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Gore had worked at one of the outlying farms and had proven his mettle. He was "proud, ambitious and persevering. He was artful, cruel, and obdurate. He was just the man for such a place, and it was just the place for such a man." Slaves could never talk back and defend themselves. Gore often saw a look or heard a word which displeased him, and subsequently doled out the severest punishment. Accusation was the same as conviction, and conviction was the same as punishment.
While Gore required the most blatant servility from a slave, he often evinced the same to Colonel Lloyd. He wanted to be the highest of the overseers and desired nothing more once he was there. He was brutal and duplicitous and had no conscience. He seemed to notice everything, and the slaves hated him the most of all the overseers.
He was young but serious, never smiling or laughing. He was not talkative or humorous. He was not reluctant to fulfill any duty his post required of him and never showed any remorse or hesitation. Douglass saw his relentless brutality as "equaled only by the consummate coolness with which he committed the grossest and most savage deeds upon the slaves under his charge."
One slave, Demby, learned firsthand the lengths to which his evil went. Demby was being whipped when he escaped into the river and refused to come out. Gore said that he would count to three and if Demby did not come out, he would shoot him. After Gore reached three, he calmly and coolly shot Demby dead.