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Of the Cowboys top 5 free agents, ESPN says the best landing spot for 4 of them is not in Dallas

The Cowboys free agent period in 2022 should be interesting.

NFL: Carolina Panthers at Dallas Cowboys Tim Heitman-USA TODAY Sports

There has been a lively debate on these pages, and elsewhere, about the Dallas Cowboys ability to re-sign their own free agents and go after others. The problem is the salary cap and the Cowboys being roughly $21 million over it at the current moment. We know they can get under that with the restructure of a few contracts and they will likely start with Dak Prescott's contact.

The debate goes further than that in Dallas, and it mainly centers on Stephen Jones and his pursuit of free agents. He generally does not like to shell out bigger contracts for “name” outside free agents, but it is true that he tries to retain their own free agents that they like. There is also the other thing that comes up at this time of year which are the cap casualties, and that can sometimes influence re-signing a player or not.

Today, let’s focus in on retaining free agents. ESPN has a list of their top 50 free agents for this year and the Cowboys place five players on that list. That is an out-sized representation for one team. And it could be trouble for a team that is currently over the cap.

In fact, of the five free agents on this list, ESPN sees four of them as better fits elsewhere.

The Cowboys top free agent is generally agreed to be Randy Gregory because of his ability, and the position that he plays. Pass rushers are highly coveted. ESPN sees a return to Dallas.

15. Randy Gregory, DE

Best team fit: Dallas Cowboys

Why it makes sense: No team knows Gregory better than Dallas. Now that his career is ascending, the Cowboys should reap the benefits with a long-term deal that both sides can appreciate. — Fowler

The Cowboys are making headlines because of DeMarcus Lawrence’s huge cap hit this year and the debate around restructuring him, or, according to some, the possibility of him being a cap casualty. Currently that last part is pure speculation, but it will be interesting o see where they come out of this at defensive end. They have Micah Parsons who is already a part-time defensive end, and depth DE Dorance Armstrong is also a free agent. Given the history with Gregory and the way they stuck with him through a lot, they probably want to reap the rewards of that long investment now. They will probably be willing to lay out the big bucks for this signing.

Next up is Dalton Schultz. The tight end kind of broke out in 2020, and then followed that up with an excellent 2021. His timing for his own bank account couldn’t have been better. Here is what ESPN sees.

23. Dalton Schultz, TE

Best team fit: New York Jets

Why it makes sense: Expect the Jets to be in the market for a safety valve over the middle for Zach Wilson, either in the draft or free agency. Dallas wants to re-sign Schultz, perhaps the most complete tight end in the class, but it can’t keep everybody. — Fowler

Schultz is probably one of the most debated of the Cowboys free agents. He’s clearly a productive player who adds value, but his position is not one that is usually highly compensated except for the elite few. Is Schultz in that elite category? You could make the case based on a small sample of stats, but Schultz doesn’t have the game-breaking ability of say a Travis Kelce or Darren Waller. The Cowboys may have to give in somewhere and save some cap dollars, and Schultz may be the place they do it.

The next one is easy.

33. Connor Williams, G

Best team fit: Cincinnati Bengals

Why it makes sense: With Quinton Spain hitting free agency, the Bengals could pair Williams with center Trey Hopkins and guard Jackson Carman, who should make a Year 2 jump. — Fowler

Every indication is that the Cowboys and Connor Williams have ended their run. Dallas benched Williams during the middle of the season (even though they eventually went back to him), and they publicly dragged him about his penalties. This one feels like a foregone conclusion.

Next up, the curious case of Michael Gallup.

40. Michael Gallup, WR

Best team fit: Chicago Bears

Why it makes sense: The Bears will prioritize a receiver who can win one-on-one matchups for quarterback Justin Fields. Gallup will be the steal of free agency if a team gets a discount due to his torn ACL. By midseason, he should be humming. Offensive coaches around the league love this guy’s game and felt he has been underutilized in Dallas. — Fowler

Before Gallup tore his ACL at the end of the season, it was pretty much thought that Dallas couldn’t afford to keep Gallup with Amari Cooper and CeeDee Lamb already on the roster. But the ACL injury threw that into doubt as it is unclear how teams will treat Gallup with the injury. His market might be driven down. Then there is the speculation about Cooper being a cap casualty. If that turns out to be true, you would have to believe the Cowboys would take some of those savings and go after Gallup. There is also Gallup himself who might decide a one-year prove-it deal would allow him to hit a better market with a completely healed ACL in 2023.

The final one also feels like a foregone conclusion.

45. Leighton Vander Esch, ILB

Best team fit: Houston Texans

Why it makes sense: Dallas declining Vander Esch’s fifth-year option sent signals that he’s not in the long-term plans. That’s OK. Vander Esch can still play a pivotal role on a defense. Lovie Smith needs a downhill thumper in Houston, but Pittsburgh could get involved here, too. The Steelers were very high on Vander Esch coming out of the draft and need linebacker help. — Fowler

As noted above, the Cowboys kind of signaled their intentions here by not picking up the fifth-year of his deal. If the market is slow for Vander Esch, maybe a reunion in Dallas is possible because the team desperately needs linebackers. But the likelihood is that he will get some decent dollars elsewhere and the Cowboys are probably already planning for that.

Of these five free agents, which ones do you think will return to Dallas in 2022?

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