<p>The stakes will be higher than ever for <a class="Link" href="https://chicago.suntimes.com/bears" target="_blank" >Bears</a> quarterback <a class="Link" href="https://chicago.suntimes.com/bears/2025/08/31/why-do-so-many-people-hate-bears-qb-caleb-williams-he-answers-exactly-that-question" >Caleb Williams</a> this season, which is saying a lot considering he’s been playing in the spotlight dating back to his time at USC.</p><p>All eyes are on him, locally and nationally, as he seeks to prove to the Bears he’s their franchise quarterback and to the rest of the NFL that he’s going to be a problem for years to come. And his team is in a similar position coming off an 11-6 season that could be the start of something big or merely another aberration.</p><p>All the while, he’ll be playing for a quarter of a billion dollars.</p><p>Williams’ first two seasons were a roller coaster, both individually and with the pieces the Bears put around him, and this is the time to steady himself. Like any first-round pick, he’s eligible for a contract extension at the end of his third season, and the market rate figures to be a five-year deal worth at least $250 million.</p><div class="RelatedList Enhancement" data-module data-align-center> <div class="RelatedList-title">Related</div> <ul class="RelatedList-items"> <li class="RelatedList-items-item"> <a class="Link" href="https://chicago.suntimes.com/bears/2026/05/14/bears-2026-nfl-schedule-release-analyze-packers-lions-vikings-thanksgiving-christmas-sunday-monday-thursday-saturday-night-football" >Breaking down the Bears’ 2026 schedule</a> </li> <li class="RelatedList-items-item"> <a class="Link" href="https://chicago.suntimes.com/halas-intrigue/2026/05/15/bears-schedule-podcast-halas-intrigue" >Halas Intrigue podcast: Talking 2026 schedule</a> </li> <li class="RelatedList-items-item"> <a class="Link" href="https://chicago.suntimes.com/bears/2026/05/14/sorry-bears-fans-at-least-one-handicapper-sees-fewer-wins-this-season-pythag-miech-vegas-sportsbooks" >Sorry, Bears fans: At least one handicapper sees fewer wins this season</a> </li> </ul> </div> <p>Teams typically know what they have in a quarterback at that stage, and the Bears’ schedule sets up in a way that they’ll certainly know the truth about Williams by the end of it.