4 former Cowboys players who failed with their new teams in 2023

It was ultimately for naught, but the Dallas Cowboys deserve their flowers for their work last offseason. Lousy showing in the NFL draft notwithstanding, the Cowboys re-signed key free agents and made brilliant trades for veterans Stephon Gilmore and Brandin Cooks, both of whom made a profound impact this year.

Though important, player acquisitions are only part of the equation. Knowing when to cut bait with players is an underrated part of a front office's job. Whether it be last offseason or dating back even farther, the Cowboys have made difficult, but necessary decisions in terms of parting with former impact players.

With that in mind, here are some former Cowboys who struggled with their new teams in 2023.

4. DE Randy Gregory (Broncos, 49ers)

Did the Cowboys dodge disaster with Randy Gregory's contract or what? During the 2022 offseason, after Dallas traded Amari Cooper, Gregory agreed to a five-year, $70 million deal with nearly $30 million guaranteed. Before the contract was made official, Gregory backed out and signed the same deal with the Broncos.

Though an embarrassing optic, the failed agreement proved to be a blessing in disguise for the Cowboys. He played just six games in 2022 due to injury and mustered two sacks, two forced fumbles and seven QB hits.

This season didn't go much better for the former Cowboy. After playing four games (three starts), Denver released Gregory. In doing so, the Broncos absorbed dead cap hits of $16.1 million in 2023 and $6.3 million in 2024.

He was swiftly signed by the 49ers, but made a minimal impact there as well. In 12 games, he compiled 2.5 sacks and four tackles for loss. For the season, he posted 45.5 player grade and 53.7 pass-rush grade from PFF.

Whether it be in Denver of San Francisco, Gregory has experienced a stunning fall from grace since leaving Dallas two years ago.