San Francisco 49ers offensive tackle Trent Williams. Kyle Terada-USA TODAY Sports

Two of the 49ers’ best offensive players, LT Trent Williams and WR Brandon Aiyuk, are seeking new and/or improved contracts, with Williams staging a holdout and Aiyuk engaging in a hold-in. Williams’ endeavor is a little more unusual, as he is 36 and under contract for three more seasons, while Aiyuk is 26 and is currently on the fifth-year option of his rookie deal.

That said, Williams continues to perform like the future Hall of Famer that he is, having earned First Team All-Pro honors in each of his first three years in San Francisco. His importance to the club’s offensive operation is unmistakable, and ESPN’s Jeremy Fowler expects the Niners to address Williams’ deal in some way.

When it comes to Williams’ contract, Fowler uses the term “rework” rather than “extend.” While there is no guaranteed money left on Williams’ deal, he is obviously in no danger of being released this season, so his $20.05M base salary for the 2024 campaign is not in jeopardy.

However, his deal now slots in fifth among offensive tackles in terms of AAV, and regardless of the length of a contract when it is signed, an NFL club’s brass cannot be terribly surprised when a high-performing player seeks additional security after the guarantees on that contract run out. Per Fowler, Williams “has conviction” in his holdout, and as a player who has secured over $170M in his playing career, he is not terribly concerned about the $50K in non-waivable fines that accrue with each day of camp that he misses.

While Williams and Aiyuk play different positions and are at very different stages of their careers, their contract situations do impact each other. As Fowler notes, Aiyuk is not budging from his “pay-me-or-trade-me” stance, and San Francisco is unwilling to authorize a contract at or near the top of a ballooning WR market that now has four players making at least $30M per season. 

The ESPN scribe says negotiations between player and team have not progressed, and that trade offers may ultimately become too tempting for the Niners to pass up.

If San Francisco does move Aiyuk, giving Williams a raise would become much easier. One way or another, the team realizes it may need to undergo a “thoughtful reset” of its salary cap in the near future, meaning that it will need to part ways with a number of high-end players in order to remain competitive over the long haul. 

Of course, quarterback Brock Purdy will likely land a massive extension next season, adding another expensive contract to a roster that currently has seven players earning between $15M-$34M per year, with a few others just below that $15M/year threshold.

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