The Chicago Bears finished the season postseason strong, but the team knows there is still work to be done to turn the current roster in to a championship-caliber one.
One area the Bears could look to bolster is at wide receiver. Defensive end and offensive tackle are the obvious candidates for Chicago to make a splash in the offseason, in free agency and the draft, there aren’t too many top-quality players at those positions heading into free agency next month.
And the draft, as we all know is ultimately a big dice roll, especially with premium positions in the latter half of the first round.
But at wide receiver, Dallas Cowboys All-Pro George Pickens could be available to the team via trade. Ian Rapoport reported that Dallas could be willing to franchise tag Pickens, who is set to be a free agent in March, for $28 million, and then subsequently trade him away for the price of around a second round pick.
If the Cowboys do choose to follow this path, there could well be a host of teams looking to acquire Pickens’ services, and the Bears make sense as a top candidate. So in this hypothetical trade scenario, Dallas trade Pickens to Chicago for a second and fourth round pick in 2026.
And in doing so, the Bears would just beat out the Packers for his services, who themselves have been heavily linked to the former Pittsburgh Steeler, with multiple Green Bay players having done some recruiting of their own to the get the soon-to-be 25 year old to come to Wisconsin.
Why Would the Bears Trade a 2nd Rounder for Pickens?
Fundamentally, George Pickens is better than any receiver that Chicago has on their roster at this point in time,
And that is not really debatable: Rome Odunze has shown promise, but fell off towards the end of the season, and the end seems to be well in sight for ex-WR1, D.J. Moore, who posted a career-low 682 receiving yards in 2025, despite quarterback Caleb Williams breaking the franchise record for most passing yards thrown in the regular season this past year, 3942.
The Bears can address the trenches in the first round – likely a defensive lineman – and then would have the opportunity to add an All-Pro player in lieu of their second and fourth round pick; it feels like a no brainer.
Do the Bears Have the Cap Space for Pickens?
Despite Chicago being over $10 million above the cap at present moment, per Spotrac, in reality they have a lot more financial manoeuvrability than one would otherwise imagine.
Per Over the Cap founder, Jason Fitzgerald, the Bears have up to almost $86 million to work with if they restructure some of their current deals on their books. It’s unlikely they would use up all of that number to make cap-relieving restructures that could put financial pressure on years in the future, but making a couple could go a long way.
The team can also alleviate their deficit by making a couple of big cost-saving moves, such as releasing inside linebacker Tremaine Edmunds, which would save them $15 million this season, and tight end Cole Kmet, which would save the Bears a little under $8.5 million.
If they are willing to make these moves financially to make space for Pickens, it could be a huge coup for the organization and another excellent offensive target for the still-developing Williams.