I agree.
CAN it be done? Certainly. You can backload the crap out of it. But we can all do the math...
Call it $20M per year. Costs $12.8M this year currently. If you actually wanted to sign Clowney (which I doubt EDC is really thinking about that and I doubt its the reason they would want to create space), you'd probably have to shave $2-3M at least off that number.
So you're signing a long term player for $20M a year, with a first year cap hit of like $10M.
Worst. Decision. Ever.
His cap hit from year 1 to year 2 would have to jump by at least $10-12M, possibly more. That's horrible cap management, and that's even if you think the cap is going to shoot up a lot next year (which is anecdotal at best at this point).
If I'm extending Stanley, I want his cap hit in 2020 to go up, not down.
Extending Judon makes more sense. If he signed for $17-18M per year, and he costs nearly $16M this year, then you could potentially save $2-3M by extending him. A first year cap hit of like $13-14M isn't that terrible, though the idea of him being in like year 3-4 of a long term deal with a $20M+ cap hit is scary. He's the kind of player, in my opinion, that when the cliff comes, its going to be a STEEP decline.