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A cruel, malicious, and sadistic man hardened by years of slave holding, Captain Anthony plays a formative role in Douglass’s early life. Captain Anthony acts as the clerk for Colonel Lloyd, which means he supervises all of Lloyd’s overseers at his various plantations. The father of Andrew, Richard, and Lucretia, Captain Anthony, though never confirmed in the Narrative, is also whispered to be Douglass’s father. In Douglass’s time, it was tragically customary for masters to impregnate their female slaves, a practice that slaveholders would profit from as it increased the number of slaves they owned. Captain Anthony is also responsible for separating Douglass from his mother at an early age, highlighting, in effect, one of the ways in which slave masters actively break down familial bonds between slaves and their families.
As both the first slave master we are introduced to in the Narrative and Douglass’s first slave master, Captain Anthony’s character introduces readers to the prototypical slave master and the relationship they share with their slaves. In particular, Douglass depicts Captain Anthony’s violence and the extent of his sadism when he recalls the scene in which he witnessed Captain Anthony whip Aunt Hester, whom Captain Anthony is curiously interested in. Both a “witness and a participant” to the beating, this scene, described with gory detail by Douglass, acts as the first instance of Douglass’s mental initiation into the terrors of slavery. Captain Anthony’s brutalization of Aunt Hester’s body and the pleasure he seems to derive from it lays out how violence is integral to slave holder’s attempts to dehumanize slaves. Furthermore, Aunt Hester’s beating at the hands of Captain Anthony illustrates the abuse that female slaves endure. In placing Captain Anthony as central to the beginning of the Narrative, Douglass exposes the evil of slavery and the harsh realities that slaves endure at slave plantations. That is, Captain Anthony’s actions and behavior toward his slaves are not unique, but commonplace.