For a second time, the Broncos allowed Garett Bolles to play deep into a contract year before extending him. After the sides previously reached an extension agreement in November 2020, Bolles inked his second Denver extension days before the team’s Week 15 game. Talks did not begin until recently. The sides did not begin to discuss a new deal — one Bolles had begun to lobby for back in 2023 — until after the Broncos’ win over the Browns, 9News’ Mike Klis notes. While Bolles held Myles Garrett without a sack, the Broncos’ upcoming bye week presumably had more to do with the timing of the negotiations.

Bolles is now the NFL’s sixth-highest-paid left tackle. Like recently extended edge rusher Jonathon Cooper, he may well have done better by reaching free agency. But Bolles wanted to stay with the team that drafted him back in 2017. The four-year, $82MM contract includes $23.7MM guaranteed at signing and features a similar guarantee structure to the one Mike McGlinchey secured. If Bolles is on Denver’s roster by Day 5 of the 2025 league year, his 2026 base salary becomes guaranteed, per OverTheCap. As the Broncos have part two of Russell Wilson‘s dead money due in 2025, they have predictably backloaded Bolles’ deal. This is a rather extreme effort, as five void years (through 2033) are attached to this deal. Bolles will count $5.8MM on Denver’s 2025 cap and just $9.2MM in 2026; the cap hits balloon past $20MM after that.

Here is the latest from the NFL’s O-line situations:

• Unable to find a reliable left tackle since letting Orlando Brown Jr. leave in 2023, the Chiefs are going with an emergency plan today. With recent signee D.J. Humphries declared out due to a hamstring injury he sustained in his Kansas City debut, the Chiefs are kicking Joe Thuney to left tackle. The left guard saw time at LT against the Raiders, who were besting second-year blocker Wanya Morris. Rather than go with Morris, the Chiefs are using Thuney at LT and backup Mike Caliendo at LG, per ESPN.com’s Adam Teicher. This will cut into the Chiefs’ elite inside trio, but with the team seeing Patrick Mahomes hit with more frequency in recent weeks, it will use this patchwork adjustment to stem the tide. A 2023 UDFA, Caliendo is making his first career start.
• On the same note, the Texans are making a change. Right tackle Tytus Howard is moving back to left guard, KPRC2’s Aaron Wilson notes. Both center Juice Scruggs and left guard Kenyon Green are out. As a result, Howard will return to the position he primarily played last season. Howard has shuffled between tackle and guard as a pro; prior to his 812-snap 2024 at RT, he played all 408 of his 2023 snaps at LG. Second-round pick Blake Fisher is in at RT.
• Trent Williams‘ recovery from an ankle injury has proven “a lot” slower than the 49ers expected, Kyle Shanahan said (via ESPN.com’s Nick Wagoner). The team is not ruling him out for the rest of the season. That said, San Francisco is now 5-8; shelving the All-Pro the rest of the way would make sense. Williams, 36, secured significant guarantees via a September reworking. He has not indicated a 2025 return will commence, but his through-2026 contract contains enticements to come back.
• The Bears should be likely to be shoppers to fortify their O-line’s interior in 2025, with the Chicago Tribune’s Brad Biggs rating that area atop the team’s list of needs. Chicago whiffed on Nate Davis and devoted low-end money to center. Left guard Teven Jenkins is a free agent-to-be who has not engaged in substantive extension talks.
• Like Bolles, Walker Little secured an extension recently. The Jaguars revealed their long-term left tackle plan, post-Cam Robinson, by signing Little to a three-year, $40.5MM extension. The first two years of Little’s deal are fully guaranteed, per OverTheCap. That comes out to $25.94MM. Although his 2027 salary is nonguaranteed, the 2021 second-rounder did well on the guarantee front as he bypasses free agency.