The San Francisco 49ers are unquestionably regretting the contract they dished out to disgruntled wide receiver Brandon Aiyuk, given how things have decomposed in the relationship between the two parties since.
And while that might be the Niners' biggest contractual talking point right now, another looming albatross hangs over the deal All-Pro defensive end Nick Bosa is currently on.
Nearly as high-profile a standoff as Aiyuk, Bosa's five-year, $170 million extension signed back in 2023 made him the highest-paid non-quarterback at the time on an annual average value. He's since been surpassed, which is understandable, but the near-$23 million cap hit for 2026 and the whopping $54.9 million hit in 2027 certainly make the remainder of his contract stand out for the wrong reasons.
Enough to catch Bleacher Report's Brad Gagnon's eye when looking at the 10 worst contracts around the league entering the new season.
Bosa's came in at No. 4, surpassed only by offensive tackle Dan Moore Jr. with the Tennessee Titans, the Tampa Bay Buccaneers with wide receiver Chris Godwin and, the unquestioned No. 1, quarterback Deshaun Watson's horrendous deal with the Cleveland Browns.
OK, so Bosa (and no one else) is in Watson's camp. But San Francisco's top pass-rusher appears for plenty of valid reasons that are worrying.
B/R is justified putting 49ers' Nick Bosa on list of worst contracts
The fact Bosa missed the bulk of 2025 with a torn ACL doesn't help matters at all, and as Sports Illustrated's Albert Breer pointed out earlier this offseason, so much will be made of the pass-rusher's future depending on how he returns from said injury.
If Bosa looks more like his old self, even if it's nowhere close to his Defensive Player of the Year efforts from 2022, the 49ers will remain happy with the contract, even if they restructure it.
However, if Bosa trends toward a decline, it's a much tougher conversation.
Here's what Gagnon had to say of the matter:
The Problem:Â The 28-year-old's production fell off markedly in back-to-back seasons before he missed all but three games in 2025. It appears he peaked as Defensive Player of the Year in 2022.
The Kicker:Â They'd have to pay Bosa just shy of $50 million simply to move on after the 2026 campaign, which likely means he's locked in at a current cap hit of $54.9 million for his age-30 campaign (highest by a mile among defensive players).Â
Should Bosa crest double-digit sacks in 2026, perhaps the Niners restructure and spread out that cap hit due in 2027, and that wouldn't be shocking whatsoever.
San Francisco might have to bank on that, too, regardless. With few other proven pass-rushers available, it needs Bosa to live up to the lofty contract regardless if B/R isn't overly impressed with it.
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