Derwin James, Tuli Tuipulotu Contract Extensions Could Complicate Chargers' Offseason

The Chargers could have some key players looking for contract extensions soon.

Derwin James Jr. | Isaiah J. Downing-Imagn Images

Plenty of questions surround the Los Angeles Chargers right now. 

Jim Harbaugh and Co. have a boatload of cap space to spend. In the neighborhood of $82 million, to be exact, in terms of expert estimations. 

But the how of spending it is complicated. The Chargers need to pay a draft class. They need to worry about attempting to re-sign free agents like Odafe Oweh and Khalil Mack. And they also need to target and potentially pay up for outside free agents, too. 

Note, though, that none of those Chargers offseason musings touch on the subject of contract extensions. 

Until now, anyway. 

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Big Chargers names headed for contract extensions?

A savvy front office headed up by general manager Joe Hortiz continues to make smart, future-minded moves that keep them both competitive and in the cap space green. 

Hence, Eric Smith of Chargers.com getting asked about whether the Chargers will do extensions with Derwin James and Tuli Tuipulotu this offseason. 

On Tuipulotu, Smith wrote this: 

“But Tuipulotu took his game to another level in 2025 with 13.0 sacks, 20 tackles for loss and 23 quarterback hits. His massive season led to Pro Bowl honors and also being named to the Pro Football Writers of America's All-AFC Team.”

Tuipulotu feels like a no-brainer, but it might hinge on just how much money the Chargers pour into Oweh and Mack. Delaying big front-loaded payments while getting a year of Oweh’s deal out of the way or another one-off deal with Mack might make sense. They have the flexibility.

Chargers S Derwin James gets a second consecutive second-team All Pro to add to an illustrious resume:
2x first-team All-Pro (2018,2021)
3x second-team All-Pro (2022, 2024, 2025)
5x Pro Bowler

When it's all said and done, he'll be one of the best to ever do it in franchise… pic.twitter.com/2jtko407gF

— Alex Insdorf (@alexinsdorf99) January 10, 2026

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Notably, James didn’t get as much of an explanation because…it’s tricky. He’s already going on 30 years old and a $24.6 million cap hit in 2026. The Chargers have plenty of cap space to get something done, but taking a wait-and-see approach and retaining the flexibility of something like the franchise tag after 2026 is always an option.

Those guys, at least, are the biggest names. Other notables slated to hit free agency after 2026 include Donte Jackson and Quentin Johnston. We'll see how Jackson's doing over the hump of 30 years old by then and if Johnston meshes well with Mike McDainel's offense.

For now, all focus on this topic goes to Tuipulotu and James.

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