An uncomfortable offseason is what Cowboys probably need, but it could backfire

The offseason for the Dallas Cowboys is barely a month old and the plan for the 2024 campaign is far from clear. After a season that ended in bitter disappointment, everything that’s transpired since has been confusing, and made things uncomfortable with the Cowboys.

Perhaps that’s the plan for the organization. The question is, if uneasiness is the goal, will it work out?

The awkwardness began when Jerry Jones said the organization will be going “all-in” this year, but nobody seems to know what that means. Even his son, Stephen Jones, isn’t sure. The executive vice president for the Cowboys mentioned at the combine how he felt the team was always all-in, an absurd notion that was met with considerable doubt.

Then, of course, there’s the indecision with quarterback Dak Prescott and his contract situation. The top brass for the Cowboys continues to say they want to keep Prescott in Dallas for a long time, yet there hasn’t been much movement about an extension. There are also rumblings the Cowboys are willing to let Prescott play his deal out and becoming a free agent in 2025.

So which is it? With the league year and free agency set to open in less than two weeks, the Cowboys need to figure it out quickly in order to operate this offseason.

Ditto for CeeDee Lamb’s expected extension and possibly Micah Parsons’ as well. Those are three huge contracts that need to be worked out and time is running out.

There is also Mike McCarthy coaching on his last year of his deal. Lame duck coaches rarely work out.

The offseason of discontent is well underway in Dallas, how will it shake out for a team that’s struggling to find the right recipe to get over the hump?

Uncomfortable is exactly what this franchise needs

The Cowboys have gone almost 30 years without winning a Super Bowl, or even making an appearance in the NFC championship game, an embarrassing fact. Some reference the country club atmosphere within the organization as part of the reason for the team’s shortcomings. Led by Jones, things are believed to be too comfortable for the players and coaches. Good is good enough because the Joneses are making money. The Cowboys remain the most valuable sports franchise in the world.

This offseason doesn’t have the same vibe. The head coach and his coaching staff are on one-year deals, including the defensive coordinator who was recently hired, and they haven’t talked about a new deal with their most important player after having his best season.

All of this has made for an uncomfortable situation inside the organization. As Michael Gehlken of the Dallas Morning News explains it, things are not warm and fuzzy with the Cowboys.

After the way the last 28 seasons, and especially the last three with McCarthy, have played out, maybe the correct response should be, ‘so what.’ The team hasn’t been successful when everyone has been fat and happy, maybe it’s time for a new approach.

If the players and coaches are uncomfortable with their status, perhaps it’s time to do something about it. McCarthy needs to feel the pressure of finding a way to get his team over the hump.

The same can be said for Prescott. Maybe the right move is adding a few voidable years to Prescott’s deal, having him to play out the final year of his contract, and then allowing him to become a free agent after next season. For as good as he’s been for the Cowboys over his career, Prescott hasn’t been good enough in the postseason, when the team needs him most. If he can’t get it done for a ninth straight season in 2024 and deliver at least a final four appearance, the writing might be on the wall, and it will be time to move on from a QB who’s been good, just not good enough. Putting more money into Prescott doesn’t feel like a wise investment if he can’t get the Cowboys near a Super Bowl.

And if this team is truly operating with a one-year all-in philosophy, perhaps they get really aggressive in free agency for the first time in over 10 years! There would be nothing wrong with Jerry Jones reverting to his old ways and truly going for it again.

Comfort be damned, what these Cowboys need is to be uncomfortable for once. Being entitled hasn’t gotten them anywhere, and this team hasn’t won enough meaningful games to feel comfortable so it’s time for a new approach.

Dallas has been the very definition of insanity, doing the same thing and expecting different results. Perhaps this new approach is necessary to get the most out the team.

Too much uneasiness is a mistake

Conversely, having the most important people all being tied to one-year contracts is less than ideal. The team is heading into an important offseason with all their coaches on a prove it deal, which affects their decision making in free agency and the draft.

Will McCarthy change his approach knowing he won’t be back if his team fails to reach their lofty goals next season? He’s come up short four years in a row, now what?

New DC Mike Zimmer will want his type of players for the defense, and the next few months will be about inputting his types of guys. However, if the team falters, Zimmer and his staff might be gone next year, and the team could be stuck with a group of his defensive players. It doesn’t feel like a wise move to be in position to have three defensive coordinators in three seasons if things go south in 2024.

Then there’s the issue with Prescott and his contract situation. It doesn’t make much sense to not do everything possible to sign your franchise quarterback who has been at the top of his game in two of his last three seasons. Playing chicken with Prescott could come back to bite the front office.

Despite not being in negotiations right now, Jerry Jones doesn’t seem to be worried about Prescott remaining with the Cowboys.

That doesn’t provide a clear answer of whether Jones means for 2024, or for the upcoming season and beyond. Getting a deal done with Prescott now would give the QB peace of mind, without one, the QB could press to ensure security for his future. In 2022, when the signal caller pressed, he had some of the worst results of his career, so putting him in a position where he must prove his worth doesn’t feel like the smart approach.

If you want one player comfortable and happy on your team, it’s the quarterback and the Cowboys are making things harder than they have to be.

2024 has the feel of a win or blow it up situation for the coaches, players, and direction of the team. If they don’t win big, the staff will undoubtedly be gone, and so will some of the veterans who haven’t been able to take Dallas to the promised land.

Conclusion: No one knows

It’s very early in the offseason to be making any statements, but that’s not how it works with Cowboys Nation. Any interviews done from the top of the organization are meticulously analyzed and scrutinized, but they do that to themselves. The Joneses rarely sound like they’re on the same page, and Jerry routinely talks in circles without meaning.

Asking fans and writers to withhold judgement until we see what happens with the upcoming contracts, in free agency, and the draft isn’t how it works with the Cowboys.

What is clear is the Cowboys have left things up to interpretation and it’s put a lot of pressure on everyone to win in 2024, or else. That’s a heavy weight to put on a team that’s already tense, and it could backfire.

However, there’s no reason a team that can’t get over the hump should feel comfortable, especially after how the 2023 season ended. It’s going to be fascinating to see how the offseason plays out for the Cowboys, and it likely leads to a boom or bust 2024 season.

Enjoy the chaos Cowboys fans!

Story originally appeared on Cowboys Wire