OSX Mavericks Trash Question why does an item remain in trash after I drag it out onto the desktop. It does indeed go to the desktop, but it still remains in the trash (OSX Mavericks). lion,etc once dragged out, it immediately left the trash.
I am really not sure what your setup is, so my answer is pure guessing.

So it happened before when I was using ParagonNTFS to delete some files from NTFS filesystem. What you need to do is boot into your Windows (BootCamp), use its built-in partition repair tool to repair the partition. Then uninstall ParagonNTFS because it will damage your NTFS partition!