It's worth remembering that security (here including the information security involved in hiding identity) is not boolean. The value of the prize matters. A pen

It's worth remembering that security (here including the information security involved in hiding identity) is not boolean. The value of the prize matters. A penny (or a diary) hidden under a mattress can be considered "secure" - three million dollars can't, especially when people know you have those three million somewhere. The first mistake this guy made was doing something that made the authorities want to know who he was, and have a good excuse for expending enormous resources (if necessary) to do that. Had he used TOR correctly, it would have been harder for them, but it's very likely they would still have succeeded. Plenty of people here are making comments that sound suspiciously like advice for breaking the law. I realize that that's not actually the case -- lessons taken from somebody who did something illegal and got caught can be perfectly applicable to someone trying to do something legal, privately. We all should be aware, though, that TOR and other privacy tools (and other non-privacy tools, like bittorrent) have a reputation for being designed for criminals, and it's not a good idea to seem to sympathize too strongly with people who use TOR to send in bomb threats.