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Which of these soon-to-be-free-agents should the Dallas Cowboys consider extending before the season begins?

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Dan Rogers
Dan Rogers
 23 days ago

The Dallas Cowboys don't have a lot of cap space next season. That shouldn't be all that surprising considering they have several of their top-talented players locked into high-priced, long-term deals. In total, the Cowboys have seven different players who will account for at least a $15 million cap hit next year, four of which will exceed $20 million.

Signing a franchise quarterback to a long-term deal immediately propels them into a group that has to operate with financial restraints. Couple that with the fact that the Cowboys have a handful of other pricey contracts, and suddenly the Dallas front office is up against a wall.

Looking ahead to next season, the Cowboys are in the hole $18.3 million, which is currently second-worst in the league. Obviously, the team will have some work to do to get under the cap, but a lot of this can be handled with some timely restructures and potential cap-saving cuts of players who are not living up to their contract.

Because this team is frugal in free agency and have a lot young, cheaper players expected to fill roster spots in the future, the Cowboys cap situation is nowhere as bleak as it may appear. However, it does mean they'll need to be very cautious about where their cap funds go, and that brings us to today's topic - which soon-to-be-free-agent should the Cowboys consider extending before their price becomes too high?

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Michael Gallup, Randy Gregory, Dalton Schultz, and Connor Williams@dannyphantom24 / Twitter

There are four players in the last year of their contract who are valuable members of this team - Michael Gallup, Randy Gregory, Dalton Schultz, and Connor Williams. All four of them are players I'd love to keep in a Cowboys uniform, but financially speaking - that's just not feasible. In fact, the Cowboys may end up losing every one of these players, especially if they have a strong 2021 season and jack up their price entering free agency next year.

Let's examine each of these players and take into account their projected cost, their value to the team, and the overall team depth of at that particular position.

Michael Gallup

The Cowboys got such a tremendous deal when they selected Gallup in the third round of the 2018 NFL Draft. He was the ninth wide receiver taken in the draft; however, only two receivers in that draft have more receiving yards - Carolina's D.J. Moore and Atlanta's Calvin Ridley, the only two first-rounders selected that year.

Gallup has played in all but two games since entering the league and has a total of 158 catches for 2,457 yards and 13 touchdowns. There is no denying his value to the Cowboys offense, and his production and availability should interest those teams needing help at the wide receiver position. While he isn't expected to command Kenny Golladay money ($18 million annually), he's every bit as good (if not better) than players like Corey Davis and Curtis Samuel, both of who got deals of roughly $12 million annually.

With Amari Cooper and CeeDee Lamb already locked down for several years to come, the Cowboys are in real good shape at receiver, and ponying up that kind of cash for Gallup is not the best way to maximize their return on those funds.

I'd love to keep Gallup, but he'll be worth more to other teams. The best we can wish for is a decent compensatory pick in 2023 when he signs elsewhere.

Randy Gregory

The front office took a gamble on Gregory when they selected him 60th overall in the 2015 NFL Draft. While he was an elite prospect from a talent perspective, he slid in the draft after failing multiple drug tests (marijuana). It looked as if the Cowboys wasted their pick as Gregory has been suspended four different times, resulting in a total of 52 games missed from violating the league's substance abuse policy - 2016 (14 games), 2017 (full season), 2019 (full season), 2020 (six games).

The Cowboys have never given up on Gregory and he still flashes great pass rushing traits. He had a solid season in 2018 where he played in all but two games and registered six sacks as a rotational pass rusher. Last year, he was underutilized like many players were under the previous coaching staff, but there are reasons to think he could take the next step under the tutelage of new defensive coordinator Dan Quinn.

Gregory is an interesting case. Despite missing so much time, the Cowboys have signed him to two different baby extensions, so there is clearly an established trust and belief with him and the Jones family. If the team could get him extended on a three-year deal for a bargain price with built-in incentives, the Cowboys might be able to secure a low cost pass rushing counterpart to DeMarcus Lawrence who offers a little bit of upside.

Quinn needs to take a hard look at him in camp, and if he gets a sense that he can unleash his talent, it could behoove the front office get an extension done before entering the final year of his deal.

Dalton Schultz

The young tight end proved to be a pleasant surpise last season after starter Blake Jarwin went down in Week 1 with a season-ending injury where he tore his ACL. Schutlz, who had been nothing more than a role playing in-line blocker, was suddenly cast as the team's pass catching tight end. All he did was reel off 63 catches for 615 yards and four touchdowns. Coincidentally, his 63 catches exactly matched Jason Witten's reception numbers during each of his final two seasons in a Cowboys uniform.

While we're still waiting to see what Jarwin can do as the primary tight end (it feels like we've been waiting forever), Schultz has already demonstrated he's a duel threat tight end. I wouldn't be all that shocked if he's actually the best tight end on the roster and not Jarwin. Blocking ability matters and Jarwin has yet to show he's an able body in that department.

This is a tricky situation. Schultz has definitely caught our attention. The Cowboys re-upped on Jarwin with a four-year, $22 million last offseason, but the team does have an escape clause after the upcoming season. They also have last year's undrafted free agent Sean McKeon who has taken on in-line blocker responsibilities and is still developing. Don't be surprised if he turns into a solid player as the Cowboys have a good history of replenishing role playing in-line blocking tight ends. While it would be nice to be able to retain Schultz, doing so would likely mean moving away from Jarwin. Keeping Schultz isn't completely out of the question, but it might take another year to reassess the situation before commiting to a new deal.

Connor Williams

You might recognize Williams as the only Cowboys offensive lineman who started all 16 games last season. He picked a good year to finally stay healthy as the team had all kinds of injury issues in 2020. Not only was he on the field, but he actually played pretty well last year. He's often criticized for his performance as he's been the weakest links on the unit since entering the league, but he took a nice step last year.

It would be great to keep Williams as he's turning into a solid player, but the Cowboys aren't likely to throw additional cap resources at their offensive line. With younger, cheaper options on the roster, the Cowboys should be able to find a quality replacement at left guard for when he leaves in free agency next season.

Taking cap implications and roster depth into consideration, which of these players would you choose to extend?

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