This chapter—“Personal Adversity and Justifying Illegal and Costly Entrepreneurial Action”—shifts even more to the dark side of entrepreneurial action in the face of chronic adversity. Specifically, in this chapter, we explore bunkerers—oil thieves—to provide a richer understanding of how individual entrepreneurs interpret their contexts and engage in entrepreneurial action that creates significant negative outcomes. We outline a personal adversity model to explain the entrepreneurial process whereby bunkerers engage in, justify, and persist with entrepreneurial action that causes substantial damage to the local environment, communities, and entrepreneurs’ health. We show how entrepreneurs claim both high and low levels of control to justify the same action and how entrepreneurs entangle themselves and others when justifying their harmful entrepreneurial action and the resulting destruction.