Question On Your CAP

So you just eat the dead money once player X retires or signs elsewhere
Yes. Some teams like the Saints include a year or two of "voidable years" at the end of a player's contract.

The benefit to the team is it keeps the current year cap hit as low as possible by spreading out the prorated signing bonus a year or two past when they likely won't re-sign the player. So a one-year contract becomes a two-year contract because of the voidable year.

Had Drew retired this year, the dead cap hit to the team's cap in 2020 would have been $21.3M. Because he re-signed (again), Mickey was able to push Drew's voidable years' cap hit a couple of more years into the future.

Eventually the Piper has to be paid... except in the fairy tale. lol