This chapter examines the complex ways in which political, economic, cultural and moral foundations shape pervasive conceptions and practices of educational leadership in Singapore. It argues that school leadership reflects fundamental socio-political values that underpin Singaporean governance: these core values are built on three pillars -- the developmental state, neo-liberalism and meritocracy. The chapter sketches the historical development of education and leadership since the foundation of Singapore as an independent republic in 1965, concluding that the instrumentalist imperative of education (preparation of a suitably qualified workforce, and cultivation of a loyal and harmonious citizenry) has dictated the purpose of schooling and thus the approach to leadership in Singapore's education system. Further dimensions of leadership are explored in terms of its 'tight-coupling' between the hierarchical layers of the education system, and at school level, a 'social compact' between school leaders and teachers, which is reinforced by a paternalism associated with Confucianism. In emphasising the tight-coupling across the whole of society and its education system, the chapter concludes by powerfully illustrating how a 'state-citizen compact' based on values of trust, dependency and self-responsibilisation are reflected in the wider community, even in the lives of low-income, ethnic minority families. [For the complete volume, "The Cultural and Social Foundations of Educational Leadership: An International Comparison. Educational Governance Research. Volume 16," see ED615841.]