Bold moves the Bears can make to win the 2025 offseason

With the 2024-25 football season officially in the books, we can go full throttle into the off season. Bears Insider is going to take a look at the NFC North and we’ll start with our own Chicago Bears.

It seems like a lifetime ago that a three-game winning streak over the playoff-bound Rams, and the lowly Panthers and Jaguars sent this team to 4-2. The signs of dysfunction were there, but erased when they beat awful teams with a belt-to-butts outcome.

Then the wheels fell off, and we know the rest.

2024 record: 5-12

Estimated cap space (via Spotrac): $65,899,494

2025 draft picks: Round 1 (10); Round 2 (39 via CAR); Round 2 (41); Round 3 (72); Round 5 (149); Round 6 (197 via PIT); Round 7 (235 via CLE) and Round 7 (242 via CIN)

Biggest priority: It’s the offensive line. Full stop. At least when we’re discussing player additions. Next would be pass rush help. The biggest thing the Bears need, though, is stability in their culture. That’s what they hope Ben Johnson and his band of thieves bring in the form of accountability, attention to detail, game planning, adjustments and so on. This isn’t supposed to be an overnight turn around, so Johnson and company have a nice runway to figure out the players that will be part of whatever this things ends up being. After the haphazard years of Matt Nagy and Matt Eberflus, making this roster and watching the game make sense is a good start. Beyond that, yeah, only Darnell Wright is really safe on the offensive line.

Notable pending free agents: Guard Teven Jenkins (26); WR Keenan Allen (33): The market value and comps on the next Jenkins contract are pretty favorable, even if you have to account for a few million annually in cap inflation costs. He’s missed a lot of time with random injuries but if Chicago can lock him for three years at that rate, the Bears will get a player they know well and has that edge to him. Allen is a tougher decision, but there’s a good case to bring him back as a veteran presence with a better offensive plan. His age makes the number of years difficult, so a deal with guarantees up front makes sense, unless the goal is get younger.

One free agent to watch: Guard Trey Smith is the top candidate to watch if he hits free agency, but I’m going to stay in the Top 50 and the interior line here (and cheat on the “one” part of this), with one position in free agency. That’s the center spot, where Drew Dalman (26 years old) of Atlanta and Ryan Kelly (31) of Indianapolis find themselves. Both are significant upgrades at a turnstile position for Chicago. Both could command higher prices, but there’s enough flexibility in the cap to make one happen without hindering other moves. It’d be easy to lean toward Dalman because of his age and the relative cost of a top-3 center versus most other positions, but Kelly is a three-time Pro Bowler with years spent alongside Andrew Luck when the Colts where a functioning team.

Draft outlook: It’s possible the Bears are in the prime spot to take the top offensive lineman on the board at No. 10. That can change depending how the board and trades fall, but keep an eye on tackles Will Campbell (LSU), Kelvin Banks Jr. (Texas) and Josh Simmons (Ohio State). A draft prospect who might rise up the board is guard Tyler Booker (Alabama). Not a top-10 type of rise but if he’s atop the board, a moderate trade down wouldn’t be out of the question. Running back Ashton Jeanty (Boise State) is getting some run in Bears talk, but this is a deep running back class, so keep an eye on the second round. I wouldn’t be surprised to see two offensive linemen go in the first two rounds, but wouldn’t blink at a mix of the trench positions on both sides of the ball. I’m also keeping an eye on the Day 2 tight ends. It’s a fairly loaded class and we’re about to find out Cole Kmet’s fit with Johnson for TE1, but there’s definitely a need to upgrade from Gerald Everett at TE2. This is a good class to do so.

Biggest question mark: Is there more house cleaning to be done? When you go 5-12 in general, but especially after being a low-key sleeper to do what the Washington Commanders did this season, there’s some problems. The Bears cleared out Shane Waldron and Eberflus, then hired the top coach, who cleaned out most of the staff remaining. We heard a lot from veteran players like Allen and Derek Walker about some things being off in training camp and the locker room during the Eberflus era. So how far did the organizational rot go? DJ Moore was an early favorite for the disgruntled locker room guy, so it was encouraging to see him and the pass catching team show up for Johnson’s introductory press conference. Time will tell when the offseason opens. If it’s not locker room issues, this question applies to how far Johnson and Poles want to tear this thing down and rebuild (retool?) in Year 1.

One prediction: A Kyler Gordon extension would seem to be a foregone conclusion after a solid campaign. He’s reportedly been singled out by Johnson and incoming defensive coordinator Dennis Allen. With Jaylon Johnson already locked in, and this looking like a prove-it season for Tyrique Stevenson, a Gordon extension gives Chicago stability at cornerback.

Bold prediction: Tremaine Edmunds is traded. Not sure how bold that is, but considering he’s making $17.4 million this year and comes with $12 million savings against the cap (around $4.8 in dead cap) if moved, its one place the Bears could look toward should they want to upgrade elsewhere in free agency. Edmunds is a fine linebacker, but he’s not the elite-level one Chicago paid him for two years ago. He’s still only 27, so there’s value either way. Bears would be looking at a third rounder at best, considering the Roquan Smith trade.

For-the-content prediction: This prediction is more something I want to see for sheer entertainment value, but isn’t out of the realm of possibility. Just more Madden-based reality. It could happen, and if it did, we’d be writing a ton about it.

Bears trade No. 10, No. 39 and Montez Sweat for Myles Garrett. For a lot of reasons for both teams, a post-June 1 trade makes the most sense, which wipes out the draft picks in exchange for future years. Cleveland is in a wasteland no matter what it does, and the Bears have a slight savings over cap hit moving Sweat before June 1. This might appeal to the Browns to maximize their known return, and the Bears have the cap space to eat this while still increasing their realized cap space for 2025. In reality, if Garrett is able to drive his destination at all, he’s more likely to end up with more ready-made winter.