Gregory is a gifted athlete with a big upside as a pass rusher, but off-field issues -- including a failed drug test at the NFL Scouting Combine and reports from NFL Media Insider Ian Rapoport that he was late to and/or totally missed two team meetings -- caused him to drop.
"There's no denying the talent, but what I hope is that the Dallas Cowboys have a plan in place, an infrastructure in place, to help this young man deal with what he is going to have to deal with," NFL Media analyst Mike Mayock said during NFL Network's draft coverage. "And I'm not just talking about when he is at the facility. I'm talking about who's he's bringing with him? Who's with him when he's away from the facility? How do you help this young man turn the corner in a positive way?"
Texas coach Charlie Strong, serving as a guest analyst on the draft coverage, agreed that what happens away from the facility is going to be the key.
"Who is he going to be surrounded by?" Strong asked. "And do they have enough leadership in that locker room to take this young man and lead him?"
That brings up another point, said NFL Media analyst Charles Davis: "Will he allow himself to be surrounded by those people? Many people get the mentors, get the people who are in their life to give them guidance, show them the right way, and guys choose to go the other way often."
Gregory is the second big pass-rushing addition for Dallas -- and the second with issues. Dallas signed free-agent edge rusher Greg Hardy, who missed the 2014 season and will miss the first 10 games in 2015 for off-field conduct issues.
"There's a lot of red flags on that line, but if they can go ahead and hunt some quarterbacks, the Dallas Cowboys could win some games. I guess everything will be hunky-dory," said NFL Network's Rich Eisen, who is hosting the network's draft coverage.