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As white settlers poured across the mountains, the Cherokee tried once again to compensate themselves with territory taken by war with a neighboring tribe. This time their intended victim was the Chickasaw, but this was a mistake. Anyone who tried to take something from the Chickasaw regretted it, if he survived. After eleven years of sporadic warfare ended with a major defeat at Chickasaw Oldfields (1769), the Cherokee gave up and began to explore the possibility of new alliances to resist the whites. Both the Cherokee and Creek attended the 1770 and 1771 meetings with the Ohio tribes at Sciota but did not participate in Lord Dunnmore's War (1773-74) because the disputed territory was not theirs. On the eve of the American Revolution, the British government scrambled to appease the colonists and negotiate treaties with the Cherokee ceding land already taken from them by white settlers. To this end, all means, including outright bribery and extortion, were employed: Lochaber Treaty (1770); and the Augusta Treaty (1773) ceding 2 million acres in Georgia to pay for debts to white traders. For the same reasons as the Iroquois cession of Ohio in 1768, the Cherokee tried to protect their homeland from white settlement by selling land they did not really control. In the Watonga Treaty (1774) and the Overhill Cherokee Treaty (Sycamore Shoals) (1775), they sold all of eastern and central Kentucky to the Transylvania Land Company (Henderson Purchase).

Despite the fact that these agreements were a clear violation of existing British law, they were used later to justify the American takeover of the region. The Shawnee also claimed these lands but, of course, were never consulted. With the Iroquois selling the Shawnee lands north of the Ohio, and the Cherokee selling the Shawnee lands south, where could they go? Not surprisingly, the Shawnee stayed and fought the Americans for 40 years. Both the Cherokee and Iroquois were fully aware of the problem they were creating. After he had signed, a Cherokee chief reputedly took Daniel Boone aside to say, "We have sold you much fine land, but I am afraid you will have trouble if you try to live there."

Not all of the Cherokee honored these agreements. Cui Canacina (Dragging Canoe) and the Chickamauga refused and kept raiding the new settlements. At the outbreak of the Revolution, the Cherokee received requests from the Mohawk, Shawnee, and Ottawa to join them against the Americans, but the majority of the Cherokee decided to remain neutral in the white man's war. The Chickamauga, however, were at war with the Americans and formed an alliance with the Shawnee. Both tribes had the support of British Indian agents who were still living among them (often with native wives) and arranging trade. During 1775 the British began to supply large amounts of guns and ammunition and offer bounties for American scalps. In July, 1776, 700 Chickamauga attacked two American forts in North Carolina: Eaton's Station and Ft. Watauga. Both assaults failed, but the raids set off a series of attacks by other Cherokee and the Upper Creek on frontier settlements in Tennessee and Alabama.

The frontier militia organized in response made little effort to distinguish between hostile and neutral Cherokee, except to notice that neutrals were easier to find. During September the Americans destroyed more than 36 Cherokee towns killing every man, woman and child they could find. Unable to resist, the Cherokee in 1777 asked for peace. The Treaties of DeWitt's Corner (May) and Long Island (or Holston) (July) were signed at gunpoint and forced the Cherokee to cede almost all of their remaining land in the Carolinas. Although this brought peace for two years, the Chickamauga remained hostile and renewed their attacks against western settlements in Tennessee, Alabama, and Kentucky during 1780. After more fighting, the second Treaty of Long Island of Holston (July 1781) confirmed the 1777 cessions and then took more Cherokee land.

Through all of this, the Chickamauga fought on but were forced to retreat slowly northward, until by 1790 they had joined forces with the Shawnee in Ohio. After the initial Indian victories of Little Turtle's War (1790-94), most of the Ohio Chickamauga returned south and settled near the Tennessee River in central Tennessee and northern Alabama. From here, they had the unofficial encouragement of the Spanish governments of Florida and Louisiana and began to attack nearby American settlements. One of these incidents almost killed a young Nashville attorney/land speculator named Andrew Jackson, which may explain his later attitude regarding the Cherokee.

Dragging Canoe died in 1792, but a new round of violence exploded that year with the American settlements in central Tennessee and northern Alabama. After two years of fighting with Tennessee militia, support from other Cherokee declined,

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