The Jacksonville Jaguars made several questionable moves during the Dave Caldwell era. One of the worst ones was trading Jalen Ramsey in 2019 instead of giving him a contract that reflected his value as one of the top cornerbacks in the league. Fast forward to 2025, and the move helped the Jags land on a list not many teams would like to be a part of.
Kristopher Knox of Bleacher Report put together a list of the 10 worst trades in the NFL over the past 10 years and included Jacksonville because of Ramsey, pointing out that they failed to maximize the assets they got in exchange for the All-Pro.
"To be fair, Jacksonville did get a strong return for the Florida State product. The Rams gave up 2020 and 2021 first-round picks, along with a 2021 fourth-rounder, to acquire the star corner," Knox wrote. "The problem is Jacksonville had a proven playmaker at a premium position and traded that for lottery tickets in the draft that didn't hit."
Knox continued, "Jacksonville used the 2020 first-round pick on pass-rusher K'Lavon Chiasson, who lasted just four years with the franchise. IT used the 2021 first-round pick on running back Travis Etienne, who remains a Jaguar but has been mostly just fine as a starter when healthy."
As Knox pointed out, the Jaguars got a pretty good return in exchange for Ramsey, and the trade would've looked much better if they had aced the two first-rounders they got. Sure, Travis Etienne remains on the roster but could change teams before the start of the regular season. Heck, even if he stays, there's no guarantee he'll get a new deal from the Jags.
On the other hand, Chaisson was underwhelming during his four-year stint in Jacksonville and only hit his stride once he joined the Las Vegas Raiders in the middle of the 2024 season. He signed with the New England Patriots in free agency and will have a chance to build off of last year.
Meanwhile, Ramsey went on to earn four Pro Bowl selections and two All-Pro designations. He's currently the subject of trade chatter, and Jacksonville has been brought up as a potential landing spot. However, the Jags don't currently have a need for him even if he switched to safety, as it's been suggested.
The Jaguars dropped the ball when they traded Jalen Ramsey
Jalen Ramsey left the Jacksonville Jaguars under less-than-ideal circumstances. Surely, he played a role in the divorce when he chose not to play because of a back injury. However, Dave Caldwell and Tom Coughlin were the adults in the room and didn't handle the situation well. Had they been less adversarial in their approach, there's a chance the former Florida State Seminole would have stayed in Duval.
If anything, the trade serves as an example of how dreadful Caldwell's tenure with the Jags was. He certainly played a role in assembling the 2017 Sacksonville defense, but re-signing players like Blake Bortles while stiff-arming game-changers such as Ramsey, Yannick Ngakoue, and Calais Campbell proves how underwhelming he was. To nobody's surprise, he left the roster devoid of talent by 2020 and got the boot that same year. Unfortunately, the Jags didn't get much better afterwards.
To replace Caldwell, the Jags hired Trent Baalke. Although he was a bit better than his predecessor, he ultimately failed to put together a Super Bowl-winning team, which is why he got the boot early in 2024. The silver lining is that it looks like the Jaguars finally found a general manager who can steer the ship in the right direction in James Gladstone.
Instead of trading away his best players, Gladstone is making a strong effort to trade for good ones. Granted, it's too early in his stint with the Jags, but you can bet that he won't make the mistakes his predecessors made or earn them a spot on an unflattering list.