Maxx Crosby is the talk of the NFL offseason right now. Despite the whispers that the Las Vegas Raiders are putting out about keeping him, everybody can see the writing on the wall. Crosby wants to play for a winner. He’s nearing 30 and has a few prime years left. He’s never come close to getting a ring and would at least like the opportunity. Las Vegas is nowhere close to giving him that. Hence why the market for the Pro Bowler is so hot, with at least 10 teams involved. However, some stand out above the rest.

Zach Wolchuk covers the Dallas Cowboys at 105.3 The Fan and is close with veteran insider Trey Wingo. He revealed on Twitter (X) that Dallas looked like they were close to a deal for Crosby, but other teams raised the price tag to two 1st round picks. He now has it on good authority that the Chicago Bears are that team, putting them on the inside track for the star pass rusher. The other team involved is the Philadelphia Eagles, who remain as dangerous as ever on the trade market.

I am getting a lot of buzz the Bears are the team offering two firsts for Crosby. Excited to chat w/ @wingoz about this at 5pm on @1053thefan

— Zach Wolchuk (@ZachWolchuk) March 5, 2026

Saw that as well but them & the Eagles are making a push

— Zach Wolchuk (@ZachWolchuk) March 5, 2026 The Bears can now make a Maxx Crosby trade work.

Two factors made it hard for many to imagine. One was their lack of salary cap space. That problem was resolved by Drew Dalman’s retirement, Tremaine Edmunds’ release, and the trade of D.J. Moore. The other was a lack of draft capital to make such a deal palatable. That changed when the Bears netted a 2nd round pick in the Moore trade. Now they have two picks in the 2nd round, meaning they can deal two 1sts to Las Vegas and still have a reasonable amount of draft currency to fill the roster with young talent.

Philadelphia does have an advantage, though. They have something they can dangle to the Raiders that the Bears can’t: A.J. Brown. It isn’t a secret that their relationship with the star wide receiver has grown frosty since last season. He isn’t happy with the state of the offense and his role in it. Conversely, Las Vegas needs wide receiver help in preparation for selecting Fernando Mendoza #1 overall in the draft next month. Packaging Brown with two 1st round picks would be a far more appetizing offer compared to anything the Bears can put forward.

🔥 Subscribe to the Untold Chicago YouTube channel to hear Chicago legends tell stories you’ve never seen in headlines — real moments, real experiences, straight from the athletes themselves.

Player YearTraded FromTraded ToSuper Bowl Win?Keyshawn Johnson2000NY JetsTampa Bay BuccaneersYes (Super Bowl XXXVII)Jalen Ramsey2019Jacksonville JaguarsLA RamsYes (Super Bowl LVI)Matthew Stafford2021Detroit LionsLA RamsYes (Super Bowl LVI)Joey Galloway2000Seattle SeahawksDallas CowboysNoRicky Williams2002New Orleans SaintsMiami DolphinsNoJay Cutler2009Denver BroncosChicago BearsNoKhalil Mack2018Oakland RaidersChicago BearsNoLaremy Tunsil2019Miami DolphinsHouston TexansNoJamal Adams2020NY JetsSeattle SeahawksNoDeshaun Watson2022Houston TexansCleveland BrownsNoRussell Wilson2022Seattle SeahawksDenver BroncosNoMicah Parsons2025Dallas CowboysGreen Bay PackersNoThe Bears must weigh the risks of this carefully.

They’ve already conducted two such blockbuster trades in the past two decades. Neither led to the elusive second Super Bowl title they’ve been chasing for over 40 years. Jay Cutler got close in 2010, but lost in the NFC Championship. Khalil Mack spearheaded a great team in 2018, but was undone in the wild card round by the Double Doink. Trading for Maxx Crosby will make them better. The problem is whether they believe he’s the missing piece to a Super Bowl run. That is up for debate.

There is no doubt that having a pass rusher of his caliber would make their defensive line formidable. However, it wouldn’t fill the voids at linebacker or safety. It also won’t solve the team’s issues at left tackle and center. This comes down to how confident Poles and head coach Ben Johnson are that they can plug those holes despite limited resources if and when the trade is completed. Based on history, the odds aren’t in their favor. Then again, those previous teams didn’t have the coach-quarterback combo that this one does.