This may or may not work, but is worth a first shot. The first method is to use the OS X "Secure Empty Trash" option, which is is available in the "Finder" application menu. Luckily permissions errors such as this can easily be overcome by emptying the Trash using alternate methods, or even delete and rebuild the hidden Trash folders. When this occurs, the Finder may show the file as being fully accessible by you, but in reality there are more restrictions under the hood, and when you try to delete the file you will be presented with an error. For instance, ACLs can allow you to fully read and write to a file, but not delete the file from the system's directory. The entries are inherited and given priority based on when they were entered, which can sometimes lead to extensive and complex permissions rules for a file that stretch way beyond merely allowing "read" and "write" access. OS X implements access control lists, which are an extensive way to manage permissions on files, and can sometimes result in bizarre permissions interpretations by the system since you can enter multiple different control entries for a specific user or group account. This usually happens when you are managing files from external disks, but it can happen with any file on the drive.
Regardless of the specifics of the error, if you cannot empty the Trash, then it is highly likely that in some hidden way you do not have enough privileges to delete the files in the Trash. One such error may be: "The operation can't be completed because an unexpected error occurred (error code -8003)," but others include a simple warning that you do not have enough privileges to perform the delete action. But there are instances when odd permissions setups for files can result in bizarre errors when you try to delete them. Usually if you come across a file for which you do not have write privileges, the system will prevent you from moving it to the Trash. The OS X Trash may sometimes give people problems where files cannot be deleted.
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