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Chicago Bears 2025 Offseason Superlatives: Cautiously Optimistic

July 18, 2025 by Windy City Gridiron

Chicago Bears OTA Offseason Workout
Photo by Michael Reaves/Getty Images

Check out part 5 of our final Chicago Bears roundtable before training camp starts!

Jacob Infante shared his Chicago Bears offseason superlatives on his Twitter page last week, and then he elaborated on those selections in this article, so several of us wanted to get in on the fun by doing our own version. We’ve been rolling these out all week, so check out our latest here, they share yours in the comment section.

Next up is our take on the most we’re Cautiously Optimistic about.

Ryan Droste: Jonah Jackson. A bad injury really derailed his time in Los Angeles, but I’m thinking that Ben Johnson and Dan Roushar can turn things around and get Jackson back to where he was during his time as a Pro Bowler in Detroit.

Jeff Berckes: Give me one Ozzy Trapilo. Ozzy Bear’s tape was like watching paint dry – about the best compliment you can pay to a tackle. I think there’s a real chance he plays significant snaps this year, and the Bears have their starting offensive line locked in for the foreseeable future. Stability in the offensive line would be the ultimate hack for this team moving forward.

Bryan Orenchuk: Cautiously optimistic that Roschon Johnson can man the RB1B role in Ben Johnson’s offense. We all know he can succeed as a short-yardage back, but can he keep the chains moving between the 20s and stay healthy while complementing D’Andre Swift? I am cautiously optimistic.

Johnathan Wood: Run Game. Everybody is worried about this after the Bears didn’t significantly upgrade a running back room that averaged a paltry 3.6 yards/carry in 2024, but I fully expect the rushing attack to be significantly better this year due to upgrades on the offensive line and at play caller. Those two things matter far more than the individual running back unless you have a truly special back. For example, David Montgomery averaged 3.9 yards/carry in Chicago but has been at 4.4 through 2 seasons in Detroit, and D’Andre Swift averaged 4.6 yards/carry in Philadelphia in 2023 before falling to 3.8 last year in Chicago. The Bears don’t have a great running back room – I expect it to be much improved in 2026 – but the running game should still be effective this year.

Sam Householder: I’m coming around on Ozzy Trapilo. At first, it seemed like a move for the future or kind of a project or something. But the further along it goes with minicamps and such, it really seems like the Bears are serious about him being the day one LT, and it seems like it could work out.

Gary Baugher Jr.: Kyle Monangai. Despite being a late 7th-round pick, I think with the way Ben Johnson uses his RBs, and the skillset Monangai brings to the team, he has a chance to have a productive rookie season. Let’s not forget there’s another Rutgers 7th-round RB in the league who has shown some very good things with another great offensive-minded HC! (Isiah Pacheco)

TJ Starman: Jonah Jackson is a move that I am definitely cautiously optimistic about. Everything that the Bears are selling has some logic to it, right? Jackson has familiarity with Ben Johnson, he played very well with the Lions prior to last season with the Rams where he was injured and (arguably) playing out of position, etc. etc. BUT he is coming off a miserable year in LA and the Bears extended him without seeing him take a single snap, so there’s nothing guaranteed here.

Josh Sunderbruch: Ozzy Trapilo. I have to admit he’s grown on me as a pick. I like his tape, and I think he was probably drafted in about the right spot.

Mongo Peanut: DE across from Sweat. Look, the DL is the biggest question mark on the roster right now. Sweat is above average, Jarrett can still contribute in stretches, and Dexter/Billings should be solid. However, Dayo Adeyingbo, Shamar Turner, and Austin Booker are largely unknowns. I’m confident that one of the three will prove to be a valuable piece across from Sweat, but it’s entirely possible that the Bears hugely underperform on the EDGE.

Donald Gooch: A non-move here – the Bears did not sign a top-dollar RB nor use significant draft capital on a running back. But there are intriguing names in that room, headlined by Swift, who Ben Johnson has already maximized when in Detroit.

Lester A. Wiltfong Jr.: While I fully expect the run game to be better with Ben Johnson calling the shots, I have some concerns about the overall position group. I’ve talked myself into the best-case scenario for the group, but I still have some doubts.

Which offseason move has you Cautiously Optimistic?

Here are the ones we’ve done so far.

  • Best Move
  • Worst Move
  • Slept-on Move
  • Surprising Move

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