The Chicago Bears had a bunch of roster needs when NFL free agency started last week. But for a second straight offseason, the Bears looked for a solution at their starting left tackle spot.

Chicago seemed to have an answer for the role when it entered the playoffs last season. Ozzy Trapilo took over as the starter toward the end of November during his rookie season and held his own to keep the job. But Trapilo injured his patellar tendon in the NFC Wild Card game in January and won’t be back until late next season.

Now, Bears general manager Ryan Poles will need to spend time and resources looking for solutions at left tackle once again.

The left tackle free agent market didn’t feature many headliners, and that was reflected in Poles’ moves during the first wave of signings. He brought back one of his own and brought in another on a one-year deal. The search will likely continue at next month’s draft, where the Bears will hold four of the first 89 draft picks.

Here’s a look at who the Bears brought in to compete for the starting left tackle spot so far.

Jedrick Wills Jr.

Poles made an interesting gamble when he decided to sign Jedrick Wills Jr. to a one-year deal.

Wills is a former No. 10 overall pick who showed that he can be a dependable starter at left tackle for the Cleveland Browns. He started 45 games over his first three seasons. But an injury derailed his career, limiting him to 13 starts over two years before he decided to sit out the 2025 season.

Wills explained that he had minimally damaged two ligaments in his knee in 2023 and that it was more of an alignment issue. Doctors went into his femur to do an osteotomy to fix the issue. He spent last season training and doing physical therapy and said he feels better now than he did a year ago.

Signing Wills felt like a low-risk, high-reward move. If Wills comes back and plays at a starter’s level, then Chicago has found a solution at left tackle until Trapilo can return, or maybe even beyond. If not, they’ll move on.

“If you go back to early in his career, before the injury, playing at a really high level, he’s a guy that we want [offensive line coach] Dan [Roushar] and [assistant line coach] Kyle [Devan] to lean into it,” Poles said. “We have phenomenal offensive line coaches. Two really good ones that do a fantastic job developing players, so they’re going to lean into Jedrick. Spent time with him. We think there’s a connection there between our coaches and him. He’s willing to put in the work. We have an unbelievable performance staff that’s going to help him get his body right so he can compete at a high level, and like any position, we want competition.”

Braxton Jones

Instead of bringing in another unfamiliar player in free agency, the Bears brought back a player they know. Or know as much as they can.

Chicago signed Jones to a one-year deal that could be worth up to $10 million. He started all 17 games as a rookie out of Southern Utah before dealing with various injuries over the next three seasons. Jones recovered from an ankle injury for most of last offseason and then missed half of the season last year because of a knee injury.

Bears head coach Ben Johnson and his staff never felt like they got a good look at Jones. He started the first four games last season. But Theo Benedet replaced him in Week 4 against the Las Vegas Raiders and held the spot as a starter for six weeks.

Chicago coaches will get a chance to see what Jones looks like healthy during the spring and the summer. That might finally answer the question of whether he can be a solution and stay on the field.

"Braxton had a crack at it early, was dealing with some things," Poles said. “I’d like to see him get back healthy to compete for that spot.”

Theo Benedet

Poles didn’t surprise many when he decided to re-sign Benedet to a one-year deal as an exclusive rights free agent.

Benedet held his own in his first full season after being an undrafted free agent in 2024. He originally was a right tackle and missed his rookie season because of injury. The Bears threw him into the left tackle competition in training camp last year, and he eventually became the starter, performing well as a run-blocker.

“We have phenomenal offensive line coaches. Two really good ones that do a fantastic job developing players, so they’re going to lean into Jedrick [Wills Jr.]. Spent time with him. We think there’s a connection there between our coaches and him. He’s willing to put in the work. We have an unbelievable performance staff that’s going to help him get his body right so he can compete at a high level, and like any position, we want competition.”

—  Ryan Poles, Bears general manager

But Trapilo held on to the job when he stepped in for Benedet because of an injury. Chicago mostly used Benedet as a swing tackle and brought him in for plays as an extra blocker. The Bears also chose to have left guard Joe Thuney start at left tackle in the NFC divisional round after Trapilo’s injury instead of having Benedet make the start.

A full offseason would benefit Benedet now that he knows he’s in the running for the left tackle spot. Benedet could make the most of his opportunity once again and show that he can become a dependable starter until Trapilo comes back later in the year.