How Chicago Bears stack up as landing spot for Trey Hendrickson

Plain and simple, no twisting or squeezing the cap, it can't be done unless they plan on cutting players next year. In fact, they probably would have a problem fitting him in their cap space this year although  they could find a way. But if they went after Hendrickson in a trade, it would be for beyond this year. It most likely would be on a contract until he's 34 years old.

Here's the issue with this type of move.

1. D-Line Spending

The Bears are already devoting the sixth most amount of their cap space to defensive line in the NFL. Next year, they're locked in for the fifth most. In 2027, they have committed the second largest amount of salary cap cash to the defensive line.

They're locked in for $25 million in cap cost to Montez Sweat through 2027. They structured Odeyingbo's deal so they're paying out $20.5 million in 2026 and $19.5  million in 2027 but only $8 million this year.

They're going to add a player who is going to command $100 million or more on a three-year extension? Maybe it's doable if they're allowed to operate with higher salary cap than other teams, but otherwise forget it.

For crying out loud, how much money do they need to spend on defensive linemen anyway?

2. Limited Restructuring

Spotrac.com modeled what a contract extension would look like for Hendrickson.

This year's cap it would be 13.667 million which the Bears can afford but they would need to restructure more deals because they still have about $14.7 million available. This amount does not include the money they need for three second-round draft picks who remain unsigned. Once that's deducted, they'll be down below $10 million, so some additional restructuring for others would be required as they head down the path toward Ryan Paceville, when they have put all of their future into dead cap space and require another roster cleansing like they had in 2022.

The model done by Spotrac has $31 million in cap space for 32-year-old Hendrickson in 2026, $36 million for 33-year-old Hendrickson in 2027 and $38 million in 2028 for 34-year-old Hendrickson.

Finding the $13.7 million this year is tough enough. Even with restructuring, it would be a terrible hit to their 2026 cap to fit in another $31 million in cap hit.

You're not restructuring to fit in $31 million deals because no one on your team even has a contract that large to do it, let alone $36 million in 2027.

It's always possible to fit in a $12 million or $14 million deal by restructuring. A deal over $31 million a year is impossible even when the cap is going up every year.

The Bears would not save money by cutting Montez Sweat in 2026. They would actually lose money against the cap, about $3.085 million after June 1 and $11.2 million before June 1. They would need to cut someone else to get back the $31 million.

They would save about $11 million in cutting Jaylon Johnson after June 1, $13 million by cutting Tremaine Edmunds and $8.4 million by cutting Cole Kmet. They save $6.2 million by cutting D'Andre Swift.

This would give them around $38 million and gone are Johnson, Kmet, Swift and Edmunds. The contract is $31 million in 2026, though.

Why $38 million?  They're already over the cap by $7.2 million for 2026 according to Overthecap.com.

If they did all of that then they could afford him. Then they just couldn't pay their draft picks in 2026 or sign anyone else in free agency. Considering they have no safeties under contract, they better start converting backup cornerbacks to safeties now to get them ready for austerity just because they would want Trey Hendrickson as another edge.

Now, in 2027 it becomes more easy to fit in a $36 million cost for that modeled Hendrickson contract because

they have $43 million in cap space for that year.

Then again, that's the year they need money for a contract extension for Caleb Williams. Quarterbacks kind of cost a lot.

3. Use

They just signed a starting defensive end. If the Bears are in the market for edge rush help, it's only for a guy who can come off the bench and relieve Sweat and Odeyingbo for a few plays on a series or take over every third or fourth series. That player would be there for depth.

The Bears have committed their big chunks of cap space for defensive ends to two players already. They simply need someone a bit less expensive who is better than Dominique Robinson and Austin Booker.

Do you go out and buy a $374,000 Rolls-Royce Cullinan when you are in the market for an SUV and you barely have sufficient cash for a Nissan or Mitsubishi?

It's all about cost and affordability. A 30-year-old edge rusher who think they should get $100 million on a three-year contract extension needs to go to teams with a bit more cap space than $14.7 million this year, minus-$7.4 million for 2027 and $43.5 million for 2027, a year when they must come up with a $50 million a year contract or more for Williams.