John Ross made an unlikely looking Cherokee chief. Born in 1790 to a Scottish trader and a woman of Indian and European heritage, he was only one-eighth Cherokee by blood. Short, slight and reserved, he wore a suit and tie instead of deerskin leggings and a beaver-skin hat. His trading post made him more prosperous than most Indians—or white men. But his mother and grandmother raised him in a traditional household, teaching him the tribe’s customs and legends. When the Cherokees embraced formal education—they were adapting quickly to a world they knew was changing—he attended school with their children. After his mother died, in 1808, Ross worked at his grandfather’s trading post near present-day Chattanooga, an important way station on the road to the West. There he encountered white settlers moving onto Cherokee land.

To a degree unique among the five major tribes in the South, the Cherokees used diplomacy and legal argument to protect their interests. With the help of a forward-looking warrior named Major Ridge, Ross became the tribe’s primary negotiator with officials in Washington, D.C., adept at citing both federal law and details from a dozen treaties the Cherokees signed with the federal government between 1785 and 1819. In the 1820s, as they enjoyed one of the most promising periods in their history—developing a written language, adopting a constitution and building a capital city—Ross became the Cherokees’ principal chief, and Ridge was named his counselor.

All the while, white settlers kept coming.

The state governments did little to discourage them, ignoring federal treaties and even abetting the taking of Indian land through bribery, fraud and coercion. When the tribes turned to Washington for redress, federal officials proved ineffectual or hostile, depending on the administration. One by one the other major Southern tribes—the Chickasaws, the Choctaws, the Creeks and the Seminoles—signed treaties that required them to uproot to the far side of the Mississippi River. But the Cherokees held out.

They finally succumbed in 1838, when they were marched 800 miles into an extremely bitter winter. The survivors of the journey to what is now Oklahoma would call it the Trail of Tears. The exodus was a communal tragedy, as it had been for the other tribes. But in the case of the Cherokees, their resistance and defeat were reflected as well in the rise and collapse of the extraordinary partnership between Ross and Ridge.

The two had met in 1813, the year Ross had a political awakening while on a trading trip through what would become Alabama. A Creek chief named Big Warrior told him a faction of his tribe had become openly hostile to European customs and settlers. These Red Sticks, as the faction called itself, were threatening civil war. Ross, only 22, recognized a hazard to the Cherokees: such a war would likely endanger white settlers, and given that whites scarcely distinguished between tribes, any retaliatory move they made would threaten every Indian. So he wrote an urgent note to the local U.S. Indian agent: “The intelligence received from the Creek Nation at this present crisis is very serious. The hostile party is said to be numerous and if assistance is not given to the Big Warrior and his party by the U.S. it is apprehensive that they will be conquered from the Superior force of the rebels.”

When Tennessee militiamen intervened that fall, the Cherokees joined them, both to protect their own interests and to curry favor with whites. Ross, whose early record shows not even a fistfight, was among the 500 Cherokees who enlisted. So was Ridge, already a renowned warrior.

The Cherokees called him “the man who walks on the mountaintop,” for his preferred means of traversing the woods; white men interpreted that as “ridge.” He would appropriate the rank he was given during the Creek War as a first name. Born in 1770 or 1771, Ridge straddled two generations: in his youth he had fought white settlers, but as a man he welcomed European traditions. “He appears very anxious that all his people should receive instruction, and come into the customs of the whites,” the missionary William Chamberlin would write in 1822. Indeed, Ridge was one of the first Cherokees to send his children to missionary schools.

Ridge’s embrace of change was initially unpopular among his tribesmen, but few questioned his loyalty. In 1807 he had helped kill the powerful Cherokee chief Doublehead for selling tribal hunting grounds for personal profit. And in 1808, when white U.S. Indian agents enticed principal chief Black Fox into proposing that the tribe move west, Ridge had been the first to protest. “As a man he has a right to give his opinion,” Ridge declared before the Cherokees’ ruling council, “but the opinion he has given as the chief of this nation is not binding; it was not formed in council in the light of day, but was made up in a corner—to drag this people, without their consent, from their own country, to the dark land of the setting sun.”

By 1813, Ridge had seen enough of politics to understand the diplomatic advantage to be gained from joining the Tennesseans against the Red Sticks. The Cherokees might even have realized that advantage had it not been for the militia leader they fought under: Andrew Jackson.

As a boy in the 1770s, Jackson had listened to stories of Indian violence toward settlers, and with no apparent understanding of their motives, he developed prejudices that he—like many Americans of his day—held throughout his life. He routinely called Indians “savages” and people of mixed heritage “half-breeds,” and he was unshakable in his conviction that Indians should be removed from the South. When news that the Red Sticks were attacking settlers reached him in Nashville, he asked: “Is a citizen of the United States, to remain under the barbarous lash of cruel and unrelenting savages?”

In March 1814, Jackson tracked the Red Sticks to Horseshoe Bend, a peninsula formed by the Tallapoosa River in what is now Alabama, and launched a frontal assault on their breastworks. His troops might have been repulsed had the Cherokees not crossed the river and attacked from the rear. Caught between two attacking forces, the Red Sticks lost nearly 900 warriors in what proved to be the decisive battle of the war.

That day, a Cherokee named Junaluska saved Jackson from an attacker, prompting the Tennessean to declare, “As long as the sun shines and the grass grows, there shall be friendship between us.” But in the peace treaty he negotiated with the Creeks, Jackson confiscated 23 million acres of land in Alabama and Georgia—some of which belonged to the Cherokees.

In 1816, the Cherokees’ principal chief, Pathkiller, sent a delegation to Washington to reclaim that land. The delegates, who included Ross and Ridge, made quite an impression while mingling with the city’s elite. Ridge sang a Cherokee song so raunchy his interpreter declined to translate it. (“It’s just like a white man’s song,” Ridge joked in his limited English, “all about love and whiskey.”) Even so, a reporter from one newspaper, the National Intelligencer, wrote that “their appearance and deportment are such to entitle them to respect and attention.”

Because of his fluency in English, Ross became one of the Cherokees’ lead negotiators, and he proved more than a match for Secretary of War William Crawford. “It is foreign to the Cherokee principle to feign friendship where it does not exist,” Ross said, implying a contrast with Washington bureaucrats. “You have told us that your Government is determined to do justice to our nation and will never use oppressive means to make us act contrary to our welfare and free will.” The treaties the Cherokees had signed generally required them to give up large tracts of land but guaranteed their rights to whatever remained. Now they wanted those rights enforced.

After more than a month of back-and-forth debate, Crawford finally relented: the United States would restore the bulk of the land the Cherokees claimed. In return, the Cherokees agreed to sell a small tract in South Carolina for $5,000 (the 2011 equivalent of $78,800) to the state government.

In a move intended to prevent local chiefs from accepting bribes to sell off Cherokee land, the Cherokee council in 1817 established a national committee to handle all tribal business. When Ross arrived at the council meeting as a spectator, Ridge led him into a private conference and told him that he would be one of 13 members of the committee. Ross was only 26—a young man in a community where leadership traditionally came with age. Just a month later, he would have to confront Andrew Jackson directly.

Jackson had been serving as a federal Indian commissioner when he launched his first effort to remove the Cherokees en masse. In 1817, he appeared with two other agents at the Cherokees’ council in Calhoun, just northeast of what is now Cleveland, Tennessee, to inform the tribe that if it refused to move west, it would have to submit to white men’s laws, no matter what any treaties might say. The chiefs dismissed the agents without hesitation. “Brothers, we wish to remain on our land, and hold it fast,” their signed statement said. “We appeal to our father the president of the United States to do us justice. We look to him for protection in the hour of distress.”

Through threats and bribery, Jackson eventually persuaded a few thousand Cherokees to leave Tennessee; Ross became the spokesman of those who remained—some 16,000 resolved to hold their ground. After years of trading land for peace, the council in 1822 passed a resolution vowing never to cede a single acre more. “If we had but one square mile left they would not be satisfied unless they could get it,” Ross wrote to Secretary of War John C. Calhoun that October, referring to state Indian commissioners who regularly tried to buy out the tribe. “But we hope that the United States will never forget her obligation to our nation.”

In 1823, Georgia officials, recognizing Ross’ growing power, dispatched a Creek chief to personally offer him $2,000 (about $42,300 today) to persuade the Cherokees to move. Ross asked for the offer in writing—then took it to Ridge. Together they exposed the bribery attempt in front of the tribal council and sent the emissary packing.

At the same time, what historians would call the Cherokee Renaissance was bringing the tribe more fully into the 19th century. Sequoyah, a mixed-blood Cherokee, distilled the Cherokee oral language into a set of 86 symbols; soon, the tribe enjoyed a higher rate of literacy than the settlers who called them savages. They started a newspaper, the Cherokee Phoenix. In 1825—after new president John Quincy Adams promised to honor the federal government’s obligations to Indians—the Cherokees began their largest public works project, building a council house, courthouse and public square in northwestern Georgia, near present-day Calhoun. They named it New Echota, in honor of a village lost to settlers years earlier.

Ridge could not hide his pride. “It’s like Baltimore,” he told a visiting missionary, comparing it to the largest city he’d ever seen.

In 1827, the Cherokees adopted a written constitution that defined a government with executive, legislative and judicial branches. That same year, they acquired new leadership: Pathkiller died, and Charles Hicks, his assistant and logical successor, followed him two weeks later. The council appointed an interim chief, but Ross and Ridge were making the decisions—when to hold council, how to handle law enforcement, whether to allow roads to be built through tribal land. The two men so relied on each other that locals called the three-mile trail between their homes the Ross Ridge Road.

If Ross aspired to be principal chief, he never spoke of it. But Ridge promoted his protégé’s candidacy without naming him, dictating an essay to the Cherokee Phoenix that described removal as the tribe’s most pressing issue and warning against electing leaders who could be manipulated by white men. Until then, every principal chief had been nearly full-blooded Cherokee. When the council voted in the fall of 1828, Ross—who was only 38—was elected principal chief by a vote of 34 to 6. The council named Ridge his counselor.

A month later, Andrew Jackson was elected president of the United States. He would test the Cherokees’ leadership soon enough, but even before Jackson was inaugurated, Georgia presented a more immediate threat, passing laws that annexed Cherokee land and extended state laws to that territory. Within two years, the state would require any whites living among the Indians—such as missionaries—to sign an oath of allegiance to the state or get out.

Ross spent much of those two years in Washington, trying to overturn the new laws. Jackson’s secretary of war, John Eaton, told Ross the tribe’s troubles had been self-inflicted: by adopting a constitution, it had insulted Georgia’s sovereignty. As the months passed and Georgia’s deadline loomed, some 500 Cherokees abandoned their homes and headed west to join earlier emigrants. Major Ridge grew alarmed: the fewer Cherokees who remained, the easier they would be to displace. He set out on a speaking tour intended to calm tribe members inclined to flee. He told large crowds that they had been targeted not because they were weak, but because they were strong and had “unexpectedly become civilized.”

“It is too much for us now to be honest, and virtuous, and industrious,” he noted sarcastically, “because then are we capable of aspiring to the rank of Christians and Politicians, which renders our attachment to the soil more strong.”

When Ross returned from Washington, he joined Ridge’s campaign, rousing crowds with his defiant oratory. He told a missionary friend that his “hopes of success were never greater.”

But more trouble was on the way: gold had been discovered on tribal land in Georgia, drawing a new wave of settlers, and President Jackson was not about to stop them. In February 1830, the tribe exercised its legal right to evict squatters; Ridge, then 60, led a two-day raid in which Cherokees burned settlers’ houses and outbuildings. After Georgia authorities sent a posse after the Cherokees, gunfire rang out through northern Georgia.

The timing could hardly have been worse: at that very moment, Congress was hotly debating the Indian removal bill, a measure Jackson had introduced to establish an “ample district” west of the Mississippi to which the Indians of the South could move. On one hand, he had said in his inaugural address, Indian emigration “should be voluntary, for it would be as cruel as unjust to compel the aborigines to abandon the graves of their fathers and seek a home in a distant land.” On the other, he made it clear that Indians could not live as independent peoples within the United States: “surrounded by the whites with their arts of civilization” they would be doomed “to weakness and decay.” They had either to submit to state laws or go.

Congress passed the removal bill that May, and by September Jackson had begun negotiating with the Chickasaws, the Choctaws and the remaining Creeks to move west. Within four years they would be under land cession treaties or on the move. Some Seminoles also left in the early 1830s, and others fought the Army in Florida for several years. But Ross refused even to meet with Jackson. Instead, he turned to the U.S. Supreme Court, asking the justices to invalidate Georgia’s removal law.

As the court’s spring session opened in March 1831, Georgia officials roamed the Capitol to rally states’ rights advocates to the idea of stripping the justices of their power to review the acts of state governments. The justices—in an act that historians would say reflected their worry over the talk coming out of Congress—ruled that they lacked jurisdiction over the Cherokees’ claims against Georgia. Chief Justice John Marshall offered their only hope when he wrote that “the Indians are acknowledged to have an unquestionable...right to the lands they occupy.”

Ross used that opinion to bring another suit, this time challenging the arrests of white missionaries who had refused to swear allegiance to Georgia. Now faced with a case involving U.S. citizens, the court was forced to act. On March 3, 1832, the justices declared the arrests unconstitutional and said Georgia could not extend its laws to Cherokee land. They also ruled that the federal government, by treaty, had the authority to protect Indian tribes from state intrusions. Taking aim at removal, Marshall wrote, “Protection does not imply the destruction of the protected.”

Ross wrote to some Cherokee delegates in Washington, “[T]here are great rejoicings throughout the [Cherokee] nation.”

But Jackson declared the ruling “stillborn.”

A month later, Major Ridge’s son John and two other Cherokees were in Washington, trying to determine whether the federal government would enforce the court’s decision. Jackson met with them only to send them home to tell their people “that their only hope of relief was in abandoning their country and removing to the West.”

Jackson’s resolve unnerved the younger Ridge. Gradually, he realized that court victory or not, his people were losing ground. But he could not relay that message to the tribe for fear of being branded a traitor, or killed. He was even hesitant to confide in his father, believing Major Ridge would be ashamed of him.

But the son underestimated his father. Major Ridge judged his people’s prospects by their suffering, and he knew the situation was far worse than anyone had dared to admit. Forbidden to meet by Georgia law, the Cherokees had abandoned New Echota in 1831. Settlers were confiscating their homesteads and livestock. By sharing his thoughts on Jackson, John Ridge helped his father come to the conclusion that the tribe had to at least consider going west.

But Major Ridge kept his feelings private, believing he needed to buy time to persuade his people to think about uprooting. At the same time, he began to wonder how Ross could remain so strident in his resistance. Couldn’t he see that his strategy was bearing no fruit?

Ross met twice with Jackson at the White House, to no avail. When Jackson offered $3 million to move the Cherokees west, arguing that Georgia would not give up its claims to Cherokee land, Ross suggested he use the money to buy off the Georgia settlers.

By spring 1833, the Cherokees were split between a National Party, opposed to removal, and a Treaty Party, in favor of it. As factional violence flared, some of the most influential Cherokees signed a letter to Ross saying their ongoing “course of policy” would “not result in the restoration of those rights” that had been taken from them. In signing the letter, Ridge acknowledged that he had softened on removal. In a closed meeting, the chiefs gave Ross until fall to resolve the impasse with the government before they made the letter public.

Under so much pressure—from the state of Georgia, the federal government and a stream of settlers—the tribe began to disintegrate. Some Cherokees—including Ross’ brother Andrew—set out for Washington to broker their own deals. John Ridge quietly continued to recruit members to the Treaty Party and make overtures to Jackson. When Ross learned of these efforts, he tried to pre-empt them, proposing to cede Cherokee land in Georgia and to have Cherokees in other states become U.S. citizens.

By then, the rift between Ross and Major Ridge was widening: when Ridge heard of the chief’s offer, he saw it not just as a bargaining ploy but as an abuse of power. Without the blessing of the other chiefs, Ridge said, Ross had no more power to make a treaty than his traitorous brother.

The majority of the tribe members remained opposed to removal, but the Ridges began advocating the idea more openly—and when they broached it at a council meeting in Red Clay, Tennessee, in August 1834, one Cherokee spoke of shooting them. Father and son slipped away unharmed, but by the end of the summer the Cherokees were trading rumors—false—that Ross and Major Ridge had each hired someone to kill the other.

In September 1834, Ridge visited Ross at his home to put the rumors to rest. They tried to talk as they once had, but the only thing they could agree on was that all talk of murder had to stop. Ridge believed Ross’ intransigence was leading the Cherokees to destruction. Ross thought his oldest friend had become soft, unduly influenced by his son.

By January 1835, the council had sent Ross back to Washington with instructions to again seek federal protection, and the Treaty Party had sent John Ridge to broker a deal. Afraid of being outflanked by the Treaty Party, Ross told Jackson the Cherokees would leave their land for $20 million. He was stalling; he knew the federal government would never pay that much. When Jackson rejected him, Ross proposed that the Senate come up with an offer. When the Senate named its price as $5 million, Ross said he would take the offer to the council but wouldn’t be bound by that figure. By then Jackson had lost his patience. In late 1835, he dispatched a commissioner to Georgia to seal an agreement with the Treaty Party leaders.

They met in New Echota, the deserted Cherokee capital. The terms were simple: the Cherokees would receive $5 million for all their land east of the Mississippi. The government would help them move and promise never to take their new land or incorporate it into the United States. The Cherokees would have two years to leave.

It was Major Ridge who outlined the final argument to those present. “They are strong and we are weak,” he said. “We are few, they are many....We can never forget these homes, I know, but an unbending, iron necessity tells us we must leave them. I would willingly die to preserve them, but any forcible effort to keep them will cost us our lands, our lives and the lives of our children. There is but one path to safety, one road to future existence as a Nation.”

On December 29, a small group of Cherokees gathered at the home of Ridge’s nephew Elias Boudinot to sign the Treaty of New Echota. After Ridge made his mark, he paused and said, “I have signed my death warrant.”

John Ross tried to overturn the treaty for two years but failed. In May 1838, U.S. troops herded more than 16,000 Cherokees into holding camps to await removal to present-day Oklahoma. Indians who tried to flee were shot, while those who waited in the camps suffered from malnutrition, dysentery and even sexual assault by the troops guarding them. Within a month, the first Cherokees were moved out in detachments of around a thousand, with the first groups leaving in the summer heat and a severe drought. So many died that the Army delayed further removal until the fall, which meant the Cherokees would be on the trail in winter. At least a quarter of them—4,000—would perish during the relocation.

Ridge headed west ahead of his tribesmen and survived the journey, but on the morning of June 22, 1839, separate groups of vengeful Cherokees murdered him, John Ridge and Boudinot. Ross, appalled, publicly mourned the deaths. “Once I saved Major Ridge at Red Clay, and would have done so again had I known of the plot,” he told friends.

John Ross served as principal chief for 27 more years. He oversaw the construction of schools and a courthouse for the new capital, and spent years petitioning the federal government to pay the $5 million it owed his people. (It wasn’t fully paid until 1852.) Even as his health failed, Ross would not quit. In 1866, he was in Washington to sign yet another treaty—one that would extend Cherokee citizenship to freed Cherokee slaves—when he died on August 1, two months shy of his 76th birthday. More than three decades later, the federal government appropriated Indian property in the West and forced the tribes to accept land reservations. Today, many of the country’s 300,000 Cherokees still live in Oklahoma.

Editor's note: An earlier version of this story referred erroneously to events having taken place in the Alabama Territory in 1813 and 1814. The territory was not organized until 1817

Adapted from Toward the Setting Sun: John Ross, the Cherokees, and the Trail of Tears, by Brian Hicks. Copyright © 2011. With the permission of the Atlantic Monthly Press.