Windy City Gridiron
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Grading the 2026 Windy City Gridiron Dynasty Rookie Draft
As we wait for the next few weeks for the Chicago Bears training camp to fire up, we are going to take a look at the Windy City Gridiron Dynasty league, review the rookie draft that took place, and analyze the 14 rosters in the league. If you missed the original introductory article on the […]
Bears sign TE Sam Roush to rookie deal, wrap up 2026 draft class
The Bears have signed tight end Sam Roush to his four-year rookie deal, the team announced on Friday. ESPN’s Adam Schefter was the first to report that the deal will be worth $7.35 million over the course of Roush’s four seasons. The signing of Roush, the No. 69 overall pick in the 2026 NFL Draft, […]
10 Most Important Bears of 2026: #3 Colston Loveland
I don’t think I’ve ever had a tight end this high on my 10 Most Important Chicago Bears list. Then again, the Bears have never had a tight end of Colston Loveland’s caliber since I’ve been writing about the beloved. Loveland can line up anywhere on the field, and he can do anything a Y […]
Is Caleb Williams above Jordan Love on the NFL Top 100?
The NFL is spending the summer releasing its top 100 players of 2025. So far, they’ve released about 30 players and we know the only Chicago Bears player so far is Montez Sweat who was ranked at 91. But here’s where it gets interesting: Jordan Love was unveiled today as the 72nd-best player in the […]
Training Camp Battle: SAF2: Cam Lewis vs Dillon Thieneman
Our next training camp battle may not be a battle at all, but any time a rookie is expected to start, there’s always an opportunity that a veteran starts in September and the rookie doesn’t start until later in the season. When we approached the 2026 NFL Draft, everyone was pretty confident the Bears would […]
10 Breakout Candidates For the 2026 Chicago Bears (Part 1)
The 2025 season was the type of storybook that most Chicago Bears fans had dreamed of over the last 15-plus years. Although it didn’t end in a Super Bowl parade, the strides made from an ineffective three-year tenure under former head coach Matt Eberflus to Year 1 of Ben Johnson were nothing short of impressive. […]
The Bear’s Den, July 10, 2026
THE DAILY SPONGIE SPECIAL Ken’s Note: Denmaster Ken is out of here for a week, but never fear, Denmaster Jack has you covered for all the exciting lists (and any actual news) M-F next week. Have fun, play nice, and give Chim a hard time. But not TOO hard. BEARSSSSSS PFF’s Best NFL Running Backs […]
All-Time Historical Bears Team Tournament: Team Sweetness vs Gridiron Greats
In the semifinals of our 2026 All-Time Historical Chicago Bears Fantasy Draft Tournament, we have Jack M Silverstein’s (1) Team Sweetness vs Lester A. Wiltfong Jr.’s (4) Gridiron Greats. Jack breaks down his full team right here, and Lester’s squad breakdown is right here. Check out each position group in the image sliders below, and […]
Linda Cohn: I love the Chicago Bears’ direction
The latest Bears Banter has dropped! The legendary Linda Cohn recently announced her retirement from her 30+ year career at ESPN. She joined the Bears Banter podcast to talk about her legendary career, what it was like being a part of SportsCenter in the 1990s, and the popularity of the “This is SportsCenter” advertisements. But […]
10 Most Important Bears of 2026: #4 Austin Booker
The Chicago Bears didn’t do anything of significance at defensive end this offseason; instead, they are banking on third-year pro Austin Booker to provide a real complement to Montez Sweat. Sweat is a pretty good football player. He was selected as a Pro Bowler a couple of years ago, and his head coach feels he’s […]
What is the Strongest Position Group in Bears History?
With so much discourse over the strength of Chicago’s pass catchers this year, as well as the concerns shared over the pass rushers, it got me thinking about previous position groups that have led the Bears and others that weighed their respective team down. Here, we take a look at some of the most noteworthy […]
The Bear’s Den, July 9, 2026
THE DAILY SPONGIE SPECIAL BEARSSSSSS Where Montez Sweat ranks among the leagues best edge rushers Hey wow! A list! Chicago Bears Film Review: Dayo Odeyingo’s Strengths and Areas of Growth 2025 Production: 1 sack, 10 total quarterback pressures, 21 total tackles, 1 Pass Defensed. $48M contract, $32M guaranteed. Strength? I guess the dude is rich. […]
NFL Network hits on the Chicago Bears’ biggest question mark going into 2026
When the Chicago Bears start training camp, one might expect the biggest topic, even more so than how the defense is going to stop anyone, to be this: Is third-year quarterback Caleb Williams primed for the MVP-style breakout other quarterbacks like Josh Allen have enjoyed? The answer to that question lies, as a recent Good […]
10 Most Important Bears of 2026: #5 Coby Bryant
Teams don’t normally get better when allowing a First Team All-Pro to leave, but that’s exactly what the Chicago Bears are hoping for this offseason with the addition of safety Coby Bryant to replace Kevin Byard III. These two are at very different places in their careers, with the 27-year-old Bryant beginning year five as […]
Training Camp Battle: RB3: Roschon Johnson vs Brittain Brown
As we move forward with our training camp battle series, we move to the offensive side of the ball, where we have an interesting development at running back. We know what the top of the Bears running back room is going to look like. D’Andre Swift and Kyle Monangai are going to be splitting the […]
Chicago Bears Question of the Day: Who will have the biggest bounce-back year?
The Chicago Bears 2025 season was a massive success by almost any standard, but that doesn’t mean that there weren’t several underperformers on the Bears’ roster. Several names didn’t match expectations, ranging from disappointing sophomore seasons (Rome Odunze), to injury riddled campaigns (Kyler Gordon and Jaylon Johnson), and underwhelming free agent signings (Grady Jarrett and […]
The Bear’s Den, July 8, 2026
THE DAILY SPONGIE SPECIAL BEARSSSSSS NFL sets key dates for Bears, league’s upcoming season The Feb. 14 Super Bowl in Los Angeles and April 29-May 1 draft in Washington, D.C., were previously set. The NFL announced other key dates for the upcoming season Tuesday. Bears and Ryan Poles Poised to Benefit From a Collapsing NFC […]
Former NFL Scout Ranks Bears OL Top Five In NFL
The Chicago Bears will enter the 2026 season with a little more uncertainty on the offensive line than they may have originally thought. Following the surprising retirement of Pro Bowl center Drew Dalman in March, the Bears looked to retool up front by drafting Iowa center Logan Jones, while also trading for New England Patriots […]
How many Chicago Bears will be selected to the Pro Bowl?
Welcome to SB Nation Reacts, a survey of fans across the NFL. Throughout the year we ask questions of the most plugged-in Bears fans and fans across the country. Sign up here to participate in the weekly emailed surveys. The 2025 season saw the Chicago Bears finish with their first winning record since 2018, and […]
2027 Bears mock draft: Improving the interior defensive line
As Bears training camp approaches, it’s natural to wonder how their roster fares compared to the rest of the league going into the 2026-27 NFL season. On paper, there are certain positions on Chicago’s roster that look stronger than others. That’s obviously going to be the case for every team, but it remains to be […]
10 Most Important Bears of 2026: #6 Luther Burden III
Considering that Ben Johnson’s 2025 offense didn’t feature one wide receiver over the others, I went back and forth on having one appear on this year’s 10 Most Important Chicago Bears list. But Luther Burden III has a chance to be really special, so I had to include him. At his NFL Combine, he only […]
Question of the Day: Which Single-Season Bears Record is Most Likely to be Broken in 2026?
With Chicago’s offense as strong as it’s been in decades, if not longer, it got me thinking about the possibility of any franchise records being broken in 2026. Let’s take a look at which ones might come down this season on both sides of the ball, starting with the offense. Passing Passing Yards in a […]
The Bear’s Den, July 7, 2026
Den picture caption: SEATTLE, WASHINGTON – JULY 06: Chicago Bears wide receiver Rome Odunze fulfills his role as the adidas Stadium Captain with the adidas Trionda match ball before the FIFA World Cup 2026 Round of 16 match between USA and Belgium at Seattle Stadium on July 06, 2026 in Seattle, Washington. (Photo by Sarah […]
10 Most Important Bears of 2026: #7 Jaylon Johnson
Last year, the Chicago Bears got only 7 regular-season games from Jaylon Johnson (and both postseason games), but I don’t think he was 100% in any of them. His offseason was hampered by a groin injury, and then during his first game (week 2 vs. the Lions), he suffered a different groin injury, this one […]
Training Camp Battle: LB2: D’Marco Jackson vs TJ Edwards
It’s time to kick off our next yearly off-season series, where we look at interesting training camp battles that could develop throughout July and August. As always, we will unveil these throughout July as we inch closer to the players reporting to training camp. Let’s kick it off on the defensive side of the ball […]