Chicago Bears offseason winners and losers: Less help for Caleb Willams, more toys for Dennis Allen

The Chicago Bears' 2026 offseason has left Caleb Williams as a clear loser despite the team's strategic focus on defense, with minimal offensive upgrades and the departure of key receiver DJ Moore without a true replacement. While Williams benefits from internal development and faith in his growth, the lack of external support makes his path harder. On offense, Luther Burden emerges as a major winner, stepping into Moore’s void as the primary playmaker, while Joe Tooney faces increased responsibility with weakened left-side line support. Defensively, Dennis Allen is the standout winner, finally getting his preferred roster with new linebackers, safeties, and versatile players like Devin Bush and Kyler Gordon. Tyreek Stevenson and Austin Booker also benefit from lack of competition at cornerback and defensive end, respectively. However, Montez Sweat is a clear loser, now expected to carry the entire pass rush burden without a true backup. TJ Edwards survives but is clearly on the way out, and Cole Komet’s fate is split—initially a winner for staying, but now a loser due to the third-round draft pick of Sam Rauch, signaling a faster timeline for his eventual replacement. The Bears’ offseason reflects a bold bet on defense and internal growth, but at the cost of quarterback support and long-term stability at key offensive positions.