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Why am I unable to delete certain files

I have backed up files under my users directory to an external hard drive.  I want to delete these files on the external hard drives but I am getting a message that states that some file names are too big and I am not allowed to delete the files or the directory they are in.  I don't understand why not.  

How can I delete the folders and all of these files from my external hard drive short of doing a reformat?
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Thank you