This chapter highlights themes which are learned in studying espionage to articulate the risk of the insider to share proprietary information. Considerable investment has been made by the US government to study the behavioral risk indicators associated with "insider threat" and espionage. Individuals with certain types of personality disorders are considered to create greater risk of insider threat than anyone identified as mentally ill. As a result of numerous espionage arrests in the 1980s, the government funded a research project that was initiated as an intelligence community project comprised of behavioral, security, and counter-intelligence professionals. The insider threat has a set of behaviors that arise out of entitlement and dissatisfaction. The psychopathic personality style is frequently identified as the constellation of character traits of greatest risk for insider threat. One of the most frequently offered rationalizations by convicted trusted insiders was that "physical security was lax; tighter security would have been more of a deterrent".