Chicago Bears’ Biggest 2026 Offseason Needs After Stunning Breakthrough Season

Kevin Byard walked off the Soldier Field turf in overtime, helmet in hand, watching Harrison Mevis’s 42-yard field goal split the uprights. Rams 20, Bears 17. Season over. The 32-year-old safety who’d just led the NFL with seven interceptions—who’d earned Pro Bowl and All-Pro honors in a career renaissance—didn’t know if he’d just played his last snap in a Bears uniform.

Somewhere upstairs in Halas Hall, Ryan Poles was already doing the math: re-sign the aging captain who’d transformed the secondary, or let him test free agency March 11th and watch him walk? The Bears had just delivered their best season since the Brian Urlacher era—11 wins, an NFC North title, and their first playoff victory since 2010. They’d beaten Green Bay in a wild-card thriller, then pushed the Rams to overtime before Caleb Williams’s third interception ended it. Championship window officially open. Rookie quarterback contract ticking like a time bomb. And an entire safety position group is about to evaporate.

When the Bears headed into November at 4-3, some betting sites were offering mighty +10000 odds for the Lombardi Trophy to head back to the Windy City. By the time Chicago had knocked off the Packers to head to the Divisional Round, those odds had come all the way down to +1400. Somebody somewhere will have been making full use of online arbitrage betting calculators, which show the exact amount punters would have had to place on all seven other potential Super Bowl winners had they backed Chicago at 100/1.

All odds conversions displayed using this betting tool: https://thunderpick.io/betting-calculators/arbitrage-hedge-calculator

Now, however, all eyes are on 2026 and the tension that GM Poles faces as the Bears’ offseason begins in earnest. Success hasn’t simplified roster decisions—it has complicated them exponentially. Playoff teams don’t get excuses for regression. The Chiefs didn’t build a juggernaut by playing it safe. Neither can Chicago.

Safety: Position Group Extinction

Here’s the crisis: Byard, Jaquan Brisker, C.J. Gardner-Johnson, Jonathan Owens, Elijah Hicks—all unrestricted free agents. That’s not roster attrition. That’s the entire depth chart walking out the door. Byard’s 93 tackles and eight passes defended anchored a secondary that desperately needed veteran leadership. Poles addressed reporters Wednesday at Halas Hall and made his intentions clear: he wants Byard back. The feeling’s mutual. But how do you commit multi-year money to a 32-year-old safety, no matter how dominant his 2025 campaign was?

Ohio State’s Caleb Downs represents the dream scenario in the draft. He’s a two-time All-American, a 2024 National Champion, and a 2025 Jim Thorpe Award winner after amassing some 257 tackles, 16 of them for loss, six interceptions, and 12 passes defended. He’s projected to be top-five. The Bears aren’t picking top-five. Trading up means mortgaging future capital when edge rushers and cornerbacks are also desperate needs. Sonny Styles, Downs’s Ohio State teammate, offers a late first-round consolation prize, but “consolation” doesn’t win championships.

This is Poles’s nightmare: pay aging stars or draft developmental prospects while Caleb Williams’s three remaining cheap years evaporate. There’s no good answer, only the least-bad options.

Edge Rusher: The Non-Negotiable Decision

Joe Tryon-Shoyinka, Dominique Robinson, and Daniel Hardy—all free agents, none irreplaceable. The Bears’ 24th-ranked scoring defense wasn’t just a secondary collapse; elite quarterbacks had clean pockets and time to dissect Chicago’s coverage. Matthew Stafford looked uncomfortable for three quarters in the playoff loss, sacked four times, but when it mattered, he had time to win.

Enter Trey Hendrickson: NFL.com’s No. 1 overall free agent, four-time Pro Bowler, former First-Team All-Pro. He’s 32. He played seven games in 2025 with four sacks after signing a one-year, $29M prove-it deal. He’s also maintained a 17-percent-plus pressure rate over four straight seasons, meaning when healthy, he’s still elite. Chicago’s been mentioned as a potential landing spot, which is agent-speak for leverage. His asking price? North of $20M annually.

Does Poles commit that money to a 32-year-old edge rusher when Miami’s Rueben Bain Jr.—6’3″, 275 pounds, 2023 ACC Defensive Rookie of the Year, 2025 All-American, 121 career tackles, 20.5 sacks—will be available in the draft? Can they even draft Bain without mortgaging future capital to trade up? Oregon’s Matayo Uiagalelei led the Big Ten with 10.5 sacks in 2024. Texas Tech’s David Bailey boasts elite speed and a 27.2-percent win rate.

This is the franchise-defining choice: pay stars now or draft prospects and hope. Rookie contracts don’t last forever. Williams has three more years before a $50M cap hit arrives. That’s three offseasons to build a champion. Poles can’t afford conservative half-measures.

Defensive Line: The Unsexy Death Sentence

Andrew Billings and Chris Williams both hit free agency, leaving gaping holes in Matt Eberflus’s rotation. Dominique Robinson, an edge/DL tweener who never developed, also departs. This isn’t sexy. Nobody writes think pieces about three-techniques. But the Bears ranked second offensively in rushing (147.3 YPG) while getting gashed defensively. The NFC North’s identity is trench warfare—Detroit, Minnesota, Green Bay all pound the rock. Losing interior beef means Jordan Love and Jared Goff have clean pockets and linebackers chasing running backs five yards downfield.

Denver’s John Franklin-Myers ranked eighth in pass rush win rate with legitimate three-down value, but he would need to be offered starter money to even consider making the move. Detroit’s D.J. Reader is 32, still stuffing runs with 10-plus solo tackles in five straight games, but how many good games does he have left—six? Ten? Tampa’s Logan Hall offers youth and “upside,” which is code for “hasn’t proven anything yet.”

Does Poles pay premium dollars for Franklin-Myers or go cheap with Reader and pray the 32-year-old’s body holds together? This is the unsexy decision separating smart GMs from desperate ones. Day 2 draft picks won’t save you immediately. Free agency depth signings won’t either. You need a legitimate starter, and legitimate starters cost money Chicago might not have if they re-sign Byard and chase Hendrickson.

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