Dallas Cowboys

Cowboys lose Randy Gregory to Broncos after contract issue

Updated Mar. 16, 2022 5:17 p.m. ET

Even the Cowboys' social media team thought it was a done deal.

And by all accounts, an agreement had been reached: five years, $70 million for star defensive end Randy Gregory to return to Dallas for the next half-decade.

But just minutes later, Gregory's path had rerouted, and the five-year veteran changed course toward Denver, opting to join the revamping Broncos in a deal that's expected to trump Dallas' offer in terms of guaranteed money.

That's not why Gregory ultimately chose to flip last-minute, though.

Dallas was hard at work over the weekend to draft up a contract that would satisfy the pass-rusher's wishes. The squad was fresh off the heels of a trade with Cleveland for wide receiver Amari Cooper, and freed up additional cap room by voiding Demarcus Lawrence's five-year, $101 million deal signed in 2019, and replacing it with a three-year $30 million contract Monday.

This cleared the runway for the ‘Boys to begin negotiating with the 29-year-old Gregory, who’d just completed his best season yet in 2021.

And from a numbers' standpoint, Dallas' offer was satisfactory.

But it was in the buried wording of the deal that things began to get tricky, and when Gregory's camp noticed some linguistic changes from the original offer, they rang the alarm bell.

According to several sources, including CBS Sports, Jerry Jones was the chief negotiator behind the push to retain Gregory, and the Cowboys owner/GM crafted a deal that would adhere to Gregory's liking — but the final language in the deal didn't work for Gregory and his agent.

The revisions proved costly, ultimately souring Gregory's relationship with the franchise and resulting in his move to Denver.

Like most of the NFL landscape, the "Undisputed" crew stood divided in assigning blame for Gregory's sudden departure. Skip Bayless took to Twitter Tuesday evening, deeming Gregory ungrateful for Jones' continued support in a career full of missteps outside the lines.

Co-host Shannon Sharpe opted for a more labor-friendly approach, however.

He acknowledged the Cowboys' right to incorporate protective language into their contracts, but added that the possibility of losing out on guaranteed money might rub Gregory the wrong way.

"If you're working on a job for six years, and you get in trouble, and then your job comes to you and says, ‘You know what, that money we paid you, we’re going to need some of that back,' you're probably going to look at them sideways."

For Sharpe, the decision is obvious. If both teams are offering similar amounts of money, and Denver relaxes the restrictions on Gregory's guaranteed money, why wouldn't he jet off to Mile High Stadium?

Sharpe also took aim at the perceived hypocrisy of branding players selfish for acting in their best interests while celebrating owners for cutting players in the name of business.

"I don't know how billionaires and teams have been able to convince their fan bases that if a player does something in the best interest of themselves they're selfish and don't care about winning," Sharpe said.

Although the specific language remains a mystery, whatever it was, it was a deal-breaker.

Gregory will now venture to the Mile High City, and Dallas is forced to watch him depart.