Drawing on research in Cuba, Spain, and the United States, this paper examines what I call loyal subjectivity, the position from which colonial Cubans expressed themselves politically. Many Cubans of African descent drew on naturalized assumptions about the loyalty generated by the unequal, paternalistic relationships idealized between whites and blacks, and members of free-colored militias and well-placed slaves often professed loyalty to the very state that subordinated them. Yet, colonial officials and the island’s creole elite routinely policed the borders of loyal subjectivity, citing the loyalty of Cubans of color when they found it beneficial and depicting slave and free alike as inherently disloyal in order to warn of social unrest. Loyal subjectivity enjoyed a long history in the Spanish Empire, but the destabilizing effects of the American independence movements threw it into question. That slaves and free people of color continued to invoke their loyalty to the king of Spain during periods of constitutional rule and anti-colonial conspiracies reveals an untold story in the history of Cuba.