I don't know a whole lot about this, but I were to spam him, I'd do the following.
Set up an SMTP server on my box. This will allow relaying of messages. It might also disguise the originating IP as 127.0.0.1 (MAYBE...)
Get an email bombing client (check Astalavista.com, I'd direct link it, but I'm sure mods wouldn't be happy).
Get a proxifying program.
Launch it.
Alternatively, you could get one of those anonymous email proggies like Quicksilver. They route your message through x number of anonymous servers to make sure it can't be traced. I don't know if you can batch-send them, but somebody could work out a script I guess.
But of course this is wrong.
