The Chicago Bears head into the offseason with two glaring needs: left tackle and defensive end — but which one should come first?

With rookie quarterback Caleb Williams entering a critical stage of his development, protecting the blind side is more important than ever. A true franchise left tackle could stabilize the offense and allow Ben Johnson's system to fully take shape.

At the same time, the Bears' defense still lacks a game-changing defensive end — the type of pass rusher who can consistently generate pressure, close games, and alter outcomes in high-leverage moments.

In this episode of The Windy City Breeze, we break down the LT vs DE debate, how each position impacts winning in today's NFL, and how free agency and the NFL Draft could shape the Bears' offseason priorities. We also discuss how Chicago's offensive direction and defensive identity factor into which move should come first.

Plus, we touch on: • The Bill Belichick Hall of Fame debate • Todd Monken's reported move to Cleveland • Ian Cunningham's potential exit to Atlanta

If you had to choose ONE — left tackle or defensive end — which should the Bears prioritize this offseason?

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