Focusing on the life trajectory of Brazilian engineer Teodoro Sampaio, this chapter discusses the possibilities for social transformation available to men of color during and after Brazilian abolition. Sampaio lived through a time when the dismantling of slavery coincided with a racialization of social status, justified by the postulates of scientific racism. His trajectory thus illuminates how an educated son of a freed mother could make his way through a society that was reinventing socio-racial hierarchies even as slavery lost its legitimacy. This chapter aims to elucidate the intricate network of relationships and endeavors engendered by a pardo, born on a large slave property, who managed to become an engineer and manumit his three brothers, who were enslaved on the same plantation where Sampaio himself was raised free. Based on Sampaio’s autobiographical texts, books, articles, and private correspondence – as well as on what his contemporaries wrote about him – this chapter will reflect on what we can learn from Teodoro Sampaio’s life about what it meant to be a free, lettered pardo man during the dismantling of Brazilian slavery.