Trash not really empty?

While poking around with DaisyDisk, I noticed on one of my other drives there is ~8GB of files in ~/Users/Username/.Trash. (Mostly a bunch of iTunes & song files)
The trash on the Dock is empty/not showing anything in it.
These seems to be files I deleted a long time ago.
Ran disk utility and Disk Warrior but the files are still there.
Why are they there and can I delete them myself?

I noticed on one of my other drives there is ~8GB of files in ~/Users/Username/.Trash.
Since it has a Users/Username folder it presumably has OS X installed on it, and I assume that "one of my other drives" means that you are not currently booted there.
If so, I think those items may have been put in the trash when you were booted from that volume, or from a volume that you subsequently cloned there. If the external volume is still bootable and you again boot from it, I think the "missing" items in Username/.Trash will probably reappear in the trash icon in the Dock. It should be safe to delete them in any event.
I'm not positive, but here is my take on this-
OS X keeps track of trash by username, and there are TWO hidden locations on a volume where user-specific trash can be stored.
For files in the startup volume, each user's trash goes into the .Trash directory in the home folder. But for external volumes, there is a different root-level folder called .Trashes, which contains numbered subfolders. Each user is identified by "User ID" - generally a number like 501, 502, etc, with 501 being the UID of the first user account created. The user's "external trash" goes into an appropriately numbered subfolder of the root-level .Trashes directory. You can't normally see the numbered subfolders even if hidden files are made visible, because .Trashes has write-only permissions for all. You can see the subfolders if you look with root privileges.
So If "Joe" is the username of the first user created, his UID would be 501. His local trash would go into /Users/Joe/.Trash on the startup disk, and his external trash would go into .Trashes/501 on the external volume. If he places files in several external volumes into the trash, each of those volumes will have a root-level .Trashes/501 folder holding his trash. Items in the local "startup-disk trash" and all the items in the various "external trashes" show up together in the trash icon in the Dock.
So if the external volume is bootable, and Joe had at one time started up from it, put items in the trash and didn't empty the trash, then those items would be left in /Users/Joe/.Trash, as per above. If now Joe boots from the internal HD, that folder will this time appear in the filesystem as /Volumes/volumename/Users/Joe/.Trash. The system, however, does not recognize items there as trash - it doesn't look there. It instead expects to find Joe's local trash in /Users/Joe/.Trash on the startup volume, and expects to find Joe's external trash in the various /Volumes/volumename/.Trashes/501 folders.
Anyway, that's my understanding - it may not all be correct.

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