Jerry Jones breaks the bank to bring back Randy Gregory: Signing grade

Dallas Cowboys, NFL Free Agency

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Jerry Jones loves his Dallas Cowboys more than anything, as he is paying Randy Gregory $70 million on a five-year deal to stay with the franchise in his free agency.

On today’s episode on why the Dallas Cowboys are the Dallas Cowboys, Jerry Jones grossly overpaid for a pass-rusher who is approaching 30 years old and has never had a 10-sack season. Randy Gregory, come get your money!

ESPN’s Adam Schefter reported the Cowboys are bringing back Gregory on a five-year deal worth $70 million. Only $28 million of that is fully guaranteed.

Gregory turns 30 years old in late November. He will be 34 years old when this contract expires after the 2026 NFL season. Loyalty may be a big thing in Big D, but what are the Cowboys doing?

Jerry Jones massively overpays for Randy Gregory in his free agency

Look. It would be absolutely fantastic if Gregory becomes a bona-fide pass-rushing beast in his early 30s for the Cowboys. Here is to him having double-digit sack seasons for the rest of time. Unfortunately, that is not going to happen. The past is the greatest indicator of future success. No matter how you slice it, Gregory is unreliable. He has never played a full season in the NFL before.

Should we root for him to succeed in Dallas long-term? Absolutely, but this move is all about the Cowboys refusing to learn their lesson. Do not pay good players great money. This is why they have not been to a Super Bowl since the Bill Clinton Administration. Only the Detroit Lions and the Washington Commanders two names ago have not been to a conference title bout more recently.

The free agency grade reflects the nickname of the city in which the Cowboys call home: Big D!

Grade: D

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