Chicago Bears Offseason Priority: Left Tackle or Defensive Line — Which Matters More?
Release Date: 01/29/2026
The Windy City Breeze
The Chicago Bulls may have just hit the reset button — hard. In a stunning sequence of moves, Chicago trades Nikola Vučević and reshapes the roster by acquiring Anfernee Simons, while also pulling off deals for Jaden Ivey and veteran floor general Mike Conley. In this episode of The Windy City Breeze, we break down what this flurry of moves means for the Bulls’ direction, identity, and timeline : • Why the Bulls finally moved on from Vucevic • What Anfernee Simons brings as a dynamic scorer • How Jaden Ivey fits into Chicago’s long-term vision • Mike...
info_outlineThe Windy City Breeze
The Chicago Bears stadium situation has reached a defining moment. In this episode of The Windy City Breeze, we break down the latest stadium update as the Chicago Bears draw a clear line in the sand with the state of Illinois, signaling mounting frustration and a possible turning point in negotiations. We also zoom out to discuss the best path forward for both the Bears and the Chicago Bulls, examining how each organization should balance patience, leverage, and long-term planning as major decisions loom. To close, we dive into coaching news, including why the Bears reaching out to two new...
info_outlineThe Windy City Breeze
The Chicago Bears received some encouraging news involving Al Harris, and it could have a meaningful impact on the direction of the defense heading into a critical offseason. In this episode of The Windy City Breeze, we break down what the Al Harris update means for defensive coaching continuity, player development, and long-term stability as Chicago continues building under Ben Johnson and Ryan Poles. We also tackle a major roster question: Is Trey Hendrickson a year too late for the Bears? With Hendrickson’s age, contract situation, and market value coming into focus, we discuss whether...
info_outlineThe Windy City Breeze
NFL executives aren’t expecting a splashy offseason from the Chicago Bears — and that may be exactly the point. As the NFL salary cap continues to rise, smart teams are redefining what it means to go “all-in.” Recent Super Bowl teams have shown that winning isn’t about maxing out spending, but about timing, flexibility, and picking the right spots to strike. In this episode of The Windy City Breeze, we break down why league decision-makers don’t expect the Bears to chase headline-grabbing free agents, how today’s free-agent market lacks true star power, and why disciplined roster...
info_outlineThe Windy City Breeze
The Chicago Bears made a quiet but significant front office decision by allowing Assistant GM Ian Cunningham to depart for the Atlanta Falcons… but was it actually the right move for the future of the franchise? On this episode of The Windy City Breeze, Pat The Designer breaks down what Cunningham’s exit means for Ryan Poles, the Bears’ organizational stability, and the long-term plan for building a contender in Chicago. Is this a sign of confidence within the front office — or could it signal a larger philosophical shift? We also dive into four surprise trade candidates that could...
info_outlineThe Windy City Breeze
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...
info_outlineThe Windy City Breeze
coaching staff and offense are starting to collide. The Baltimore Ravens have officially requested permission to speak with Bears offensive coordinator Declan Doyle, raising important questions about offensive continuity and stability as Chicago continues building around its young core under head coach Ben Johnson. How real is the threat of losing Doyle, and what would it mean for the Bears’ offensive direction moving forward? At the same time, former Dolphins Associate Head Coach and running backs coach Eric Studesville has emerged as a name to watch for Chicago’s vacant RB coach...
info_outlineThe Windy City Breeze
Are the Chicago Bears actually legitimate Super Bowl contenders, or are we getting ahead of ourselves? 🐻⬇️ On today’s episode of The Windy City Breeze, Pat the Designer breaks down the real case for why the Bears belong in the Super Bowl conversation and where the skepticism still makes sense. This isn’t a hot take episode. It’s a full-scope discussion around quarterback play, roster balance, coaching, defense, playoff trends, and timing — the same factors that decide who actually survives January football. We discuss: • What separates real contenders from feel-good playoff...
info_outlineThe Windy City Breeze
Could injuries to Rome Odunze and Luther Burden derail the Chicago Bears offense in their crucial matchup against the Green Bay Packers? In this episode, Pat the Designer breaks down how Odunze’s availability and Burden’s health impact the Bears’ offensive identity, spacing, and game plan under Ben Johnson. We discuss what this means for Caleb Williams, the passing game, and whether the Bears can generate explosive plays if both receivers are limited or unavailable. Is this a temporary setback… or a major problem heading into Packers week? ⬇️ Join the discussion Do the Bears need...
info_outlineThe Windy City Breeze
Caleb Williams just put together his most complete performance as a Chicago Bear in a dominant showing against the Cleveland Browns, and it may officially be his best game in a Bears uniform so far. In this episode of The Windy City Breeze, Pat the Designer breaks down what made this performance different. From command of the offense, improved pocket presence, timely throws, and situational awareness, to how Ben Johnson’s game plan finally unlocked the best version of Caleb Williams. We discuss: Why this may be Caleb Williams’ best game as a Bear How his decision-making and confidence...
info_outlineThe 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?
Follow, rate, and review The Windy City Breeze for daily Chicago Bears coverage and offseason breakdowns.