Part of the answer to violent crime prevention is to understand the route that those who have committed violent crimes have traveled in order to find ways to guide others from the road leading to such violence. An investigation of the lifelong personal and environmental factors affecting 37 men who were executed in 1997 focuses on distinctions between men in two categories based on heinousness of violent crime. The study aimed to identify risk factors and events that preceded the violent event and to compare the constellation of variables of the men who committed particularly heinous murders characterized by extreme rage and brutality with those whose crimes and criminal histories were characterized mostly by property crimes without intentional harm to people. Descriptive results suggest differences between the two groups of men related to 19 variables and the emergence of two diverse profiles of risk factors and life experiences.