Chicago Bears left-tackle duties remain unsettled after 17 camp practices, with a five-man competition centered on Braxton Jones, Ozzy Trapilo, Kiran Amegadjie, Theo Benedet, and Caleb Williams. Benedet has surged, starting three straight practices with the ones and earning clean first-team reps, signaling a potential turning point in protection for Williams. The staff craves clarity, not a revolving door, and the upcoming joint session with Buffalo plus the second preseason game are viewed as pivotal for an opening-week decision.

Jones brings starting experience but has shown warts, while Trapilo has athleticism and run-blocking upside but needs to speed his feet. Amegadjie has missed time due to injury but is back in the mix, and Benedet has been the breakout case on tape, offering versatility on both sides. The Bears aim to solidify the job for Week 1 vs. Minnesota, yet a midseason reassessment remains on the table. For fantasy, the LT spot directly impacts Williams’ pocket time, run game tempo, and overall offense efficiency as Chicago finalizes its protection plan.

The Chicago Bears’ left-tackle competition has shifted from a two-man race to a three-way audition, with Theo Benedet emerging as a dark horse contender alongside Braxton Jones and Ozzy Trapilo. Benedet, an undrafted free agent, found himself in the three-man left tackle rotation during the last Sunday’s preseason opener against the Dolphins after an injury to Kiran Amegadjie. He rotated with Jones at times for the first team, drawing praise from OL coach Dan Roushar who noted Benedet’s dramatic spring-to-now growth and his relentless work ethic, keeping him squarely in the fight for a starting spot as the preseason continues.

Following that showing, Benedet continued to split first-team reps with Jones in practice, while Trapilo worked on the right side with the second unit. The plan appears to be a rotation strategy to evaluate all three, meaning Benedet’s roster chances hinge on continued improvement and consistency. While he insists he’s a long shot for the job, Benedet has captured the attention of the coaching staff, signaling that the Bears’ offensive line could be more competitive than initially anticipated this season.

As Roushar emphasized, Benedet’s growth has been among the most notable in the group, suggesting a future where depth and versatility up front could shape Chicago’s offensive performance. The unfolding battle remains open, making Benedet a player fantasy managers should monitor closely for potential lift in pass protection and run blocking if he earns a starting role.

The Bears used their first real look at the 2025 rookie class in the preseason, and it offered a hopeful signal for fantasy rosters. Colston Loveland and Luther Burden III flashed as potential Week 1 contributors in a Chicago offense that envisions pairing two tight ends with DJ Moore on the outside. Loveland showed awareness and dependable hands, even if not every route was crystal-clear, while Burden displayed speed and route-running bursts that could translate into meaningful targets down the line. Ozzy Trapilo held his own against second- and third-string rushers in the left-tackle duel with Braxton Jones, suggesting Chicago may have stability on its blind side, though injuries and rotation could shape Week 1 plans. The Bears also leaned on Bagent and Keenum in the two-minute drill, reinforcing Loveland’s role as a safety valve and hinting at a polished rookie who can climb the ladder as the playbook tightens. The weekend produced a 24-24 tie with the Dolphins, but the rookie performance felt like a blueprint for added fantasy upside as the season approaches.

Beyond Loveland and Burden,Trapilo, Hyppolite, and Newman impressed enough to keep eyes on the depth chart. Loveland’s early connection with Tyson Bagent and the quarterback’s comfort level with a tight-end pair could unlock a more pass-friendly Chicago approach, particularly in two-tight-end sets Johnson used in college. Burden’s speed and contested-coverage ability stand out as a potential spark plug for the offense, with development likely to coincide with Loveland’s progression. The left tackle competition revealed enough to believe Trapilo could be a viable swing tackle and occasional starter, affording Moore and Moore-like options more room to operate. In short, the Bears’ rookies looked ready for the jump, and fantasy managers should monitor how the coaching staff deploys Loveland and Burden as September nears.

Chicago’s big offseason story line centers on the left tackle battle. Braxton Jones and Ozzy Trapilo headline a competition that also features Theo Benedet and Kiran Amegadjie, with the latter sidelined by injury. Head coach Ben Johnson has signaled patience, stressing joint practices and preseason action as the deciding factors rather than rushing to a starter.

Chicago’s interior upgrade—Jonah Jackson, Drew Dalman, and Joe Thuney—shapes the overall protection plan, but the true test is in the live game reps. If Trapilo seizes the job, Fields could enjoy better clean pockets and more play-action efficiency; if Jones holds, the line gains stability but the floor for upside remains tempered. Benedet and Amegadjie provide solid depth behind the top contenders.

Fantasy relevance centers on protection and timing. A winner at left tackle could unlock higher passing efficiency for Fields and more consistent targets for receivers. The Bears’ preseason rotation—Jones, Trapilo, Benedet, and Amegadjie—will clue fantasy managers in on Week 1 projections, while the Dolphins clash adds extra urgency to evaluate the depth chart and potential early-season lineup.

In short, Chicago’s O-line evolution could shift Fields’ ceiling this season, with left tackle stability potentially boosting passing efficiency and play-action effectiveness across the passing game.