Big decisions are looming for the Cowboys this offseason, as they try to maintain one of the league’s most talented rosters. Two key pieces to the team – who both happen to be pending free agents coming off of significant injuries – are defensive end Randy Gregory and wide receiver Michael Gallup. 
The former has already undergone knee surgery, according to ESPN’s Todd Archer. While the issue bothered him throughout the season, it didn’t cost him any time (unlike one missed game because of COVID-19, and a calf strain that landed him on IR). Overall, the 12 games Gregory was able to play in was tied for the second most in his career, mainly as a result of multiple suspensions.
The 29-year-old is set to hit free agency for the first time in his career. The Cowboys signed him to an extension in September of 2020, keeping him in the fold through this past year. He responded with six sacks, three forced fumbles and one interception, as he was a key member of Dallas’ impressive defensive unit. According to David Helman of Cowboys.com, owner and general manager Jerry Jones recently expressed optimism in being able to bring Gregory back: “Knowing our time together and some of the pluses and some of the times that we’ve had to work through and some of the not-so-fun things, that will serve us well”, he said.
Meanwhile, Gallup is scheduled to have knee surgery next week, writes Michael Gehlken of The Dallas Morning News. The 25-year-old tore his ACL at the beginning of the month, ending his season. He ended up with the lowest receiving yards of his four-year career, but his 2019 season (66 catches for 1,107 yards and six touchdowns) alone should earn him plenty of suitors if he hits the market. With a great deal of money already committed to Amari Cooper, and CeeDee Lamb eligible for an extension as early as next season, the Cowboys may very well have to keep only one of Gallup or breakout tight end Dalton Schultz, who is also a pending UFA.
Both players are expected to make full recoveries, and be available for the start of the 2022 season. Whether or not they will playing in Dallas by that point remains to be seen.