On Saturday, TMZ Sports reported Gregory's friends are "deeply concerned for his well-being," while other sources close to the defender believe he's "drifted from football" and think his playing career might be over after the latest setback.
The 24-year-old Florida native was suspended for "at least one year" by the NFL in January for violating the league's substance-abuse policy. He'd have to apply for reinstatement and get the application approved before returning to action.
Cowboys owner Jerry Jones said he disagreed with the ruling during a radio appearance on 105.3 The Fan, adding in a press conference the defensive end was "genuine in his rehab process," per Patrik Walker of 247Sports.
"We anticipated [the suspension of Randy Gregory]," Jones told the radio station. "We knew the circumstances. We don't agree with them, but we do know the circumstances."
Dallas invested a second-round pick in Gregory during the 2015 NFL draft. He was originally projected as a first-round selection after a pair of standout seasons at Nebraska, but a failed drug test at the scouting combine caused his stock to drop.
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He's appeared in 14 games across his first two professional seasons, tallying 20 tackles and one sack.
The Cowboys drafted defensive end Taco Charlton out of Michigan in the first round of the 2017 NFL draft Thursday night. He'll likely fill the front-seven void the team hoped Gregory would assume two years ago.
It's unclear how the latest reported failure of a drug test could impact his one-year suspension.