Trouble deleting trash files from an external drive?

Question

They are from my passport for MAC.
I have tried doing from terminal as well and most did delete however there are a lot of files that won't. I am getting a message pop up then when I click continue it just disappears and trash is still full.  Would love some help on this please.

Answer 1

Apparently;
error
-50
paramErr
error in user parameter list
Not sure what it means though.
I usually use rm -rf as it ignores permissions errors I think. Or at least attempts to.
The man page for the RM command is below.
NAME
     rm, unlink -- remove directory entries
SYNOPSIS
     rm [-dfiPRrvW] file ...
     unlink file
DESCRIPTION
     The rm utility attempts to remove the non-directory type files specified
     on the command line.  If the permissions of the file do not permit writ-
     ing, and the standard input device is a terminal, the user is prompted
     (on the standard error output) for confirmation.
     The options are as follows:
     -d          Attempt to remove directories as well as other types of
                 files.
     -f          Attempt to remove the files without prompting for confirma-
                 tion, regardless of the file's permissions.  If the file does
                 not exist, do not display a diagnostic message or modify the
                 exit status to reflect an error.  The -f option overrides any
                 previous -i options.
     -i          Request confirmation before attempting to remove each file,
                 regardless of the file's permissions, or whether or not the
                 standard input device is a terminal.  The -i option overrides
                 any previous -f options.
     -P          Overwrite regular files before deleting them.  Files are
                 overwritten three times, first with the byte pattern 0xff,
                 then 0x00, and then 0xff again, before they are deleted.
     -R          Attempt to remove the file hierarchy rooted in each file
                 argument.  The -R option implies the -d option.  If the -i
                 option is specified, the user is prompted for confirmation
                 before each directory's contents are processed (as well as
                 before the attempt is made to remove the directory).  If the
                 user does not respond affirmatively, the file hierarchy
                 rooted in that directory is skipped.
     -r          Equivalent to -R.
     -v          Be verbose when deleting files, showing them as they are
                 removed.
     -W          Attempt to undelete the named files.  Currently, this option
                 can only be used to recover files covered by whiteouts.
     The rm utility removes symbolic links, not the files referenced by the
     links.
     It is an error to attempt to remove the files ``.'' or ``..''.
     When the utility is called as unlink, only one argument, which must not
     be a directory, may be supplied.  No options may be supplied in this sim-
     ple mode of operation, which performs an unlink(2) operation on the
     passed argument.
     The rm utility exits 0 if all of the named files or file hierarchies were
     removed, or if the -f option was specified and all of the existing files
     or file hierarchies were removed.  If an error occurs, rm exits with a
     value >0.
NOTE
     The rm command uses getopt(3) to parse its arguments, which allows it to
     accept the `--' option which will cause it to stop processing flag
     options at that point.  This will allow the removal of file names that
     begin with a dash (`-').  For example:
           rm -- -filename
     The same behavior can be obtained by using an absolute or relative path
     reference.  For example:
           rm /home/user/-filename
           rm ./-filename