AI…Artificial Intelligence. It’s been a major component of our sci-fi fiction for decades. While Skynet hasn’t gone online, and we don’t see robots walking around downtown, with the advent of large language
models, we are seeing a massive increase in the number of AIs available and the use of AI in numerous contexts. So, I wondered what AI would say about the ideal Chicago Bears 2026 offseason for free agency and the draft. Would it match up with what our best experts and analysts have suggested, or would it deviate from the consensus recommendations? For this exercise, I gave Grok (the X version of AI) a single prompt, asking it to map out the ideal Chicago Bears 2026 offseason.
Here is what Grok said, with my comments on each section, assessing how well I think Grok did at coming up with answers. Grok starts off with a summary statement of where the Bears are at after the 2025 season and the cap situation.
GROK: The Chicago Bears are coming off a strong 2025 season, finishing 11-6, winning the NFC North, and securing their first playoff victory in 15 years before bowing out in the Divisional Round. With quarterback Caleb Williams breaking franchise passing records and the team showing marked improvement under head coach Ben Johnson, the foundation is solid. However, defensive inconsistencies—particularly against the run, where they allowed 5.0 yards per carry—highlight key needs. The offense is young and talented, but the defense requires reinforcements in the trenches and secondary to push for a deeper playoff run.
Currently, the Bears are projected to be $4.3M to $17.4M over the 2026 salary cap, but strategic moves can flip this into $50M+ in space. With 27 pending free agents, including a loaded safety group, GM Ryan Poles must balance retention, external additions, and the draft (starting at No. 25 overall). As a fellow Bears enthusiast (noting that emoji in your profile), here’s a realistic yet aggressive ideal offseason blueprint to build a Super Bowl contender
GOOCH: Nothing too controversial with this take, but also nothing we didn’t already know about this Chicago Bears team. Grok identifies the defensive issues the Bears had, particularly against the run, and that the Bears have work to do in building out their defensive line and defensive secondary this coming season. Grok correctly identifies the fact that the Bears’ current cap situation is a bit unclear, with estimates that vary significantly. So let’s get into the meat of Grok’s recommendations.
GROK Step 1: Salary Cap Management
The Bears start over the cap, but restructures and cuts can create flexibility without gutting the roster. Focus on converting base salaries to bonuses for high-cap players like WR DJ Moore, EDGE Montez Sweat, and LB Tremaine Edmunds to spread hits over future years. Potential cuts include TE Cole Kmet (if underperforming) and aging depth pieces to free up $10M-20M more.Projected Moves and Impact:
Move
Players Involved
Cap Savings Created
Restructure Contracts
DJ Moore ($19M cap hit), Montez Sweat ($18M), Tremaine Edmunds ($15M)
$30M+
Post-June 1 Cuts
Potential: Ryan Bates (OL, voiding), Cole Kmet (TE, bubble)
$10M-15M
Extensions with Lower Caps
D’Andre Swift (RB), Braxton Jones (OT)
$5M-10M deferred
Total Projected Space
–
$50M-60M (aggressive scenario)
This aligns with expert breakdowns showing the Bears can easily hit $50M+ by being proactive. t positions them to retain talent and pursue top free agents without mortgaging the future.
GOOCH: Well, as we can see here, Grok isn’t nearly as bearish (heh) as our Josh Sunderbruch is on the Bears creating cap space – but whether or not the kind of restructuring that Grok envisions here is possible, or even likely, is a real question we have to consider. Further, some of the decisions Grok makes here are at odds with what most analysts and reporters think will happen I think there is a consensus among Bears analysts that one of the obvious moves will be to cut Tremaine Edumnds contract – not restructure it. DJ Moore is more often identified as a potential trade candidate than a restructure candidate – but if the Bears do keep him then a restructure might be in the offing to create space.
And I agree with Grok that Sweat is a good restructure candidate. Grok is inclined to cut Cole Kmet, which would save about $9 million in cap space, but I doubt that is a move the Bears are likely to make. Grok lists Braxton Jones as an extension candidate – but as we know Braxton Jones is a free agent – and very unlikely to be retained by Chicago. As for extending Swift – that’s at least in the realm of possibility – but paying older running backs is usually a bad idea.
Back to Grok for free agency:
GROK Step 2: Free Agency
With newfound space, prioritize re-signing core defenders while targeting veteran upgrades on the defensive line—where the Bears need pass-rush and run-stopping help. Avoid overpaying for WRs (strong internal group: Moore, Odunze, Allen) and focus on value deals. The 2026 class is stacked with EDGE rushers and WRs, but Bears needs skew defensive.Key Re-Signings (Internal Free Agents):
Kevin Byard S 2yr/$18M
Veteran leader; stabilizes secondary amid expiring deals.
Jaquan Brisker S 3yr/$25M
Breakout star; extension locks in young talent at a discount.
C.J. Gardner-Johnson DB 2yr/$16M
Versatile slot DB; big 2025 season warrants retention.
Nahshon Wright CB 2yr/$10M
Emerged as starter; cost-effective depth.
Andrew Billings DT 2yr/$8M
Solid run-stuffer; bridges to draft picks.Let walk: Jonathan Owens (S), Joe Tryon-Shoyinka (DE)—replace with upgrades.
External Signings:
Trey Hendrickson EDGE Bengals 2yr/$52M
Top FA pass-rusher (No.1 overall in rankings); pairs with Sweat for elite duo. Addresses run defense woes.
John Franklin-Myers DL Jets 3yr/$45M
Versatile lineman; adds interior pressure and depth.
Rashid Shaheed WR Saints/Seahawks 2yr/$12M
Speedy depth/slot option if needed; low-risk upside.These moves cost ~$50M but fit under the created space, emphasizing defense as fan discussions suggest.
GOOCH: Well, I would be thrilled with this offseason plan that Grok has laid out for the Bears – but it strikes me as too optimistic in many respects. Grok has the Bears resigning both Byard and Brisker – I can only guess that in doing so these are back-loaded contracts, given the external signings Grok predicts. Brisker is difficult to nail down in terms of price given his concussion history, but whatever his market value, I’m pretty convinced he is not in the Bears plans. And I think Grok has underbid the Byard contract considerably. Yes, his age and position should keep him out of the stratosphere, but coming off a career season, someone is going to give him a considerable contract. I highly doubt 2 years at 18 million total av is going to cut it.
I think someone is going to pay Nashon Wright much more than Grok predicts as well, and I highly doubt it will be the Bears. I think you could probably get Billings cheaper than Grok projects, and CJ Gardner-Johnson was cut twice last season. While I think he resurrected his career with the Bears – that commitment seems high to me as well. On the other hand – there is no way Trey Hendrickson is signing a 2-year contract. It will be three years at minimum, and more likely four. I do expect the Bears to add to their defensive line this offseason – but that contract commitment just doesn’t seem practicable given the Bears’ cap situation. Rashid Shaheed has been a weapon for the Seahawks. I fully expect them to re-sign him.
Back to Grok for the draft:
GROK Step 3: 2026 NFL Draft
The Bears hold six picks, including No. 25 in Round 1. With offense largely set (thanks to 2025 picks like TE Colston Loveland), flood the draft with defensive talent—focusing on DL/EDGE for trenches dominance, then secondary and LB. This mock draws from recent projections, prioritizing best player available with need alignment.Mock Draft Picks:
1 (25) Kayden McDonald DT Ohio State
Dominant interior disruptor (67 tackles, 9.5 TFL, 3 sacks in 2025); bolsters run defense immediately.
2 (57) Dillon Thieneman S Oregon
Versatile safety (can play deep/slot); insurance if FA losses occur, with high upside.
3 (89) Zion Young EDGE Missouri
Explosive edge depth; complements Hendrickson/Sweat rotation.
4 (TBD from Rams) Beau Stephens OG Iowa
Interior OL depth; protects against Bates voiding.
5 (TBD) Zxavian Harris DT Ole Miss
Run-stuffing backup; builds DL pipeline.
7 (TBD) Harrison Wallace WR Ole Miss
Late-round flyer for WR depth/special teams.This draft class adds immediate defensive impact while keeping costs low on rookie deals.
GOOCH: I’m a big fan of this draft, and it is certainly possible those players will be available for the Bears in the first three rounds. McDonald is one of my favorite choices for the Bears’ first pick, and Daniel Jerimah recently mocked Thieneman to the Bears (but in the First Round). Based on my own mocks (using PFF’s 2026 mock draft simulator), McDonald has only been available at pick 25 around 33% of the time. Thieneman has been available in the 2nd round about 50% of the time. And Zion Young in the third about 10% of the time. Particularly after Young’s strong Senior Bowl performance, I expect you’ll have to take him in the 2nd round to have any shot at him – and there’s a decent chance he won’t be there at pick 57.
Grok has the Bears retaining Braxton Jones, so no surprise to see that a tackle wasn’t in the offing, but since we know it is very unlikely that happens, a tackle might need to be a Bears pick in the first three rounds. I’m a fan of Zsavian Harris, so I like the 5th round pick as well. And since we are unlikely to keep Edmunds, as Grok predicted, we likely need a linebacker in there as well. Interestingly, Grok missed the fact that the Bears have a second 7th-rounder in the upcoming draft.
Back to Grok for the conclusion:
Final Outlook
This offseason transforms the Bears into a top NFC contender by fortifying the defense—creating a ferocious front with Hendrickson, McDonald, and existing stars like Sweat—while retaining secondary stability. Offensively, young weapons like Williams, Odunze, and Swift continue developing. With $10M-20M leftover for mid-season adds, the Bears could target 13+ wins and a Super Bowl push in 2026. Bear down!
GOOCH: Well, I can’t argue against this final outlook if the Bears were to follow Grok’s plan. Ultimately, though, I don’t think Grok did a very good job and projecting market value for the Bears free agents or potential free agent acquisitions, and I’m not convinced the Bears can or will restructure contracts along the lines that Grok discussed. Further, Grok made some errors (listed Shaheed as being a Saints FA, forgot a 7th round draft choice the Bears have) – which is a fairly common situation with AI as it stands today.
So, how did Grok do? Can we replace Ryan Poles with Grok or some other AI? Or do humans still rule the roost in making decisions for NFL franchises? Do you like Grok’s offseason, and do you think it is realistic? Let us know in the comments!
