A former top-10 draft pick is getting a second chance—and the Chicago Bears may have just made one of the sneakiest moves of the NFL offseason.
With Caleb Williams entering a crucial phase of his career, Chicago just added a high-risk, high-reward protector to the offensive line.

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Bears Take a Calculated Gamble on Former Top-10 Pick Jedrick Wills in Offensive Line Shake-Up

The Chicago Bears continue reshaping their roster ahead of the 2026 NFL season—and their latest move could quietly become one of the most intriguing signings of the offseason.

On Wednesday, Chicago agreed to a one-year deal with former Cleveland Browns first-round pick Jedrick Wills, bringing the once highly regarded tackle into a revamped offensive line competition.

The signing, first reported by ESPN’s Adam Schefter, adds a player with legitimate starting experience and high draft pedigree to a Bears roster determined to defend its NFC North title.

At first glance, the deal may seem like a simple depth addition. But dig deeper, and the move reveals a calculated gamble by Chicago’s front office.

A Top-10 Talent Searching for Redemption

Jedrick Wills entered the NFL with enormous expectations.

Selected 10th overall in the 2020 NFL Draft out of Alabama, the 6-foot-4, 307-pound tackle was viewed as one of the most polished offensive linemen in his class. Cleveland quickly installed him as its starting left tackle, and Wills delivered an impressive rookie campaign.

He started immediately and earned PFWA All-Rookie Team honors in 2020, helping anchor one of the Browns’ strongest offensive lines in years.

Over the next several seasons, Wills remained a consistent presence up front, eventually starting 57 games for Cleveland.

But what once looked like a promising long-term career began to unravel due to injuries.

During the 2023 season, Wills suffered a significant MCL injury, and lingering knee issues continued to affect his availability. The setbacks eventually forced him to sit out the entire 2025 season while focusing on recovery and rehabilitation.

Now healthy again, Wills enters the 2026 offseason with one mission: prove he can still play at a high level.

Chicago is giving him that opportunity.

A Strategic Move for the Bears

For the Bears, this signing isn’t about headlines—it’s about flexibility and protection.

The team has been carefully addressing the offensive line during the early stages of free agency. Chicago previously re-signed tackle Braxton Jones on a one-year deal, but the position group still lacked depth and competition.

Adding Wills instantly changes that.

The former first-rounder brings experience at left tackle and the physical tools to compete at multiple spots along the line. At the very least, he provides valuable depth. At best, he could push for a starting role if he regains his previous form.

For a one-year contract, the risk is minimal.

But the potential reward could be significant.

Protecting the Franchise: Caleb Williams

Every offensive decision the Bears make right now revolves around one player: Caleb Williams.

The young quarterback represents the franchise’s future, and Chicago understands that protecting him will be essential if the team hopes to build on last season’s success.

After emerging as a contender in the NFC North, the Bears are under pressure to maintain offensive momentum. That starts with keeping Williams upright.

Adding Wills provides another experienced body capable of protecting the edge—one of the most critical responsibilities in modern NFL offenses.

Even if he doesn’t win a starting job outright, Wills strengthens the unit and creates competition that could push the entire offensive line to improve.

A High-Upside Lottery Ticket

There’s no guarantee Jedrick Wills returns to the form that once made him a top-10 pick.

Injuries can derail even the most promising careers, and Chicago will need to see how his knee responds during training camp and the preseason.

But if the former Alabama standout is truly healthy again, the Bears may have stumbled upon one of the most intriguing reclamation projects of the offseason.

A player who once anchored Cleveland’s offensive line now has a chance to revive his career in Chicago.

And if that gamble pays off, the Bears might have quietly secured a valuable protector for their franchise quarterback—without sacrificing long-term financial flexibility.

Sometimes the smartest offseason moves aren’t the loudest ones.