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Perhaps because of his education, or his grandfather's influence, Greenwood realized the benefits of assimilating with White society. While he deplored the encroachment of Settlers onto Choctaw land, he encouraged other reforms, such as education and improved farming methods. At age 22, he became Chief of the Western Division of the Choctaw Nation, where he worked to abolish the ancient "blood for blood" system of avenging violent crimes through blood feuds. Meanwhile, he repeatedly pleaded with government officials to stop the infringement of Settlers onto his people's land, asking that they be left alone in return for adopting these reforms.
But it was not to be. As more and more Settlers poured into Mississippi, pressure mounted on the Choctaw to cede their remaining lands and depart to new territory in Oklahoma. Andrew Jackson's election in 1828 convinced many Choctaw leaders that removal would be inevitable. After passage of the Indian Removal Act in 1830, the Chiefs of the other two districts resigned and the Council elected Greenwood LaFleur as the first Principal Chief of the Choctaw Nation. He drafted a treaty with what he believed to be the best terms possible for the Choctaw and sent it to Washington. The government sent representatives to Mississippi to negotiate with the Choctaw. LaFleur and other leaders selected what they hoped was the best land available in Oklahoma and believed they would be compensated by being allowed to keep some land in Mississippi. LaFleur and other chiefs signed the Treaty of Dancing Rabbit Creek in 1830, ceding most Choctaw lands in Mississippi and a storm broke loose.
Neither the Jackson Administration nor Mississippi authorities had any intention of honoring the provisions in the treaty allowing any Natives to stay on reserved lands in the state and become American citizens. A faction of the Council, furious with the chiefs and leaders who had signed the treaty, directed their ire at LaFleur and worked to have him deposed as Principal Chief. LaFleur's nephew was elected in his place. LaFleur did receive a grant of land and the right of his unmarried and minor children to continue living with him. A few other families also receive land, but most of the Choctaw Nation began their own Trail of Tears trek in 1831-33. In fact, it is the description of this Trek by a Choctaw leader as a trail of tears and death that gave the whole process of removing the Southeastern Tribes the name by which it is still known today.
Greenwood LaFleur decided that the best course of action for him was to move forward and not look back. He became a Mississippi State Senator and friends with Mississippi leaders such as Jefferson Davis. He was an admirer of Napoleon Bonaparte and named his plantation Malmaison, after Napoleon's country retreat. He became a successful planter and businessman, dying as the Civil War wound down in 1865.
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