The Chicago Bears are candidates for a higher-end defensive tackle or safety with the No. 25 overall pick in Round 1 of the NFL draft, as well as potentially a second-tier pass-rusher, but there is a growing case for the franchise to use that asset as fortification for a suddenly questionable offensive line.
Specifically, the Bears have serious concerns at the left tackle position after rookie Ozzy Trapilo injured his knee during the team’s opening playoff game against the Green Bay Packers in January. Trapilo, a second-round pick who found his way into a starting role on the left side down the stretch of the 2025 campaign, won’t likely be back until the end of next season.
That leaves Chicago with a formerly undrafted player out of Canada heading into his third pro season in Theo Benedet, as well as Braxton Jones returning on a one-year deal to fill the gap on Caleb Williams‘ blindside. The Bears also signed first-round bust Jedrick Wills Jr., drafted 10th by the Cleveland Browns in 2020, after he sat out all of 2025 due to injury issues.
Charlie Kravitz of ESPN, who co-hosts the “Dominique Foxworth Show,” suggested on April 10 that Chicago’s most important draft initiative must be solidifying the left tackle position.
“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, and I know Caleb can make up for a lot of things with avoiding pressure, but you don’t want him to get into the bad habits of his rookie year.”
Tackle Position Uncertain in This Year’s NFL Draft, Particularly in Late First Round
GettyLeft tackle Monroe Freeling of the Georgia Bulldogs.
Kravitz noted Caleb Lomu of Utah, Monroe Freeling of Georgia and potentially even Kadyn Proctor of Alabama as options for the Bears in the mid-20s, while conceding that Francis Mauigoa of Miami will already be off the board.
However, Foxworth noted that there isn’t really an overwhelming prospect at the tackle position in this year’s class.
“The tackle spot feels a lot like the receiver spot this year, where there’s not really someone who is clearly [a can’t-miss player],” Foxworth said.
Given the lack of certainty regarding which tackles might still be on the board at No. 25 and what each player could potentially give the Bears on the left side during his rookie year, Kravitz floated a different idea.
“Maybe do you trade your picks and try and get Trent Williams,” he suggested. “Trade some draft capital, get Trent. He’s 36 [years old]. He’s still a freak athlete.”
Williams is actually 37 currently and will play next season for the San Francisco 49ers at 38 years of age.
“They are in a win-now situation,” Foxworth said of the Bears following their 12-5 NFC North Division-winning campaign in 2025. “Yeah, I like that. Package em up, go get Trent.”
Trading for Trent Williams Represents Massive Risk for Bears
GettyLeft tackle Trent Williams of the San Francisco 49ers.
Williams presents a few significant issues as a trade target.
The first is that San Francisco is positioned to contend for a championship yet again in 2026 if the team can remain healthy, and losing the 12-time Pro Bowler and reigning second-team All-Pro left tackle would not be conducive to their chances at finally finishing the job after losing twice in the Super Bowl under head coach Kyle Shanahan.
Williams is entering the final year of his $83 million contract and the 49ers are working hard to convince him to agree to a contract restructure/pay cut to whittle down his $46.3 million salary cap hit.
If they can’t, Williams may become available at some point this offseason. But that leads into concern No. 2, which is that he will likely cost the Bears their first-round pick.
That is a considerable asset to surrender for a player in his late 30s who will be a free agent next spring and potentially command a sizable contract, as well as to whom Chicago would have to pay $33 million in 2026.
Paying Williams next year would be a feat for the franchise given its current cap circumstances. Keeping him beyond 2026 would be an expensive risk due to his age. And trading a first-round pick for one season of a player — even an all-time great who still has plenty left in the tank — is an unacceptable use of a valuable resource unless doing so carries the Bears to their first title since 1985-86.
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