Ok, so I removed the Desktop Manager software because it was a very outdated version. I download the latest and greatest version and setup the problem BlackBerry so he can copy software and music and what not. I then resent the Service Books. I then looked at his user account on BES and under User Properties/Redirection/Message Forwarding/Redirect to BlackBerry device was set to False. I changed this to True and all seems to be happy. Thanks for the heads up on the Service Books.
If a user is configured for BIS and is using Desktop Manager software, is there a proper way to move the user to BES?