byMickey Spagnola,Kyle Youmans,Patrik Walker&Kurt Daniels

FRISCO, Texas- Football season is getting closer and closer.

The Cowboys are set to depart for training camp in less a month. That's when we'll get the first up-close look at Brian Schottenheimer's first season with this revised roster and coaching staff. When we get to Oxnard, that's when we'll start to get some real answers about this 2025 Cowboys team.

But what are the questions? We've compiled our annual list of pressing questions that need answers heading into the regular season. The staff writers, consisting of Patrik Walker, Tommy Yarrish, Nick Eatman, Mickey Spagnola, Kyle Youmans and Kurt Daniels, weigh in on some of the pressing issues.

Today, we'll dissect next year's potential free agents and see which player has the most to prove entering the final season of their contract.

9) Who has the most to prove in his contract year?

Mickey:Will give you three, almost a dead heat. First, wide receiver George Pickens. While Pickens is in the final year of his four-year contract having signed with Pittsburgh as a second-round draft choice, the dynamic receiver must show he can be a co-No. 1 receiver along with CeeDee Lamb and maybe most of all that he has matured, putting those emotional outbursts the Steelers detested behind him. This guy has the ability to become one of the top free agent receivers next year, meaning big money never really achieved as a second-round pick. Second, defensive end Sam Williams. The Cowboys were expecting big things from Sam last summer before suffering that torn ACL during training camp, missing the entire season. Here is another second-round draft choice with first-round ability who will have a chance to show he's one of the top defensive ends in the NFL. Seems he is successfully rehabbing following knee surgery and will get every chance to demonstrate his ability. Now must take advantage of this opportunity to further market himself in free agency for 2026. And lastly cornerback Kaiir Elam, Buffalo's former first round draft choice the Cowboys acquired in a trade. Another guy with a great opportunity to reset his career course the final year of his deal. Even when Revel and Diggs return, the Cowboys still will need another corner.

Kyle:Without a doubt for me, it's George Pickens. No one could see more benefit or more loss by how their 2025 season goes than the Cowboys' newest weapon. He has quickly become one of the most feared receivers in football after just three years in the NFL but had a sour ending in Pittsburgh which resulted in his trade to Dallas. Because of this, his season could set a league-wide perception in one of two ways.

The ideal scenario would see Pickens piecing together an incredible season and pairing with Dak Prescott and CeeDee Lamb to create an offensive core for Dallas. This would prove that the rumors in Pittsburgh were nothing more than situational frustration and doesn't define who Pickens is as a player. If he's able to do so, he'll prove doubters across the league wrong and take his spot in line to sign a massive second contract anywhere he wants next season.

Patrik:Well there is certainly no shortage of answers to this question. I'll go with Sam Williams though, and for good reason. When Dorance Armstrong and Dante Fowler departed in free agency one year ago, the onus was on Willams, a former second-round pick, to have a breakout season to help stabilize things along with Micah Parsons and DeMarcus Lawrence. Nowadays, Lawrence is in a Seahawks' uniform and Williams played zero snaps in 2024 after suffering a torn ACL early on in last year's training camp. And with Fowler having returned, adding to the fact the Cowboys used a second-round pick in this year's NFL draft to acquire Donovan Ezeiruaku, one year after spending a second-round pick on Marshawn Kneeland I think you see where I'm going with this. Williams knows full well he'll need to hit the ground running to establish himself as the man to beat (outside of Parsons) in that room, and that he's a full go after the injury. Oh, and did I mention he's also in a contract year and set to become an unrestricted free agent in 2026, needing to have a breakout season for that reason as well? Mhmm.

Kurt:Given the number of one-year free-agent contracts the Cowboys signed, and those acquired in trades who came with one season remaining on their deals, there's a mess of players trying to earn big paydays for 2026. But there are also three homegrown talents who may still need to prove they deserve a second contract: tight end Jake Ferguson, wide receiver Jalen Tolbert and defensive end Sam Williams. Though there is depth at tight end, Ferguson at least has a Pro Bowl on his rsum and can perhaps blame a down 2024 campaign on injuries, which might provide Sam Williams a little leeway as well after he tore his ACL a year ago. However, Tolbert has no such excuse. He's improved in each of his first three seasons but has yet to truly solidify himself. With George Pickens now taking some of the pressure off, perhaps Tolbert can finally make his mark in 2025.