Hello Frank,
Thanks for that info and for choosing the Apple Support Communities. If we understand correctly, you are having an issue with emptying the Bin on your Mac, as you empty it and restart your Mac and the Bin isn't empty as expected. To help isolate this, use safe mode to start up your Mac as it does the following things:
- Verifies your startup disk and attempts to repair directory issues, if needed
- Loads only required kernel extensions
- Prevents Startup Items and Login Items from opening automatically
- Disables user-installed fonts
- Deletes font caches, kernel cache, and other system cache files
Log in to your user account and test the issue while in safe mode and then restart normally and test the issue again.
How to use safe mode on your Mac - Apple Support
Cheers!