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The case for and against re-signing the Cowboys top 5 free agents

The Cowboys must make a decision this offseason on these five players.

Washington Football Team v Dallas Cowboys Photo by Wesley Hitt/Getty Images

The Dallas Cowboys are preparing for 21 players to hit the open market as unrestricted free agents in a few weeks. With the team $21 million over the cap, they are going to have to make some hard decisions. They will not try to re-sign all of them, but will make some strategic decisions once the team re-structures some of the bigger contracts on the roster. Dallas has some easy re-structure decisions to make like with Dak Prescott’s contract, others will not be so easy. Amari Cooper and DeMarcus Lawrence, in particular, seem to be questions marks in terms of re-structure or release.

But in this moment, a few weeks before the new league year actually commences, the Cowboys have five prominent free agents. Four of them end up on most Top Free Agents lists around the internet, and one of them may not be as sought after league-wide, but definitely has the Cowboys’ attention.

Let’s look at the reasons for and against re-signing each one.

Randy Gregory

Case for: The Cowboys have shown incredible patience with Gregory as he battled his mental health issues over the years. Now that he seems on the path to wellness, they want to cash in on that investment. Gregory also plays one of the most important positions in football and he seems to be close to reaching his potential as a football player. His build and skills are almost prototype for the position.

Case against: Because of the position he plays, Gregory could command a pricey contract. Pass rushers are always in demand and Gregory should have plenty of good reps left in his career after putting little wear on his tires so far. That could drive up his price. The Cowboys could also replace him by using a combination of other defensive ends and Micah Parsons without breaking the bank.

Dalton Schultz

Case for: Schultz has broken out over the last two years and has become a primary target for Prescott. The Cowboys drafted him and wasted a couple years of his rookie contract so they would love to keep the homegrown product and reap the benefits. He put together some very strong games late in the season when the rest of the offense was inconsistent.

Case against: Like Gregory, the price to keep Schultz might be too high at a time when the Cowboys are navigating cap constraints. They could obviously make room to sign him, but it could cost them at other positions to do so. They also have Blake Jarwin as a ready substitute, a player they believed in and gave a hefty contract to a few seasons ago.

Michael Gallup

Case for: You can never have enough weapons in the passing game in the modern NFL. Gallup represents a high-quality package and is the Cowboys’ best deep threat. He is also one of the best at controlling his body to make spectacular catches along the sideline. He adds a dimension to the offense that none of the other receivers can claim.

Case against: His injury could hamper him for all of 2022. ACL tears are notorious for bothering players, especially at skill positions, for another season after their recovery. Also, the Cowboys have a lot of money tied up in Amari Cooper, and down the line they will need to extend CeeDee Lamb. Maybe there is not enough pie to go around at the position.

Connor Williams

Case for: While the fanbase, and the Cowboys brass, were annoyed by the constant penalties, Williams actually graded out well by PFF and several other sources. The Cowboys saw what happened when they benched Williams and tried to replace him in-season. They found that they missed his play. Finding offensive linemen is not always easy.

Case against: Those penalties. The Cowboys found themselves behind the chains too often because of a Williams’ hold. And while Williams has improved his strength and ability to hold his base against powerful defensive tackles, he is still perceived as a weak link along the line and a place to improve.

Jayron Kearse

Case for: While he isn’t ranked on the free agent lists like the other four on this list, Kearse was extremely important to the Cowboys defense in 2022. Dan Quinn used him all over the field, including safety (box and single-high), linebacker, and slot corner. He was one of the Cowboys top defenders last season and helped fuel the defense’s turnaround.

Case against: Kearse signed a one-year deal that was very cheap last offseason for a reason. He just hadn’t excelled during his career. Is he a one-year wonder? Would the Cowboys be shelling out a multi-year deal to a player who had one great season that was not truly representative of his abilities?

Given all this, what is your priority list (1-5) for re-signing these free agents?

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