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Bears OTAs may answer the question fans have been asking all offseason

We are wondering the same thing.
Chicago Bears head coach Ben Johnson
Chicago Bears head coach Ben Johnson | Kamil Krzaczynski-Imagn Images

The day has finally arrived as the Chicago Bears are back on the field for OTAs, and they get underway.

Chicago's players will be practicing for the next few weeks before their summer break. There are an overwhelming number of storylines going into OTAs that Bears fans are going to be monitoring before training camp starts in the last week of July.

While there are a lot of questions about the defending NFC North champions, one keeps coming up besides the pass rusher situation. This question is more important than anything the Bears will have to answer in 2026.

Who will be protecting Caleb Williams' blind side in 2026?

There is currently a three-way battle going on at left tackle after Bears general manager Ryan Poles announced back in January that Ozzy Trapilo would miss a good portion of the 2026 season. The Bears will have to decide between Braxton Jones, Theo Benedet, and Jedrick Wills Jr.

Jones is expected to be the favorite heading into OTAs, as he has experience with Bears head coach Ben Johnson's scheme from last year. Over the offseason, Jones has received praise from Johnson and his personal offensive line coach, Terron Armstead, for his preparation heading into the 2026 season, as He works through the mental hurdles of losing his starting job and battling last year's injury.

Benedet was the second-string left tackle last year, replacing Jones for over a month before Trapilo took over at left tackle late in November. There are starting traits to Benedet's game: he is a strong run blocker but struggles in pass protection.

Wills hasn't played on the field in over two years, having sat out 2025 to recover from his injury. He feels like the long shot to not only win the left tackle job, but to make the roster.

Read more: Bears coach praises Tyrique Stevenson for what fans didn't see

There is no position more important than the one that protects Caleb Williams's blind side, so the Bears need to pick the right starter. Jones might have the lead at the moment, but a lot can change over the next few months and flip the position battle on its head.

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