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Windy City Gridiron

https://www.windycitygridiron.com/ | 883 entries published

A Chicago Bears community

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2026 Bears mock offseason: Free agency and draft moves after playoffs

The Bears’ season is over. It’s time for a mock offseason. I’ll be making my picks for free agency, the draft, open coaching positions, and which cuts, trades, and restructures to make to create some cap space. You know the drill. Let’s get into it. Bears coaching hires I originally had this article starting out […]

7 days ago | 1 read

Question of the Day: Do you like the Bears playing International Games?

Earlier today, the NFL announced that they’ll play a 2026 regular season game in Madrid, Spain, and a game in Paris, France, which brings the confirmed number of such games in the league’s International Series to eight. UPDATE: NFL Commissioner Roger Goodell announced they’ll also play a game in Mexico City. The NFL will also […]

8 days ago | 1 read

The Bear’s Den, February 2, 2025

THE DAILY SPONGIE SPECIAL BEARSSSSSS 2026 visions of Pete Crow-Armstrong, Caleb Williams, the pope and World Series watching at Gallagher Way That’s a trio. Bears begin offensive-coordinator search after Ravens hire Declan Doyle to same position Interesting to see what they are doing. Bears’ Nahshon Wright Earns Another Award for Breakout Season After signing a […]

8 days ago | 1 read

We want YOU to answer these free agency questions about the Chicago Bears!

We’ll occasionally have staff roundtables here at Windy City Gridiron, where members of our team answer a few questions about the Chicago Bears, but today I wanted to flip the script. I guess you can call this a reverse roundtable, because I want you, our WCG members, to answer these three questions. 1) Of all […]

9 days ago | 1 read

The Chicago Bears: 2026 Best Dressed Team

Blitz Fits (@blitzfits via Instagram), a sports and fashion media platform, has named the Chicago Bears the 2026 Best Dressed Team. Blitzfits, founded by Moses Anoh in September of 2019, combines football, fashion, culture, and lifestyle onto one platform. Quarterback Caleb Williams reposted BlitzFits’ post naming the Bears the NFL’s best-dressed team to his Instagram […]

9 days ago | 0 reads

Two Bears listed in PFSN’s Top 100 Free Agent list

We’re about five weeks away from NFL Free Agency, and with the salary cap expected to jump from this year’s $279.2 million to a projected $301.2 to $305.7 million, the Chicago Bears (and the other 31 teams) will have more to play with. The Bears didn’t have much cap wiggle room at season’s end, but […]

9 days ago | 2 reads

Could Bears get their new Ozzy Trapilo this year in the draft?

As much as Chicago Bears fans might not like to admit it, they now have a priority even higher than fixing the defensive line: finding a left tackle. With Ozzy Trapilo going down due to a serious patellar tendon injury that will require a long recovery, this team’s left tackle for the 2026 season might […]

10 days ago | 0 reads

Bears lose OC Declan Doyle to Ravens in same role

Chicago Bears offensive coordinator Declan Doyle will be leaving to become the offensive coordinator for the Baltimore Ravens, ESPN’s Adam Schefter reported on Monday. Doyle, 29, will be taking over offensive play-calling duties for Baltimore, according to Schefter’s report. With their new head coach Jesse Minter coming from a defensive background, their offensive coordinator hire […]

11 days ago | 1 read

GOOCH vs Grok: What AI thinks the Ideal Chicago Bears Offseason would be

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 […]

NFL

11 days ago | 3 reads

Here’s the real problem with the Ian Cunningham-Falcons comp pick saga

Ever since the Chicago Bears hired Ryan Poles and Ian Cunningham to their respective general manager and assistant GM positions back in 2022, I saw people talking about it.  That for the first time since the NFL had instituted its new rules awarding compensatory draft picks to teams that had a minority coaches and/or executive […]

NFL

11 days ago | 0 reads

The Bear’s Den, January 30, 2025

THE DAILY SPONGIE SPECIAL IAN CUNNINGHAM Bears lose assistant GM Ian Cunningham to Falcons Georgia native Cunningham is Atlanta’s new GM. All of these articles are about the same if you want to save time, just read one of them. Falcons hire Ian Cunningham as new GM Falcons announce Ian Cunningham as their new GM […]

11 days ago | 3 reads

Report: Ian Cunningham to become Falcons GM

Ian Cunningham, the Chicago Bears’ assistant general manager, is set to become the general manager for the Atlanta Falcons, according to multiple NFL insiders. Cunningham has served as the assistant general manager and right-hand man to GM Ryan Poles for the past four years. Before coming to Chicago, he was an assistant director of player […]

11 days ago | 1 read

Chicago Bears’ Defensive Player of the Year is Kevin Byard III

Yesterday, the Chicago Bears announced that quarterback Caleb Williams was their Offensive Player of the Year, so naturally, the Defensive Player of the Year announcement was coming today, and All-Pro safety Kevin Byard III was “Honored” with the honor. The 32-year-old Byard has played some damn good football since signing with the Navy and Orange […]

NFL

11 days ago | 0 reads

This new ranking shows again how much of a hit Ben Johnson has been for Bears

Chicago Bears fans don’t need any more proof that Ben Johnson is the perfect coach for this team. But I’m sure you won’t say no to some more. ESPN’s Bill Barnwell put together his rankings of the best head-coaching hires of the last five years—a total of 37 overall. And guess who has already cracked […]

12 days ago | 1 read

Ben Johnson is on the Mount Rushmore of Bears head coaches

In the middle of the season, when the Bears were on a roll, I had some fun and put out an AI-generated image of Ben Johnson on Mount Rushmore with George Halas, Mike Ditka, and Lovie Smith, and declared that he was already the Bears’ fourth-greatest coach in team history. Most fans rolled their eyes […]

12 days ago | 1 read

The Bear’s Den, January 29, 2025

THE DAILY SPONGIE SPECIAL BEARSSSSSS Senior Bowl: Can the Bears find a Round 1 starter at tackle? Cornerback? Safety? Yes? No? Maybe? Good news for Bears: Edge rushers are ‘hands down’ the strength of the draft We could sure use a couple. Chicago Bears stadium bill passes Indiana Senate, but changes likely The Indiana Senate […]

12 days ago | 2 reads

Bears Joe Thuney is a Nominee for the Protector of the Year Award

For the first time ever, the NFL will honor the best offensive lineman in the league with the Protector of the Year Award, and as I speculated nine months ago, the Chicago Bears do indeed have a legitimate candidate for the award. Earlier today, ESPN’s Jeremy Fowler broke the news of the six nominees for […]

12 days ago | 0 reads

Chicago Bears’ Offensive Player of the Year is Caleb Williams

The Chicago Bears have named quarterback Caleb Williams their Offensive Player of the Year for the 2025 season. Williams had a great sophomore year from his growth as a young player, his first career playoff victory, and breaking franchise records. Overall, he took a big leap forward. Williams finished the 2025 season with 3,942 passing […]

12 days ago | 0 reads

Final 2025 QB Rankings

It’s time for the final installment of our QB rankings for 2025. I felt we could publish them because, at this point, I don’t think Drake Maye or Sam Darnold’s play in the Super Bowl will affect their spots. They’ve both proven where they should be ranked. As a reminder, these rankings are not just […]

NFL

13 days ago | 1 read

Bears Question of the Day: Which Player Most Exceeded Expectations in 2025?

Few expected the 2025 Chicago Bears to make the playoffs, let alone win the NFC North outright. Suffice it to say, it took some exceptional performances throughout this unforgettable season that propelled these Bears to an 11-6 record. With the recent addition of CB Nahshon Wright, four Bears players made the Pro Bowl with OG […]

13 days ago | 3 reads

The Bear’s Den, January 28, 2025

THE DAILY SPONGIE SPECIAL BEARSSSSSS Good news for Bears: Edge rushers are ‘hands down’ the strength of the draft Good news indeed. Colston Loveland eyeing major breakthrough as Bears flip the page to next season Bears tight end Colston Loveland had a promising rookie season with 58 receptions, 713 receiving yards and six touchdowns, plus […]

13 days ago | 2 reads