Does sound like you know him better than I do :)

Back in the early 2000s I was the guy helping sort out John's open email relay complaints at my ISP. A few other random things too. We hosted the EFF and Internet Archive so my life was pretty busy. I've been less of a fan of the EFF over the years as they've adopted some fights that I think they're on the wrong side of (IE: fighting for censorship) but... ohwell...