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It's actually surprisingly hard to get OPSEC right, because most of the time you either don't think what you're doing warrants a huge amount of resources spent prosecuting you, or you don't realise how big it is until it's too late.

One of the biggest links from the Silkroad owner's identity outside of tor was the fact that he promoted his own site in the early days, using an alias he had used to ask questions on stackoverflow. He probably didn't realise how important good OPSEC was until much later in the game.

I recently had the chance to help the FBI in an effort to catch a child abuser in collaboration with an NGO. It was very interesting to see how "techies" can piece together a scary level of detail about someone's identity using everyday things like the clothes they wear (if they bought them online) or how their house is decorated. Details of how were withheld from us, but the suspect got caught.