We only have a few more players in our Cash, Stash, or Slash series. We have been looking at several key veterans and will decide in the next 12 months if they should receive an extension (Cash), if the Bears should cut ties (Slash), or if they should wait and see how things go (Stash).
Today, we pivot back to the offensive line to take a look at guard Jonah Jackson. We’ve already looked at Thuney, where we said he was absolutely a “Cash.” The series started with Darnell Wright, who was not only a “Cash,”
but he’s a “Cash” this month. And we also looked at Garrett Bradbury, who we said needs to be a “Slash” after this season.
Based on performance, Jonah Jackson is 100% a “Cash” player. But the question is, how many offensive linemen are the Bears comfortable paying on large contracts moving forward?
Jonah Jackson: Cash
I think before we look at Jackson, let’s look at the Bears’ offensive line construction. I think you see Wright and put his name in ink at tackle at a large salary. I think we look at Thuney and know that he is going to be here at a fairly large salary as long as he wants to be here.
But when you look at the other two positions, the Bears will have Logan Jones almost certainly starting at center in 2027, 2028 and 2029 on a rookie salary. I also think it’s almost impossible to think that the Bears LT isn’t going to be on a rookie contract for the next few years. I think the Bears will either be starting Ozzy Trapilo, or they are going to head back to the draft and find a new LT if Trapilo’s knee injury is too much for him to overcome.
I think if the Bears have two starting offensive linemen on rookie contracts, there will absolutely be enough cap space for the Bears to pay a third offensive lineman on a veteran contract. Jackson is currently signed through the 2027 season. If Jackson plays as he did in 2025 in 2026, he absolutely needs a contract extension after this season.
I’ll be the first to admit that I was a little hesitant on the Jackson trade last year. I know Jackson was solid in Detroit (with Ben Johnson), but his time with the Rams was a mess, and I was concerned that his Rams season was more of what was ahead for Jackson. I was wrong.
Jackson not only returned to his Detroit form, but you can argue it was the best season of his career. No, Jackson didn’t receive the accolades, but really great offensive line analysts like Brandon Thorn and Duke Manyweather thought his play last year was as good as any other interior line play in the league. In a recent article for Bleacher Report, Thorn had Jackson ranked as the 10th best guard (both sides combined) in the NFL.
Jackson will be 30 heading into the 2027 season, but there’s no reason to think he can’t put together a few more strong seasons in Chicago. As long as his performance in 2026 matches 2025, the Bears should ink Jackson to an extension and help solidify the right side of the offensive line for the next half-decade.
