49ers left tackle Trent Williams signed a new two-year, $50MM contract this offseason, one that he said will “probably” be his last, per ESPN’s Nick Wagoner.
Williams, who will turn 38 years old in July, is entering his 16th season in the NFL with 12 Pro Bowls and five All-Pro selections (three first-team, two second-team) to his name. Retirement has been a topic of discussion for a few years, but his latest deal with San Francisco seems designed for him to hang up his cleats after the 2027 season.
That decision may still be dependent on his performance level as he enters his 40s. He has maintained an extremely high standard of play with Pro Bowl and All-Pro recognition in his last four healthy seasons. But Williams will face an extremely tough test over the next two seasons: at least four matchups with reigning Defensive Player of the Year Myles Garrett, who arrived in the NFC West this week in the Rams-Browns blockbuster. If Williams can consistently handle him, he may believe he still has a few more years left in the tank.
With a $265MM quarterback under contract, the 49ers will want to have their future left tackle situation figured out before Williams retires in the hopes of a smooth transition on Brock Purdy‘s blind side. The team currently lacks a clear successor, but the same was true when San Francisco’s last elite left tackle, Joe Staley, retired in 2020. Rather than target a rookie, the 49ers traded for an established veteran in Williams, though his medical situation made him available for a steep discount. There is plenty of time to figure out their long-term plans at the position, though some kind of draft investment in 2027 would seem warranted.