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Simon Legree appears about midway through the story when he buys the main character, Uncle Tom, at a slave auction; Tom previously belonged to a much nicer master who was actually planning on setting him free eventually but was unfortunately murdered by loan sharks, causing Tom to be taken away from a relatively kind ownership and put up for sale where he could be bought by a monster such as Legree, illustrating another tragic injustice of the slave trade system.
On the plantation, Uncle Tom refuses to participate in the abuse of other slaves, firmly maintains his strong Christian ideals despite all Legree’s efforts to “break” him, and helps inspire hope in the other slaves, which Simon Legree will not accept. At the climax of the book, Legree orders Uncle Tom to help him track down two female slaves who he had witnessed escape, but Tom absolutely refuses to harm a woman. As a result Legree eventually has Tom beaten so badly that he dies from his injuries, and even Quimbo and Sambo feel bad afterwards. Shortly after the beating, George Shelby, a man from Tom’s previous family of owners arrives at Legree’s plantation in an attempt to take him back, having regained the ownership rights to him, only to find him dying. In the 1987 film version, Legree then insults Tom again in front of George's son, Christopher, who responds by furiously throwing several punches, knocking him down into the mud before leaving.
Due to the book’s unprecedented depiction of slavery at its worst, which the character of Simon Legree fully embodied, it was extremely controversial for its time to the point that is is considered a major contributing factor to the American Civil War. Legree is remembered as one of the most despicable characters in all of classic literature, and has influenced many later stereotypes of villainy.