Surveyor, penkeeper, overseer, slaveowner, and landholder Thomas Thistlewood (1721–86) was a white English immigrant to British colonial Jamaica who lived there from 1750 until his death. Canonical readings of Thistlewood’s archive quarantine his intellectual pursuits from his brutal plantation oversight, which included serial rapes of enslaved women. Taking a necessarily integrative approach, this essay analyzes Thistlewood’s diaries in conjunction with his reading notes, identifying the literary-scientific valences of his perpetration and documentation of rape. It argues that violence against enslaved women was central to Thistlewood’s Enlightenment thought and plantation management, in addition to considering the political stakes of choosing a language to describe his interactions with enslaved women. It proposes that antiracist feminist theory and art have the potential to critically disrupt analyses of slavery’s archives that threaten to reproduce or even exacerbate their violence.