They were well aware of the issues he had at Nebraska. They knew he tested positive for marijuana at the scouting combine. They knew he had anxiety issues. They had him in at Valley Ranch for a pre-draft visit to get a better feel for him and if he was worth the trouble.
They decided he was.
Their faith in Gregory is now being tested with a four-game suspension to start the 2016 season for violating the NFL's substance abuse policy.
The easy thing to say is cut Gregory. Another way to look at it is to say perhaps the NFL should look at altering its policy regarding marijuana, assuming this is in fact the substance that got Gregory suspended. As society's feelings toward marijuana change, maybe someday the NFL's will too.
But that doesn't help the Cowboys on the field in 2016.
The Cowboys were hoping Gregory could do in 2016 what DeMarcus Lawrence, their 2014 second-rounder, did in 2015. Lawrence went from zero sacks as a rookie in the regular season to leading the Cowboys with eight.
Gregory did not have a sack last year, his season derailed early because of a high ankle sprain in the season opener after he had an electrifying training camp and preseason. I went out on a limb and said he would be the NFL's defensive rookie of the year.
With Greg Hardy, Jeremy Mincey and Jack Crawford set to become unrestricted free agents and Hardy almost assuredly not returning, the Cowboys had a need for pass-rushing help before Gregory's suspension was announced.
A great need becomes even greater with Gregory missing a quarter of the season.
Do the Cowboys get in the free-agent game and make a play for perhaps the biggest prize, Miami's Olivier Vernon? He gave Tyron Smith problems when the teams met last season. Do they look at Bruce Irvin or even a Jason Pierre-Paul? Do they continue to go with a quantity over quality approach and look for bargains to be a part of Rod Marinelli's desired rotation?
In the draft they could be in position to take Ohio State's Joey Bosa at No. 4. Eastern Kentucky's Noah Spence might be the best pass-rusher available, but he was kicked out of the Big Ten for a drug problem. Could the Cowboys really roll the dice again after what has happened to Gregory?
The suspension is disappointing on many fronts, because Gregory is an engaging kid, but he has a problem. The Cowboys knew it. They thought they could help him beat it. They still have a duty to help him, and that in turn could help them in the future.
A lot of people across the league will snicker at the Cowboys for taking a chance on Gregory and getting burned. The holier-than-thou attitude is off-putting when every team takes chances on players. Every team.
The Cowboys took a chance on Gregory last year. They don't need to turn their backs on him now. The right thing is to help Gregory and hope he can develop into the pass-rusher they so badly need.