He signed a four-year, $19.7 million rookie deal that included an $11.9 million signing bonus and $19.7 million guaranteed, per Spotrac, and it gave him a $1 million base salary and a $4.4 million cap hit for the current season.

In May, Cleveland exercised its fifth-year option on the lineman’s contract, which means he’ll make $14.2 million in base salary and carry a $14.6 million cap hit to protect the blind side of whoever lines up at quarterback.

Shortly after, Bleacher Report’s Gary Davenport predicted that the Browns would ink Wills to a five-year, $88 million extension with $48 million guaranteed, largely to free up more financial flexibility for a team allocating a ton of guaranteed money to Deshaun Watson.

“This is a financial decision for the Browns. Deshaun Watson’s fully guaranteed contract puts a massive strain on Cleveland’s cap space every season. Having Wills on the books for over $14 million in 2024 takes away that much more wiggle room for GM Andrew Berry,” Davenport wrote. “That makes this a relatively easy decision. Provided that Wills doesn’t completely fall apart in 2023, he’ll be signed to a long-term extension in 2024 that affords the team more cap flexibility.”

Cleveland doesn’t have to rush into anything. It could easily wait until the heart of the 2024 offseason to decide whether it wants to offer Wills an extension.

But this injury, which limited the left tackle to just eight games played in 2023, complicates everything because Andrew Berry and the rest of the front office have fewer chances to see whether his progress is legitimate or the result of a small sample size before making a bigger, lengthier monetary commitment.

“In the moment, in the season, you felt it because he was healthy and was playing well. But as you go back and watch a lot of the tape over and over, he’s doing a nice job in the run game and the pass game. He’s winning his one-on-one matchups,” Cleveland head coach Kevin Stefanski told reporters, per Mary Kay Cabot of Cleveland.com, at the NFL owners’ meetings during the 2023 offseason. “Never perfect because it’s hard to be perfect as a left tackle in this game. But he played well. I really think if he stays healthy, the trajectory continues to ascend.”

Wills entered the league as a promising prospect who could theoretically thrive at either tackle spot after playing right tackle at Alabama. He excelled in both run- and pass-blocking schemes, displaying great athleticism, solid footwork and few notable weaknesses.

However, transitioning from the SEC to the NFL is a difficult task, and Wills’ professional career has featured both ups and downs.

Per Pro Football Focus, his stats—limited as they may be for offensive lineman—haven’t always been positive, dating back to his inaugural campaign in 2020:

Wills, even when healthy, has consistently struggled to remain effective in run-blocking situations, and he regressed in both phases during his healthy portion of the 2023 calendar.

He was picking up steam as the season progressed after a brutal start against the Cincinnati Bengals, putting together his three best pass-blocking performances of the season in his final three appearances and thriving as a run-blocker against the San Francisco 49ers in Week 6 and the Arizona Cardinals in Week 9. But can the Browns bank on that growth?

They won’t be receiving any more live-action information now that he’s out for the season, and that puts a lot of pressure on the front office and scouting department.