For the first time, young Frederick begins to see the darker side of Captain Anthony, and yet Douglass, in retrospect, describes his “Old Master” with magnanimity and even pity. Anthony was “not by nature worse than other men” (27). Indeed, had he been raised in the North, in a free society, Anthony “might have been as humane a man as are members of such society generally” (27). Instead, he appeared an “unhappy man” who “wore a troubled and at times a haggard aspect” and often was seen “walking around, cursing and gesticulating as if possessed by a demon” (27-28).

On one occasion, Anthony refuses to protect a young slave woman, Frederick’s cousin, who has been beaten by the overseer, Mr. Plummer. “Old Master” blames the young woman for the beating, tells her she probably deserved it, and orders her to return to work. Another young slave woman named Esther, who possesses the “curse” of “personal beauty,” is brutally whipped by Anthony because she is being “courted” by Ned Roberts, one of Colonel Lloyd’s slaves, and she refuses to stop seeing Ned even when Anthony orders her to do so (29-30). Douglass strongly implies that Anthony wanted to keep Esther for himself.