This chapter provides a reinterpretation of Modesto Brocos’ well-known painting, Redenção de Cã. Its goal is to resituate the notorious canvas within the complex transitions from bondage to freedom that began in the 1870s and lingered through the 1910s. It argues that Redenção is a painting just as much about a black nineteenth-century emancipationist past as it is about a whitened twentieth-century post-emancipation future. This argument calls into question previous interpretations that have been reluctant to interrogate what is to be made of the Black characters in the canvas and how Brocos – whose contact with Afro-Brazilians began in the 1870s, during his student years, and intensified after 1890 – drew from direct contact with the formerly enslaved to paint his enigmatic portrait of bondage redeemed.