Cowboys Completely Blew Randy Gregory Negotiations and Lost Him to the Broncos

Randy Gregory
Randy Gregory / Julio Aguilar/GettyImages

The Dallas Cowboys entered free agency with some tough decisions to make offensively. Defensively, the priority appeared simple: do what they could to keep the group together. The 2021 Cowboys defense was the best unit the franchise has put forth in a long time. It would occasionally hemorrhage yards but recorded more takeaways than any other defense in the NFL. It gave the Cowboys the best turnover differential in football and played a large role in capturing the team's first divisional title since 2018.

The biggest piece hitting free agency comes in the form of defensive end Randy Gregory. Gregory is a good story for the Cowboys, who brought him aboard despite suspensions for substance abuse plaguing the early part of his career. Gregory steadied out and became an extremely productive player in 2021, as he notched six sacks, 17 quarterback hits, and three forced fumbles in only 12 games. He's widely viewed as one of the top edge players available on the market and the Cowboys were going to have to make a competitive offer to retain his services.

On Tuesday, it appeared they did just that. Reports emerged Dallas had reached an agreement with Gregory on a five-year deal worth $70 million. Pricy, to be sure, but about what Gregory was projected to earn.

But then, disaster struck. Two hours later, news broke that Gregory was actually signing with ... the Denver Broncos. Not the Cowboys. A complete reversal. A coup for Denver and a gut punch for Dallas. The drama!

This does not happen very often in the NFL, but it can happen. Nobody can put pen to paper until tomorrow, when the negotiating period ends. Sometimes, things happen between the agreement and the date when the actual signing of the contract happens.

But the Gregory situation was a very quick turnaround. It took less than three hours for him to back out of the deal with Dallas and find a new one elsewhere. How could this have happened?

Apparently, the Cowboys fiddled with the language in the contract after they reached an agreement with Gregory. He did not like that, and so he immediately called the Broncos to tell them he was headed to Denver.

Reading between all the various lines, the narrative the Cowboys would like to have out there is that they wanted additional security in the contract to ensure they'd get their money back should Gregory find himself in trouble again. However, it does appear that Dallas tried to add that after an initial agreement had already been reached. Or at least after all parties felt comfortable enough with their progress that they released information to the media. Everyone felt like they were past the point of no return. But they weren't.

It's brutal for the Cowboys and it's tough to argue that they didn't blow this badly. It is probably smart of them to ask for additional language in the contract that covers all possible bases considering Gregory's history of substance abuse. But however they went about negotiating that was very poorly done. There clearly was a universe in which the Cowboys were protected and Gregory stuck around. Dallas had it within reach. Then they tried to change things and it backfired.

The Cowboys still have the likes of Demarcus Lawrence and Micah Parsons. Losing Gregory will not lead to the defense falling apart. But Gregory is a good player and a legitimate game-changer when he's on the field. Jerry Jones has an awful lot of money tied up in this version of the team. Results are expected immediately. Managing to lose their third or fourth-best defender due to language snafus in the contract is nearing disaster.