Over a week after the start of free agency, the San Francisco 49ers have, by and large, enjoyed a successful period.
They acquired a future Hall of Fame wide receiver in Mike Evans, added another target in Christian Kirk, extended key pieces like Eddy Piñeiro and Jake Tonges, traded a third-round pick to the Dallas Cowboys for Osa Odighizuwa, and brought Dre Greenlaw back to the Bay—moves that suggest the 49ers have had the strongest free agency so far.
However, one key move is still missing, one ESPN identifies as the 49ers’ biggest weakness.
**ESPN thinks Trent Williams' contract is the 49ers' biggest issue**
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Dec 14, 2025; Santa Clara, California, USA; San Francisco 49ers offensive tackle Trent Williams (71) enters the field prior to the first half against the Tennessee Titans at Levi's Stadium. Mandatory Credit: Cary Edmondson-Imagn Images | Cary Edmondson-Imagn Images
"One future Hall of Famer whose status remains up in the air is Trent Williams. Before free agency, there were reports that the 49ers were considering trading or releasing Williams," wrote [ESPN's Bill Barnwell](https://www.espn.com/nfl/story/_/id/48227677/2026-nfl-free-agency-barnwell-20-contenders-weaknesses-signings-trades-draft).
"Those reports felt mostly like an issue with guarantees. Williams is due $31 million in 2026, none of which is guaranteed. That changes Friday, when Williams is due a $10 million bonus.
"If the 49ers don't want to pay that bonus (or the broader $31 million), they'll decide on Williams' future before Friday.
"From the star tackle's perspective, the time to make a decision would have been weeks ago. If Williams was going to hit the open market, the time for him to get there would have been before free agency, when every team still had plenty of cash to throw around.
"In the Niners waiting until mid-March, Williams won't have the same sort of market or chance of landing something in the ballpark of $31 million if he's released.
"Both sides know that, which is why Williams wanted to have a resolution on that decision two weeks ago -- and why the 49ers now hold the leverage in those negotiations."
This is a pivotal move for the 49ers if they are to keep hold of Williams. The offensive line isn’t competitive as it stands, and while Williams, at 38, is beginning to decline slightly, the 49ers still need to protect their quarterback, Brock Purdy. It’s already an area of the field the front office has not consistently prioritized in building elite talent.
This is not a problem the 49ers can afford to overlook. Strengthening the offensive line is critical to both short-term performance and long-term stability. If they fail to address it, pressure on Purdy will increase, and their chances of competing deep into the season will suffer if he is out for a long period again.