I've had a trash can on my Mac that refused to empty for about a year. The reason being that a folder in the trash refused to disappear no matter what I did.
I followed all the Mac guides for what to do when this happens, none of them worked.
In the end I plugged the disk, my media store, into my Windows PC, ran Checkdisk; to no avail, then tried to manually delete the files.
It turns out that the Mac is happy to put nested directories with ridiculously long file names onto a Fat32 format disk thereby violating the MAX_PATH rules and rendering portions of the disk forever undeletable.
In the end I had to laboriously rename directories from 2345523000802340980980232452352398098123423 to "s" and eventually managed to arrive at a final directory name I could actually delete.
So. When your Mac file system seems screwed, fix it with a PC!
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