Two weeks after the Chicago Bears’ trade acquisition of former Pro Bowl guard Jonah Jackson, the team extended him but didn’t take on much more future liability in the process. We’ll take a deeper dive into Jackson’s one-year extension and how it’ll impact the Bears moving forward.

During the week leading up to free agency, general manager Ryan Poles and his staff sought an aggressive journey to fortify the team’s interior offensive line. After Trey Smith was franchise-tagged at the combine, it became clear that the team would be required to get creative to accomplish their offseason goals. First, the front office sat down with multiple agents at the combine to gauge the potential markets of the top names. Those names included Will Fries (who missed all but five games in 2024 with a broken tibia), Aaron Banks (who has struggled with consistency), Mekhi Becton (who had a career year under the best offensive line coach in the game), and of course, Drew Dalman, who the Chicago Bears ultimately signed to a three-year, $42 million at the start of the legal negotiation period.

Once Poles and his staff realized there was far more risk in a shallow free agent class than a reward, he aggressively pursued trade options. Within 24 hours, the Bears had a pair of new starting guards. Jonah Jackson was the first of the two moves. The former Detroit Lion was acquired for a 2025 6th-round pick. The next day, the Bears made the first shocking move of the offseason, landing All-Pro Joe Thuney for a 2026 4th-round selection.

When healthy, Jackson has played at a Pro Bowl level. That led him to sign a three-year, $51 million deal with the Los Angeles Rams at the start of last year’s negotiation period. Unfortunately for both parties, a training camp injury and a position change led to a disappointing lone season in Los Angeles. This opened the door for first-year head coach Ben Johnson to acquire someone he knew.

Jackson’s remaining two-year contract that the Bears acquired was in question. While Spotrac had his cap hit sitting at $17.5 million for 2025, and $17 million for 2026 due to a pair of $8 million roster bonuses, Over The Cap had terms slightly different, with consecutive cap figures of $11.83 million over the next two seasons. A few days after the trade was made official, the NFL Network’s Tom Pelissero reported that the team had given Jackson a one-year extension. It confused fans, especially coming off a poor season in 2024.

It took a few days to get the final numbers and overall details from the one-year extension, but they are finally complete. Let’s take a look.

The Terms Of Jackson’s New Contract

Three years, $52.5 million with $17.5 million in fully guaranteed money.

On the surface, the Bears added an additional year for a similar average annual value onto his existing contract ($17.5 million), right? That’s how the contract would appear on the surface.

In reality, all the Bears did was switch Jackson’s $8 million roster bonus (that was due a few days ago) and convert it into a $10.5 million signing bonus. The 28-year-old will see a slight increase in his base salary for 2026 ($12.25 million) and be owed his original $8 million roster bonus if he’s not cut or restructured by March 16th of next year. Overall, he receives a little extra guaranteed money but will function on a “prove it” basis after this season.

Jackson’s cap hits are as follows:

2025: $10.5 million ($17.5 million in dead space)

2026: $25 million ($18 million potential savings before March 16th, with a $7 million dead figure)

2027: $17 million ($13.5 million potential savings before a $230,000 workout bonus in April, with just $3.5 million in dead money)

What The New Contract Actually Means

For starters, Jackson’s new average value of $17.5 million ranks 11th in overall cap hit for interior linemen. If he plays to the level he did in Detroit, this isn’t a bad deal, even if the cap hit doesn’t look pretty in 2026. More importantly, for ownership, there’s a slightly lower cash flow on the back end of this deal. After an expensive start to this offseason, the season ticket price increases can only go so far. For an ownership group like the McCaskey family, cash flow on a year-to-year basis will always be a big factor in how aggressive the team can be in acquiring and/or extending players.

From a football perspective, it’s a little easier to understand. Jackson’s cap hit in 2025 was lowered by $1.33 million, and the structure should give him all the motivation he needs to play the best football of his career this season. It seems unlikely that the Bears will roll into the 2026 season with Jackson’s $25 million cap hit. If he plays well enough to stick around, they’ll likely convert his $8 million roster bonus into a signing bonus or something along those lines to lower the cap liability for next season.

If Jackson cannot regain his previous form, it will make a decision before March 16th much easier. Sure, they’ll eat $7 million in dead space, but they’ll save $18 million in the process. According to Over The Cap, the Bears’ are projected to have $54.522 million in cap space with an assumed $295.5 million cap. This figure, of course, only accounts for 29 players on the roster, none of their upcoming draft class next month, or anything else for next season. Not to mention any future extensions of current players like Kyler Gordon, Jaquan Brisker, or Thuney. The good news: They’ll have multiple avenues to clear cap space, including releasing players like Tremaine Edmunds ($15 million savings), D’Andre Swift ($7.5 million savings), or even a more surprising move like Cole Kmet ($8.4 million savings).

With the cap hits of Jackson and Jarrett expected to double next season, there’s a strong possibility that Poles is setting up a situation where more creativity will be required to have maximum cap fluidity. If all goes well, they’ll have considerably fewer holes heading into next offseason and won’t need to worry about making five-plus impact moves.

How This Impacts The Bears’ Draft Plans

There’s still plenty of uncertainty regarding the Bears offensive line beyond 2025. Left tackle Braxton Jones is heading into a contract year, which just saw a well below-average left tackle in Dan Moore get $21 million annually. In addition to Jones, new left guard Joe Thuney comes to Chicago with one year remaining on his current deal. It is expected that the team will extend him in the next few months, but with the price of the guard market exploding, fans should expect something above $20 million per year. Couple that with Jackson playing on essentially a one-year deal, and fans should reasonably expect them to spend at least one of their first four picks on an offensive lineman. Depending on how they feel about Jones, don’t be surprised to see a left tackle early and a developmental interior lineman with their third or fourth pick. After all, free agency and veteran trade acquisitions are rarely long-term fixes.

Step 1 of the Bears’ overall goal has been completed. They’ve found three new starters on their offensive line, and all three can be considered plus-players. This should give second-year quarterback Caleb Williams a much better chance for success in 2025. With that in mind, most successful teams stay in contention by drafting and developing players in the trenches. Jackson and Thuney should be considered stopgaps, even if they are around for the next two or three seasons. This is a good class for offensive linemen, so Chicago would be wise to continue to add talent to that group. More importantly, fans should not get too wrapped up in placing expectations on any young lineman they draft. The goal of the draft is always more focused on the long term. With Dan Roushar at the helm of their offensive line development, fans should learn to trust the development taking place. Johnson’s success as a play-caller is rooted in elite offensive line play, so no one should expect his philosophy to change any time soon.