The Chicago Bears were always something of a long shot to make a blockbuster trade this spring that addresses one of their two major weaknesses — offensive tackle and edge-rusher — but now the biggest potential splash the team could have made to improve its O-line is off the board.
Left tackle Trent Williams reached an agreement on a contract extension with the San Francisco 49ers on Monday, April 20, which knocks down his salary cap hit this season but adds an extra year and more overall money to the deal by stretching it out through 2027.
“49ers and 12-time Pro-Bowl LT Trent Williams reached agreement today on a two-year, $50 million extension that now contractually ties him to San Francisco through the 2027 season, per @eliteloyaltysp,” ESPN’s Adam Schefter reported via X.
Bears Were Viable Trade Suitors for Trent Williams Amid Uncertain Contract Negotiations With 49ers
GettySan Francisco 49ers left tackle Trent Williams.
San Francisco and Williams had been engaged in contract negotiations for several weeks, as the LT was set to cost the team north of $46 million in 2026.
The potential savings of more than $33 million on a second-team All-Pro heading into his age-38 campaign rendered a trade one possible outcome of the 49ers-Williams saga, and Chicago’s need at left tackle is significant enough that hopping in on talks, had they ever arisen in earnest, would have represented a reasonable win-now move for the Bears.
Charlie Kravitz of ESPN each said as much during an edition of the “Dominique Foxworth Show” last week.
“That team took such a step forward last year when they were playing Ben Johnson ball and had an improved offensive line,” Kravitz said. “And they had really unfortunate circumstances with their left tackle and [Drew Dalman’s] retirement at center. They have to handle that.”
“Maybe do you trade your picks and try and get Trent Williams?” Kravitz continued after mentioning some rookie options the Bears could select with No. 25 overall selection.
“They are in a win-now situation,” Foxworth responded. “Yeah, I like that.”
Bears Have Made 2 Modest Moves at Left Tackle This Offseason
GettyOffensive tackle Ozzy Trapilo of the Chicago Bears.
Chicago has made two moves at left tackle this offseason since losing starter Ozzy Trapilo to a knee injury late in the team’s Round 1 playoff victory over the Green Bay Packers in January. Trapilo’s torn patellar tendon is likely to keep him sidelined for the bulk of the 2026 campaign.
The Bears brought back Braxton Jones on a one-year contract after he battled injuries last season and the team subsequently benched him for 2024 undrafed rookie Theo Benedet.
Benedet remains on the roster, while Chicago also picked up Jedrick Wills Jr., the No. 10 overall pick of the Cleveland Browns in the 2020 draft who has since become a bonafide bust. Wills played in just 13 games across his final two campaigns in Cleveland (2023-24) before sitting out all of last year in an effort to get fully healthy.
Because of the Bears’ investments at left tackle — as minimal, though multiple, as they may be — Todd McShay of the Ringer reiterated on his show Monday that the wind in Chicago is blowing toward an upgrade at edge-rusher or safety with the No. 25 pick.
The Bears also own pick Nos. 57 and 60 in Round 2, as well as the 89th selection in Round 3, so the team could get creative and try to move up. There is a case to do so for an offensive tackle, as McShay expects a run on the position to begin in the mid-to-late teens in Round 1, after which the available talent will fall off precipitously.
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