Trash does not empty completely

My trash had over 300 files when I emptied it. Nearly all were emptied, but 8 remain. The empty operation keeps running, but doesn't do anything, and I have to relaunch Finder to get out of the loop. Most of the remaining items are system files for a WD external drive.
The eight don't take up much space, and I am tempted to just let them be, but I am worried this might be a symptom of a larger problem.

actually they might got deleted ... but the file name may be still showing there...sO better check "info" of trash before deleting the next time you do so. and sometimes if the iteams are locked it could happen. better to restart your computer. Even when i delete some files in the trash. The trash becomes empty. but finders memory is still not emptied. even i do restart my computer my hard-disk couldnt be free sometimes . But aftr few dayz of use, automitacally free space created in the hard disk. SO BEFORE DELETING ANYTIN CHECK OUT ITS USED MEMORY, DEN U COULD ACTUALLY GET TO KNOWN THE FILE IS REALLY GOT DELETED OR NOT ! TNX..

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I have tried ctrl / Alt Empty Trash.
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8037 Zürich
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Hi Melo
Here goes...
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/dev/disk0
   #:                       TYPE NAME                    SIZE       IDENTIFIER
   0:      GUID_partition_scheme                        *251.0 GB   disk0
   1:                        EFI EFI                     209.7 MB   disk0s1
   2:                  Apple_HFS Macintosh HD            250.1 GB   disk0s2
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   0:     Apple_partition_scheme                        *100.7 MB   disk1
   1:        Apple_partition_map                         32.3 KB    disk1s1
   2:                  Apple_HFS DiskDrill               100.7 MB   disk1s2
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Filesystem   1024-blocks      Used Available Capacity iused   ifree %iused Mounted on
/dev/disk0s2   244277768 220264736 23757032    91% 55130182 5939258   90%   /
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WARNING: Improper use of the sudo command could lead to data loss
or the deletion of important system files. Please double-check your
typing when using sudo. Type "man sudo" for more information.
To proceed, enter your password, or type Ctrl-C to abort.
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1          /Users/Shared
23259          /Users/murraymilne
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PS: How would DISKDRILL help me? What are cleverfiles?

Trash does not empty completely

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