It was widely reported earlier this week that the Denver Broncos were planning to release veteran linebacker Randy Gregory, who the team signed ahead of the 2022 season on a five-year, $70 million contract but has ultimately failed to live up to that deal.

Gregory missed the majority of his first year with the team due to injury, and he’s only appeared in 10 games with just three sacks since joining the team. He was removed from Denver’s starting lineup in Week 4, signaling the team planned to move on.

The Broncos threw the league a curveball, however, as they ultimately found a trade partner in the San Francisco 49ers.

Gregory will be shipped off to a San Francisco team that is 4-0 and seen by many as the early Super Bowl favorites. General manager John Lynch and coach Kyle Shanahan hope to revive the 30-year-old’s career and bolster a scoring defense that already ranks third in the league while sitting at fifth in total defense.

A second-round pick in 2015 for the Cowboys, availability has been a concern for Gregory, who has never played a full season due to a combination of suspensions and injuries. When on the field, however, he’s been fairly productive. He totaled six sacks in both the 2018 and 2021 seasons despite playing in just 14 and 12 games, respectively.

The 49ers are looking for that level of production coming off the bench as they search for their first world championship since 1994.

Let’s break down who won the surprising trade between the 49ers and Broncos.

Per ESPN’s Adam Schefter, here’s the compensation for both parties.

49ers Receive: LB Randy Gregory, 2024 seventh-round pick

Broncos Receive: 2024 sixth-round pick

Comp update: Broncos are trading pass rusher Randy Gregory and a 2024 7th-round pick to the San Francisco 49ers for a 2024 6th-round pick, per sources.

— Adam Schefter (@AdamSchefter) October 6, 2023

Trevor Ruszkowski-USA TODAY Sports

This is the kind of luxury move you can make when you have the benefit of Nick Bosa and a supporting cast of edge rushers that includes solid players like Drake Jackson and Clelin Ferrell. The Broncos — likely desperate to make a deal — will eat a roughly $10 million payout to Gregory for this season, while the 49ers only owe Gregory the veteran minimum this season, according to Schefter.

The cap hit would increase significantly beginning next season until the end of his contract in 2026, but his deal is also not guaranteed beyond this season. That gives San Francisco a lot of flexibility to move on if things don’t work out down the stretch this year.

Broncos will pay Randy Gregory roughly $10 million for the remainder of this season.

49ers will pay Gregory the veteran minimum for the remainder of the season.

Gregory has three years left on his contract; none of it is guaranteed after this season.

— Adam Schefter (@AdamSchefter) October 6, 2023

Banking on significant production from Gregory, especially at this point in his career and given his recent performance, is certainly a bit of a gamble. But San Francisco doesn’t have much skin in the game here, and if Gregory is even a modest contributor, it will probably end up looking like a good trade.

Even if he’s not, the 49ers could pull the plug on the experiment after this year essentially no worse for the wear, minus a one-year veteran minimum salary and a sixth-round pick.

Maybe this move never amounts to anything. Maybe it will finally give Shanahan’s team the boost it needs to finally capture the Lombardi Trophy. Either way, it’s hard to imagine it will end up looking like a loss for San Francisco.

Grade: A

Ron Chenoy-USA TODAY Sports

It’s pretty apparent that the Broncos were trying to cut their losses here after making a free-agent move that just objectively did not work out. Gregory never became a major contributor, and he had recently been outplayed by some younger players on the roster.

Denver seemed fully content to release Gregory, but instead it was able to find a willing trade partner. However, it won’t save the team from paying him the bulk of his remaining salary for this season, so this move really just amounts to the same result as the team releasing him, except it picked up some late-round draft capital and saved a bit of cash.

Given the fact that Gregory’s time in Denver was obviously at an end, this was probably the best the Broncos were going to do. This isn’t a bad deal in a vacuum, but it’s hard to give them a lot of props for successfully moving on from a contract they never should have given out in the first place.

If Gregory figures things out on a Super Bowl-contending team, things are only going to look worse for Denver.

Grade: C+

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The offseason for the Dallas Cowboys is starting a little sooner than we had hoped after the team suffered a 23-17 loss to the San Francisco 49ers in the Wild Card game on Sunday. The attention now turns to the upcoming 2022 season and how the team can take steps to improve their ball club. One of the first things this organization will do is to figure out which of their own free agents they intend to keep. There are a lot of tough decisions ahead, but one of the biggest ones is how to deal with edge rusher Randy Gregory. While he’s a guy most fans would love to bring back next season, that might not be the smart thing to do. Here are three reasons why the Cowboys should pass on re-signing Gregory.

They can’t afford him

First, we want to put a little disclaimer here. The Cowboys can afford any player they want if they genuinely want that player. Contracts can always be finagled to fit a new deal if the front office feels that’s a good use of their money. So, what we’re really saying here is that the organization won’t feel that he’s worth the investment.

Gregory had a good year and put a lot of great things on tape during the first half of the season. He started 11 total games this season, which is 10 more than what he had started the previous six years. Granted, two of those years he never stepped onto the field due to season-long suspensions, but even during the three seasons he played at least 10 games, he only managed one start. This year, he was a fixture at the right defensive end position. He missed one game early in the year while being out on COVID reserve and then four more in the middle of the year after suffering a calf injury.

He finished the year with six sacks matching the career-high he had in 2018. It’s unclear what his market value will be this offseason. He’s still under 30 and has very little mileage on his body due to all the time he’s missed. Gregory’s production did slow down as the season progressed. He failed to record a sack in the final five regular-season games (six counting playoffs), and he did himself no favors with some untimely penalties on Sunday. He’s still a skilled edge rusher that several teams will covet.

Many have suggested that the Cowboys should be able to retain Gregory on a team-friendly deal, but that seems a little optimistic. He’s already signed two different one-year extensions for a bargain price, so one could argue he’s already given the team enough of a discount. With his one true chance to cash in on some money, you have to figure Gregory and his agent will maximize this opportunity, and there stands a good chance that it won’t fall within the amount that Stephen Jones is willing to pay for his services . Don’t fret though, the Cowboys can still come out of this with a premiere pass rusher, which leads us to reason number two…

Make Micah Parsons an edge rusher

It’s not required to typecast the Cowboys star rookie into one specific position. In fact, it would be a mistake to do so. His skill set is so rare that they’d be foolish to limit his contributions to just one facet of the game. That’s why this “lionbacker” should be used as needed to do whatever. Oddly enough, that’s exactly what happened for them to discover just how remarkable of an edge rusher he is.

Parsons led the Cowboys with 13 sacks this year, but what’s incredible about this accomplishment is that he did so with limited pass-rushing reps. With the team deploying him several different ways, they have only scratched the surface on what he could be as a true pass rusher. His 19.4% pressure rate was the highest in the NFL, and who’s to say that he might not turn into one of the game’s best edge rushers? There is certainly enough quality film to justify experimenting with this idea. An elite edge rusher is more valuable than an elite off-ball linebacker any day of the week. Not only that, but it’s much easier to find a viable off-ball linebacker in the draft to where the team could backfill Parsons linebacker reps with a brand new rookie in the upcoming draft. Or even sign a moderately-priced veteran.

The Cowboys have some other options

With DeMarcus Lawrence and Parsons under contract, the Cowboys will enter the new season with some quality edge-rushing players even if they lose Gregory. They also have a couple of depth guys as well. The team drafted Chauncey Golston in the third round this past year and they also have the veteran Tarell Basham under contract. Unlike the one-year deals the Cowboys offered to most of their free agents last offseason, Basham got a two-year deal so the team has him in their back pocket if needed.

They also should consider trying to bring Dorance Armstrong back if the price is right. A fourth-round pick back in 2018, Armstrong’s rookie deal has expired and he’s coming off his best season as a pro. He’s taken advantage of time missed from both Lawrence and Gregory and logged 507 defensive snaps (56%), which is a career-high in playing time. Armstrong has made the most of it with five sacks, 37 tackles, and a forced fumble. He’s even blocked a punt as well as scooped up a Parsons sack/strip/fumble and returned it for a touchdown.

Ultimately, we’d love Gregory to return. Having him on this squad makes this defense better. However, after looking at things carefully, the Cowboys might be better served to go another direction if his asking price is too high.

What about you? Would you find a way to re-sign Gregory or let him walk in free agency?

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