Mock trade has Chicago Bears acquiring Bengals' rookie pass rusher

With NFL teams having wrapped up their minicamps and OTAs, the biggest ongoing story is still the Cincinnati Bengals and the two major contract holdouts on their defensive line. Trey Hendrickson is coming off back-to-back seasons of 17 or more sacks and wants a pay raise, while rookie Shemar Stewart is refusing to sign his rookie deal until a contentious and somewhat bizarre clause is removed.

While Hendrickson and the Bengals are reportedly back at the negotiating table, the standoff with the rookie Stewart has no end in sight as both sides remain dug in. This situation could soon enter uncharted waters, with Stewart allowed to re-enter the NFL Draft in 2026 if he does, in fact, hold out all season without signing his deal, though a trade would be a far more likely outcome before things got that far.

That's the scenario that Mitchel Milani of Bleacher Report explored on a recent episode of B/R's NFL Daily live show. When listing potential trade partners for Stewart, Milani started with the Chicago Bears. In this scenario, the Bears would send Cincinnati a second-round pick and a third-round pick, both for the 2026 NFL Draft, and in return, they would get the promising young pass rusher.

As Milani correctly points out, Stewart is exactly what Bears defensive coordinator Dennis Allen looks for in a defensive end. He's huge, fast, and he's got freakishly long arms and raw strength. Milani also identified Chicago's ongoing weakness at defensive end. Yes, they've got Montez Sweat, and they made a splashy, high-risk/high-reward free agency signing in Dayo Odeyingbo, but the depth remains a major concern.

Trading Stewart is likely a non-starter for Cincinnati

This is an admittedly fun scenario to imagine, and I think it would actually benefit the Chicago Bears. Stewart has incredible upside and, if coached up to his full potential, could one day win multiple Defensive Player of the Year awards. But the floor for him is incredibly low, which is why I never liked the idea of spending a top first-round pick on him.

But a second and third for Stewart? That's a more acceptable risk, especially since, if all goes according to plan for Chicago this year, those picks will end up being close to the very back of each round. With that in mind, this could be a good deal for Chicago.

Shemar Stewar — Mark Hoffman / Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

Unfortunately (or fortunately, depending on your point of view), there's just no way the Bengals let things get this far out of hand with Stewart. As aforementioned, they're already back at the negotiating table with Hendrickson after what seemed like an irreconcilable chasm between the parties, and I imagine they'll eventually come around with Stewart and give him the contract he's demanding.

Not only would trading their first-round pick without ever getting a glimpse of him in a game be a huge embarrassment for the organization, but it would set them back another year in their quest to return to the Super Bowl. Cincinnati's defense needs all the help it can get after a disastrous 2024 season, and letting their high-upside pass rusher go, even in an equitable trade, would surely signal to the players and to the fans that the team does not expect to be a serious contender in 2025.

Chicago will almost certainly enter training camp without Stewart, and that's probably best for all parties involved.

Shemar Stewart — Phil Didion/The Enquirer / USA TODAY NETWORK via Imagn Images

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