My Top Chicago Bears of All Time – And Why This Stadium Drama Has Me Fired Up


This season two bonus episode of The Shawn Mackey Show was personal. Before we kick off season three, I wanted to put a bow on something that’s been rattling around in my brain for years—my all-time greatest Chicago Bears list based on the players and personalities I’ve actually witnessed in my lifetime.

And yeah… I cheated a little.

But when you’re talking about legends, history, and one of the most iconic franchises in the NFL, sometimes you’ve got to bend your own rules.

#10 – Devin Hester

Let’s start with electricity.

The opening kickoff return in Super Bowl XLI. I still get chills thinking about it. One of the most explosive players I’ve ever seen. Special teams? Offense? Defense? It didn’t matter.

Hester changed games. Period.

And when he finally earned his Pro Football Hall of Fame induction in 2024, it felt right. Some guys are exciting. Some guys are clutch.

Hester was both.

#9 – Charles Tillman

The Peanut Punch.

Nobody did it better. Timing, awareness, physicality — that wasn’t luck. That was craft.

44 forced fumbles in his career. Think about that. He didn’t just tackle you. He took the ball from you.

And he embodied that defensive mentality that defined Bears football for decades.

#8 – Wilber Marshall & Otis Wilson

Yeah, I doubled up.

These two were absolute junkyard dogs in that 4–6 defense. You can’t talk about that legendary unit without mentioning them.

Marshall was instinct. Wilson was fury. Together, they made life miserable for quarterbacks.

Without them, I don’t know if the rest of that defense becomes what it did.

#7 – Jim McMahon

The Punky QB.

Swagger. Attitude. Edge.

The only quarterback in my lifetime to lead the Bears to a Super Bowl victory. He wasn’t perfect. He wasn’t politically correct. He wasn’t quiet.

He was Chicago.

And that matters.

#6 – Richard Dent

Super Bowl MVP.

Relentless pass rusher. Franchise sack leader.

Dent didn’t just collapse pockets — he destroyed game plans. Offensive coordinators lost sleep because of him.

#5 – Brian Urlacher

From safety in college to Hall of Fame linebacker.

Urlacher carried that defensive torch for the next generation. The leader of the Super Bowl XLI era defense. Fast, smart, physical.

He was the bridge between eras.

#4 – Dan Hampton & Steve McMichael

If you want to understand dominance, start in the trenches.

These two were monsters in the middle. You double one? The other beats you. You single one? You’re in trouble.

Everything that 1985 defense became started up front.

#3 – Buddy Ryan

The architect of the 4–6 defense.

Innovation. Aggression. Chaos.

He built a scheme that overwhelmed offenses. That defense wasn’t just talented — it was engineered to suffocate opponents.

#2 – The Entire 1985 Roster

I don’t care if that’s cheating.

That team wasn’t just a roster. It was a cultural moment.

#1 – Walter Payton

Sweetness.

When the league names the Man of the Year Award after you, your impact goes beyond stats.

He defined excellence — on and off the field.

No debate for me. He’s number one.

Now… The Stadium Drama

Here’s where it gets complicated.

The Bears possibly relocating to Indiana? Hammond? Arlington Heights? Breaking the lease at Soldier Field?

I get the business side. I get leverage. I get negotiations.

But identity matters.

If they stay the Chicago Bears and just play across state lines? Maybe I can live with that.

If they rebrand?

That’s different.

I’ve been a Bears fan for over five decades. That connection isn’t just about football — it’s about where I’m from.

And that’s why this situation hits differently.

Looking Ahead to Season Three

We’re pivoting toward the Chicago Cubs.

Baseball season is here. New signings. Trades. Expectations.

But don’t worry — if the Bears stadium situation blows up, you know I’ll have thoughts.

That’s what I do.

Opinionated. Unedited. Unpredictable.


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