Failure to Empty Trash I have an iMac20 with OS 10.6.8 and an external hard drive. It appears that recently the Trash has an large amount of items. When I try to use Secure Empty Trash it counts the number of items to be deleted, then starts the deletion process and fails after a short time.
You could try using terminal.
I suppose that you can not remove the files from external drive trash (Mac use separated trashed for each drive). 

In order to remove external drive files try this:


Open Terminal
Write: cd /Volumes/{Your External Drive Name}/.Trash
Check that your files are there with: ls -la
Remove them using: sudo rm -rf ./*
It will ask your password


With that you should be able to remove your files.
You can do the same for your local drive but the .Trash folder is on your user folder instead of the drive root.