One Key Position Battle Is Already Taking Shape for the Chicago Bears

The Chicago Bears addressed several roster needs during the first waves of free agency. But one of the team’s most important positions is still very much up for grabs.

According to ESPN reporter Courtney Cronin, the Bears are heading into the offseason with a true competition at left tackle, one that could end up being one of the biggest storylines of training camp.

At the center of it are two players the team believes could claim the job: Jedrick Wills Jr. and Braxton Jones.

Jedrick Wills Arrives in Chicago With Something to Prove

Cleveland Browns offensive tackle Jedrick Wills Jr. (71) against the Philadelphia Eagles | Eric Hartline-Imagn Images

The Bears brought in Wills this offseason on a one-year deal with a clear message. He’s here to compete.

Wills, the No. 10 overall pick in the 2020 NFL Draft, did not play during the 2025 season while recovering from a complicated knee injury that originally occurred late in the 2023 season while he was with the Cleveland Browns.

The recovery process turned out to be more involved than a typical knee rehab.

“I had minimal damage to my ligaments,” Wills explained when discussing the injury. “It was more of an alignment issue from where I got fell on.”

He later clarified the procedure required to correct the issue.

“It wasn't my knee; they had to go into my femur and do what was called an osteotomy to kind of correct my alignment. So my knee is healthy. It took a little bit longer than just the regular injury, but it's doing better now.”

For Wills, the 2026 season represents an opportunity to reset his career after injuries disrupted his trajectory in Cleveland.

Braxton Jones Isn’t Giving Up the Bears’ Left Tackle Job Easily

Chicago Bears offensive lineman Braxton Jones (70) blocks against the Atlanta Falcons | Jamie Sabau-Imagn Images

While Wills may bring the pedigree of a former first-round pick, the semi-incumbent shouldn’t be overlooked.

Jones has quietly been one of the Bears’ most durable offensive linemen since arriving in Chicago.

Drafted in the fifth round in 2022, Jones has already made 44 starts for the Bears and re-signed this offseason on a one-year deal worth up to $10 million.

After dealing with injuries last season, Jones enters the offseason healthy and motivated to keep the job he held since his rookie year and before his turbulent 2025 season that sent him to the bench.

That experience could matter when the competition begins.

A Third Name in the Mix for the Bears’ Starting Job

Chicago Bears offensive line Luke Newman (65) and Theo Benedet (79) run during the Rookie Minicamp | Kamil Krzaczynski-Imagn Images

The Bears also have another developmental option in their offensive tackle room.

Theo Benedet is expected to factor into the competition as well, giving the coaching staff another player to evaluate as they determine the best combination along the offensive line.

Still, the battle will likely come down to Wills and Jones, and, perhaps, an early draft pick.

Could the Bears Draft Their Left Tackle of the Future?

Chicago Bears general manager Ryan Poles speaks at the NFL Scouting Combine | Kirby Lee-Imagn Images

There’s another wrinkle to this conversation that could reshape the entire competition: The 2026 NFL Draft.

Even with Wills and Jones battling for the job this summer, the Chicago Bears still have a long-term question at left tackle. Jones is currently on a one-year deal, and Wills signed a short-term contract as well. Neither move guarantees a permanent solution to protecting Caleb Williams’ blind side.

Because of that, the possibility of Chicago selecting an offensive tackle in the first round remains very real.

General manager Ryan Poles has repeatedly emphasized building through the trenches, and the Bears hold the No. 25 overall pick, a spot where quality offensive line prospects can still be had.

Drafting a tackle wouldn’t necessarily eliminate the Wills-Jones battle. Instead, it would raise the stakes. A rookie would enter the mix immediately and potentially push for the starting job, especially if he’s a first-round pick.

Left Tackle Matters More Than Ever for the Bears

Chicago Bears quarterback Caleb Williams (18) calls the snap count from shotgun | Matt Marton-Imagn Images

For Chicago, stability at left tackle is critical. Protecting franchise quarterback Caleb Williams will remain one of the organization’s top priorities as the offense continues to grow under head coach Ben Johnson.

That’s why Cronin’s observation carries weight. The Bears may have filled several defensive holes this offseason, but the left tackle job remains unsettled, and the answer may not emerge until the pads come on in training camp.