It’s common to portray the Chicago Bears’ impending quarterback dilemma as Justin Fields against a strong group of draft prospects, but that’s not always the complete picture.

It’s expected that the Bears would trade Fields, ideally for first-round value, if Chicago chooses Caleb Williams or Drake Maye with the first or second overall pick in April. The rookie will then likely start right away. However, there are also circumstances where the organization signs an experienced signal-caller to either teach and support the franchise quarterback or act as a bridge starter for the team’s starting quarterback until the player is ready to take the reins.
Under those circumstances, Chicago may be considered for a few pending free agents, including Denver Broncos quarterback Russell Wilson, Washington Commanders quarterback Jacoby Brissett, and Cleveland Browns quarterback Joe Flacco.
The bookmaker BetOnline listed the Bears as favorites to sign Wilson, who is almost expected to look for a new team when free agency opens in March, on Thursday, December 28.

The Bears have 8-1 chances to acquire Wilson, according to BetOnline’s estimates, which were reported by JP Finlay of NBC Sports via X. Chicago is joined at 8-1 by a few clubs that could require a quarterback; the Commanders and Las Vegas Raiders are at 7-1, while the Minnesota Vikings are currently the betting favorites at 5-1.
The Athletic’s Dianna Russini also contributed a piece outlining Denver’s long-standing intentions to cut ties with Wilson in the upcoming summer.

According to league insiders, Russell Wilson anticipates being cut by the Denver Broncos in March, Russini said on X. “The quarterback has been starting for nearly two months, knowing that the organization was probably going to move on [from him] after this season.”
Wilson, who frequently makes an effort to manage the narrative surrounding himself and his profession, addressed X on Thursday with a message of his own.
Prior to the 2022 season, Wilson, a nine-time Pro Bowl player and Super Bowl winner with the Seattle Seahawks, signed a five-year, $242.6 million contract with the Broncos.

Over the course of the next two seasons, Denver will owe the 35-year-old quarterback $85 million in dead money, which should allow whichever team decides to sign Wilson to do so at a fair price. That does not imply that he will give a steep discount, though, since Wilson has quietly produced strong results in 2023 in spite of the harsh criticism that has surrounding him.
Denver will owe the 35-year-old quarterback $85 million in dead money over the course of the next two seasons, which should allow whichever team chooses to sign Wilson to do so at a reasonable cost. But despite the severe criticism that has surrounded Wilson, he has quietly generated good results in 2023, so it does not mean he will provide a large discount.