Before OTAs kicked off last week, the Chargers and S Derwin James agreed to terms on an extension to make him the highest paid safety in NFL history. James eclipsed Ravens S Kyle Hamilton's $25.1M AAV contract with his own $25.2M per year deal. In all likelihood, a second extension increases the chances that the All-Pro safety will finish his career with the Chargers.
Full contract figures for James' extension have been revealed via OverTheCap.
The Chargers made Derwin James the highest paid safety in the league, but also gave themselves some long term flexibility.
The year to year cap hits for the Chargers on James' extension are as follows:
2026: $24.6 million
2027: $20.5 million
2028: $27.6 million
2029: $27.5 million
As James heads into his age 30 season, a valid question is whether his contract would be frontloaded or backloaded. With the full dead money/cap savings figures from year to year, it appears we have an answer. James' deal comes with $54.5M guaranteed and $41M guaranteed at signing. In 2026 and 2027, James will have roughly $32 million paid out in guaranteed salary.
That brings us to 2028. In what would be his age 32 season, the contract numbers work out to roughly $15.6 million in cap savings if James was to be cut. The 2028 and 2029 seasons have roster bonus due dates, but importantly no guaranteed salary for the Chargers. If the Chargers were to move on from James in 2029, they'd save $21.5 million against the cap.
As with a lot of Ed McGuire-negotiated Chargers deals, the money is indeed frontloaded. James scores a lot of money at signing while the Chargers have some roster flexibility later on if there is a decline in performance. In an ideal world, that doesn't happen for the Chargers or James. But we've seen LA's front office move on the cuttable years of deals for vet players before.
Ultimately, the Chargers had to secure an extension with James to avoid the prospect of him hitting free agency next year. In the first season of new DC Chris O'Leary's defense, James' versatility and ability to play at all three levels of the defense will be incredibly valuable. The star safety had back-to-back second-team All-Pro nominations in 2024 and 2025 while playing in now Ravens HC Jesse Minter's defense. The sky is still the limit for James as he heads into his ninth NFL season.
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