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Weird. Try doing it from the console by entering:

sudo rm -R /Users/your_user/.Trash/

Type the command EXACTLY as written above (notice the "." before Trash) and replace "your_user" with your user name.

 

You could also try fixing file permissions before executing the command.

If you have more than one volume (disc), you might also try removing the contents of their .Trash folders from the terminal.

 

It could also be a corrupted Fat32 drive, like in this guy's post:

http://fredericiana.com/2007/11/01/osx-leo...sh-always-full/

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