It’s like there are two realities in the NFL, one where 31 teams mostly operate, and another one centered around Frisco, Texas that is the unique and puzzling world of the Dallas Cowboys. The latest example of how the Cowboys, which is to say the Jones family that owns them and makes the top level decisions, continually march to the beat of a different kazoo is the ongoing saga of Dak Prescott’s extension.

For most of the teams in the league, it is a fairly straightforward bit of logic to figure out something like this. First, you decide if you want to go forward with your incumbent as your franchise quarterback. Then you contact him and his representation, open negotiations, figure out something both sides can agree too, and get it done. This is a good time of year to start since things are otherwise rather slow outside the scouting staff (who are in their busiest time) and there aren’t that many distractions. Getting things hammered out in a timely manner is an advantage since other teams might also be working out a new deal with their franchise quarterback, and that will usually nudge the price for yours up. Even if you can’t get things worked out expeditiously, getting started just buys time to work on the sticking points and eventually get to the deal.

For reasons that escape us, Dallas chooses instead to follow a different blueprint. They play a waiting game, even acting hard to get in some aspects. R.J. Ochoa’s report linked above was inspired by this tweet from NFL insider Ian Rapoport.

This appears to clears the path for Dak Prescott to test free agency in 2025. https://t.co/HAA34sKKjF

— Ian Rapoport (@RapSheet) March 26, 2024

The whole idea of letting Prescott test free agency is at least puzzling, and in ways a bit alarming. The first concern is that the odds of improving the quarterback position by moving on from Prescott are dismal. Barring a real collapse this season, the team is not going to have the draft capital to get a top college quarterback in 2025. That collapse seems hard to envision given that Prescott would be trying to put his best performances on the field to increase demand for his services, and Mike McCarthy is also coaching for his future with the team.

You can make an argument that the ownership is trying to subtly handicap their own team’s chances through their lack of action in free agency, but that is more likely just their habitual stubbornness in refusing to spend any real money there. Even If they could manage to get a high draft pick, all college quarterbacks are a gamble, with no assurance they are going to work out, especially as rookies. And that would still leave them with about $40 million in dead cap for Prescott, which is a chilling prospect for the team’s cap maven Stephen Jones.

Part of this is another rather unique aspect of the Cowboys way, the convoluted and often ambiguous way Stephen and his father Jerry express things. As Rapoport says, there is a “mutual understanding” about the situation, but no clarity about what that entails.

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This has led to rampant speculation about the real strategy. One possibility is that this all points to a rebuild in 2025 with a new coaching staff as well as a new quarterback. The crushing exit from the playoffs at the hands of the Green Bay Packers could be a reason for this, with the owners possibly concluding that Prescott is never going to be able to take the team further than he has so far.

Another factor is that Dallas continues to be the most valuable sports franchise in the world, with diversified income streams that continue to grow no matter what the results on the field. In a way, the Dallas Cowboys have morphed into Cowboys, Incorporated. Their operation as a business is paramount and on-field success is just a by-product that has little effect on the balance sheet, at least in the minds of the Jones family. They put more effort into penny pinching to boost the bottom line than winning titles. This is a direct result of Jerry clinging ferociously to the general manager role and the resulting attention it brings him as the team’s chief spokesman, with Stephen also exhibiting similar fondness for the constant attention of the media. They are driven too much by ego and the way the spotlight stokes it.

If the ownership is showing no real commitment to bringing Prescott back, he likely lacks any dedication to the organization. This points to going into free agency as the more lucrative path for him if he can put a good performance together this season, which he is certainly going to try to do. He has a no-trade clause in his current contract, but if someone were to approach the team about wanting to acquire him, he might well waive that in order to secure a massive payout for himself. That could be an attractive option for his employers as it could net them the draft capital to buy a ticket in the annual quarterback draft lottery.

There is a flip side. That mutual understanding might well include assurances that the owners do intend to work out an extension for him, just in their own sweet time. Josina Anderson, who seems very plugged into the team, offers that side of things.

Anderson’s reference to the history of Prescott’s previous contracts is particularly noteworthy. It’s not like we haven’t seen this song and dance before, both with the quarterback and with other players like Ezekiel Elliott. The management plays their games with contract negotiations, the players just wait them out, sometimes holding out as well, and eventually the owners blink first, usually winding up paying more than they might have if they had just engaged in some good faith and honesty.

Those two traits seem markedly lacking in Dallas. Egos play a big role here, as Jerry and Stephen lack the self-awareness to perceive their own inadequacies at the negotiating table, often preferring to use the media in ham-handed and ineffective attempts to court public opinion to sway the players. The agents involved are too smart to fall for that particular trick and keep cashing in.

All this has to be a strain on McCarthy, who is waging his own battle for his future. The offense goes as Prescott goes, and the prospect of having a disgruntled quarterback who might want to resort to the option of holding out has no good side. Meanwhile, McCarthy still has to worry about the entire roster as well. He is still working on doing what he can. His recent comments about free agency not ending are pertinent. The team can still acquire more players before the draft, after the rookies are selected, and up to and into the regular season. Evidence of this are the recent reports that the team is still looking at Elliott and Dalvin Cook to fill out the running back room. There are thoughts that they could bring one in to be insurance behind a rookie drafted to start, but it also might be the plan that Rico Dowdle will be the starter they back up. Elliott in particular could fill a short yardage/goal line role that was lacking last season with Tony Pollard and company. In any case, just because they have not accomplished much with their usual stingy approach in free agency, it does not mean they are done.

It’s all just more signs of the dysfunction we have lived with for years. The owners and head coach don’t even seem to be in the same book, much less on the same page. The approach to contracts is almost designed to create friction and ill will. The plan remains intentionally opaque. We can only wait and see how this all plays out, with pessimism certainly justified.