From Adrian Chen's Gawker long-read about that recent bust of the web's biggest online illegal drug marketplace:
The lesson of the Silk Road takedown isn't that Ulbricht was sloppy about security. It's that the idea of a world famous, anonymous illegal market is fatally contradictory. Ullbricht made some technical mistakes, but his biggest one was conceptual: buying his own hype that high-tech tricks would let him implement a radical free market fundamentalism that could never work politically.
Read the whole piece. Related: Chen's profile of Ross William Ulbricht.