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Randy Gregory debacle reveals the problems with the Cowboys front-office

The Cowboys front-office is under fire for a poor decisions that could be causing a rift.

Dallas Cowboys v New Orleans Saints
The brain trust outsmarted itself again.
Photo by Jonathan Bachman/Getty Images

The NFL legal tampering period has been an emotional roller coaster for fans of the Dallas Cowboys. First came the welcome news they had agreed to a new three-year deal with DeMarcus Lawrence. That freed up needed cap space while avoiding a major hole to fill. Then came reports that some of that cap space was going to re-signing Randy Gregory, lifting spirits even higher. But then came the plunge as news broke that Gregory changed his mind at the last minute and was instead going to the Denver Broncos. It left us confused and wondering what happened.

The answer is not hard to figure out. It seems that once again the team, or more specifically the owners, outsmarted themselves.

This is just the latest symptom pointing to a major problem for the Cowboys. While the past few days started to reveal that there is indeed a plan for the team, this bit of underhanded maneuvering to gain an advantage, along with some ridiculous nickel-and-diming in other cases, unfortunately seems to be very much a part of that plan. This is just the most recent and glaring example.

The opening chapter of this year’s story of how badly the Jones family, and especially Stephen Jones, keep messing up was the much-reported incident of him talking with the media about how the contracts of Amari Cooper and Lawrence were big problems for the salary cap. He kept with his stance that the cap is a hard line that the team has to meet. Then the team proved just how false that concept is. With a couple of restructures, the trade of Cooper, and the Lawrence deal, they went from being in the red in cap space to having one of the best cap situations in the league.

According to Over the Cap, they now have over $28 million in space, the seventh most in the NFL. With La’el Collins expected to be released at some point, that should increase, although how they handle that will determine if it is just $1.3 million or $10 million. In any case, they now have the room to do just about whatever they want. Re-signing Gregory was apparently one thing that new space was earmarked for. Now they have blown that up, and in addition to losing a key part of the defense, they have to do something to try and soothe what may be some bad feelings on the part of Lawrence, who gave them a very team-friendly deal. If part of selling Lawrence on his new deal was to bring Gregory back, he probably is feeling a bit burned.

We discussed the Randy Gregory saga in an emergency episode on the Blogging The Boys podcast network. Make sure to subscribe to our network so you don’t miss any of our shows! Apple devices can subscribe here and Spotify users can subscribe here.

Dallas already had done some damage to the culture with the ham-handed way they dealt with Cooper. There was absolutely no reason to air all the dirty laundry in the media. While there is evidence that management and the staff had soured on Cooper due to various behind the scenes issues, dragging it all out was never needed. All this should have been kept inside the building. Negotiating through the media is sadly a well established trait for the Joneses, and it always has negative consequences whether the team wins or loses. Most of the time, it is not an overall victory for management as they get forced to cave late or see players they want going somewhere else that offers a promise of better or more honest treatment.

These incidents are not accidents, but a result of an intentional “hard-nosed” way of dealing with their roster. Contract negotiations are treated as a zero sum game far too much rather than focusing on finding a way for both sides to come out ahead. Not only is it being reported that they changed a deal after it was verbally agreed upon, the they also seemed to “nickel and dime” the contract the way that has created so many problems in the past. It also reflects the attitude of the Joneses that they are smartest people in the room. But all too often, the only ones they outsmart are themselves.

Now there is a report that the Gregory mess is a sign of dysfunction at the top.

For years, Stephen has been taking on more and more of the day-to-day operations of the team, with cap management and contract negotiations a big part of his portfolio. But Jerry still gets involved in the personal negotiations, as the tweet above indicate. If that is at all close to the truth, then we have the potential for a rift and possible power struggle within the Jones family. That is a very negative development, at least in the short term.

This is all on the Jones family. They are the only ones who can fix this, and the prospects for that are dim because it would require a couple of very stubborn people changing themselves. What we have learned through all this is that there is a plan for the team, and for a brief time it seemed to be paying dividends. Unfortunately, Stephen Jones’ ineffective and counterproductive approach to contracts and managing the cap, primarily in this case his focus on what should be minor issues and his underhanded way of throwing in things at the last minute, are embedded in that plan. There have been self-inflicted and avoidable wounds this season, and that is a far too familiar pattern. Now they have a lot of damage control to manage. That is always hardest when the ones trying to smooth things over are the ones who created the problem in the first place.