Episodes

  • Learning more about Bears free agent signing Kalif Raymond. Is he culture cornerstone?
    Apr 3 2026

    Kalif Raymond followed Ben Johnson from Detroit to Chicago this offseason, and it sounds like he could be a new tone setter for the team. Longtime Bears report Dan Pompei dug into Raymond as a player and a person, and Kenneth Davis and Alex Shapiro share their thoughts on Pompei's story, plus Raymond's fit with the team.



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    26 mins
  • Chicago Bears Top 30 Visit Tracker
    Mar 31 2026

    The Bears are in the latter stages of their draft preparation and taking a closer look at some young prospects. Kenneth Davis and Alex Shapiro go through the list of players who have reportedly paid a visit to Halas Hall and share their thoughts on what those players could bring to the team.



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    33 mins
  • Chicago Bears Mock Draft 2.0 - Rebuilding The Defense
    Mar 24 2026

    The NFL draft is one month away, so Kenneth Davis and Alex Shapiro put together their second mock draft of the year. The guys rebuild the defense, from front to back, inside and out... and they can't help but add another offensive weapon, too. Learn about the new crop of prospects!



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    30 mins
  • NFL Draft March Madness: Making A Bracket For The Bears No. 25 pick
    Mar 20 2026

    It's Bears Bracketology on Da Windy City podcast! The crew created a bracket of 16 players whom the Bears may select with the No. 25 pick. Alex Shapiro acts as Director of College Scouting. Kenneth Davis acts as GM. The pair go through the bracket until only one player remains as THE pick for the Bears this year.



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    50 mins
  • Remaining Free Agents Who Can Help The Bears
    Mar 13 2026

    The biggest names in free agency have mostly found their new homes, but there are still players on the market who can help the Bears win football games this season.



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    Not Yet Known
  • Bears free agency breakdown: Deep dive into offseason additions
    Mar 12 2026

    The Bears have begun reshaping their roster in earnest with the opening of free agency legal tampering. Kenneth Davis and Alex Shapiro break down the new names, both big and small, and share their thoughts on how they'll fit into the team this season. Plus, should the Bears make a move for Maxx Crosby after the Ravens backed away from their blockbuster deal?



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    1 hr and 10 mins
  • How Bears can fill holes left by DJ Moore, Drew Dalman and Tremaine Edmunds
    Mar 6 2026

    Next man up. The Bears have big holes to fill with the departure of three key players. Kenneth Davis and Alex Shapiro share their thoughts on how Ryan Poles and Ben Johnson can use their assets most effectively through the draft and free agency.



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    50 mins
  • Bears roster reshape begins with three HUGE moves
    Mar 6 2026

    Free agency hasn't even opened, and the Bears will already look much different in 2026. Some moves were expected. Others were massive surprises. Kenneth Davis and Alex Shapiro break down all the news and share how it will affect the team moving forward.



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    43 mins