The political development of Davao indicates a pattern of leadership marked by tough, unconventional, and high-handed authority. Politicians who exhibit this kind of leadership are recognized and voted to power. They utilize coercive forces and offer the rhetoric of violence and toughness, and a sense of authority that is less of a strongman but that of a political operative adept at reading the sentiments of political loyalty of violent forces. This paper aims to show how frontier politics are interlinked with the politics of prowess as the defining dynamics in Davao. The paper relies on the biographies of politicians who are considered as having shaped not only Davao but have shaped from Davao the conduct of national politics as well. It argues that Davao’s local politics and politicians are closely entwined with and to some degree consequential to the national political development. It examines how the politics of prowess, are reflected in the ability of a political leader to mobilise local, national, and regional state, private, social, and political resources for the advancement of their political career.