Since the 1960s, archaeological and historical explorations have been concerned with understanding the evolution of inequality cross-culturally. Every generation of scholars has sought to understand the transformation from egalitarian bands to today’s world of ‘savage inequalities’. Archaeology has accumulated the data to engage in cross-cultural synthesis of global archaeologies and histories. But some areas are still underrepresented. In this chapter, I draw from recent archaeological research in on the East African Coast to evaluate the cultural trajectories of communities that flourished during the region’s medieval period leading to the emergence of socially and politically hierarchical chiefdoms, polities, and states. Contrary to earlier migration theories, the current reconstruction strengthens the view that the adoption of agriculture, market-based exchange, and urban centered state structures were the main catalysts for building communal and personal wealth in medieval Africa as in other regions around the world. Networks of interaction were crucial in connecting emergent cities to their hinterlands and to merchants across the sea. The chapter answers two crucial questions. How and in what ways did regional trade serve as the kernel upon which the medieval Swahili state arose? What were the mechanisms through which emerging elites manipulated economic and political power?