The problem of the insider threat is extremely challenging to manage as it involves trusted entities who have legitimate authorization to the information infrastructure of an organization. It has been reasoned that the framing of the Fraud Pentagon may assist in predicting and preventing white collar crimes such as fraud. The Fraud Pentagon considers the elements of motivation, capability, rationalization, opportunity and arrogance which converge in a crime scenario. The current study considers the value of using the Fraud Pentagon in examining insider attacks. This paper evaluates this theoretical framing from an insider threat perspective, thereby assisting researchers, organizations and information security practitioners in understanding its complexity and its application to the insider threat problem.