Let’s keep this incredibly simple for the brain trust in Santa Clara.
Do the San Francisco 49ers actually want to compete for the Super Bowl this upcoming season?
Yes or no?
If the answer is yes, they need to sign left tackle Trent Williams to a contract extension. End of discussion. Roll the credits. There is no middle ground, no bargain-bin compromise, and certainly no replacing a player of his caliber.
So why do I get the sense things are more complicated?
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He’s a surefire Hall of Famer who protects the franchise quarterback, and right now, he’s got the front office by the throat. His agent is even playing games — why else do you think ESPN representative regurgitation machine Adam Schefter tweeted out that the Niners and Williams were in an impasse on Tuesday, roughly 90 minutes before Niners’ general manager John Lynch spoke to the media at the NFL Draft Combine in Indianapolis?
The only difference between this latest shakedown and the previous ones — where Williams simply held out of training camp until the Niners folded like a cheap card table and gave him everything he wanted — is a March 20 deadline. That’s when he has a $10 million option bonus vesting. And if there is one thing agents love more than fully guaranteed money, it’s a hard deadline.
The football solution to this conundrum is as obvious as a false start. Williams has repeatedly said he wants to play until he’s 40. That’s easy enough to oblige.
Add another year to his contract, guarantee both seasons, and kick the void-year dead-cap hits down the road to 2028 or beyond. By then, the NFL salary cap will make today’s dollars look like Monopoly money and the 49ers will have oodles of cap space to absorb the blow. Crisis averted. Williams stays, the Niners remain contenders, everyone is happy.
But there is an irrational option at play in this situation:
The silent, spreadsheet-driven killer of championship windows — ownership cheapness.
If the 49ers were to cut Williams in the coming days with a post-June 1 designation, the dead-cap hit makes the decision non-sensical. He’d count roughly $13.3 million against the cap in 2026 and $20.8 million in 2027, give or take some actuarial nonsense. You might as well keep him at those prices.
But here is the real prize for the suits: By cutting Williams, the Niners would save a staggering amount of actual, real-world cash. More than $30 million for the upcoming campaign.
Remember last year? When the Niners sat out the meaningful parts of free agency and cut useful players? That wasn’t salary cap gymnastics. That was cash preservation.
Because there’s the NFL’s salary cap and then there’s Jed York’s cash budget.
The Niners are currently No. 1 in the NFL in projected cash spending for 2026 (this includes Williams’ current deal), per OverTheCap.com and they haven’t engaged with a single open-market free agent yet.
Last year’s budget was $334 million in cash spend. Word I’m hearing is that number is staying relatively static.
So forget the cap. Follow the cash.
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This should be a testy negotiation, but one that results in a new deal.
But is a new Williams deal in the best interest of York’s growing sports conglomerate? What’s more important? The 49ers or 49ers Enterprises?
Last year, the Niners valued the ledger over the roster.
And while they swear that was a one-time thing, the question has to be asked: What’s to make 2026 different from 2025?
The Niners can prove it was a cheap fling by re-signing Williams and engaging in some serious free agency battles.
But if they do the indefensible — if they decide to move on from Williams for fiscal reasons — why prolong the inevitable?
If you decide your starting left tackle in season you believe you can contend for a title is going to be Austen Pleasants or a rookie taken at pick No. 27, you’re unserious.
So don’t stop with Williams.
Tear the whole roster down and start from scratch.
It’ll save a lot more cash that way.
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