I don't think he would be fooled. You could send him material anonymously in snail mail, maybe. You could ask questions that will make him think (without stating the ttatt, let him figure it out himself) You could just get into his google and get a lot of stuff popping up at him from various sites that don't support the WT, like this one, JW Facts, silent lambs, etc.
That won't work, the WT firewall would go up immediately. As far a mail, it's hard enough to get him to open non anonymous mail, and as far as google, he barely uses the internet. Not the most technologically savvy person.
Even better, tell him to read the James book on the Library.
It was written by Ed Dunlap and edited by Raymond Franz. In my opinion its the precursor to In Search of Christian Freedom,
This might work, I wonder if there is a "favorites" option and I could bookmark it for him.