Chicago Bears May Already Be Regretting Free Agent Signing Before Training Camp

We haven't even hit training camp yet and the Chicago Bears may already be regretting one of their free-agent signings.

Chicago Bears general manager Ryan Poles. | David Banks-Imagn Images

When the Chicago Bears signed Jedrick Wills in free agency, they were expecting the veteran to compete for the starting left tackle job against Braxton Jones and others.

The Bears knew Wills would be a roll of the dice considering how his career had been a major disappointment and he didn't play a single snap in 2025, but he also came very cheap, so that lessened the risk.

So far, it doesn't look like Wills is off to a good start in his first year with the Bears and Chicago is on track to regret the decision to sign the former first-round pick.

Jedrick Wills' uninspiring offseason

Cleveland Browns offensive tackle Jedrick Wills Jr. | Eric Hartline-Imagn Images

Wills has been very quiet this offseason, with the exception of a few updates that haven't exactly been inspiring.

After hearing nothing about him at OTAs, Wills was sidelined for at least one practice of minicamp for an undisclosed reason, and when he returned to action for the next session, he was working with the third-team offense at left tackle.

That is not a good sign for his chances of offering legitimate competition for the starting job, nor is the fact that Jones has gotten all of the first-team reps at left tackle this spring.

"Braxton Jones has taken all the first team reps at left tackle this spring, months removed from re-signing with the Bears on a one-year contract," ESPN's Courtney Cronin wrote. "While the Bears won't get to fully evaluate any play in the trenches until the team is in pads, Jones has the inside track to claim the left tackle job in a competition that has also included Kiran Amegadjie and Jedrick Wills Jr."

Perhaps things will change during training camp, but right now it looks like Wills may not even make the roster, let alone secure a starting or top backup job.

Why Bears may regret Jedrick Wills signing

Former Cleveland Browns offensive tackle Jedrick Wills Jr. | Scott Galvin-Imagn Images

Yes, Wills only signed a $1.2 million contract, and yes, he can be cut without penalty. However, the Bears can still regret signing him, even with the no strings attached financially.

The regret comes from the Bears choosing Wills when they could have potentially signed a player to offer better competition and a reliable backup if that player went on to lose said competition.

Now, the Bears may have to scramble before the start of the 2026 season to find a reliable backup if Wills gets cut and other options like Theo Benedet and Kiran Amegadjie fail to inspire enough confidence as backups in Chicago.