Readers first hear about Captain Anthony, Douglass's first master, and Colonel Edward Lloyd at the start of chapter two. Douglass explains:
"My master was Colonel Lloyd's clerk and superintendent [Captain Anthony]." (ch. 2)
This is the most basic relationship between Douglass and Captain Anthony, but it does not explain the significance of their connection. Simply stated, Captain Anthony supervised the workings of Colonel Lloyd's plantation, and was therefore the master of Douglass, as well as the other slaves on the plantation.
Soon after Frederick Douglass is put under the authority of Captain Anthony, he sees his Aunt Hester being abused. Aunt Hester was a favorite of Captain Anthony, but one day she chose to disobey Captain Anthony and go out with another slave:
"Aunt Hester had not only disobeyed his orders in going out, but had been found in company with Lloyd's Ned; which circumstance, I found, from what he said while whipping her, was the chief offence." (ch. 1)
Aunt Hester had gone to see one of Colonel Lloyd's slaves; they were likely romantically involved, and it appears that Captain Anthony got jealous. This interaction between Aunt Hester and Colonel Lloyd's slave got her into serious trouble, and Douglass had to witness her brutal punishment. Captain Anthony called Aunt Hester horrible names and beat her:
". . . after rolling up his sleeves, he commenced to lay on the heavy cowskin, and soon the warm, red blood (amid heart-rending shrieks from her, and horrid oaths from him) came dripping to the floor." (ch. 1)
Briefly stated, Colonel Lloyd was the employer of Captain Anthony, and Captain Anthony was Douglass's master. One of Colonel Lloyd's slaves was associated with Douglass's aunt. This connection led to Frederick Douglass witnessing someone he loved being brutal beaten.
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