While it may not have been his intention, Chicago Bears quarterback Caleb Williams had to be aware to some extent of how viewers would react to his sit-down with Las Vegas Raiders star Maxx Crosby.
Ditto for Crosby.
Heading into the 2026 offseason, the duo’s remarks during their face-to-face are sure to be on repeat as prognosticators use them to bolster their speculation.
Bears’ Caleb Williams Helps Fuel Trade Speculation
Caleb Williams Talks Up Maxx Crosby Amid Bears Trade Speculation
Williams joined Crosby on the latter’s “The Rush” podcast, which premiered on Tuesday. It featured an hour-long conversation that often boiled down to one star-level athlete showing respect for another.
Williams and the Bears defeated Crosby’s Raiders during the 2025 regular season.
Fittingly, it was part of a disappointing season for Las Vegas that has left Crosby’s future in question.
He has refrained from demanding a trade publicly, but there is increasing speculation thathe could seek a new home, or be made available this offseason as the Raiders look to retool. A five-time Pro Bowler, Crosby would undoubtedly elevate the Bears’ stagnant pass rush.
The chat drew attention from fans and media alike, but there are two significant hurdles.
Bears Trade Idea for Maxx Crosby Could Face Challenges
Crosby has recorded double-digit sacks in four of his seven seasons in the league, and all but two when he has played in at least 15 games. He tied Bears edge Montez Sweat with 10.0 sacks in 2025. It was a step up from his injury-shortened 2024 campaign.
However, Crosby is signed through 2029 on a three-year, $106.5 million contract. He also has a $35.8 million cap hit in 2026.
The Bears can get it done, but they could end up needing to part with players.
ESPN’s Bill Barnwell suggested the Bears explore trading wide receiver DJ Moore, noting that Crosby’s contract does not have a signing bonus. The Raiders would incur a $5.1 million dead cap hit while his new team would owe $60.6 million over the next two seasons.
There is another $53.9 million in non-guarantees for the 2028 and 2029 seasons. That gives the Bears an out if they need it, should they pursue Crosby in a trade.
Barnwell noted the difficulty of defining Crosby’s trade value.
In Barnwell’s suggestion, part of an article exploring options leaguewide on February 16, the Bears would send their 2026 first-round pick–No. 25 overall–to Las Vegas along with Moore in exchange for Crosby and a fifth-rounder in 2027.
Bears Have Been Down This Road
The Bears have dealt for big-time pass rushers plenty of times in their history, from Sweat to Julius Peppers, and even former Raiders star Khalil Mack.
Mack was 27 in his first season with the Bears. His tenure lasted four seasons. Crosby turns 29 in August. Sweat turns 30 in September. Behind them are Austin Booker, Dayo Odeyingbo, and Shemar Turner.
Booker showed well as a pass rusher last season, but is slight of frame for the run game.
Odeyingbo and Turner are both stouter against the run, but are also better suited as interior pass rushers.
Even if the Bears choose to pursue Crosby and are ultimately successful in complementing Williams and the offense on the defensive side, they need to inject more youth up front. Draft picks are the way to do that.
Depending on how the draft shakes out, it could remain the most viable option for the Bears.
