The Los Angeles Chargers will have plenty of re-evaluations to make by the time we arrive at the 2027 offseason. Perhaps, with the right amount of flexibility again and ample draft capital, we can see some real decisions start to be made on the part of the front office. There's also a world, though, where the same decision-makers won't even be in power by the time we get there.
Either way, the Chargers will have a number of contract scenarios to deal with this offseason—especially with things getting tighter in the near future as Justin Herbert's contract bumps up closer to $60 million and Tuli Tuipulotu's extension (hopefully) kicks in.
Donte Jackson will be a free agent, and while there's certainly a chance he's moved before the trade deadline, the Chargers may need to think seriously about the rest of the room before they let him walk. Dalvin Tomlinson, Bud Dupree, and Troy Dye will all be in the same boat—veterans entering their third or fourth contracts that can likely be brought back at a relatively low price.
The most complex contract situation for next offseason, though, rests squarely on Daiyan Henley, and it's not one that's been discussed much to this point in the season. When he's at his best, Henley is a cornerstone of this defense. He's performed admirably over the past two seasons in that regard, especially considering the adversity he faced in 2025.
But there are still some inconsistencies in his game that could make Los Angeles hesitant to pay him as a top player at this position. What his future looks like, then, will likely be one of the major storylines of the offseason for the Chargers—and the decision hasn't gotten any easier through five weeks.
Daiyan Henley should be back with the Chargers, but the decision isn't as clear cut as that
Henley burst onto the scene as a real weapon for the Chargers in his sophomore season in 2024, posting 147 combined tackles, eight passes defended, and one sack over the course of the season. He didn't earn an All-Pro nod for that campaign, but he looked, to many around the organization, like a sure-fire future candidate for that sort of recognition.
In many ways, he's become one of the primary leaders of this Chargers defense over the past couple of seasons, and his constant intensity and production as a tackler justify that role.
It's not as though inside linebacker is paid as a premium position, either, so we're not talking about putting Los Angeles' entire contract balance out of whack here with an extension for Henley. The highest paid inside linebacker in the NFL, right now, is Roquan Smith—who's on a five-year, $100 million deal with the Baltimore Ravens. Henley's pay grade, on the high end, would hopefully come in somewhere closer to Zack Baun and Azeez Al-Shaair's—somewhere around $17 or $18 million annually.
That's still a large jump, though, from the $3.9 million cut of the cap that Henley is taking on in 2026. And there are enough inconsistencies in his game that it's reasonable to think the Chargers will at least consider their options here.
Henley has struggled somewhat in coverage throughout his career, and those inconsistencies have carried over into this season. According to Pro Football Focus's system, he's graded out as the 62nd-best out of 72 qualified linebackers in terms of pass coverage, allowing 11 receptions on 16 targets and failing to post a PBU through five games. While linebacker performance is more difficult to quantify than that of other positions, that tracks relatively with what we've seen from him over the past year or so.
At the same time, what does this linebacker room look like if the Chargers don't pay up to retain Henley? Denzel Perryman returning on a one-year deal seemed like a stop-gap solution to account for Junior Colson's injury issues. Dye will be a free agent after this season as well. That leaves Los Angeles with just Marlowe Wax and Del'Shawn Phillips currently under contract beyond this year at the position.
It's also important to note that Henley's tackling and pressure production seem to be on par with his breakout 2024 campaign to this point in the season.
Is this front office willing to pay top positional dollars to keep Henley in the fold? There's no clear answer here—at least not yet. And Henley's inconsistencies, combined with the uncertain future of the room as a whole, don't make finding one any easier.
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