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Bears OTAs gave first warning about a failed offseason bet

Is he even going to make the cut?
Cleveland Browns offensive tackle Jedrick Wills Jr.
Cleveland Browns offensive tackle Jedrick Wills Jr. | Eric Hartline-Imagn Images

The Chicago Bears certainly made an interesting move in the offseason to address their offensive line concerns, but OTAs might have made the picture clearer.

One move that got the fan base's attention was the Bears signing offensive tackle Jedrick Wills Jr. on a one-year, $1.2 million contract. This is considered a risky signing because Wills hasn't played football since 2024, having sat out last season with a knee injury he suffered two years ago.

Wills was brought in to compete at the left tackle position with Braxton Jones and Theo Benedet as the Bears look to replace Ozzy Trapilo for the first part of 2026 with his injury recovery. Once Wills and the Bears arrived at OTAs, there was a kind of radio silence about how he performed, as more attention focused on how great Jones looked, leaving Wills in a tough spot.

Jedrick Wills Jr. might not make it through Bears training camp

It is really up in the air whether Wills will even make the Bears' 53-man roster, as he will be a roster bubble candidate. Jones and Benedet will have the advantage since they know Bears head coach Ben Johnson's scheme better from having played in it last year.

Johnson has already been praising Jones in OTAs, leaving the door wide open for him to win the job. That does not bode well for Benedet or Wills.

Benedet was not high on the list to win the job anyway, as he was average at best last season at left tackle, replacing Jones before Benedet himself was replaced by Trapilo and never got his job back. Wills is already at a massive disadvantage in winning the left tackle job and even staying on the roster.

The Bears did not get a slouch player in Wills, though, as he has plenty of NFL experience after being the 10th overall pick by the Cleveland Browns back in the 2020 NFL Draft. He started 57 of 58 games before his knee injury in 2024.

There's a chance that Wills will get some looks at right tackle as well, with the Bears looking to make him a swing tackle. That would be his key to making the 53-man roster if he can.

Read more: Lamar Jackson said what Bears fans know well about Declan Doyle

The left tackle position battle at training camp will be fascinating to monitor throughout July and August, but the chances of Wills making it may not be great. Still, with his experience, he's got a shot to make some noise and be a depth player on this Bears team.

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