Renaissance Florence paid homage to the values and rights associated with freedom. It was governed by a body of citizens rather than by a prince, and Florentines did not take their right of self-government for granted. Indeed, Florentines treated freedom as both prerequisite and ultimate expression of virtue. Yet, somehow Florence also was the scene of a burgeoning of urban-domestic slavery. Was this simply a mismatch of rhetoric with sociological reality? This chapter explores the life and times of Leon Battista Alberti, author of the most penetrating exploration of the slavery-into-freedom dialectic of any modern Western writer. Because of his own life circumstances, including illegitimacy, Alberti was able to see the essence of the slave condition, and its dialectical relation to freedom, and express it cogently in his writings.