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Can the Dallas Cowboys Afford to lose Connor Williams in 2022?

The Dallas Cowboys have some interesting decisions coming in the next year as Randy Gregory and Michael Gallup are in the final years of their contracts. One player that doesn’t get talked about enough for a potential contract extension is left guard Connor Williams.

Though unlikely, with the money the Cowboys have invested along the offensive line, Williams is an ascending player who has gotten better each of his three years in the National Football League.

Bleacher Report’s Brad Gagnon took a look at the free-agent market in the 2022 offseason and made the argument that Williams is the pending free agent the Dallas Cowboys can least afford to lose.

If you read this space, you know I’m a fan of Williams. He isn’t the greatest player, but he’s been solid throughout his time in Dallas and, as Gagnon points out in his piece, had his best year in 2020.

When everything went to crap along the offensive line, Connor Williams was the last man standing from the projected starting offensive line. At the same time, the abilities and productivity of Michael Gallup and Randy Gregory put them at the front of the line when it comes to pending free agent contract extensions.

Even as much as I love the passing game and want to give Dak Prescott all of the weapons, finding pass rushers with Randy Gregory’s ability is a difficult task. Assuming the Dallas Cowboys feel like they have to make a choice, to me, the choice is clear: It’s Randy Gregory.

Michael Gallup’s been great. This has nothing to do with the type of player he is. It has everything to do with the reality that the Dallas Cowboys have Amari Cooper and CeeDee Lamb also playing wide receiver.

Considering the depth available in the NFL Draft and a player like Simi Fehoko in-house, the Cowboys have options to supplement their wide receiver corp if they were to allow Michael Gallup to walk in free agency.

With the ability to creatively create cap room through contract structures and restructures, and an increasing cap over the next several years, it’s not out of the question that the Dallas Cowboys find a way to keep Williams, Gallup, and Gregory.

It would likely take some hometown discounts from one or all three, but the Dallas Cowboys could find a way to make it all work if they wanted to. Still, it’s unlikely they’d sacrifice either Gallup or Gregory to keep Williams in place despite his improved play.

What do you think?

John Williams

Written by John Williams

Dallas Cowboys optimist bringing factual, reasonable takes to Cowboys Nation and the NFL Community. I wasn't always a Cowboys fan, but I got here as quick as I could.

Make sure you check out the Inside The Cowboys Podcast featuring John Williams and other analysts following America's Team.


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  1. Williams has been fine, and improved yearly as players should. Some other team will overpay him more than likely.

    This team, historically, has given too many second contracts, although I think we are improving slowly in this area.

    As a team, you have to keep trying to get younger.

    Williams will and should go. If we are unable to replace his level of production, then we need to replace coaches and or those in scouting, neither of which I believe is the case.

    The guy is a JAG. We should be able to get 90% (at least) of what he provides with a first year replacement, who has been in our system for a year or two, ie: McGovern, who is next man up.

    Accepting this kind of roster evolution is the only way to truly evaluate organization and player development.

    Fearing this evolution results in poor contracts and suspect depth, imo.

  2. Yes, definitely extend Connor Williams now and do the same for Gallup and Gregory. These are all successful draft picks who are not quite yet superstars. We should be able to entice and negotiate them to a second contract. In the case of Williams, he is still improving but won’t command top ten guard pay. If the Cowboys draft a blue chipper who beats him out in the future (unlikely) then you have exceptionally reliable depth and avoid fiascos like last year.

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