Cowboys avoided all-time bad contract following shocking Randy Gregory release

The Dallas Cowboys have assembled one of the finest rosters in the NFL. Like any team, though, Dallas has made some regrettable moves that set the franchise back. Trading Amari Cooper is the example most folks would point to in that regard, as it loomed large in last year's playoff loss against the 49ers.

Trading Cooper paved the way for the Cowboys to negotiate an extension with pass rusher Randy Gregory, who was coming off his most productive season as a pro in 2021 with six sacks, 17 quarterback hits, three forced fumbles and 43 pressures.

Gregory and Dallas ultimately agreed on a five-year deal worth upward of $70 million with nearly $30 million guaranteed. It seemed like a gross overpay for a player who had trouble staying healthy, navigated off-field troubles early in his career and never became the consistent game-wrecker the team hoped he'd be.

At the eleventh hour, though, Gregory backed out of his agreement with the Cowboys and signed the same contract with the Broncos.

Less than two years into that mega-deal, Denver shockingly released Gregory on Wednesday to allow more opportunities for its young core.

Broncos release Randy Gregory, saved Cowboys from all-time bad contract

The Cowboys should be counting their blessings right now. While it stands to reason that Gregory would've been more productive the last two seasons if he stayed in Dallas, sometimes the best moves in free agency are the ones that don't happen.

At the end of the day, Gregory had three sacks in 10 games with the Broncos. His injury troubles have reared their ugly head and he didn't have the production to show for it, which prompted Denver to inherit dead cap hits of $16.1 million in 2023 and $6.3 million in 2024.

Gregory was a nice player for the Cowboys, but is he overrated by the fan base?

Dorance Armstrong had as many sacks last year (8.5) that Gregory has combined the last three seasons. Armstrong signed a two-year, $12 million contract with Dallas, including $6 million guaranteed after the Gregory agreement went haywire.

Armstrong has two sacks in four games this season and is second in the NFL with an incredible 17.2% run stuff rate, per Next Gen Stats. He's more available and productive than Gregory for a quarter of the price.

There's already heated debates on social media about whether the Cowboys should bring Gregory back to fortify an already-lethal defensive front.

It's tough to say if the fences can be mended after Gregory left Dallas at the altar over language in his contract and we wish nothing but the best for Gregory in his future endeavors, but the Broncos swooping in saved Jerry Jones and Co. from one of the worst contracts in modern NFL history.

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