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5 key pending free agents that the Cowboys should retain

The Dallas Cowboys will have some tough choices to make as they shape their roster in the coming months and that begins with deciding on their own free agents.
Credit: AP
Dallas Cowboys defensive end Randy Gregory (94) celebrates during an NFL football game against the Washington Football Team, Sunday, Dec. 12, 2021 in Landover. (AP Photo/Daniel Kucin Jr.)

DALLAS — The Dallas Cowboys have a lot to do this offseason. They’re currently over the salary cap, have 21 free agents to make decisions on, and have high-priced players who might need to be released in order to make all of the money work in 2022. 

Despite all of the possible turnover, the team will take the same approach that they’ve had over the last nine years. With Stephen Jones at the helm, Dallas won’t sign any of the best players available on the open market and you can expect them to sit out the first wave or two in free agency.

Instead, the Cowboys will look inward first before filling their holes with moderately priced players after the elite options are gone. Since Dallas drafts well, the philosophy has worked out OK, but perhaps the team would win more consistently if the front office was not as rigid about their methods. 

Either way, there will be changes in Dallas. They won’t re-sign 21 players and they’ll have to find a way to add players to replace the ones they lose on the open market. The team probably will have no problem walking away from the majority of those 21, but here are five of their own free agents that the Cowboys should prioritize bringing back:

Defensive end Randy Gregory

The Cowboys are in a bit of a pickle at defensive end. With the rumors that the team might cut DeMarcus Lawrence, it would leave the defense short at a premium position. Even if the Cowboys keep Lawrence, they need a bookend to help get to the quarterback.

Gregory had his best season in 2021, tying his career-high with six sacks, four tackles for a loss and picked up his first NFL interception. Those were all high marks for Gregory, even as he was limited to just 12 games.

The Cowboys finally saw Gregory’s potential pay off after years of strife and they would be wise to keep a player who is 29 years old but doesn’t have much wear and tear on his body. 

Double-digit sacks for the next few years are possible for Gregory and the defense needs to keep all the edge rushers that they can. Cost is the only issue with Gregory, he’s going to be expensive and the franchise tag isn’t out of the question. Regardless, the Cowboys need to make keeping Gregory an offseason priority.

Wide receiver Michael Gallup

Bringing back Gallup might prove tricky since he will be coming off a torn ACL suffered in December. The WR missed eight games in 2021 which obviously saw his production dip, but Gallup has a 1,100-yard season under his belt and was a reliable outside threat for Dallas. 

Gallup will command a sizable contract and will be just 26-years old when the new league year begins. Even if Gallup misses some time early in the 2022 season, he’ll prove to be worth any multi-year deal the Cowboys would give him. If the roster construction philosophy is to re-sign the draft successes, that should include Gallup. 

If the team moves on from fellow wideout Amari Cooper, Gallup would be able to step in and be a solid No. 2 receiver opposite CeeDee Lamb. Perhaps the team gets him at a discount or on a short prove it deal because of the injury, but any way you look at it, Dallas would be wise to keep Gallup to keep the offense humming. 

Safety Jayron Kearse

Kearse was one of the more unheralded signings around the league last year. Defensive coordinator Dan Quinn maneuvered Kearse like a chess piece, moving him around the defense and using him as a tight end eraser over the middle. The veteran safety split time around the line scrimmage and in the secondary, leading the team in tackles and had a career-high 10 passes defensed.

Kearse’s career year led to him being named the most improved player for the Cowboys. 

Quinn got Kearse to play his best football, and, with the DC returning to the fold, the team should consider bringing back the versatile safety as well. With the Cowboys being up against the cap, Kearse likely won’t break the bank and should be an affordable piece that can make a big impact. 

Punter Bryan Anger

He might not play a big money position, but the Cowboys need to do what they can to retain Anger, who was a second-team All-Pro punter this past season. Special teams were a much-improved unit for the Cowboys in 2021 and Anger was a big reason why. 

Anger had 24 punts downed inside the 20-yard line, the hangtime on his punts helped allow opponents to gain just 6.5 yards per return – third fewest in the league – and his net average yards of 44.5 led the NFL.

After suffering through some rough seasons with Chris Jones, Anger came in and was one of the best punters in the game. If the Cowboys want to continue to win on special teams, Anger should be brought back.

Safety Malik Hooker

Hooker was a late addition to the Cowboys during training camp, but he played better as the year went on. While recovering from a torn Achilles tendon that he suffered in 2020, Hooker wasn’t ready to play until later in the summer. Dallas added him for safety depth and the move paid off.

Hooker has the pedigree to be a good player and he fits the Cowboys salary-wise. A former first-round pick out of Ohio State, Hooker hasn’t been a star, but he’s a solid safety. If he can stay healthy, the Cowboys could have an under-the-radar player coming into the prime of his career.

Hooker was behind Quinn favorites Keanu Neal and Damontae Kazee, and even Kearse last season, but with no guarantee that any of them will return, Hooker might be looking at a starting spot in the secondary if the Cowboys retain him. Coming off a season where he was regaining his strength after a major injury, Hooker could be a successful reclamation project in Dallas.

The Cowboys are forever in need of safety help; Hooker might be someone who can stick around and help be an answer to the position’s woes.

Which impending free agent do you most want to see the Cowboys re-sign? Share your thoughts with Ben on Twitter @BenGrimaldi.

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