Bears 2026 Offseason Needs, Part 4: Caleb Williams' Blindside Is Wide Open, and Bridge Tackles Don't Come Cheap

The Bears cycled through four left tackles last season. Four. Braxton Jones won the job in training camp, got benched after four starts, and landed on injured reserve. Theo Benedet replaced him and held the fort for eight games before an injury opened the door for Ozzy Trapilo. Trapilo, a second-round rookie who hadn't played left tackle since 2022, stepped in during Week 12 and proceeded to look like the long-term answer—earning a 77.7 PFF pass-blocking grade as a starter and finishing as the third-highest-graded rookie tackle in the NFL from that point forward.

Then, in the fourth quarter of the Bears' Wild Card comeback win over the Packers, Trapilo went down with a torn patellar tendon. Just like that, the one position that had finally stabilized was ripped open again.

This is different from the center situation we covered in Part 3.5. Drew Dalman retired and isn't coming back. Trapilo is coming back—Ryan Poles said as much at the Combine. But "coming back" and "ready to start Week 1" are not the same thing. Poles expects Trapilo to miss most of the 2026 season. That means the Bears need someone to protect Caleb Williams' blindside for the majority of a year in which anything less than a deep playoff run will be considered a disappointment. And as Brad Biggs of the Chicago Tribune put it: "Good luck finding bridge left tackles. Good ones aren't gonna be signing one-year deals for budget buys. It's a tricky spot."

He's right. It is.

About This Series

With free agency opening March 11 and the NFL Draft set for late April in Pittsburgh, the next two months will define whether the Bears can turn a breakthrough season into sustained contention. This week alone, the Bears have created approximately $44 million in new cap space by trading DJ Moore to the Bills, releasing Tremaine Edmunds, and processing Drew Dalman's retirement. Per Over The Cap, that puts Chicago at roughly $33 million in cap room—12th in the NFL. The flexibility is there. The question is how to spend it.

Over the coming days, we'll be breaking down each of the Bears' biggest offseason needs in a multi-part series. For each position, we'll examine why it needs to be addressed, who the realistic options are in both free agency and the draft, and how Poles might navigate the cap crunch while keeping this team's championship window wide open. Here's what's ahead:

Part 1: Safety — Zero safeties under contract. The most urgent hole on the roster.
Part 2: Defensive Tackle — Poles is targeting speed and violence up front. The Combine confirmed it.
Part 3: Edge Rusher — Montez Sweat needs a running mate. The cap says it won't be Crosby.
Part 3.5: Center — Drew Dalman's shocking retirement blew a hole in the NFL's best O-line.
Part 4: Left Tackle (today) — Caleb Williams' blindside is wide open, and bridge tackles don't come cheap.
Part 5: Linebacker & Secondary Depth — The Edmunds fallout and what comes next.

What Was Lost

To understand the scope of this problem, you have to understand how improbable Trapilo's emergence was in the first place.

The Bears drafted Trapilo 56th overall in the 2025 draft out of Boston College, where he played right tackle. He was viewed as a high-floor prospect with good size and polished technique—a developmental piece, not an immediate starter on the blind side. When he lost the training camp competition to Jones and was moved to backup right tackle behind Darnell Wright, most people wrote him off as a future swing tackle. Then Benedet got hurt before Week 12, and Trapilo was thrust into his first career start at left tackle against the Steelers.

He allowed one pressure. Zero sacks. Zero quarterback hits. PFF gave him an 88.4 pass-protection effectiveness grade. And he never gave the job back.

Over his six regular-season starts, Trapilo played all 418 offensive snaps and earned a 77.7 PFF pass-blocking grade—better than every rookie tackle in football except Kansas City's Josh Simmons. He allowed just 13 pressures in that stretch. PFF ranked him as Chicago's sixth-highest-graded offensive player from Week 12 on and a top-10 offensive rookie overall. His best games came against Green Bay: a 79.5 grade in Week 16 and a 75.9 in the Wild Card, where he posted an 85.9 run-blocking grade—the second-best mark of any tackle that weekend. The Bears went 4-2 in his starts, including the playoff win that ended his season.

For the full season, including his limited early snaps and the Week 4 disaster against Maxx Crosby that tanked his overall numbers, Trapilo finished with a 70.0 PFF grade (36th among 89 qualifying tackles), allowed two sacks and 15 pressures across 491 total snaps, and drew just two penalties. A right tackle by trade who hadn't played the left side since 2022, playing that well that fast in that situation. The son of former NFL lineman Steve Trapilo was ascending on a steep trajectory—and then the patellar tendon gave out in the game's final drive.

Poles addressed it directly at the Combine. "We expect him to come back and heal from it," he said. "There's a plan in place. I can't get into the timelines or anything like that, I just don't know. But, yeah, we expect him to be back and be himself. Pretty significant injury that he's got to get through, but in terms of affecting his overall career or next year, I don't see that being an issue."

That's the good news: Trapilo's career isn't in jeopardy. The bad news is everything between now and whenever he's ready to play again.

What's Already in the Building

Poles outlined the framework at the Combine. Darnell Wright and Jonah Jackson are staying on the right side. Joe Thuney is not moving to left tackle—that's "only something they want to do in a pinch," the same pinch that led to Thuney starting there in the Divisional Round against the Rams (where, to his credit, the offensive line didn't allow a single sack). The left tackle job is open. And the in-house candidates are, charitably, limited.

Theo Benedet is the most likely internal starter, and the Bears have already re-signed him. The 24-year-old undrafted free agent out of UBC in Canada started eight games at left tackle in 2025 and showed a clear split: he's a capable run blocker (PFF ranked him fourth among all tackles in ESPN's run block win rate) but a below-average pass protector (55.4 PFF pass-blocking grade, 74th out of 89 tackles). His overall PFF grade of 57.4 ranked 72nd. It's worth noting that eight starts is a limited sample, and drawing firm conclusions from that body of work comes with some caveats. He allowed two sacks and seven penalties. Ben Johnson's own assessment was blunt: "Inconsistent, to say the least." And when it came time to pick a left tackle for the Divisional Round, Johnson chose Thuney over Benedet. That tells you something about the coaching staff's confidence level. Benedet is a floor option—a guy who can hold the fort until Trapilo returns—but he's not someone you want starting 14 games protecting a franchise quarterback's blind side.

Kiran Amegadjie, the 2024 third-round pick out of Yale, has played a total of six games since being drafted and spent all of 2025 on injured reserve. The coaching staff is high on his development in theory, but as AtoZ Sports noted, "this staff hasn't seen much out of him in a live game environment." He may project better as a guard. Counting on him to start at left tackle in 2026 would be reckless.

Braxton Jones is the wild card, but he's a free agent now. The 26-year-old started 44 games at left tackle for the Bears over four seasons—the most extensive starting experience of anyone in this conversation. His 2024 season was strong (career-best 80.8 PFF pass-blocking grade) before a fractured ankle ended it early. But 2025 was a disaster: a 55.5 PFF overall grade, benched after four terrible starts, then a knee injury that put him on IR. Spotrac projects his market value at a modest two-year, $9.5 million deal. If the Bears could bring him back for $5 million or less as a depth piece to compete with Benedet, it would make sense. But banking on Braxton Jones as the starter at this point feels like running back the same experiment that failed in September.

Offensive line coach Dan Roushar was the most honest about the situation. Asked on Terron Armstead's podcast whether the starting left tackle was already in the building, Roushar said: "There's guys that have traits, but not consistent enough. So that's to be determined." He then added that premium positions like left tackle usually require "draft capital or an asset we currently don't have."

The Trent Williams Question

If you've been following this series, you know the pattern by now. In Part 3, it was Maxx Crosby—the transformative player every Bears fan dreams about who seemed unlikely just a week ago. With the Bears aggressively clearing cap space this week, though, who knows what might be cooking up there. In Part 3.5, it was Tyler Linderbaum. At left tackle, the dream name is Trent Williams.

Williams is a 12-time Pro Bowler, five-time First-Team All-Pro, and a future Hall of Famer who PFF ranked as the third-best tackle in football last season. He's 37 years old and entering the final year of a restructured deal that carries a $38.84 million cap hit—the fourth-highest among non-quarterbacks in the NFL. The 49ers want to bring him back. Williams wants to stay. But the two sides have been locked in a contract standoff since February, and as of March 4, NFL Network's Mike Garafolo reported that there has been "no progress" on a revised deal.

If the 49ers release Williams—either before or after June 1—he would immediately become the most sought-after offensive lineman on the market. Multiple outlets have named the Bears as a potential suitor. CBS Sports noted that Ben Johnson "isn't afraid to make bold moves to upgrade Caleb Williams' surroundings." Bleacher Nation called the idea of pairing Williams with All-Pro left guard Joe Thuney "a dream team of sorts." Heavy.com described it as "a longer-shot and far more expensive, but also potentially a Super Bowl type of move."

Here's the reality check: even on a reworked deal, Williams would command significant money for a player entering his age-38 season. The Bears have roughly $33 million in cap space and still need to address center, safety, defensive tackle, edge rusher, and linebacker. ESPN's Adam Schefter has indicated that Chicago is more likely to target players in the $10 to $15 million range than make mega-splash signings. Williams is a one-year, maybe two-year rental at most. The 49ers' GM John Lynch said at the Combine that he feels "very positive" about getting a deal done. And even if Williams does hit the market, the Bears would be competing with the Packers, Steelers, Cowboys, and every other tackle-needy team in football.

Williams to Chicago would be spectacular. It would also require everything to break right: the 49ers releasing him, the Bears winning a bidding war, and the cap math somehow working alongside all the other holes on this roster. Don't hold your breath. But don't completely rule it out, either.

The Free Agent Market

The realistic headliner in free agency is Rasheed Walker, the Packers' 26-year-old left tackle who has started 48 games over the last three seasons and hasn't missed a single game in that stretch. Walker is a former seventh-round pick out of Penn State who replaced David Bakhtiari in 2023 and never looked back. Green Bay declined his fifth-year option and is expected to let him walk now that 2024 first-round pick Jordan Morgan is ready to take over.

Walker's durability is real. His production is murkier. Pro Football Focus graded him at 64.6 overall in 2025—52nd out of 89 qualifying tackles. That number is dragged up by a respectable 70.0 pass-blocking grade (41st) and dragged way down by a 55.4 run-blocking grade (71st). He allowed five sacks, up from three in 2024, and committed nine penalties. Sports Info Solutions charged him with nine blown blocks in the run game—as many as his 2023 and 2024 seasons combined. NFL.com's boom-or-bust analysis pointed out that while Walker has allowed 19.5 sacks since becoming Jordan Love's blindside protector (tied for 12th-most among tackles), his low quick-pressure rate "suggests the sacks might be more on Love's indecision than Walker's execution." There's some truth in that. There's also the fact that his career 69.8 PFF overall grade ranks 45th out of 83 tackles with 1,000-plus snaps since 2022. Albert Breer of Sports Illustrated put it plainly: Walker is "good, but not great."

The problem is that "good, but not great" at left tackle costs a fortune in a thin market. Spotrac projects a four-year, $81.1 million deal ($20.3 million per year). Bleacher Report's Kristopher Knox estimated four years, $85 million. The Athletic projected four years, $82 million. Breer said he expects Walker to get "over $20 million per year." In a class where Walker is the clear top free-agent left tackle by default, scarcity is doing the pricing—not production.

Walker also has an off-field wrinkle. He was arrested at LaGuardia Airport on January 23 after telling a Delta Airlines employee that his checked bag contained a locked firearm. The gun was legally licensed in Wisconsin, and Walker's attorney said he was unaware of New York's laws. He was charged with two felony counts of criminal possession of a weapon, released on his own recognizance, and has a court date on March 19. His attorney has expressed confidence the case will be dismissed, and the NFL has not yet reviewed the matter under its personal conduct policy. It's possible the arrest suppresses his asking price slightly—but in a market this starved for left tackles, it's unlikely to make a dramatic difference.

Beyond Walker, the free-agent tackle market is thin. Jermaine Eluemunor of the Giants posted strong pass-blocking numbers (76.7 PFF pass-blocking grade, 20th among all tackles) at a projected cost of $8.7 million per year, but he played 1,083 of his 1,088 snaps at right tackle—not left—and his 14 penalties ranked 88th out of 89 qualifying tackles. Flipping him to the blind side is a gamble. Cam Robinson posted a career-best 92.1 percent pass block win rate with Cleveland in 2025 but has been inconsistent throughout his career and turns 30 this year. Jawaan Taylor, just released by the Chiefs, is a solid pass protector when he's not getting flagged—and he gets flagged a lot. There are veteran bridge options at various price points, but none of them inspire confidence as someone you'd trust to start 14-plus games protecting Caleb Williams' blind side.

The Draft Path

This is where the conversation gets interesting, because the 2026 offensive tackle class is deep—arguably the strongest position group in the entire draft. CBS Sports has seven offensive linemen ranked among the top 25 overall prospects, and the strength extends well into Day 2. The Bears hold the 25th overall pick and, thanks to the DJ Moore trade, the 60th pick as well. They also already hold the 57th pick. They have options.

The top-tier tackles—Utah's Spencer Fano and Miami's Francis Mauigoa—will almost certainly be gone by the 25th pick. Fano is the consensus OT1, a scheme-versatile lineman whom PFF's Trevor Sikkema described as having "All-Pro potential." He didn't allow a single sack or hit across 822 snaps in 2025. Mauigoa could go as early as the top 10. Neither is realistic for Chicago.

The names that could be there at 25 are more compelling than you might expect.

Kadyn Proctor, Alabama. Proctor is unlike any prospect in this class. At 6-6⅝ and 352 pounds, he's a mammoth who squats 815 pounds, benches 535, and power cleans 405—earning the No. 2 spot on Bruce Feldman's Freaks List. He started 12 games at left tackle in 2025 despite playing through a torn labrum suffered during pregame warmups before the season opener, and he won the Jacobs Blocking Trophy as the SEC's best blocker. At the Combine, he posted the highest vertical jump (32.5 inches), the second-fastest 40-yard dash (5.21), and the third-best broad jump (9-1) ever recorded by a 350-plus-pound lineman. His arm length measured 33⅜ inches—adequate, despite early speculation that short arms might force a move inside. Mel Kiper has him ranked 25th overall. The Draft Network has mocked him to the Bears. The concerns are real—Proctor can struggle against speed rushers off wider alignments, his weight management has been a question (he played at 365-370 early in 2025 before trimming down), and some evaluators project him as a guard long-term. But the upside of a player this massive, this athletic, and this nasty as a finisher is enormous in a gap- or man-blocking scheme.

Caleb Lomu, Utah. If Proctor is the power play, Lomu is the finesse option. He's a true left tackle with excellent lateral quickness, loose hips, and smooth footwork—the kind of mover who mirrors speed rushers with ease. His 2025 tape was impressive: 823 snaps, zero sacks allowed, a 97.9 percent pass block win rate, and just four penalties. At the Combine, he said joining the Bears' veteran offensive line would be "amazing," adding, "I love the learning that it brings as a young player." Daniel Jeremiah comped him to the Seahawks' Abraham Lucas. The knock is play strength—CBS Sports gave him a B grade at the Combine, noting that "his punch lacked the power displayed by others." He needs to get stronger to hold up in the run game at the next level, and CBS projects him as a "late first round or early Day 2" selection. He could be there at 25.

Monroe Freeling, Georgia. At 6-7, 315 pounds with a 4.93 40-yard dash and a 33.5-inch vertical, Freeling has prototypical tackle size and the athleticism to match. CBS Sports praised his "fluidity and lateral quickness" at the Combine. He's raw compared to Proctor and Lomu but offers the kind of physical ceiling that could make him a long-term starter. He could slip to the late first round.

At No. 60—the pick acquired from the Bills—the Bears could target someone like Caleb Tiernan out of Northwestern (four-year starter, 97.0 percent pass block win rate in 2025), Max Iheanachor from Arizona State (one of CBS Sports' top-25 overall OL prospects), or Blake Miller from Clemson (another four-year starter whom PFF praised for his "great posture and balance in pass protection"). This draft class is deep enough that quality starting-caliber tackles could be available well into Day 2.

The Sun-Times' reporting from the Combine made the case plainly: "If they believe there are enough quality left tackles in the draft, their best move probably is to look for one there. If that pick works out and Trapilo bounces back, there's nothing wrong with having a surplus at such a valuable spot." Ryan Poles seemed to agree, telling reporters: "Sometimes there are years where there's a run, where they're all gone. Sometimes there's a lot of them, and there are a couple of guys sitting there waiting for you."

The Bottom Line

Left tackle is different from the other positions in this series because it comes with a built-in timeline. Trapilo is expected back. He played well enough as a rookie to suggest he can be the long-term answer. The question isn't whether the Bears need a franchise left tackle—it's whether they need a bridge for 2026, a long-term investment, or both.

The bridge path means leaning on some combination of Benedet, a returning Braxton Jones, or a mid-tier free agent, then using draft capital at other positions of need. The investment path means spending real resources—either $20-plus million on Rasheed Walker or the 25th overall pick on someone like Proctor or Lomu—to address the position with a player who can start immediately and compete with Trapilo for years.

The most likely path probably involves a little of both. The Bears use the draft to address left tackle—this class is deep enough that a quality starter could fall to 25, and the 60th pick gives them a second bite at the apple. They bring back Jones or sign a budget veteran to compete with Benedet in camp. If the draft pick wins the job, great. If Trapilo comes back sooner than expected, even better. If the 49ers somehow release Trent Williams and he wants to come to Chicago for a restructured deal, you find a way to make it work and worry about the cap later.

The one thing the Bears cannot afford to do is nothing. Last season's left tackle carousel—four starters, three benchings, one training camp competition that dragged into December—was a dysfunction that Ben Johnson inherited and managed his way through. He's not going to want to run it back. The Bears won 11 games and made the Divisional Round despite that chaos. They're not going to get that lucky twice.

As Dan Roushar said: premium positions require premium resources. The Bears have the cap space. They have the draft capital. And they have five days until free agency opens to figure out how to deploy both.

Next up — Part 5: Linebacker & Secondary Depth. The Edmunds release changes the equation. We'll break down what comes next.