This chapter looks at the complex emerging colonial society that combined a remnant of indigenous inhabitants, white settlers, African slaves, and free men and women of different races. It also discusses asymmetrical human interactions among the races—whites, blacks and mulattos, and Amerindians and mestizos—and pays much attention to conflicting and overlapping hierarchies and social structures that developed on the island, as well as to the ways in which particular groups and individuals challenged those structures and hierarchies. Lastly, in this chapter I expand on the thesis of the “Two Cubas”: one, an urban, official, and mercantilist Havana, the region’s navigation hub; the other, the Cuba of the east, peasant, remote, relaxed, and rebellious, where smuggling and tobacco-farming predominated.