During the first three decades of the twentieth century, a cluster of self-educated workers that called themselves obreros ilustrados (enlightened workers) sought to dominate the means of knowledge production, reproduction, and documentation. The discourses produced by this group of working-class intellectuals did not challenge but complemented the elite's contempt towards the laboring masses. In order to be legible in the “Archive of Puertorriqueñidad”—an archive crossed by centuries of colonialism, slavery, and imperial violence—these ragged intellectuals created various layers of exclusions that silenced those individuals that unapologetically upheld their Blackness. These silencing practices not only had power in the moment in which they took place but also influenced later historical production. To explore these dynamics, this paper uses the stories of Juana Colón and Mateo Pérez Sanjurjo. Both were highly-respected Black illiterate labor organizers that were absent in the historical narratives obreros ilustrados wrote about the labor movement. Ultimately, this article seeks to create counterarchives by unearthing, imagining, and retelling the lives of those that were not deemed worthy of being represented in the historical record.