This book synthesises cutting-edge scholarship on artificial intelligence, democratic theory, and educational leadership with three long-standing intellectual pillars of the author's work: Deweyan pragmatism and inquiry-based moral reasoning, non-foundational epistemology, and moral craftsmanship as the practical enactment of ethical leadership. The book examines how AI is reconfiguring agency, authority, and public reason; how algorithmic systems threaten or support democratic life; how educators and civic leaders can cultivate ethical judgment in AI-mediated environments; and how institutions can design governance structures that protect transparency, accountability, and the public good. The distinctive argument is that educative leadership--leadership that intentionally cultivates inquiry, critical consciousness, and collective learning simultaneously at personal, institutional and system levels--is essential to preserving democratic integrity against the combined risks of algorithmic misinformation, surveillance capitalism, digital authoritarianism, and cyber insecurity.