In June, Teven Jenkins made it known attempts from his camp to pursue a Bears extension were unsuccessful. His latest comments on the matter provide further clarity on the timing of a potential deal being worked out. 
The fourth-year offensive lineman said on Monday (via ESPN’s Courtney Cronin) the Bears informed his agents any potential extension would take place no earlier than the team’s bye week. As a result, Jenkins will be a pending free agent in 2024 through at least Week 7. Plenty will depend on his level of play as he continues to operate along the interior.
Jenkins entered the league with the expectation of being able to serve as a right tackle starter. He struggled in that role, but moving to guard allowed him to take a notable step forward. The 26-year-old was PFF’s third highest-rated guard in 2022, and he ranked 14th last season, one in which he missed the first four games of the campaign. Jenkins (who took snaps at both left and right guard in 2023) would up his market value with another strong showing this fall.
Chicago has 2022 fifth-rounder Braxton Jones in place on the blindside with 2023 10th overall pick Darnell Wright at the right tackle spot. The former has two years remaining on his rookie deal, while the latter can remain under team control through 2027 via the fifth-year option. Pairing those two with a Jenkins extension would ensure stability up front for the Bears.
Jenkins in particular and the team as a whole will face expectations on an offense featuring a new quarterback (Caleb Williams) and several acquisitions at the skill positions (led by running back D’Andre Swift and receivers Keenan Allen and Rome Odunze). The play of the offensive line will be key, of course, and Jenkins’ financial future will be determined if he continues his strong guard play and convinces the Bears to make a multi-year commitment in him.
Chicago is currently projected to have over $47MM in 2025 cap space, so affording a second Jenkins contract should be feasible. If the team elects not to extend the Oklahoma State alum, he could look to benefit from the upward trajectory of the guard market in free agency.