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Bear With Me: The 10-Year Cutler-versary (With Jack M Silverstein!)

In this episode, Jack M Silverstein joins Robert S. in a moment of reflection on the trade that brought Jay Cutler to Chicago. Was it worth it? How does he rank among all-time Chicago QBs? All of this and more in this latest episode of Bear With Me!

Chicago Bears Introduce Jay Cutler Photo by Jim Prisching/Getty Images

Hey Bears fans! You may not have realized it, but this Wednesday (April 3rd) is the 10-year anniversary of the now-infamous Cutler trade. It’s been ten years. Crazy, right?

With that in mind, I brought in WCG Historian Jack M Silverstein to help me dive deep into Bears History to answer two major questions:

  1. Was the Cutler Trade Worth It?
  2. Is Jay Cutler still the Best Bears’ Quarterback Ever?

And while answering these questions we also cover...

  • Tony Romo vs Jay Cutler: What makes them different?
  • How the Bears might’ve won Super Bowl XLI
  • How Jay Cutler may have affected Charles Tillman’s Hall of Fame case
  • Why Mike Martz traded Greg Olsen
  • Could Kyle Orton have been “the guy”?
  • A sneak peek at a confidential project the WCG Staffers have been working on
  • And much, much more....

Give it a listen and let me know what you think!

Feedback rocks, so please provide it! Whether positive or negative, I want to make something that you want to listen to. Comments about length, content, frankly anything you have an opinion on is welcome. Bear Down, and thanks for Bearing With Me!