You can learn together. If everyone who gets up to speed then takes responsibility for getting two more people up the curve it won't take long before everyone is PGPable. We need a way to get exposure beyond Web denizens into the world the politicos inhabit. It's a marketing problem. I hope he does.
Someone starts packet-sniffing for the correspondence.
Letters from Dad end up being front page news. Mr. Clinton gets encryption religion. John Doerr Key point, political celebrities are probably already tuned into the privacy issue, just say the word paparazzi, but we keep talking about cryptography. This is not a technical issue, it's a human issue. Visions of hackers on virtual motorcycles, prying into Clinton's private email will drive the point home.