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All-Time Historical Bears Team Tournament: Team Sweetness vs Gridiron Greats

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 then vote for the GM who drafted the best in the poll.

QUARTERBACKS & RUNNING BACKS

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Linda Cohn: I love Bears’ direction

Linda Cohn: I love 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 we didn’t ignore Chicago, she talked about what it was like covering Michael Jordan in the 1990s, her thoughts on Caleb Williams and Ben Johnson and the current direction of the Bears, and she even talked a little Blackhawks as well!

When we talked about...

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10 Most Important Bears of 2026: #4 Austin Booker

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 coming off his best season yet, but the Chicago Bears need more than just him rushing off the edge in 2026.

They need the 23-year-old Booker to develop into a consistent and reliable threat, which is why he’s the most important defensive player on my...

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What is the Strongest Position Group in Bears History?

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 position groups in recent memory. We discussed the weakest groups here, so now let’s discuss the strongest.

What is the strongest position group in Bears history?

While I had planned on finishing this piece shortly after the last one about a month ago, we’ve...

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The Bear’s Den, July 9, 2026

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. Other than that, I’ve got nothing.

POLISH SAUSAGE
Bills to hold two practices at their new stadium in August

Must be nice to have a new stadium this August

The Mark Sanchez trial is once again delayed, to September 8

The former Bear is in...

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NFL Network hits on the Chicago Bears’ biggest question mark going into 2026

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 Morning Football segment highlighted, in the trenches.

During a discussion of the most pressing issues the Bears must address when training camp kicks off later this month, former NFL offensive lineman Willie Colon and NFL Media insider Stacey Dales hit heavily on the big men...

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10 Most Important Bears of 2026: #5 Coby Bryant

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 a pro, and Byard, who turns 33 next month, about to enter his eleventh season. Bryant is younger, more athletic, and more versatile, but does that translate to him being a better football player?

Byard may have lost a step, but he more than made...

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Training Camp Battle: RB3: Roschon Johnson vs Brittain Brown

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 carries. As long as the two of them remain healthy, there will be very little room for any other running backs to get any carries on this offense.

But we are all football fans; we understand the running back position. It carries a physical pounding,...

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Chicago Bears Question of the Day: Who will have the biggest bounce-back year?

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 Dayo Odeyingbo).

The unfortunate reality is that not all of these players will have a bounce-back season in 2025, though I suspect a few from this list will absolutely turn around the narrative.

Which Chicago Bear will have the biggest bounce-back season in 2026?...

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The Bear’s Den, July 8, 2026

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 North

SI crap on a slow news day. Read at your own SI tolerance level.

POLISH SAUSAGE

Von Miller now regrets choosing Commanders over Seahawks

Hindsight is a hell of a drug.

2027 free agent negotiating window will open a day after the Combine ends...

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Former NFL Scout Ranks Bears OL Top Five In NFL

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 center Garrett Bradbury.

Bradbury looks to be a possible short term answer, with Jones the center of the future if all goes to plan. The team also signed undrafted free agent center Jaren Kump out of Utah.

The left tackle position also remains somewhat of...

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How many Chicago Bears will be selected to the Pro Bowl?

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 with team success came individual notoriety as four players made the Pro Bowl: Guard Joe Thuney, center Drew Dalman, safety Kevin Byard III, and corner Nahshon Wright.

Four of those players no longer play in the Windy City, so if the Bears can keep the...

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