playing any football next season.
This logjam should sound familiar to Cowboys fans. The team was in a similar spot the last time its quarterback was looking for a contract extension, in 2019. At that time, Prescott was coming off a big season and was looking to cash in before the final year of his rookie contract, which had been one of the best bargains in the sport. But the Cowboys also needed to get deals done with Elliott, Amari Cooper, Collins, and Lawrence that offseason. Most of those guys got their money, including $50 million in guaranteed money for Elliott.
Prescott, though, did not get paid that offseason. And the following offseason, with Lawrence still in need of a deal, the Cowboys made him their priority and used the franchise tag on Prescott, who was coming off another monster campaign. Dallas could have signed Prescott for around $30 million per year had the sides gotten a deal done before he played on the tag. But that didn’t happen, and even after Prescott suffered a gnarly ankle injury that ended his season after five games, his price went up. The Cowboys eventually gave Prescott a four-year, $160 million deal in the 2021 offseason—which was in line with the quarterback market at the time. The deal included a no-trade clause and an agreement not to use the franchise tag on Prescott if he played out the full four years. So not only did Prescott get $10 million more per year than he would have had the Cowboys been more proactive, but he also got protection against this sort of thing ever happening again.
That brings us to now, when the Cowboys and Jones are trying to play hardball with Prescott once again—only this time, the quarterback has all the leverage. There is no looming threat of the tag. The Cowboys can’t trade Prescott to a team he doesn’t want to play for, so there’s really no incentive for him to get a deal done now. And after the going rate for franchise quarterbacks reached $55 million per year this offseason, Prescott, who’s coming off the best season of his career, could soon become the NFL’s first $60 million quarterback. If he hits free agency, that number could be even higher.
Getting to free agency is a dream scenario for a star quarterback—which is the main reason teams never let it happen. We’ve never seen a QB like Prescott—who has no obvious question marks in his game—hit the open market in the NFL. Drew Brees was a free agent in 2006 and had New Orleans and Miami fighting over him, but the Dolphins backed out because of legitimate concerns about his surgically repaired shoulder. Kirk Cousins was the big free agent prize of the 2018 offseason, but he was considered a fringe top-10 quarterback (if that) when he left Washington, so there were questions about his value. Tom Brady made it to free agency in 2020, but he was coming off his worst season in years and was well over 40 years old by that point. He wasn’t a long-term solution for any team. Prescott, meanwhile, just turned 31, he finished second in MVP voting last season, and he has been a top-five quarterback, statistically speaking, since entering the league in 2016. There are no questions about his ability or his age. Nothing like this has ever happened before.
Jones’s patient and stubborn negotiating tactics have worked out for him in the past, but Prescott has gotten the better of him before by waiting him out. And it doesn’t sound like Jones is in a rush to make a deal happen.
“Contracts isn’t the end-all solution, and some of the best decisions that I’ve been a part of with the Cowboys have been when we didn’t have contracts one way or the other, with a player on our team or some other team,” Jones said, via ESPN. “So I quit a long time ago getting bent out of shape about having anybody under contract or not. And there’s all kinds of other things other than a contract that could change the outcome of him being under contract—injury, the level of play—so you can’t just pick that and say, ‘That should give you a better feeling about our team,’ or me a better feeling. The whole thing has a lot of moving parts.”
Jones seems to be under the impression that he still has some level of control in this situation. That the market, which has seen lesser quarterbacks like Jared Goff and Tua Tagovailoa recently sign massive deals, has not already locked him and his starter into a record-breaking salary. That something could happen over the next few months that will change the math. That his stubbornness will pay off and “waiting for a few more leaves to fall” will pay the same dividends it used to back in the good old days. Well, let’s humor Jerry, go over all of the possible outcomes for Prescott and the Cowboys this season, and figure out how they could affect the quarterback’s future. We’ll start with the best possible (and least likely) scenario for both parties.
Dak plays well, and the Cowboys win the Super Bowl.
Hahahahaha. Ahahahaha. HAHAHAHAHAHA.
Sorry, just had to get that out of my system. Take one look at the Cowboys depth chart, and you’ll understand why this is such a wild idea. There are some big names at the top of the roster, including Prescott, but this year’s team is concerningly thin further down the depth chart. Lamb is one of the best receivers in the game, but he’ll be surrounded by what’s left of Brandin Cooks and someone called Jalen Tolbert in the wide receiver room. Jake Ferguson is a fine tight end but little more than that, and last year’s second-round pick, Luke Schoonmaker, is coming off a disappointing rookie season. Somehow, Elliott is the team’s starting running back again, which isn’t a good thing. And the once all-powerful offensive line is still good, but it features a rookie starting at left tackle and another one potentially starting at center. And, no, I do not trust Mike McCarthy to make it all work.
What would happen next: Prescott now owns the Cowboys, and Jerry writes him into his will. After retiring in 2028, Prescott wins Dancing With the Stars and is later elected president of the United States.
Dak plays well, and the Cowboys crash out of the playoffs (again).
OK, that’s more like it. The Cowboys remain a flawed but talented team with a very good quarterback and questionable coaching—as they have been dating back to the Tony Romo days. They’re built to play well during the regular season and lose to the first good team they come up against in the playoffs, only for Jones and Co. to act shocked every time it happens.
When it inevitably happens again this season, Prescott will be blamed for it. It doesn’t matter whether that’s fair; it’s just the reality for any big-money quarterback in today’s NFL. And typically for good reason. Quarterbacks, more than any other individual on the team, determine the outcomes of games. If a team loses in the playoffs, there’s a good chance its quarterback didn’t play well enough to win—or the other team’s quarterback just played better. While that has certainly been the case in Dallas at least once or twice over Prescott’s career, his individual statistics suggest he deserves better than his 2-5 postseason record. Compare Prescott’s performance in his postseason losses to the league-average performance for losing quarterbacks in the playoffs:
Prescott’s Performance in Playoff Losses Since 2016
Prescott has played poorly in some of the losses, most notably against the 49ers in two of the past three seasons. But those are really his only playoff stinkers. He’s played at an elite level in some of the Cowboys’ most devastating losses, including the 2016 divisional-round loss to Green Bay, in which Prescott went 24-for-38 for 302 yards and three touchdowns but was outdueled by Aaron Rodgers.
Prescott’s Five Playoff Losses
Prescott hasn’t been the issue. At least not the main issue. That’s been the defense, which has surrendered more than 30 points per game in those five playoff losses. In an alternate universe—or on a more well-rounded team—Prescott might be viewed in a totally different light.
Joe Burrow is the NFL’s highest-paid quarterback by average annual salary. He’s also the only active quarterback who has beaten Patrick Mahomes in the playoffs, and he has earned a clutch reputation thanks to his postseason success. In just two playoff trips, Burrow’s already racked up five wins. But compare his performance in playoff wins to Dak’s performance in playoff losses, and you might understand why these labels don’t mean much and shouldn’t be factored in when negotiating contracts.
Playoffs: Prescott’s Losses Vs. Burrow’s Wins
Prescott is not some regular-season fraud who gets exposed in the postseason. He just hasn’t gotten the breaks that others have in January. And Dallas hasn’t provided him with the team or coaching staff to overcome the bad luck. When QBs enter contract negotiations, we often look at it from the team perspective: Can this guy really take X team to a Super Bowl? But with all the leverage he holds, Prescott is in a position where he can flip the question and ask whether the Cowboys have what it takes to bring him to a Super Bowl. After another early playoff exit, the answer could be obvious.
What would happen next: Despite the Cowboys’ best effort to re-sign Dak after the season, he realizes that his best opportunity to win a Super Bowl is somewhere else, and he signs a record-breaking deal with another team.
No matter where Prescott signs, whether in Dallas or elsewhere, the overall numbers aren’t likely to change. It would be three or four years, right around $60 million per season. We’ve never seen a quarterback as talented as Prescott hit free agency, but Cousins has been a free agent twice, and while he was able to land significant deals in both cases—including the first fully guaranteed multiyear contract for a quarterback—he didn’t have an intense bidding war that drove up his average annual salary.
The offers Prescott would receive in free agency would likely align with any offers Dallas sends between now and then. But other teams may have the financial flexibility to structure the deal in a more enticing way—fewer years and with more guaranteed money, perhaps—and some will be able to offer a more realistic shot at winning a ring. Even if the contract offers from other teams aren’t necessarily greener, the grass they might offer certainly could be.
Dak plays well, and the Cowboys finally get past the divisional round.
Still no Super Bowl, but the Cowboys are going on nearly 30 years without having reached an NFC title game. If Prescott leads that charge, he could ask for a blank check, and Jones would have no choice but to sign it. This actually may be the worst-case scenario for Dallas, even if it would be its best finish in decades. It would give the front office false hope that an aging and top-heavy roster is only one or two moves away from winning a title. That kind of thinking last year is why Prescott is currently without a deal …
And if Jones applies the same line of thought when Parsons asks to get paid next offseason, you can see how that could get messy down the line. Sorry, Micah, we can’t give you that billion-dollar contract you deserve. We need the money to make room for DeAndre Hopkins and Jadeveon Clowney. We’re trying to win a Super Bowl here. Just reread this article next summer if you want an idea of how it could go. The Cowboys will have more cap space available in 2025, but that’s before we account for any potential deals for Dak, Lawrence, or Martin. For the Cowboys to have enough money to truly go “all in” for a Super Bowl next season, Jones would likely have to play contractual chicken with Parsons and put off forking over a bunch of money to his best player.
Worst of all, leading the Cowboys to a conference title game would probably be enough to earn McCarthy, who is also entering the final year of his contract, a big extension.
What would happen next: A happy Jones gives Prescott whatever he wants. That ends up being a three-year, $180 million deal that includes $150 million in guarantees and provides enough time for the quarterback to sign one last big-money deal before he eventually retires. Parsons is forced to play on the franchise tag in 2025, but Dallas keeps its roster mostly intact. McCarthy signs a new four-year deal that also gives him some control over roster decisions. The Cowboys, under this regime, never make it back to the NFC championship again.
Dak plays poorly, and the Cowboys don’t make the playoffs.
It’s hard to say what a bad Prescott season would look like because we haven’t seen one in a long time. The worst season of his career came in 2017, when he averaged fewer than 7 yards per attempt and finished with a passer rating under 90 (the only time either of those things has happened for Dak). Prescott also averaged minus-0.04 expected points added per dropback that season, which remains the lowest mark of his career. He then got off to a poor start in 2018, but after a big second-half push, he hasn’t looked back.
Since 2019, Prescott has ranked fourth in the NFL in EPA per dropback, seventh in average yards per dropback, and sixth in passer rating, per TruMedia. His worst season during that run came in 2022, when he dealt with horrid turnover luck and threw a league-leading 15 picks. Outside of those 15 plays, Prescott was one of the most efficient quarterbacks in the NFL, so it wasn’t surprising to see him put together an MVP-caliber season in 2023, when his turnover luck improved.
If Dak has a bad season, assuming he’s in good health, it will likely be the result of poor luck or a sudden decline in his physical talent. With Dak entering his age-31 season, it’s a bit too early to be putting him on washed watch, and a down year will probably be viewed as a statistical aberration. Prescott has a long enough track record to earn the benefit of the doubt. But that likely wouldn’t stop Jones from trying to use a bad showing to save some money on a contract. Prescott’s team, and the other 31 front offices that can offer him a deal, have access to the same numbers we do, so it’s not likely to work.
What would happen next: With questions about Dak’s performance (and age) being asked after a poor season, he doesn’t look to make any dramatic changes and takes a five-year, $300 million deal with the Cowboys that makes him the NFL’s highest-paid player and provides him with long-term security. Jones feels good because he got Prescott to sign for an extra year, but this can’t be considered a win since the quarterback is making about $10 million more per season than he would have if the Cowboys had gotten this deal done in 2023. Sure, Dallas gets a few more years of roster control, but there will be nothing stopping Prescott from asking for a new deal once all the guaranteed money on his next one runs out.
Dak gets injured, and the Cowboys make the playoffs without him (the Cooper Rush timeline).
If this happens and Cooper Rush leads the Cowboys to the playoffs, I want the entire organization tested for performance enhancers. From the front office to the coaches to the last player on the roster. Hell, even the grounds crew should be tested. There was a brief time when it appeared that Rush was a quarterback capable of leading this team to wins. With Dak out injured in 2022, Rush led the Cowboys to four consecutive wins and played efficiently enough to create some questions about Prescott’s value on a stacked roster. But Rush answered those questions by playing poorly in a loss to the Eagles, which ended his run as the team’s temporary starter.
Rush is your typical game-managing quarterback. He lacks arm talent and the quick processing we see in today’s stars. Plus, he doesn’t have the accuracy and timing that we see in the successful system QBs. The 2022 Cowboys had enough talent on offense to prop up a quarterback like Rush. The 2024 Cowboys do not.
But let’s just say this does happen. What would that look like? I’d imagine the Cowboys defense would be dominant under Mike Zimmer and the offensive line would have to play like one of the top units in the NFL. The cost to maintain the roster heading into 2025 would make paying Prescott a near impossibility, and having seen Rush take the same roster to the playoffs, Jones wouldn’t feel the need to do it, anyway.
What would happen next: The Cowboys may not have the money to pay Dak or any established QB in this scenario, but they do have some future first-round picks they can use to trade up to draft a quarterback. With Shedeur Sanders on the board, Jones can’t resist the urge to make one last splash move and brings in the son of his former star defensive back Deion Sanders.
Dak gets injured, and the Cowboys do well without him (the Trey Lance timeline).
If you consider this more realistic than the Rush timeline because Lance was talented enough to be drafted third not too long ago, you need to watch this:
Lance threw FIVE interceptions in one preseason game and didn’t play much better in his other two appearances this August. The Cowboys took a smart flier on Lance when the 49ers discarded him last season. Lance was seen as a developmental project and a possible replacement for Prescott if he were ever to leave Dallas. That is no longer the case, and with Lance barely clinging to the bottom of the quarterback depth chart, I won’t even consider the possibility that he could lead this roster to a successful season.
What would happen next: Even more pain and misery for Cowboys fans.
Dak gets hurt, and the Cowboys implode.
This is the one scenario in which the Cowboys could, in theory, end up getting Prescott to agree to a bargain deal. Next offseason he’ll be heading into his age-32 season, and in this case, he’d be coming off the second major injury of his career. He’d have only two playoff wins to his name and plenty of question marks about his capacity to be a top quarterback in this league. Signing a lucrative deal—but one that doesn’t reset the QB market—to stick with a team that makes earning money easy off the field could be an attractive option if Prescott’s longevity is in question.
But as we learned this offseason, when a 36-year-old Cousins got a $180 million deal from Atlanta after tearing his Achilles in 2023, even injured quarterbacks get paid. Prescott and the Cowboys already know that’s the case. In 2020, the Cowboys quarterback suffered a season-ending ankle injury while playing on the franchise tag. This was back when Prescott’s track record of success wasn’t so long, but even that didn’t stop him from getting top-of-the-market money the next offseason. And not only did Prescott become a $40-million-a-year quarterback, but he also got the no-trade clause and the protection from the franchise tag that have provided him with the leverage he currently enjoys.
Obviously, a season-ending injury would not be ideal for Prescott, but it’s not likely to affect the offseason market for his services.
What would happen next: Jones allows Prescott to hit free agency, thinking he’ll come back after teams concerned by the injury refuse to give him a top-of-the-market deal. A long line of teams is willing to pay top dollar for one of the five or six best quarterbacks in football. Only Jones is surprised by this, and the Cowboys owner ends up caving and giving Prescott the contract he’s desired this whole time. That’s how this will always end. Jones seems to be the only person who doesn’t realize it yet.
