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Win now or a bright future? Examining the soon-to-be expiring contracts of the Cowboys top players

The Cowboys have a stacked roster, but there is work to do to keep it that way.

Dallas Cowboys v Washington Commanders Photo by Rob Carr/Getty Images

The Dallas Cowboys are a good football team. They are coming off two consecutive 12-win seasons, and many are expecting big things this year. The front office has had some tough contract decisions in recent years and that has resulted in some valuable veterans from the past leaving the team. Players like Amari Cooper, Ezekiel Elliott, Randy Gregory, La’el Collins, and Dalton Schultz have all left Dallas over the last 14 months.

While some are gone, new talent has arrived. With great drafts that include CeeDee Lamb, Trevon Diggs, Micah Parsons, and even Tyler Smith, the Cowboys are poised to keep this ball rolling. However, time is again dwindling down on some veteran players. Does this mean that the window of opportunity is running out?

Today, we’ll look at the contracts of 14 of the Cowboys most important veteran players and get a feel for whether there is a sense of urgency to win now or if the future remains bright for this team.

On Friday, Rabblerousr and I went through these contracts on the latest episode of The Star Seminar, so make sure to check it out!


Four of the Cowboys' key starters on offense are in the last year of their contract, including three players on the offensive line. Four more have contracts that expire the year after that. Here is a contract breakdown of the important starters on offense, courtesy of spotrac.

As you can see, the Cowboys have some questions along the offensive line. They did draft Tyler Smith last year so they’ll have four more years of player control with him, but outside of that, it gets a little dicey.

Who’s likely to return

We know the Cowboys are committed to Dak Prescott and it’s only a matter of when and how much in terms of what that looming third contract looks like. We know it’s going to be a lucrative deal and something the front office will have to work around financially when it comes to balancing the books and keeping enough talent around him.

Terence Steele was slapped with a second-round tender this offseason which gives him the first of many pay increases. Despite being an undrafted free agent in 2020, he’s developed into a quality tackle and it would be odd to see the team just let him walk away. Expect a contract extension soon for Steele.

The Cowboys exercised the fifth-year option on CeeDee Lamb which is just a precursor to the interest they have in retaining him long-term.

Who’s on their way out

The Cowboys' aging lineman may very well finish out their current deal and call it quits. That seems very likely for Tyron Smith who has battled to stay healthy for several years now. Zack Martin could be a different story. It wouldn’t be shocking to see him sign a short-term extension if the veteran is up to sticking around a bit longer. He’s still playing at a high level and has a strong résumé of durability, but a lot could change two years from now.

We suspect Brandin Cooks is on a two-year rental. With an extension coming for Lamb and money invested in Michael Gallup, it would be hard seeing them throw additional funds at wide receiver. The Cowboys didn’t use an early draft resource at receiver, so they still have a lot of questions outside of their main three.

Who remains a question mark

The Cowboys placed the franchise tag on Tony Pollard and released Ezekiel Elliott. However, they only used a sixth-round draft resource on a running back with Deuce Vaughn, meaning they don’t have any definitive answers outside of Pollard.

Another big question is center Tyler Biadasz. Last year some thought he could be replaced by Iowa center Tyler Linderbaum, and the Cowboys had a chance to draft him, but passed in favor of Tyler Smith. That turned out great for two reasons. First, Smith is a future star in this league, but second, Biadasz continued to get better. In fact, he earned Pro Bowl honors last season. The Cowboys would love to retain the player they once traded up to get, but he won’t come cheap.


Recently, the Cowboys have reinvested in some of their key defenders but they still have several players in the secondary who are in the last year of their contracts. Here are the contracts of the key defensive players courtesy of spotrac.

Secondary is a big one for Dallas. Not only are the three players listed above in the last year of their deals, but the same is true for a couple of other guys, Malik Hooker and Jourdan Lewis. They did re-sign Donovan Wilson this offseason and have second-year corner DaRon Bland under player control for the next three years, so it’s not all bad. Plus, they got a young corner who’s about to get paid, which brings us to...

Who’s likely to stay

We all expect Trevon Diggs to get a contract extension. From the moment he was stolen in the second round of the 2020 draft, he’s been over-performing. His 11-interception, All-Pro season in 2021 was quite the sight to see and he followed it up with another Pro Bowl season last year. If the Cowboys don’t extend him prior to the start of the season, there’s a good chance he’ll get hit with the franchise tag next year.

Micah Parsons will also get a huge second contract, but that is still a ways away, especially when you factor in that fifth-year option that the Cowboys will inevitably exercise.

Who’s on their way out

With money coming for Diggs, it seems a foregone conclusion that Stephon Gilmore is just here as a one-year rental. There’s a small chance he could return on a team-friendly deal next offseason, but we’ll have to wait and see on that one.

DeMarcus Lawrence took a pay reduction/small extension to stay in Dallas last offseason, and it worked out for both sides. With a rising talent like Sam Williams on the roster and the team’s continued success in finding low-cost veteran depth (Dante Fowler this time), the most likely outcome is that Tank finishes out his current deal and calls it good.

Many thought the team wouldn’t retain Jayron Kearse after his breakout season in 2021, but the front office surprised us and signed him for two more years. Will that happen again next offseason? With the investment in third-round pick DeMarvion Overshown, it already appears the Cowboys are scoping out Kearse’s replacement.

Who remains a question mark

Just when you think Leighton Vander Esch has played his last snap in Dallas, the Cowboys surprise us by re-signing him. He’s under control for two more years and with not a lot of proven options from younger players who have been recently added, LVE remains “the guy” at linebacker. A lot could change in two years with good upside players like Damone Clark and the before-mentioned Overshown on the team, but until we see it, Vander Esch’s value to the team remains high.


The opportunity the Cowboys have right now is huge. They are loaded with talent and some of these key pieces will ultimately go away before long. That said, the Cowboys have proven themselves capable of replenishing talent. Just looking at the top superstars on the team right now, some of them weren’t on the team a few short years ago. Additionally, the Cowboys have rising/already proven stars in all of the money five positions, and they won’t be going anywhere for a while.

Do they have a great chance to make something happen now? Yes.

Do they have a great chance to make something happen later? Also yes.

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