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17) Who Cashes In On A Contract Year?


(Editor's Note: Over the next month, the staff of is looking to answer the 20 biggest questions facing the team heading into 2021. Today, we'll take a look at some of the Cowboys' biggest contract considerations.)

FRISCO, Texas – The Cowboys aren't strangers to contract negotiations by this point.

From Dak Prescott to Amari Cooper to Ezekiel Elliott and DeMarcus Lawrence, there has been a high-profile deal to discuss every season for the past four years. Recent offseasons have been marked by which star player was in need of a new contract.

With Prescott finally agreeing to a new deal back in March, the drama has subsided substantially – for now. But even with most of this team's star players locked up for the long-term, there are some situations worth wondering about. The Cowboys have a handful of noteworthy players entering contract seasons, and it'll be time to speculate on their futures before too long.

So why delay, when we can speculate heading into training camp?

17) Which Player In A Contract Year Cashes In?

David Helman: One way or another, I have to assume Michael Gallup is going to see a nice pay day in the near future. Consider the fact that Curtis Samuel just signed a three-year, $34.5 million contract this spring – and Gallup already has comparable stats after three years to what Samuel did during four seasons with the Carolina Panthers. If he is healthy and on his game in 2021, Gallup should be able to angle even higher. Kenny Golloday just signed in New York for $72 million – and Gallup is on a fairly similar trajectory. With the salary cap trending back in the right direction, Gallup is in a great position to capitalize.

Nick Eatman: Lots of options here. I think if I had to pick, I'll go with Leighton Vander Esch. That's not to say that Connor Williams, Gallup or Gregory won't get big deals as well. But LVE is a former All-Pro and when he's healthy, he's probably better than all of these guys. I think Vander Esch will be hungry and ready to prove himself. Now, of course, he has to stay healthy and that's easier said than done for him. But when he's out there running around and making plays, he can be as good as any inside linebacker. Something tells me he's going to thrive in this defense with Dan Quinn. I think he gets a big contract and it wouldn't surprise me if it's here – that is if he's willing to return although the Cowboys did decline his fifth-year option.

Jonny Auping: I'll go with Michael Gallup. I get why he is overlooked on a team with Amari Cooper and CeeDee Lamb, but Gallup's athleticism is wildly underrated and he has complete control over it in a way that you can see in the versatility of his catches. He doesn't need a lot of balls thrown his way to step up and make huge plays, and he already has a knack for coming through in the fourth quarter. Sharing receptions with those two guys will probably mean that his season total statistics won't blow anyone's mind, but I think he'll put together enough huge games and big plays to impress a lot of teams that want a big upgrade to their receiving corps. Maybe the Cowboys will do what it takes to retain him next offseason, but I don't think they'll be able to do that at a low price tag. My only advice to fans is not to lose too much sleep over the prospect of paying him or losing him. Just enjoy what he does this season to earn his next contract, because he's a great player, a great person, and he'll make plays that will be fun to watch.

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