I honestly don't believe Chicago was under great fire to trade Keith. They are facing about $7.6M in cap penalties if Keith retires early. If he played at least one more season with them that number reduces to $4.3M. Bowman must've felt he was still useful and if I was him I'd be leary of those cap recapture penalties. Right now Chicago will owe $5.5M and $2.2M in dead cap space if he retires at seasons end. They are assuming a lot of risk on this.
The only way the Oilers had leverage is if Keith threatened to retire if he wasn't traded to the Oilers for next to nothing. But he's got friends on that team, he's worked with Bowman for years. I can't imagine he'd want to burn his reputation down over this.
This could probably just stay in the Keith thread, but... I'll bite.
Chicago was going to move Keith. He's a Blackhawks legend at the end of his career. They weren't going to say to him "no, we won't trade you to be near the child you didn't get to see at all in the last year". Even Stan Bowman isn't that big of an asshat.
The thing is, the Oilers weren't the only option. They could have certainly exposed Keith to Seattle, and even if Seattle doesn't bite on that (I'm not sure what else Chicago is having to expose), they could make a side-deal to get Seattle to take Keith. If what Chicago wants is salary cap space to make a hard run at Seth Jones with, then they'd probably make it happen with whatever B or C tier asset it'd take over negotiating with the Oilers into August. And who knows what Vancouver is thinking if both Edler and Hamonic are gone and they've missed out on whatever defenseman they're targeting (*cough*Larsson*cough*).
Beyond that I think the salary retention was not a huge problem for the Oilers considering the real dollars are much lower and actual money is relevant to the Daryl Katz. They've taken a bath during the pandemic and they were missing payments to hotels and shit before all that. Getting to 81.5M cap dollars on the nose so they can use as much of Klefbom's LTIR relief as possible without actually spending money is possibly something that informed the Keith deal as much as anything else.