4 Cowboys Players With Most to Prove Entering Contract Years

OTAs are right around the corner for the Dallas Cowboys, with June 1 set as their first day for the voluntary workouts. Mandatory minicamp follows shortly after, with these sessions taking place June 16-20.

The Cowboys typically have excellent attendance at the OTAs, thanks in large part to the example set by team leaders. While completely voluntary, it's a good chance to get up to speed with offseason changes and to begin building chemistry with new teammates.

For the following four players, it's also an opportunity to prove themselves deserving of a new contract. Each of these players is in the final year of their current deal and must find a way to convince the front office they deserve another contract.

Sam Williams, EDGE

Dallas Cowboys defensive end Sam Williams looks on during the game against the Green Bay Packers. | Jerome Miron-Imagn Images

After recording 8.5 sacks over his first two seasons in the league, Sam Williams was set for a larger role in 2024. Unfortunately, he never got that chance with a torn ACL suffered during training camp putting him on the shelf.

He returned in 2025, but recorded just one sack on the season. He then signed a one-year "prove-it" deal with the Cowboys, hoping that he can show more explosion off the edge with a full year removed from his surgery. Williams has expressed excitement to work with new defensive coordinator Christian Parker, which could be the exact boost he needed to get back on track.

Luke Schoonmaker, TE

Dallas Cowboys tight end Luke Schoonmaker runs after a catch during the second half against the Minnesota Vikings. | Raymond Carlin III-Imagn Images

A second-round pick in 2023, Luke Schoonmaker has yet to establish himself as a consistent weapon. He had just eight receptions for 65 yards as a rookie, but began to shed the dreaded bust label in 2024. When Jake Ferguson suffered a knee injury, Schoonmaker delivered and finished the season with 27 catches for 241 yards.

Those aren't overly-impressive numbers, but the progression was encouraging. 2025, however, saw Schoonmaker regress, picking up 132 yards on 14 receptions. He now finds himself battling with Brevyn Spann-Ford and undrafted rookie Michael Trigg for a spot, and could be in danger of not making the team. If he does, Schoonmaker will still have plenty to prove before hitting free agency.

DeMarvion Overshown, LB

Dallas Cowboys linebacker DeMarvion Overshown looks on before the game against the Baltimore Ravens. | Jerome Miron-Imagn Images

As far as talent goes, DeMarvion Overshown has plenty to spare. During the 2024 season, the former Texas Longhorn was a menace, recording 90 tackles, five sacks, and one pick-six. That season ended prematurely though, with Overshown suffering a torn ACL, MCL, and PCL in Week 14. This was just one year after missing his entire rookie season with a torn ACL.

Entering his fourth year in the league, Overshown needs to prove he can stay healthy. If so, he can secure a massive deal. If not, he could stand to lose millions of dollars as he enters free agency in 2027.

George Pickens, WR

Dallas Cowboys wide receiver George Pickens reacts during the game against the Philadelphia Eagles. | Kevin Jairaj-Imagn Images

Like Overshown, there's no doubt that George Pickens has the talent to secure a massive contract. In his first season with the Cowboys, Pickens had 93 receptions for 1,429 yards and nine touchdowns. He was a complete nightmare for opposing defenses, but wasn't able to hit the open market as an unrestricted free agent this offseason.

Instead, he was given the franchise tag by the Cowboys and now has to prove himself worthy of a new deal. Again, the concern isn't talent, but rather his maturity.

This was questioned often throughout his time with the Pittsburgh Steelers and while things went well overall in 2025 with the Cowboys, Pickens has to show that he can stay happy and focused for more than one year before securing a huge deal.

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