The Chargers are entering the 2026 offseason with something every NFL front office dreams of: flexibility. With a projected league-best cap space that could approach $100 million, the opportunity is there for Los Angeles to reshape its roster and finally make the leap from potential to production. After years of playing second fiddle in their own city, this might just be the moment the Bolts flip the script.
A Golden Opportunity - But a Tightrope Walk
Let’s be clear: this isn’t just about having money to spend. It’s about spending it wisely.
The Chargers are walking into the offseason with only about half their roster under contract. That gives them room to maneuver, but also means they’ll have to make some tough calls - and fast.
Enter Jim Harbaugh. The new head coach isn’t afraid of bold decisions, and he’s going to have to make a few right away.
One of the biggest will be what to do with Derwin James Jr. He’s got one year left on his deal, and letting a player of his caliber inch closer to free agency without a plan would be a mistake.
James is a tone-setter - the kind of player who defines a defense. Locking him up long-term should be near the top of the Chargers’ to-do list.
And while the cap space is a major asset, don’t forget about the draft. The Chargers hold the 22nd overall pick, and with a roster that still has more questions than answers, that pick could be a key piece in building out a more complete team. Whether they go best player available or target a specific need, it’s a chance to add a young, cost-controlled contributor to a team that’s looking to contend.
The Herbert Factor
Justin Herbert is locked in through 2030, but his contract - while deserved - is one of the heftiest in the league. The numbers are eye-popping: a signing bonus north of $16 million and an average annual salary over $52 million. That said, there’s a real possibility the Chargers could restructure his deal to create up to $17 million in cap relief this offseason.
We’ve seen elite quarterbacks do this before. When a team is close to contending, the best signal-callers often buy into the bigger picture. If Herbert’s willing to restructure, it could be the difference between adding a star and settling for depth.
Weapons Wanted
Here’s where things get interesting: Herbert doesn’t have a clear-cut No. 1 receiver on the roster. There are a few solid options in the WR2/WR3 range, but no one who consistently demands double coverage or changes the way a defense plays. That’s a problem - especially in a division where you’re going to need to score points in bunches.
Expect the Chargers to be active in both free agency and the draft when it comes to pass-catchers. Whether it’s a big-bodied outside threat, a dynamic slot weapon, or a tight end who can stretch the seam, this team needs someone Herbert can trust in crunch time. If they can find that go-to guy, it could unlock a new level for the offense.
High Stakes, High Expectations
Let’s not sugarcoat it - the pressure is on. The Chargers have had talent before, but what they haven’t had is consistency, health, and the ability to close out games when it matters most. They’ve also been hamstrung by cap issues in recent years, which makes this offseason all the more critical.
This is a make-or-break moment for the front office. With Harbaugh now in the building and Herbert in his prime, the window is wide open - but it won’t stay that way forever. The decisions made over the next few months will shape not just the 2026 season, but the trajectory of the franchise for years to come.
The Herbert-Harbaugh pairing still has the potential to be something special. But potential doesn’t win playoff games.
Execution does. And now, with the resources in hand, it’s time for the Chargers to execute.