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Chargers' Derwin James extension is already starting to backfire before it kicks in

We knew Derwin James' extension was a bit of an overpay. But with the Tuli Tuipulotu ordeal still unsolved and James seeming set to head to the IR, it's already starting to backfire.
ByG.C. Bellchamber
Jun 17, 2026; El Segundo, CA, USA; Los Angeles Chargers safety Derwin James (3) during minicamp at The Bolt. Mandatory Credit: Kirby Lee-Imagn Images
Jun 17, 2026; El Segundo, CA, USA; Los Angeles Chargers safety Derwin James (3) during minicamp at The Bolt. Mandatory Credit: Kirby Lee-Imagn Images | IMAGN IMAGES via Reuters Connect

Make no mistake—Derwin James Jr. is still one of the league's best safeties, and as the connective tissue of the Los Angeles Chargers defense, he's absolutely integral to any sort of major success Chris O'Leary is going to find within his scheme.

That makes the pair of injuries he's faced this season—to both his wrist and his hamstring—highly concerning. Earlier this week, Jim Harbaugh announced that James had faced a setback in his rehab for the latter injury that could send him to the injured reserve. On Saturday, the Chargers made that move official—which means that James will need to miss at least the next four games.

Granted, O'Leary has done a solid job keeping the secondary intact even with James and top cornerback Donte Jackson out for the past couple of weeks. But an extended absence for James is a ceiling-limiter for that unit in terms of consistency and viability. He's simply too versatile, both in coverage and working downhill either as a run defender or a blitzer, to be replaced by anyone on this roster.

That's why Los Angeles was right to extend him this past offseason. But as this season unfolds, and James remains out while a Tuli Tuipulotu extension still has not come to fruition, there's plenty of room to question the three-year, $75.6 million value of the contract before it even kicks in.

Derwin James is absolutely integral to the Chargers—but the reality is that he won't be the best safety in the league for long

Again, James is still one of the most integral players to any defensive scheme across the NFL when he's active. Under Jesse Minter's scheme, he started to take on more of the nickel role that's become popular across the NFL, and his ability to consistently provide whatever the Chargers need as essentially an extra defender in the secondary or on the blitz is almost unparalleled across the league. Across the three games he's played this season, James posted 21 combined tackles, two pressures, and one PBU.

Even just from simple counting stats—which often don't define defensive players that well—that's a massive amount of impact in just that trio of appearances.

But by granting James that $75.6 million extension, they made him the highest-paid safety in the league, at least on an annual basis, for the foreseeable future. That deal surpassed Kyle Hamilton of the Baltimore Ravens by $100,000 annually, and there aren't currently any safeties approaching the end of their deals that are likely to rival that amount. The only exception might be Brian Branch, who has been too limited by injuries in recent seasons to truly project an extension much north of $20 million annually.

Hamilton, though, was just 24 years old at the time of signing his contract. James is already north of 30, and Los Angeles will likely be paying him at the rate of a high-profile edge rusher until his age-35 season. They do have an out—that comes with $6 million in dead cap—in 2028, but we can set that to the side for now.

Because what also matters, in the immediate sense, is the extension for Tuipulotu. The Chargers still have not locked down their star pass rusher long-term on the back of his 13-sack campaign in 2025. Sure, his production is down this season. But if he walks, where can Los Angeles turn? This seems to be Khalil Mack's final NFL season, and Akheem Mesidor certainly isn't ready to take over alpha pass-rushing duties. The Chargers need Tuipulotu to return next season, and even $1 or $2 million of flexibility there on an annual basis could be the thing that makes the difference.

There's not truly an argument to be made that James shouldn't have been extended. But if one comes at the cost of the other—and James continues to struggle with his health over the next couple of season—we may easily look back at this moment as a sort of inflection point for the Los Angeles defense.

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