Douglass recalls one of his earliest experiences with the extreme cruelties of enslavement. Captain Anthony had one day refused to intervene when Mr. Plummer, a brutish overseer and drunkard, had excessively beaten a young woman who was, in fact, Douglass’s cousin through his Aunt Milly. Not only were her neck and shoulders covered with scars from a cowhide, but Mr. Plummer gashed her head open with a hickory club. She arrived before Captain Anthony with her face covered in blood. Douglass had expected his old enslaver to become enraged. Instead, he told the young woman that she deserved the beating and demanded that she return home immediately, otherwise, he would give her another beating himself. Clearly, the old enslaver disliked “being troubled by such complaints” (92). Douglass explains how hearing the complaints of enslaved people would make the office of the overseer impossible. The enslaver would himself become the overseer, which was too difficult for one who enslaved many people.

There were occasions, however, when enslavers outdid overseers in their ability to mete out violent punishment. Douglass recalls a beautiful young aunt, Esther, who lived with Captain Anthony. A young man named Ned Roberts, just as attractive as she and a favorite of Colonel Lloyd’s, courted her.