Money quote in the last paragraph: "When we get into things like this," [Judge William Downing] said, "anonymizing stuff, that’s well over my head technologically, then it becomes very murky and hazy." That sounds to me like the judge likely wouldn't have known what a TOR node was if the police had told him these guys were running one. Technology isn't slowing down, so how can we make sure the law keeps up?
He is willing to admit that it goes over his head, which presumably also means that he'd be willing to read up on it or seek advice if necessary. The biggest problem isn't judges who doesn't know everything - they have to deal with cases covering every possible discipline and can't possibly know everything about everything put before them. The problem is when they believe they do, or don't care, or don't want to admi…
(I wouldn't trust either the defense nor the prosecution to provide me with neutral information via their selected experts.)