Chargers pay Derwin James, but what’s the structure?

The Los Angeles Chargers gave safety Derwin James record-setting money, but it remains to be seen how the deal pays out.

Derwin James is a great player, and on Wednesday morning, a great player got paid.

The 26-year-old star safety received a four-year extension worth $76 million, including a whopping $29 million the first year and $42 million guaranteed. All told, both the guaranteed money and the average annual value resets the safety market for the two-time Pro Bowler.

Chargers pay Derwin James a record-setting amount

For the Chargers, this was the only move to make. James had been at each training camp practice to avoid being fined, but he wasn’t participating while his representation negotiated an extension off his fifth-year option. With the contract now done, James returns to work with a little more than three weeks before the start of the regular season.

Now, the big question is how the guarantees are structured throughout the contract.

The Chargers know they have a potentially mammoth extension coming next offseason for quarterback Justin Herbert. That money, assuming it’s tacked onto the end of the rookie deal, will begin in 2025.

Last week, I wrote about James’ contract situation and what might shake out considering everything Chargers general manager Tom Telesco has to think about. I was close:

The historical high-water marks for safeties are $84 million in total value (Landon Collins), $18.4 million annually (Minkah Fitzpatrick) and $38 million guaranteed (Jamal Adams).

For James, that could mean something such as five years, $93 million and $40 million guaranteed. That would be historical in all three main aspects. For the Chargers, they could front-load the guaranteed portion, and essentially make the extension two years and $40 million with minimal dead money over the final three campaigns.

Ultimately, this would protect general manager Tom Telesco against sunk costs if James can’t shake the injury bug, all while giving him what amounts to three team options.

Again, structure matters. This is especially true with James, who has played only 36 of a possible 65 games so far in his career.

We’ll have to wait to see how Telesco set everything up, but considering my predictions on annual money and guarantees were almost a perfect match, I’d expect James to essentially be on a three-year deal — including this season — and then have a pair of team options.

Regardless, good for James, who has fought through significant injuries to showcase his talents, and earn one of the richest deals for a defensive player in NFL history.

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