
The Dallas Cowboys have been able to keep some key players like DeMarcus Lawrence and Dalton Schultz in the offseason. But sadly, they’ve also lost some big names to trades and free agency. We all knew this offseason would be a tough one. The salary cap struggles meant cuts and trades would be necessary. We knew the roster would look different, but it’s never easy to say goodbye to players, especially ones who have had long-term spots on the team.
In less than a week’s time, the Cowboys lost four critical players: Connor Williams, Amari Cooper, Cedrick Wilson, and Randy Gregory. One was a trade, two were free-agent pickups, and one actually was supposed to be on the Cowboys for a whole 90 minutes. At some point in their time in Dallas, each one of these players made a key play or helped their team win a game. Now, they will be wearing different jerseys in 2022.
Everyone in Cowboys Nation has their opinions about who should have stayed and who should have left, but we wanted to do our own ranking of the four biggest players who left the team so far. We will go in order of who the team will miss the least to who the team will miss the most.
Updated list of Cowboys moves: pic.twitter.com/J6hPTNSSKa
— Jon Machota (@jonmachota) March 15, 2022
Ranking the 4 biggest Cowboys losses of the 2022 offseason
4. Connor Williams, Guard
You probably saw this one coming. The 2021 season made Williams an easy goodbye. But before we talk about that, we can reminisce just a bit on his impact in Dallas. Williams was drafted out of Texas in the second round of the 2018 NFL Draft. The former Longhorn became an immediate starter at left guard for Dallas.
One positive thing Williams brought to the team was his durability. Williams started in 51 of 57 games in his four years with the Cowboys. In 2019, he missed the final five games of the season with an ACL tear. However, after that, he played all but one snap in the 2020 season. These good times were sadly overshadowed by a rough 2021 campaign. The 24-year-old was a penalty machine. He led the league in holding penalties and ruined several key moments with false start and holding flags.
Despite all of this, Williams remained at the top of several top free-agent lists due to his young age, durability, and potential. This year, several NFL teams are in need of strong offensive line talent. The Cowboys will undoubtedly have a starting role to fill as well. But the Miami Dolphins capitalized on Williams. The AFC team signed him to a two-year, $14 million deal with $7.5 million fully guaranteed. Passionate Cowboys fans took to Twitter to troll Miami and let them know their true thoughts on the guard.
There is a chance he cleans up his act and does well for the Dolphins, but the Cowboys certainly won’t miss the 2021 version of Williams. From here, it’s incredibly hard to rank the next three. They were all players we hoped would remain in Dallas.

3. Cedrick Wilson, WR
Although Wilson isn’t a starter like Williams was, he certainly brought a lot of value to the team. Before free agency rumors even began, The Landry Hat made a list of reasons why Cedrick Wilson should be a priority. The Joneses didn’t seem to agree. They let one of the most reliable backups on any NFL roster walk in free agency. We always knew that Wilson had earned himself a more lucrative salary with a breakout 2021 campaign, but we thought the Cowboys would be able to keep him around.
Wilson is also heading to the Miami Dolphins, signing a three-year, $22.8 million deal. Miami was hoping they’d land Cooper but instead picked up Wilson. While there is no denying that Wilson isn’t at the caliber that Cooper is, he certainly isn’t a garbage signing. Wilson is ready to be a No. 2 receiver who gets a high snap count and makes an impact on a roster.
After catching just 22 passes and having no starts in his first three years with Dallas, Wilson took advantage of several injuries throughout the Cowboys’ WR trio to have a stellar 2021 season. The former sixth-round pick started in four games and had 602 yards and six touchdowns in the 16 total games he played. The receiver didn’t look like a backup.
Cowboys WR Cedrick Wilson has caught a touchdown, a 2-point conversion and five other balls in addition to completing a pass for 31 yards
— Jori Epstein (@JoriEpstein) January 3, 2022
It’s Cedrick’s world, we’re all just living in itpic.twitter.com/XcNs8zSlUb
The Boise State product was also willing to fill in wherever needed. According to his official stats, he is five for five on passing with 111 throwing yards and one throwing touchdown. Wilson was well-liked by his head coach, teammates, and others. No longer having him on the wide receiver depth chart may be a problem for Dallas next year.

2. Randy Gregory, DE
This loss was upsetting for a whole slew of reasons. On a surface level, Gregory was a long-time presence on the Dallas defense. In 2021, Gregory had the ninth-best pressure rate amongst pass rushers. There was only one game last year (against Tampa Bay in Week 1) where he did not record a single QB pressure. His sack numbers may not be the highest, but he had 19 tackles, a tackle for loss, three forced fumbles, a fumble recovery, and an interception last year.
The biggest issue with losing Gregory is that he leaves a huge void in a defense that already has positional needs this offseason. The Cowboys need another linebacker or edge rusher to work alongside Micah Parsons and DeMarcus Lawrence. However, there’s a reason we put Gregory at No. 2 instead of Cooper.
The now Bronco has spent way too much time off the field, whether that be for injuries or for suspensions. Gregory has never played more than 11 games in a season and has never totaled more than 6.0 sacks. Lawrence and Parsons were far more crucial to the defense than Gregory.
After being drafted in 2015, Gregory missed most of the 2016 and the entire 2017 season. In 2021, he missed time with COVID and a calf strain. His 11 starts in 2021 were a career-high and Denver is hoping he is going to continue projecting upwards.
The other issue is how the Cowboys lost him. While many reporters are up in arms about the situation, no matter who you feel is at fault, Dallas lost Gregory due to contract clauses. The front office wanted to put a clause in his contract that would void any guarantees if Gregory was fined or suspended. The team claimed it was a clause in everyone’s contract, but it was apparently absent from Dak Prescott’s.
Many questions regarding the Randy Gregory contract language matter. Explained here: pic.twitter.com/845SnQCpK3
— Andrew Brandt (@AndrewBrandt) March 16, 2022
After everything was all but secured, the front office tried to change the wording and Gregory said see you later. His agent said he’d never seen that language in a contract in his 30 years. Regardless of what really happened behind closed doors, the point is that the Cowboys couldn’t get it done.
Unlike Dallas, the Broncos are making moves this offseason. They’ve signed Russell Wilson and re-signed linebacker Josey Jewell. Gregory will likely join Bradley Chubb as a starting outside linebacker in the Broncos’ 3-4 defense. Although Gregory leaves big shoes to fill, his off-the-field issues and injuries make him less of a loss than Cooper.

1. Amari Cooper, WR
The rumors that Cooper may be leaving Dallas started very early on. Ahead of 2020, Cooper signed a five-year, $100 million. That deal had an out because it had no guaranteed money left at the beginning of 2022. The Cowboys’ choice not to restructure that contract last off-season was already a sign of foreshadowing. The receiver made a whopping $20 million to have a subpar year in 2021.
Both Stephen and Jerry Jones expressed their frustration with Cooper’s production given his pay. Plus, cutting the receiver would help the team save $16 million towards the salary cap. Fans quickly realized that Cooper’s exit seemed inevitable. While some argued that the fact that the Cowboys were able to save money and get some draft help in return for Cooper was a good thing, most argued that the Browns were the clear winners in the trade.
Remember that Dallas gave up a first-round pick to acquire the wide receiver from the Raiders in 2018. Now, they’re getting rid of him for a lousy fifth and sixth-round pick. The Browns are landing a top NFL talent for almost nothing. Yes, they have to pay $20 million in 2022, but if things don’t work out with Cooper, they can get out of the contract after one year.
https://twitter.com/1kalwaysopen_/status/1502725429416837127?s=20&t=ra7DUac2ZArS5yMdHx4Fhg
So, yes. Cooper didn’t perform the way he could’ve in 2021. But now the Cowboys have a giant gap in the wide receiver corps with Wilson and Cooper gone. The team is losing a no-doubt starter. While they were able to secure Michael Gallup to a five-year contract worth $62.5 million, Gallup is currently recovering from ACL surgery. What if Gallup is never the same when he returns in 2022?
Another thing to point out is that Cooper and Dak Prescott had chemistry. Cooper has been a go-to target for Dak for three years. Since 2018, the two have connected for 23 touchdowns. Here are some more stats to prove Cooper’s impact:
Since 2018, when Cooper was in the game…
- Prescott was 28-16
- The Cowboys averaged over 28 points per game
- Prescott averaged over 297 passing yards per game
- Prescott’s completion percentage was 67.9%
Without Cooper…
- Prescott was 3-6
- The Cowboys averaged 20.2 points per game
- Prescott’s average dropped to 223.1
- Prescott’s completion percentage dropped to 63.5%
If you’re going to pay Prescott the big bucks, why aren’t you going to prioritize a guy who helps him perform well? All in all, the Cowboys’ only hope in this trade being worth it is that Cooper has a low chance of success with Baker Mayfield or some unknown quarterback at the helm in Cleveland. It’s likely his absence may come back to haunt Jerry Jones.

