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Uncertainty surrounds Trent Williams' contract. The 49ers and their star tackle must bridge a gap in guaranteed money to keep him in San Francisco.

The San Francisco 49ers have been aggressive in addressing their roster this offseason, filling a number of key holes in free agency and putting themselves in a strong position moving forward.

But even after all the moves, one major issue still looms over the organization. The contract situation of left tackle Trent Williams. While San Francisco added pieces across the roster, including at wide receiver and along the defensive front, the offensive line remains tied to Williams’ future. And right now, that future comes with some uncertainty.

Earlier this offseason, reports surfaced that the 49ers were at least open to the idea of trading Williams amid ongoing contract tensions. At the center of the issue is the lack of guaranteed money remaining on his current deal, something that doesn’t sit well with the 12-time Pro Bowler as he enters what is effectively the final year of his contract.

Williams is set to earn $31 million in 2026, but none of that money is currently guaranteed. A key date has already come into focus, with a $10 million option bonus looming. From the team’s perspective, the goal is to reduce Williams’ massive $38.8 million cap hit. From Williams’ side, the priority is just as obvious, to secure more guaranteed money.

ESPN analyst Bill Barnwell recently outlined a potential solution, suggesting a middle ground that could satisfy both sides while keeping one of the league’s premier tackles in San Francisco.

“The 49ers likely want to pay Williams something closer to the $21.9 million he made in 2025, which would make sense. Finding common ground on a deal that guarantees Williams $25 million in 2026 and $30 million in 2027 would be smart for a team that doesn’t have a replacement for the 12-time Pro Bowler,” Barnwell wrote. “And while Williams might want to become the highest-paid tackle in league history one more time and top Rashawn Slater’s $28.5 million average salary, there isn’t really a market to pay him that sort of deal in free agency right now.”

For the 49ers, committing that level of guaranteed money would be significant, especially considering the rest of the roster. Quarterback Brock Purdy carries the highest guaranteed figure on the team for 2026, and even that structure reflects careful cap management. At the same time, Williams’ value to the offense is undeniable. Even at 38 years old, he remains one of the most dominant left tackles in football and a cornerstone of Kyle Shanahan’s system.

There’s also the question of leverage. If Williams were to hit the open market earlier in the offseason, he may have had a stronger chance of landing a massive deal. But with free agency well underway, teams have already allocated much of their cap space, limiting the likelihood of a contract near his current number.

That dynamic works in the 49ers’ favor but it doesn’t eliminate the need to reach a resolution.

Ultimately, San Francisco finds itself balancing short term versus long term planning. The team still does not have a clear successor in place at left tackle, making Williams even more valuable in the immediate future.

A compromise, as Barnwell suggests, could be the best outcome for both sides. Because while the 49ers have checked off plenty of boxes this offseason, their most important move might still be the one that keeps their future Hall of Fame left tackle protecting the blind side for at least a little while longer.