Cowboys not planning to extend any impending free agents before 2022

Gallup, Gregory and Vander Esch profile as the Cowboys' top three 2022 free agents. Each could be elsewhere next season, depending on their respective performances this year. Dallas’ upcoming free-agent crop does not bring the kind of high-stakes drama of recent offseasons, when the Cowboys either doled out big-ticket extensions (in the cases of Ezekiel Elliott, Amari Cooper and DeMarcus Lawrence) or stood down (in the case of Prescott). But Gallup and Gregory could enhance their value with quality contract-year performances, making the Cowboys pay more come 2022 — if they view the starters as long-term pieces.

Cooper’s status will affect Gallup’s. It appears Dallas recognizes there is only room for one of the two on its 2022 squad, with Gehlken adding that the Cowboys expect Gallup to see a big market as a free agent. Cooper’s $20 million average annual value contract becomes easy to shed next year, with the Cowboys saving $16 million in cap space and taking just a $6 million dead-money hit if they cut the former trade acquisition. Cooper, 27, is two years older than Gallup. An either/or scenario creates an interesting subplot for the Cowboys’ passing attack this season.

The Cowboys making Gregory prove it is logical, even though they did extend the talented defensive end through 2021 despite his persistent off-field issues. Gregory will be 29 by the time his contract expires, and the former second-round pick has been suspended four times during his career. He is, however, set to be a full-time starter for the first time. This season stands to make a major impact on Gregory’s value ahead of what could be his only notable contract agreement.

Dallas might enter an either/or situation at linebacker soon. The Cowboys are set to deploy first-round pick Micah Parsons this year, potentially leaving Vander Esch and Jaylon Smith to vie for a slot alongside him in 2022. The Cowboys did not pick up Vander Esch’s fifth-year option, due to his injury troubles. Shedding Smith’s deal next year would saddle the Cowboys with $6.8 million in dead money. How Vander Esch performs this year, and his health status at the end of the season, will largely determine his free agency value.