There is much research published on Corporate Social Responsibility (CSR); what it means, what it looks like, how to do it and the benefits for an organization. There is a lot less research on Corporate Social Irresponsibility (CSI) although people have experienced this facet more frequently. This book offers a timely, interdisciplinary exploration of how corporate executives navigate the moral ambiguity between CSR and CSI. While CSR is often idealized as ethical and strategic, and CSI dismissed as aberrant or deviant, this work challenges that binary by showing how both can co-exist within the same organizations, leadership decisions, and legitimacy strategies. Drawing from executive psychology and behavioral ethics the book advances a new conceptual framework: corporate social behavior is shaped not by fixed moral commitments but by the dynamic interplay between psychological characteristics, contextual pressures and the strategic management of legitimacy. The research offers a realistic, behaviorally grounded lens for scholars, practitioners, and educators seeking to understand the contradictions of modern corporate leadership. It is especially relevant in today's climate of increasing scrutiny of corporate virtue signalling, reputational risk, and executive accountability.