This paper is the 19th Jaime V. Ongpin Memorial Lecture delivered by the author last 21 October 2020. The first section discusses inequality and its double-edged nature with respect to inclusive growth and development. The paper then elaborates on the related features of oligarchy and dynasty—two elements of inequality in the Philippine context. The author emphasizes the importance of analyzing the impact of the patterns of leadership for political dynasties, and the structure of the economy as regards potential business oligarchy. He outlines a three-point reform agenda to tackle the deep roots of inequality in the Philippines, focusing on social protection against aggregate shocks, and further enhancing competition in the political sphere and the market economy.