This chapter tells the stories of three young people, living in the northeastern city of Recife, on the cusp of freedom during Brazil’s last decade of slavery. Their stories unveil the malleability of Brazilian bondage in its last gasp but also place in sharp relief the limitations and contradictions of both urban freedom and liberal modernity in a city structured by slavery. In highlighting the continuity and intersectionality inherent in urban struggles for freedom, the chapter seeks to open windows on relational dynamics that shape cities across the globe.