This book focuses on understanding values-based leadership in rules-based organizations. It assists leaders, whether they are Board Members, CEOs, Executives, or Middle to Lower Management, in understanding how to enact and embody values/virtues-based leadership. Of particular interest to readers are the discussions around primary data collected from participants at three levels of leadership in the military who responded to a vignette and interview. The results of the case study are used in conjunction with current trends or practices that are considered unethical and questionable behavior which undermine trust and integrity in organizations. By using a case study from the military, the highly codified rules-based organization illustrates the tensions, contradictions, and paradoxes that leaders face and provide a teachable moment for leaders in all industries the complexities in achieving virtue eudaimonia. In doing so, the book also illustrates the tension and complexities between an individual’s multiple subject positions, organizational rules and values, and the ability to have agency.