His method of hiding his activity was saving drafts in gmail... roughly on par with what I'd expect most people to do to maintain "privacy".
At first you would want to encrypt the information. Then you would like to have some method of transfer that does not stick out and could hide the intent to transfer encrypted data. Perhaps with the help of some steganography tool. And you would make sure that nobody identifies you in the process by using tools like Tor. This "I hope they don't notice" method is just gambling.