I know what you mean, but in a way I find it strangely reassuring that the head of the CIA is (in some respects at least) plain old old-skool dumb.
It tends to confirm me in my suspicions that the media-projected image of ruthlessly efficient and mindbogglingly smart intel apparatchiks is a fantasy, and that the reality might be more like Burn After Reading[1]
Is it worse than any other free email provider? None of them have two factor login by default and they all have sketchy password reset policies/mechanisms. Brennan is 60 years old. He's probably been using AOL since the 90's. He felt no need for change. A lot of our top leadership are boomers and will have boomer habits.
If you read that article you'll see this is more of a social engineering hack on Verizon than AOL. Verizon gave up all sorts of information about him which made answering AOL's password reset questions easy for them. Its scary how much you can do to a person if you know the last four digits of their credit card.
This is yet another example where things like S/MIME would have helped, but apparently we're all content with completely unencrypted emails. I suspect guys like Brennan prefer email unencrypted anyway, except when things like this happen to him personally.
Not really, but they are definitely on the bottom of the trusted list. That being said, the WTFs in this story would be the same if it was yahoo, gmail, etc. The problem is that the emails were forwarded out from his work network.
What does this article have to do with Google and Facebook's CEOs?
edit: No, seriously. I can't see how the CIA is the most powerful information gathering agency on the planet. Even restricting to government organizations, the NSA likely has far more access to information. Allowing for private organizations, Google/Facebook likely know far more about individual people than any government agency does given Google Analytics, Facebook Like buttons, etc. strewn around virtually every public internet page.