NFL Trade Deadline Winners and Losers: Jaguars, Chargers Among Standout Teams

In the blink of an eye, the sun is already setting on the 2026 NFL trade deadline. With nine weeks of play in the books, many teams are starting to figure out who they are, prompting plenty of action around the league on the trade front.

This year has featured a bit of everything, including blockbuster swaps for stars, savvy swaps, and picks galore. As the home stretch of the season approaches, which front offices stood out for the work they did?

Below, we’ll dive into the top NFL trade deadline winners and losers, ranging from teams that made moves to capitalize on assets or contention windows to squads that committed some errors along the way. 

Also woven in are PrizePicks payouts for outcomes such as making the playoffs, winning a conference, or winning Super Bowl LXI.

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2026 NFL Trade Deadline Winners

The following teams either struck while the iron was hot to capitalize on the chance to pursue a championship or came to terms with the harsh reality of where they sat and adjusted accordingly.

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Jacksonville Jaguars

The Jacksonville Jaguars made it clear that they’re going all-in at this deadline. Regardless of whether their aggressive moves wind up paying off in the form of a ring in February, it’s hard to not love this approach from 36-year-old general manager James Gladstone. 

Ironically, none of the Jags’ swings had anything to do with improving the offense. Instead, a defense that currently ranks third in EPA/play allowed (RBSDM) adds S Jessie Bates from the Atlanta Falcons for a 2027 second-round pick and a 2028 fifth-rounder. That’s far from it, though.

Entering the fold are two DTs, too. Davon Godchaux isn't a household name, but snagging him from the New Orleans Saints for just a 2028 conditional sixth-round selection is masterful work. 

The jaw-dropper was undoubtedly landing Jordan Davis from the Philadelphia Eagles. While giving up a first-round pick in 2027 and a second-rounder in 2029 is almost surely an overpay, Davis was a plus player as recently as last year (28 pressures and 43 stops, via Pro Football Focus) and could be the swing piece on a title team.

Now, the pressure is on Jacksonville to get to and win the big game to prove that this was all worth it.

Chicago Bears

It became abundantly clear out of the gate that the Tennessee Titans’ season was going down the drain, and GM Mike Borgonzi didn’t shy away from acknowledging that fact with his actions.

This fall, a swap with former Kansas City Chiefs coworker Ryan Poles and the Chicago Bears allowed him to stock the draft pick cupboard even more.

Tennessee sent all-world DT Jeffrey Simmons and a 2028 fifth-round pick to Da Bears in exchange for a 2027 first-round pick, 2027 fourth-round pick, and 2028 first-rounder. Losing that many assets is hard to stomach, albeit with an ideal endgame similar to Jacksonville.

Simmons has made an impact right away in his first two games as a Bear, recording 10 tackles and 2 sacks already. The four-time Pro Bowler is shoring up one of the club’s biggest weaknesses, which is all you can ask out of a contender.

This would’ve been an awesome offseason move; making it happen in-season is tremendous.

Las Vegas Raiders

Sometimes, one team’s misfortune is another’s time to shine. In this instance, a poor showing on Monday Night Football against the Buffalo Bills made the Minnesota Vikings enter desperation mode at the QB spot.

The Las Vegas Raiders obliged with a trade in the closing hours of deadline day, completing one of the best feel-good arcs lately by sending Kirk Cousins home in exchange for a 2027 third-round pick.

Cousins was far from perfect in his nine games as a Raider, but his 97.1 passer rating and 62.1 QBR were both his best marks since he was last in Minnesota in 2023. Not only that, but he also tossed 20 TDs while sitting seventh among qualified signal-callers in adjusted EPA/play at 0.226.

The Raiders signed Cousins to allow #1 overall NFL Draft pick Fernando Mendoza to sit and learn for a bit. Not only did the franchise accomplish that, but it also exited the Cousins business at the right time while recouping some nice capital in the process. 

That’s elite maneuvering by a front office that might just be on the upswing. It’s a win for the Vikings, too, as they don’t need Cousins to even sustain this level of play to be scary.

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2026 NFL Trade Deadline Losers

The transactions these teams made might prove detrimental in the grand scheme of things. Elsewhere, it’s sometimes the moves you didn’t make that can see you land in this category of organizations.

Los Angeles Chargers

To say this has been perhaps the most disastrous season in the history of the Los Angeles Chargers somehow wouldn’t be an understatement. Not only is L.A. the only team in the sport with fewer than two wins, but it’s the only winless squad standing entering Week 10.

Whenever an 0-8 team preaches wanting to give things a run the rest of the way, it simply rings hollow for everyone on the outside. Despite some late reporting that the Chargers were “more receptive” to trades, not moving off veteran pass rusher Khalil Mack is a loss.

In fairness to Los Angeles, it did send the expiring contract of LB Daiyan Henley to the Denver Broncos for a 2027 fourth-round pick and 2028 fifth-round pick. That gets kudos, but GM Joe Hortiz left a ton of meat on the bone here.

Indianapolis Colts

The Indianapolis Colts are bottoming out after firing GM Chris Ballard and are clearly building for the future. 

Netting a 2027 third-round pick and 2028 fifth-round pick from the Seattle Seahawks for star guard Quenton Nelson is a solid doing, as is sending DT DeForest Buckner and WR Keenan Allen to the San Francisco 49ers. Heck, even getting picks out of WR Josh Downs from the Kansas City Chiefs is nice.

With that said, two missed opportunities may loom large elsewhere on offense. They cast a dark cloud over the good.

The aforementioned Vikings were reportedly eyeing Colts field general Daniel Jones for a trade, only to go on and get Cousins. They were tabbed as a team to watch for star RB Jonathan Taylor, too, as were clubs like the Denver Broncos and Seattle Seahawks.

Offloading Jones’ money would’ve been splendid, and it remains to be seen whether the organization will be in a contention window by the time Taylor's current deal is up in 2028. If not, risking another year of age or even an injury could make a non-transaction in 2026 iffy at the absolute best.

Pittsburgh Steelers

We’re going way back in time for the first leg of breaking down the Pittsburgh Steelers’ 2026 trade cycle. To kick off the month of October, the club finally marked the end of the CB Joey Porter Jr. era by sending him off to the Dallas Cowboys. 

Was receiving a 2027 sixth-rounder and 2028 second-rounder a fitting conclusion, though? Forget how Porter’s Cowboys tenure started — he was operating at a borderline Pro Bowl level in the two years prior for Pittsburgh. Nothing about his early-year holdout or the franchise’s policy of not doing deals in-season passed the smell test.

Then there’s the matter of not getting QB Aaron Rodgers a trusted pass catcher in his final NFL season. At 6-2, the Steelers need all the help they can get to complement budding star RB Jaylen Warren and keep pace with the Cincinnati Bengals in the AFC North.

Failing to do so and losing out on the Josh Downs sweepstakes doesn’t mean this year will be a flop for those behind the Steel Curtain, but it sure could make winning multiple postseason games much more difficult.

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As we gear up for the unofficial second half of the 2026 NFL season, playoff races will only heat up. On the other end of the spectrum, non-contending clubs must also strike a balance between competing and securing a nice slot in the 2027 NFL Draft. 

Regardless of where you think each franchise will go after the trade deadline, you can make plenty of NFL predictions on PrizePicks

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