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Six contract-year Cowboys who can cash in by having a big season in 2021

In Dallas or elsewhere, there are some big numbers at stake for these players.

Syndication: The Enquirer
It could be his year to finally get paid.
Kareem Elgazzar/Cincinnati Enquirer via Imagn Content Services, LLC

Professional athletes in team sports have a double agenda. They want to win titles with their franchise, but they also are very much in the business of maximizing their earnings. Fortunately for all, the two are mutually supporting goals. Hitting free agency after your team has done well tends to lead to bigger paychecks. The so-called contract year, or the final year of their old deal, is when those future riches can be secured.

As our One Cool Customer compiled earlier this year, the Dallas Cowboys have 34 players who are on expiring contracts this season. Obviously not all will have years that will lead to big paydays, and some will likely end their careers. But several can land significant raises with a good season. Here are the ones that could be laughing all the way to the bank.

DE Randy Gregory

There is no more moving redemption story in the NFL than that of the Cowboys’ pass rusher. If you have access to The Athletic, the recent piece on his road to redemption is worth every second it takes to read it. He is poised to finally get the kind of contract his talent merits but his personal struggles kept from happening. Last year saw him flash some of what he can bring to the table, even though he may have not been fully unleashed, as he noted, and was quoted earlier by our David Howman.

As much as the 2020 season could prove to have been a springboard, Gregory believes he was denied opportunities last year. He thought he had fulfilled the obligations from his indefinite 2019 suspension after a year away from the team, but the NFL saw it differently. His reinstatement was delayed because the NFL didn’t drug test during the pandemic, so Gregory did not have the opportunity to prove he was clean. The league allowed him to return to the facility at the start of the season but prevented him from playing the first six games, apparently to see if he could handle a deliberate reintroduction.

For the rest of the season, Gregory’s opportunities behind Aldon Smith were limited.

“I felt there was a little bit of favoritism going on … refusing to let me outshine their favorite,” he says. “They knew I could do it, so they did what they could to keep me at bay. I had my times when I was angry. I used to talk to Peter about it, and the best thing I could do was just go out there on the field with the plays they give me and make those plays worth it. I did that, but I truly felt I got robbed of a year last year.”

Now with Dan Quinn calling the shots on defense, we could see Gregory really explode, and he is physically almost untouched by the battering most pass rushers endure. If he does have the season anticipated, he is going to be one of the most desired players at one of the most valuable positions in the game.

It may be expensive for the Cowboys to keep him, but they have invested so much in his recovery that they will surely try. This is a rare case of loyalty running both ways in the NFL. That does not mean he will give Dallas a hometown discount. It doesn’t mean he won’t, either. If he remains healthy, someone is going to seriously enrich him.

G Connor Williams

In 2019, he was viewed as the weak link on the offensive line. In 2020, he was the rock. Every other projected starter from the beginning of the season ended it on IR. Availability is not called the most important ability for no reason.

Continuity on the offensive line is vital. All the other starters are locked in for a bit, so the Cowboys should be willing to make a good offer to him to remain, buthere will likely be other interested suitors. Williams may not be the elite player that Zack Martin is, but he is going to get a nice chunk of change out of this somewhere.

WR Michael Gallup

The bad news for Gallup is that he is pretty clearly WR3 for the Cowboys. The good news is that the two receivers ahead of him are Amari Cooper and CeeDee Lamb, who are one of the best one-two punches in the entire league. He had an 1,100-yard season in 2019, and still managed 843 last year with Cooper and Lamb eating up catches and a motley crew of quarterbacks throwing passes for the last three-quarters of the year. Many teams will rightly see Gallup as an upgrade at WR2, and someone will probably think he has WR1 potential. It is highly unlikely he remains in Dallas, but that shiny new contract will at least make him feel better.

That could also be good news for either Cedrick Wilson or Noah Brown, or possibly both. Neither should get an eye-popping new deal, but if Gallup does move on, the team will want some experience behind Cooper and Lamb. It could mean a nice offer, just not one big enough to make this list.

TE Dalton Schultz

When Blake Jarwin was lost for the season, Schultz stepped in and proved he was a legitimate starting tight end. He may retain that job, but even if Jarwin winds up ahead of him on the depth chart, Schultz will be attractive to many. That probably includes the Cowboys, although they should have a max price they will pay for him. One way or another, he should get starter money in 2022.

LB Leighton Vander Esch

The Cowboys declined to pick up his fifth-year option during the offseason. That may turn out to be the best thing that could have happened financially for Vander Esch. He had many issues last season, but if that was truly just a symptom of the defensive travails of the team, he will be poised to get a nice second contract a year earlier than he would have. We certainly hope Quinn will make better use of him. The large infusion of new talent on the defensive line should work in his favor as well. Most are projecting him to line up as the WILL alongside Micah Parsons at MIKE. If Parsons is as good as most think he is, and those interior defensive line issues do get resolved, Vander Esch should play well enough to draw a lot of interest. The Cowboys may not be among those pursuing him, however, as they drafted Jabril Cox and still have Jaylon Smith under contract. If the latter also has a better season for the same reasons Vander Esch should, then LVE will probably wind up in a different uniform next season.

QB Garrett Gilbert

OK, this one is partly humorous. He is certainly not in line for an eight figure annual salary. But he is dirt cheap for a QB2, which seems to be what the staff is trying to make him. If Dak Prescott remains healthy, Gilbert may triple his salary just by standing on the sidelines the entire season. Just having a year and a half’s experience in the system may make him worth that to the team. And then who knows? He could move on after football to become the next Dan Orlovsky, only without the Carson Wentz man-crush.