This paper takes an innovative approach to understanding Islamic radicalism and militancy by utilising charismatic leadership theory to understand the critical role of charismatic leaders in the evolutionary development of the modern Islamist movement's most radical and militant strains. The study of charismatic leadership, rather than focusing exclusively upon the individual leader, is concerned with understanding the complex interplay of social, cultural, historical, psychological and ideological dynamics that create a context conducive for the emergence of the charismatic leader-follower relationship. Consequently, this paper offers critical insights into the phenomenon of Islamic radicalism and militancy. To this end, I argue that the charismatic leader has acted as the vehicle for the evolutionary development of the more radical and militant strains of political Islam. To support this contention, I identify a chain of charismatic leaders stretching across the entire chronology of the modern Islamist movement, reflecting an increasing radicalisation and propensity towards violence with the rise of each leader. I argue that these leaders have emerged during ever present and intensifying perceptions of crisis within communities of potential support, due to the transformative charisma phenomenon in Islamic radicalism and militancy. This innovative and multidisciplinary approach to mapping the evolutionary roots of modern Islamist terrorism will reveal the critical factors at play in the evolutionary development of contemporary Islamic radicalism and militancy from its roots in Islamic modernism in the late 1800s to today’s ‘self-generating mini-groups’