Randy Gregory flipped on Jerry Jones and the Cowboys faster than a coin toss
Randy Gregory (l.) is heading from Arlington to Denver. source: Getty Images The new NFL year officially begins tomorrow at 4 p.m. EST, but free agency is already on and popping with many big moves, trades, and releases being confirmed. When you woke up this morning, you may have heard that the Dallas Cowboys had retained the services of defensive end Randy Gregory, agreeing to a long-term extension. Well, just hours later, news broke that Gregory flipped the script on Jerry Jones and decided to take his talents to the Mile High City Denver.
Jones is an owner that loves to take care of players he’s drafted and makes it a point to re-sign them. He likes to keep his guys in the Cowboy family, so Gregory switching up like this at the last minute has got to hurt. And it’s not like the deal he’s accepted from the Broncos isn’t much different from what the Cowboys offered. It’s a five-year deal worth $70 million with $28 million guaranteed. And most of that guarantee will come over the first two years of the contract.
The fallout that is sure to follow this story should be interesting. The Cowboys have stood behind Gregory through all of his issues with drugs and several suspensions since he was drafted in 2015. I’m not saying he necessarily owed them anything because the NFL and professional football are a business, but it’s the way it went down. Gregory reportedly was all set to stay in Big D, then of course, we know what happened from there. Free agency is looking like the wild wild West out here right now.
Apparently, some type of “ behavioral clause” was inserted into the deal, which led to Gregory deciding to leave Dallas. Dem’ Boys just lost a tremendous edge rusher. And those are highly coveted in today’s pass-happy NFL. Losing Gregory will likely mean a shift in free agency and draft strategy for Dallas. Gregory recorded six sacks in 12 games last season. Now the Cowboys need to replace his production and his presence in the lineup.
We’ll see how Jerry bounces back from this because the Cowboys took a big ‘L’ here. Whether that behavior clause was the straw that broke the camel’s back or not, Jones must now must go shopping for a player to line up opposite of DeMarcus Lawrence on the D-Line. Luckily for Jones, this happened at the beginning of the free-agent signing period, so some pretty good options are still in play for Dallas. Chandler Jones is out there, Von Miller is available even though he’s Tweeting about Denver (and they just added Gregory), and even Jadeveon Clowney remains an option for the Cowboys. Hopefully, Jerry and the Cowboys don’t fumble the next routine handoff.
Three NFL Teams That Can’t Afford To Screw up 2026 NFL Draft
These NHL Playoff Sleepers Shouldn’t Be Counted Out
WrestleMania 42 Grades: Night 1 Disaster, Night 2 Delivers
Ranking the Greatest Stoner Athletes of All-Time
Are the Detroit Pistons in Trouble After a Rough Game 1?
Best Value Betting Picks Ahead of 2026 NFL Draft
- UFC Winnipeg Betting Picks: Best Bets for April 18th Card
- NBA Play-In Picks: Best Player Props for Hornets vs Magic, Warriors vs Suns
- Friday April 17th Expert MLB Betting Picks, Predictions
- NHL Betting Picks April 16: Top Plays for Final Regular Season Games
- MLB Picks Today: Best Bets for Diamondbacks vs Orioles and Cubs vs Phillies
- NBA Play-In Picks: Best Bets for Warriors vs Clippers and Magic vs 76ers
- NBA Play-In Player Props: Donovan Clingan, LaMelo Ball Headlines Best Picks

