The assimilation of former militants into leadership roles as traditional rulers or corporate leaders in Nigeria presents significant challenges to national security and governance. This article explored these concerns through two case studies: His Royal Highness Ateke Tom, an ex-militant who became the Okochiri monarch, and Dokubo Asari who transitioned into a business leadership role with the Niger Delta People’s Volunteer Force (NDPVF). The primary objective of this study was to assess their effectiveness in contributing to regional stability, economic development, and governance while addressing issues of legitimacy, reconciliation, and ethical governance. Utilizing a comparative analysis, the study examined the dual roles of these ex-militants in post-conflict leadership and their impact on the Niger Delta region. The research was grounded in conflict resolution and governance theories, providing a theoretical framework to understand the complex dynamics of their leadership roles. The findings revealed that while integrating ex-militants into leadership can foster economic growth and stability, it also raises concerns about the legitimacy of their authority and the long-term sustainability of peace in the region. The study recommended harnessing the potential of ex-militants in leadership positions by promoting inclusive governance, enhancing community participation, and ensuring that their roles do not undermine national security. By retracing their paths from militancy to leadership, this research highlights the need for careful management of such transitions to achieve positive outcomes in post-conflict regions.