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Windy City Gridiron

A Chicago Bears community

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The Bears have more cap flexibility than you think

Let’s address the elephant in the room: the Bears have negative cap space heading into the 2026 NFL offseason. It’s not the abundance of resources fans are used to seeing. Chicago has been big spenders almost every year that Ryan Poles has been their general manager. Last year was no exception: they traded for both […]

Bear & Balanced: Change is in the air for the Chicago Bears

The NFL offseason is the time for change. The Chicago Bears’ front office has seen a change as assistant general manager Ian Cunningham has left for the Atlanta Falcons. Chicago’s coaching staff lost running backs coach Eric Bieniemy to the Kansas City Chiefs and offensive coordinator Declan Doyle to the Baltimore Ravens. And we’ll soon […]

The Bear’s Den, February 3, 2025

THE DAILY SPONGIE SPECIAL BEARSSSSSS Rams WR Puka Nacua: Bears QB Caleb Williams had me ‘sweating like a mother’ after TD pass to Cole Kmet We’d rather have had Puka crying like a toddler after a massive, crushing upset… but it is what it is… Chicago Bears Insider Says DJ Moore Conversation Has Gone Too […]

Chicago Bears’ Rookie of the Year is Colston Loveland

Earlier today, the Chicago Bears named tight end Colston Loveland, the tenth overall selection in the 2025 NFL Draft, as their Rookie of the Year. In any other year, the Bears could have honored wide receiver Luther Burden or running back Kyle Monangai, but this year, it was the dynamic Loveland who took home the […]

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 […]

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 […]

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 […]

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 […]

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 […]

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 […]

Chicago Bears’ Special Teams Player of the Year is Cairo Santos

Yesterday, the Chicago Bears named kicker Cairo Santos as their Special Teams Player of the Year, which was well deserved, because in a season full of clutch moments, Santos had a hand in several of their comebacks. His understanding of the Soldier Field winds is something he’s learned in the last six years in Chicago, […]

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 […]

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 […]

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

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

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 […]

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 […]

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

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 […]

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 […]

Chicago Bears Question of the Day: Who gets a second contract next season?

For the first time in a long time, it feels like the Bears have waves of young talent that they can build upon. This is mostly exciting news. Mostly. It also means that Ryan Poles has entered a new phase of his roster building process – evaluating several of his first draft picks for second […]

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 […]