
While in Connecticut, Elias accepted Christianity and later collaborated with others in using Sequoyah's syllabary to translate the New Testament into Cherokee. He did well at school, but illness forced him to return home. Not before he'd met a young White woman, Harriet Ruggles Gold, from a Connecticut family with roots back to the Pilgrims. He courted her by letter. His cousin, John Ridge, had also found love in Connecticut. These two cross-race marriages caused controversy in Connecticut and forced the eventual closure of the mission school, but both young couples stuck to their guns and their families eventually decided to support them. Elias and John married the women the loved regardless of class and race. In 1825, the Cherokee National Council accommodated these and other marriages by allowing full Cherokee citizenship to children of a Cherokee father and White mother, something not allowed in traditional matrilineal society.

Despite the Supreme Court's decision upholding Cherokee rights to their Native land, Congress passed the Indian Removal Act of 1830 and President Jackson was intent on enforcing it. Elias began to see that Removal was inevitable and believed the best thing to do was to make the most favorable terms with the Americans, and leave before they were forced out. In this opinion, he was opposed by the National Council and John Ross, who still opposed Removal. Tempers flared between Natives who sided with Ross, and those who sided with Boudinot and the Ridges, who advocated acquiescing to Removal. Ross forbade Elias from publishing pro-Removal articles in the Phoenix and Elias resigned. In addition to his work on the Phoenix, Elias had written and later published an "Address to the Whites", arguing his reasons why the Cherokee should not be expelled from the homeland. A minor gold strike in Georgia sealed the Cherokee's fate. Elias and other Treaty Party leaders, including the Ridges, signed the Treaty of New Echota in 1835, ceding all Cherokee land in Georgia. John Ross, the Principal Chie at the time, refused to sign. Despite this, the Treaty was ratified.
Elias, dealing with Harriet's illness and eventual death, placed some of his children in school and sent others west with relatives before going to visit Harriet's family in Connecticut. When he returned to Georgia, he married another New England woman who had been a school teacher in New Echota, before migrating West to Oklahoma. He was by now destitute, and received assistance from a missionary society to settle in Park Hill and return to assisting with translating the Bible. Elias' second wife, Delight Sargent, died even as they settled into their new home. As the tragedies of the Trail of Tears unfolded in 1838-1839, anger boiled over at the men who had signed the Treaty of New Echota. On June 22, 1839, a group of Cherokee assassinated Elias outside his home. That same day, Major Ridge and John Ridge were also killed, and Elias' brother Stand Watie was severely wounded. Elias' children were sent to their respective grandparents in Connecticut.
The roots of this internal blood feud would run deep in the Cherokee Nation for decades, exacerbated by hardship and later, by the Civil War. Stand Watie later took revenge on a man whom he had believed killed his uncle, Major Ridge. He was tried for murder, and his attorney was his own nephew, Elias C. Boudinot, who later became a Confederate States Senator for Indian Territory.
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