In 1818, Boudinot was enrolled in the American Board of Commissioners for Foreign Missions (ABCFM) School in Cornwall, Connecticut. During the time Boudinot was enrolled in boarding school, the Cherokee were petitioning “the government for aid to [educate] the Nation” and show that the Cherokee were willing to “accept white civilization”. Just as the petition was being drafted, Elias Cornelius, an agent from the American Board of Commissioners for Foreign Missions befriended Watie and became his educational benefactor. Elias Cornelius was founding a new school for people of all ethnicities and was “seeking to add representatives from southern Native American groups” and chose Boudinot as one of the students. It was later in life that Watie took the name Elias Boudinot in honor of the man responsible for his education.

Boudinot’s religious education began in 1808 at the age of 6 while studying at missionary school. In 1818 Elias Cornelius and other missionaries conducted schools in the Cherokee Nation in parts of what are now North Carolina, Georgia, and Tennessee, which Boudinot was then enrolled in. This missionary influence greatly impacted the religious beliefs of Boudinot, and in 1820 he officially converted to Christianity. Christianity became a large focus in his work with the Cherokee Nation and in 1824 he collaborated with others in order to translate the New Testament for his people.

In 1828, the Cherokee Nation released its first issue of the Cherokee Phoenix with Boudinot as its editor. Due to his unique qualifications (in addition to his exceptional education he was fluent in English and Cherokee) and having raised money for its establishment, Boudinot was the natural choice. Though ostensibly a bi-lingual newspaper, during his tenure as editor Boudinot printed only 16 percent of the paper's content into the Cherokee language; the journalist Ann Lackey Landini explains this discrepancy as demonstrating that the Cherokee Phoenix was foremost intended to influence white Americans outside of the Cherokee Nation. Between 1828 - 1832 Boudinot wrote numerous editorials arguing against the movement to remove the Cherokees from their Eastern lands instigated by Georgia and supported by president Andrew Jackson. Over a roughly four year period his editorials emphasized to its (largely) white readership that Georgia's disregard of the Constitution and past federal treaties with the Cherokees would not only hurt the Cherokees' progress in acculturating but also threatened the fabric of the Union. The Cherokee editor's arguments were adaptive and ingenious. His various avenues of argumentation included (but were not limited to) offering tangible evidence of Cherokee progress in "civilization" (conversion to Christianity, an increasingly Western educated population, and a turn toward lives as herdsmen and farmers, etc.) to indictments of the "easy" way in which treaty language was distorted by removal advocates for their own purposes.

In 1832 while engaged in a speaking tour of the North to raise funds for the Cherokee Phoenix, Boudinot received word that the Supreme Court had sustained the Cherokees' rights to political and territorial sovereignty within Georgia's claimed boundaries. Initially jubilant, the Cherokee editor soon after received the sobering news that President Andrew Jackson would not enforce the Court's decision, thereby leaving the Cherokees to Georgia's mercy. In this context, Boudinot began publicly advocating for his people to secure the best possible terms with the United States and make a treaty of removal. His changed position brought him widespread enmity from his countrymen. Former friends in the Cherokee government turned against him and his prominent relatives, John and Major Ridge, also recently "converted" treaty advocates, impugning their patriotism and denying them a fair hearing in council. Principal Chief John Ross later forbade Boudinot from discussing his pro-removal arguments in the pages of the Cherokee Phoenix. Facing censorship, Boudinot resigned his position in protest in the spring of 1832.

The Cherokee Phoenix

The first newspaper published by a Native American tribe gave a “voice to the American insiders” who were forced to become “outsiders”’. The premier edition of the Cherokee Phoenix was called the Tsalagi Tsu-le-hi-sa-nu-hi, and it “came off the small union press on February 21, 1828”. The Cherokee Phoenix office regularly received around one hundred newspapers from publishers far and wide because it was respected so much throughout the United States as well as Europe.The next year the second edition of the Cherokee Phoenix was called Cherokee Phoenix and Indians’ Advocate, its title reflecting in an effort to repel the white settlement and the Indian Removal Policy. Boudinot used the paper to present his arguments about Indian Removal.

An Address to the Whites (1826)

This speech was delivered in the First Presbyterian Church in Philadelphia, May 26, 1826. Boudinot spoke to illustrate the similarities between the Cherokee and the whites, and the changes that were being made in the Cherokee culture to match the United States. His purpose in doing so was to solicit donations for a national academy and for printing equipment in order to further “civilize” and “Christianize” the Cherokee population. Following the speech, a pamphlet was created under the same title, highlighting Boundinot’s original speech. An Address to the Whites was well received and “proved to be remarkably effective at fund-raising”.

Indian Removal was brought on by the discovery of gold in Cherokee territory, the growth of the cotton industry, and anti-Cherokee feelings that were prevalent in the Southeast. During 1838 to 1839, American soldiers evicted the Cherokee Indians from their Southeastern home to Indian Territory in present day Oklahoma. The path in which the Cherokees were marched during this removal was named the Trail of Tears due to the estimated 4,000 deaths that occurred along the way.

The Indian Removal Act, of 1830, was passed by the United States Government calling for all Indian peoples living east of the Mississippi River to be removed from this area and sent west. While the majority of the Cherokee lead by Chief John Ross opposed this act, Boudinot saw Indian Removal as inevitable and wished to secure Cherokee rights through a treaty before they were moved against their will. The belief of Boudinot and a small number of followers caused a division within the group and Boudinot used all of his skills as a writer and his persuasiveness in speech to gain the upper hand in the influence Indian Removal, even releasing a written attack on Chief John Ross, who opposed his ideas.

In 1832 Boudinot stepped down as editor of the Cherokee Phoenix due to its support of anti-removal views, but he continued working for promotion of the Indian Removal. The Treaty of New Echota was signed by Boudinot and his companions, giving up all Cherokee land east of the Mississippi River, without the consent of the Cherokee government or the approval of Chief John Ross.

In 1837 Boudinot relocated to the Western Cherokee Nation in the northeast quarter of what is today Oklahoma. He arrived impoverished and was forced to secure a loan from the American Board of Commissioners for Foreign Missions to finance the construction of a modest house in Park Hill. Reunited with his longtime collaborator Samuel Worcester, Boudinot returned to his vocation as a translator of the Gospel.

The hopefulness of Boudinot's new life ended abruptly shortly after the survivors of the Trail of Tears arrived in their new land. Following a council in which the "old settlers" and John Ross's supporters failed to reach an agreement of unification, a band of Cherokees met secretly to pronounce judgement on the Treaty Party leaders. On June 22, 1839, a group of Cherokees (probably supporters of Ross) murdered Elias Boudinot outside of his home. His cousin and uncle, John and Major Ridge, fell to Cherokee assassins on the same day. The trio were killed in accordance with the Cherokee "blood law" that made selling tribal land without the General Council's consent a capital crime. The Treaty Party leaders were also killed because many survivors of the Trail of Tears blamed them for the misery of their forced emigration.

Though John Ross denied any connection to the killings, Boudinot's brother Stand Watie blamed the Principal Chief. After the murders, followers of Watie and Ross engaged in violent conflict that lasted until a tenuous peace treaty was arranged by the United States in 1846. But the bitterness remained. During America's Civil War, the two factions once again split, Watie's supporters siding with the Confederacy, Ross's with the Union. The Treaty Party leaders murders were directly responsible for the violent post-removal factionalism that compounded the misfortune of the Cherokee Nation.