5 moves Cowboys should make before 2021 season begins

Extend Randy Gregory

The Cowboys’ front office has had its issues in recent years when it comes to timing. Had they given quarterback Dak Prescott the extension he desired years ago, he’d likely be seen as a great value right now. Instead, Prescott was inked to a massive four-year, $160 million deal this offseason.

On the other end of the spectrum, signing players like running back Ezekiel Elliott and linebacker Jaylon Smith to contract extensions early have resulted in lackluster returns. When it comes to the timing of these deals, being able to properly predict future production is key.

That’s why we think the Cowboys should seriously consider extending defensive end Randy Gregory right now. The 28-year old pass rusher appears to be on the brink of a breakout season. And the fact Dallas didn’t re-sign starter Aldon Smith in the offseason means the Cowboys are banking on Gregory’s future production being sky-high.

While Gregory’s troubling past is cause for concern, he finally appears to be on track to become a consistent force for Dallas. And because premier pass rushers are hard to find, and often very expensive in free agency, the Cowboys should try their level best to lock him down to a team-friendly deal while they still can.