The one player the Cowboys should extend right now

The Dallas Cowboys have done a fairly good job of drafting players in recent years. As a result, many of their drafted stars have signed extensions in Dallas that represent a good portion of the team’s salary cap. And this is an area where the Cowboys’ brass has struggled.

The biggest example of course being the front office’s failure to extend the contract of quarterback Dak Prescott early on. The two sides allowed negotiations to linger on for years resulting in the Cowboys using two franchise tags to retain Prescott, although the last one was simply a placeholder as a new four-year, $160 million deal was agreed upon earlier this year.

But if the Cowboys had simply agreed to a deal in a more timely fashion it would have saved the team millions in salary cap space. Knowing when and when not to extend players has been a big issue in Dallas.

The Cowboys have found themselves swimming in difficult financial waters after players like running back Ezekiel Elliott and linebacker Jaylon Smith have severely underperformed since signing their extensions. There is a fine line to walk between being cautious and being proactive.

In the case of the above contract examples, the importance of accurately predicting a player’s future value is paramount. Getting an ascending player locked down to a team-friendly contract extension before they have a breakout season is the key to striking great deals in the NFL.

And the Cowboys have an opportunity this summer to do just that. Dallas would be wise to start exploring the idea of extending the contract of 28-year old defensive end Randy Gregory right now, as the former second-round selection is primed for a career performance in 2021.

The downside of signing Gregory to a long-term deal is obvious. This is a player that has been unreliable in the past due to his various drug-related suspensions. Gregory has played just 38 games for Dallas since being drafted out of Nebraska in 2015.

But Gregory believes his issues are behind him to the point where he hopes the media stops referencing his past as part of his narrative. And if the Cowboys agree, they’d best try to sign him to something long-term now as the young defender enters into a contract year in Dallas.

Last season, Gregory didn’t start a single game playing behind former All-Pro pass rusher Aldon Smith. And although he played just 10 total games, Gregory still had the second most quarterback hits on the team with 12. He ended last season racking up 21 total tackles, 3.5 sacks, and three forced fumbles while only playing 25% of the team’s defensive snaps.

The Cowboys felt so good about his play, they essentially made him their starter opposite DeMarcus Lawrence by not re-signing Aldon Smith this offseason. And so far through his first full offseason training program since he was a rookie, Gregory appears to be on pace for a breakout performance.

Premier pass rushers demand top dollar in free agency. The Cowboys know this fact very well. In 2019, defensive end Robert Quinn was able to rack up 11.5 sacks in Dallas opposite Lawrence. Quinn ended up inking an impressive five-year, $70 million deal to join the Chicago Bears as a free agent last year.

The fact is, the Dallas Cowboys have held the door open for Randy Gregory’s return for years. And the player would likely be inclined to return the favor by signing a team-friendly deal to remain in Dallas. If the Cowboys believes his troubles are truly behind him. getting a contract extension done before the regular season kicks off could potentially save the team millions.