It doesn't sound like he's been very careful. Between sleeping with random women who his supporters claim are CIA agents of some sort, and using the same password for different secret files...

But truthfully how hard would it be to honeytrap this guy? Suppose you go with my child pornography scenario, your sexy blonde Swedish secret agent only has to get close enough to slip a USB key into Assange's luggage so that when he flies through LHR customs can stop him and discover it. And if he checked any luggage it would be even easier.

> Considering Assange has probably been pretty careful and paranoid

You'd expect that, wouldn't you. But then his whole career show less risk-aversion than most people. To put it mildly.