Yes it does matter. The right thing to do is transparency and that's what's happening here. If Bad Person & Associates are doing evil, they're not going to get a break just because their messages also contain personal love letters.
I had a much better opinion of Stratfor until now. They were plotting how to best sell misinformation. Misinformation that could start a war in which millions could die. They thought they could get away with this shit.
I'm sure many HNers have sent joking emails concerning their work to fellow coworkers. It happens in almost every office. I'm not saying that's the case here, but you never know.
"To initiate a war of aggression, therefore, is not only an international crime; it is the supreme international crime differing only from the other war crimes in that it contains within itself the accumulated evil of the whole."