As the adoption of electronic health records has reached unprecedented levels and continues to rise rapidly, the issue of criminal activity related with unauthorized patient data acquisition, black market distribution, and illegal exploitation/use becomes increasingly important. This article will provide a historical review of recorded data breaches that resulted in extensive patient data leaks as well as subsequent efforts of monetization via black market structures that utilize the anonymity and counter-tracking environment that the dark/deep web and cryptocurrency provide. It will also focus on the methods and tools used by the villains, the types of vulnerabilities that can result in a successful attack, as well as latest developments and future trends in the field of scientific, technical, and legal/regulatory countermeasures that can be employed in order to prevent sensitive health data from falling into the wrong hands.