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On Christmas morning 1837 Colonel Zachary Taylor and nearly 900 men—Regulars of the 1st, 4th and 6th Infantry regiments, plus 132 Missouri militiamen and a handful of Delaware Indian guides—cautiously approached a wooded hummock on the marshy edge of south Florida’s Lake Okeechobee. What they saw was not encouraging: The hummock bristled with the rifle barrels of some 400 Seminoles. Between Taylor’s position and the hummock stretched a half-mile swamp of 5-foot-high, razor-edged saw grass, knee-deep water and thick mud. The Seminoles had cut swaths in the saw grass to create open fields of fire.

For Taylor it was a poor battleground, but his orders were to “destroy or capture” any hostile Seminoles he encountered. Colonel Richard Gentry, commander of the Missouri militiamen, advised Taylor to encircle the hummock and trap the enemy. According to soldiers present, Taylor questioned Gentry’s courage and ordered a frontal assault, to be led by the Missourians. Taylor’s plan was to have the militiamen retreat at the first fire and re-form behind the Regulars. Their waiting enemy had other plans.

Many of the Seminoles carried breech-loading Spanish long guns with rifled bores, which were considerably more accurate and faster to reload than the soldiers’ muzzle-loading smoothbores. Shortly past noon the militiamen started struggling across the expanse of tall grass and muddy water, all the while taking fire from the Seminoles. Within moments Gentry fell mortally wounded. After sustaining heavy losses, the volunteers broke and ran for their horses, too shattered to re-form. Meanwhile, the Seminoles dashed forward to take scalps.

Next in were the 200-plus Regulars of the 6th Infantry (a third of whom the Seminoles soon killed or wounded, including every officer but one and nearly all noncoms) and the nearly 300 men of the 4th Infantry. The regiments at first withdrew under fire, then re-formed and pressed the Seminoles back to their camp on the lakeshore. Taylor then sent the 200-man 1st Infantry on a flanking maneuver, which finally drove the Indians from cover. The Seminoles withdrew from the lake and scattered eastward, having lost an estimated 11 dead and 14 wounded. Taylor’s losses were 26 dead and 112 wounded. Faced with so many casualties, he was unable to pursue the enemy. Two days later, after Taylor’s able-bodied men had buried the dead and tended the wounded, he led his bloodied force on the slow march back to Fort Gardner on Lake Kissimmee, more than 100 miles north up the Kissimmee River.

The Seminoles had confronted a military force nearly twice their size and stalled it long enough to ensure the escape of their women and children. However, within a few weeks officials in Washington, D.C., had declared the Battle of Lake Okeechobee the greatest victory of the Second Seminole War, and Taylor its greatest hero. Taylor was promoted to brigadier general and soon given command of all U.S. troops in Florida. The spin on this battle typified the official hype the government used to sell this long, ill-conceived war to a wary and increasingly disapproving public.

The U.S. Army and the Seminoles fought three wars between 1816 and 1858. The focus of the first war was the wresting of Florida from Spain, while the third was essentially a mop-up operation to flush the few remaining Seminole holdouts from their hiding places deep in Big Cypress Swamp and the Everglades. But the Second Seminole War, fought from 1835–42, cost upward of $30 million—more than the annual federal budget at the time—and resulted in the deaths of nearly 1,500 soldiers (mostly from disease), the forced removal from Florida of between 3,000 and 4,000 Seminoles, and the deaths of countless more.

The conflict was the direct result of the nation’s unbridled desire for territorial expansion, and of President Andrew Jackson’s Indian removal policy. It was a program he had been pushing since his 1814 defeat and relocation of much of the Creek Nation. In the decade that followed the Creek War, 11 treaties—nine of which Jackson himself negotiated— stripped the southern tribes of threequarters of Alabama and Florida, as well as parts of Georgia, Tennessee, Mississippi, Kentucky and North Carolina, all to make room for white settlers. In 1823 a compliant U.S. Supreme Court supported Jackson’s course by declaring it illegal for Indians to hold title to land.

Jackson believed Indians posed a threat to the peace and tranquility of the American nation and should be relocated or eliminated. He formalized his policy in 1830 by selling the concept to Congress, which passed the Indian Removal Act by the narrowest of margins. Over the next few years Jackson continued his campaign to remove the “Five Civilized Tribes”—the Cherokee, Chickasaw, Choctaw, Creek and Seminole— and drive them west of the Mississippi. Some of the Indians tried nonviolence, in the hope assimilation might prove viable. The Cherokees of Georgia fought extradition in the courts. They declared themselves a nation, wrote a constitution and argued for sovereignty before the U.S. Supreme Court—which, improbably, ruled in their favor in 1831. However, neither Georgia nor Jackson honored or enforced the law, and by the end of the decade U.S. forces had driven the Cherokees west on the infamous Trail of Tears.

Jackson declared that all “disaffected” bands that resisted expulsion were to be “dispersed or destroyed.” In his 1833 message to Congress he made his position—and his personal feelings— clear regarding those Indians who chose to fight displacement:

They have neither the intelligence, the industry, the moral habits nor the desire of improvement which are essential to any favorable change in their condition. Established in the midst of another and a superior race, and without appreciating the causes of their inferiority or seeking to control them, they must necessarily yield to the force of circumstances and ere long disappear.

Those who had the misfortune of standing in the way of America’s progress thus faced two choices: move west or die.

By 1834 Jackson had turned his gaze again on Florida and the Seminoles. Eleven years earlier the Treaty of Moultrie Creek had directed the Seminoles to surrender all land claims in the territory and move to a 4-millionacre reservation in central Florida. It also bound them to remain peaceful and to apprehend all runaway black slaves and other fugitives for the government. For its part the government would provide cattle and hogs, an annual annuity of $5,000, an interpreter, a blacksmith and an Indian agent, and keep all whites from encroaching on Indian land—the latter an unenforceable provision. The agreement came with a 20-year shelf life.

Less than nine years later—just two years after the passage of Jackson’s Indian Removal Act—the parties signed another treaty under highly questionable circumstances, whereby the Seminoles were ordered to relocate to Arkansas Territory within three years and to surrender all runaway slaves.

Besides wanting them removed to facilitate white settlement, Jackson harbored a personal resentment toward the Seminoles for their practice of sheltering and adopting runaway slaves into the tribe. Although the Seminoles themselves practiced a form of slavery, the blacks whom they called slaves lived a much freer existence than those in bondage to many white masters. They lived apart with their families and worked at their own trades, simply turning over to their nominal masters a small portion of what they earned or grew. Many blacks living with the Seminoles had intermarried within the tribe, a fact that galled Jackson. Part of his mission, as he saw it, was to seize all runaway slaves and return them to their rightful white masters.

Arkansas offered little to tempt the Seminoles, with its dry summer heat, winter snows and hostile tribes. According to several Army officers present at the treaty negotiations, the Indians had been “wheedled and bullied into signing.” Seeking to justify its actions, the government argued that the Seminoles were not originally from Florida anyway and had no real ties there.

Some of the Seminoles moved out by the deadline; most, however, believed strongly in their right to remain in Florida and resolved not to leave without a fight. The situation on the reservation rapidly heated to the boiling point. In early 1835 the Indian agent at Fort King, a former Georgia congressman named Wiley Thompson, took it upon himself to remove from office the chiefs who did not agree to move, and he refused to sell any more powder and lead to the Seminoles.

In the midst of this fray an angry young warrior with natural leadership capabilities emerged. He was called Osceola, and he made his intentions clear: “The white man shall not make me black. I will make the white man red with blood; and then blacken him in the sun and rain…and the buzzard [shall] live upon his flesh.” He refused to abide by the treaty, and when he spoke defiantly to Thompson, the agent had him placed in irons overnight. It was an affront Osceola would not forget.

Soon after, a group of seven whites assaulted five reservation Seminoles as they sat at their campfire. Two armed Indians arrived on scene, and by the time the affair had ended, three whites and one Indian lay wounded, another Indian dead. In retribution a band of Seminoles attacked and killed a soldier on a mail run. In November the hawkish Seminoles judged one chief who had agreed to relocate a traitor to the tribe, and Osceola killed him. It became clear war would come—and soon.

That fall Brig. Gen. Duncan Lamont Clinch, commander of U.S. forces in Florida, wrote to Washington, requesting additional troops. The government promptly sent 500 volunteers, under Brig. Gen. Richard K. Call, and four companies of Regulars. The Indians were already at war. Through year’s end Seminole war parties raided white settlements and sugar plantations and at some point attacked a militia wagon train, killing eight and wounding six.

On December 28 Osceola returned to Fort King for the express purpose of killing agent Thompson. The war chief and his band waited outside the fort, and when Thompson emerged, they opened fire. The Indian agent went down with 14 bullets in his body. Osceola and his men then killed nearly all the occupants of the sutler’s cabin and took whatever booty they fancied.

Eclipsing even this deed was another event that same day that sent a shock through the entire country. Five days earlier the Army had sent two companies of soldiers under Major Francis Langhorne Dade from Fort Brooke to support the agency at Fort King, which was considered—rightly, as events had shown— susceptible to Indian attack. Dade had posted no flankers or scouts, a stunning lapse considering his companies were marching directly through hostile Indian territory. Worse yet, in the morning chill on the 28th the troops had buttoned their coats—over their cartridge boxes.

A party of 180 Seminoles led by Micanopy, the tribe’s highest-ranking chief, had been following them for five days, concealed by the tall grass that bordered the trail. Suddenly a single shot rang out as Micanopy fired a ball that struck Dade in the heart. The rest of the war party then opened fire, killing about half the soldiers in the first volley, as the others clawed desperately for their cartridge boxes. The survivors managed to unlimber their lone cannon and drive back the Seminoles, but the Indians continued to pick off the soldiers one at a time. The troops hastily set up a triangular breastwork, but the Seminoles’ fire was remarkably accurate, and within hours they had killed all but a few soldiers. Only one would survive.

The day after the Dade Massacre, Clinch—ignorant of the defeat—set out from Fort Drane, some 20 miles from Fort King, with 750 men, including 500 volunteer militiamen. His objective was a watery maze of islands and peninsulas known as the Cove of the Withlacoochee, a Seminole stronghold southwest of the namesake river. Clinch arrived there on New Year’s Day but did not find the shallow ford he had anticipated. Though the river was swift and deep, Clinch determined to cross his troops—five and six at a time— in a dugout canoe they had found. It was a monumentally ill-conceived move.

All the Regulars had crossed and were resting in a clearing when the surrounding hummock came alive with shouts and gunfire. The Indians, hiding in the saw grass, took a harsh toll, until Clinch ordered a bayonet charge and managed to temporarily dislodge the attackers.

As concealed Seminoles sniped at the Regulars, Clinch ordered a retreat. Meanwhile, the militia under Call had fashioned a makeshift bridge, and they covered the Regulars’ withdrawal. The chastened army marched back to Fort Drane, with four men dead and 59 wounded. Ironically, within two months Maj. Gen. Edmund Gaines —Clinch’s superior—would have practically the same experience at exactly the same spot and, after sustaining numerous casualties, would be rescued at the last minute by Clinch.

It was beginning to look like a long war. Complicating matters was a bitter rivalry between Gaines, an impulsive veteran Indian fighter in command of the nation’s Western Department, and Maj. Gen. Winfield Scott, the tall, pompous commander of the Eastern Department. While Gaines felt the war might be ended through negotiation, Scott was a true believer in Indian removal. The decision was Scott’s to make; the Army had placed him in charge of the war, and he intended to fight it to a successful conclusion. Scott’s subsequent 5,000-man grand campaign, however, proved a dismal failure; in March his forces crossed the Withlacoochee only to find the Seminole villages deserted.

That same month Call, former commander of the volunteers, was appointed territorial governor, and the War Department soon authorized him to launch a campaign against the Cove, using militia and volunteers. He set out that fall, but again the Withlacoochee was flooded, and Call had brought no axes for construction of a ferry or bridge. After several weeks of futile pursuit he too withdrew his forces, his efforts no more successful than those of Clinch, Gaines or Scott. The Army relieved Call of command and on December 9 turned over the reins to Maj. Gen. Thomas Sidney Jesup, another experienced Indian fighter. With the Seminoles continuing to raid plantations and settlements with impunity, 1836 had been a disastrous year for the Army.

Jesup was the first commander to realize the U.S. Army was in- volved in a guerrilla war, and he decided the only hope for success lay in wearing down his opponents. In addition to his 7,000 Regulars, he solicited thousands of short-term volunteers, acquired the use of a brigade of Marines, and even got the Navy and other maritime units to patrol Florida’s coast. Rather than put a large force in the field, he dispatched several small, mobile units to harass the Seminoles, capturing some and pressuring others to surrender. It was slow going, but eventually it became clear to the Indians their enemy had an unlimited source of men, whereas their own numbers were gradually but inexorably dwindling. Compared to the previous year, 1837 proved a turning point.

Part of Jesup’s strategy was to entertain no discussion with the enemy unless it was to surrender. On at least three occasions he used subterfuge to achieve his objective. First, Jesup asked Coacoochee, a leading Seminole chief, to come in under a flag of truce to discuss terms; when he did, Jesup had him imprisoned. On another occasion Jesup sent a delegation of Cherokees to try to convince the Seminoles to relocate; when Micanopy and others came in to meet with them, Jesup seized the Seminoles, over the protests of the Cherokees. In October 1837 Osceola himself requested a parley with Jesup; the general agreed, and when the war chief appeared, Jesup had him jailed as well. Within a few months Osceola took ill and died.

Many Americans had come to view the young Osceola as a heroic warrior, fighting for his homeland against impossible odds, and they were incensed at Jesup’s treachery. When Osceola died in captivity, they were outraged—as were many Army officers. By then even Congress was growing disenchanted with the war, although it would continue to fund the conflict for years.

By 1838 the fighting had subsided considerably, but the Seminoles continued to resist. Less than two months after Taylor’s debacle at Lake Okeechobee, and after two more embarrassing encounters with the Indians, Jesup—with the knowledge and support of his officers—wrote an extraordinary letter to Secretary of War Joel Roberts Poinsett, stating there was no end in sight to the conflict and urging the government to abandon its plans to relocate the Seminoles. He recommended ending the hostilities with a truce that granted the Seminoles a reservation in southern Florida. He had already met with Seminole leaders (this time honoring a truce flag), who had agreed to stop all hostilities if they were allowed to remain south of Lake Okeechobee.

But the administration of newly elected President Martin Van Buren— a scaled-down puppet of Andrew Jackson—did not concur; in a profoundly wrongheaded move it rejected Jesup’s proposal. Poinsett ordered him to resume the campaign. Jesup then called the Seminoles to a council, ostensibly to give them the bad news. Having been tricked by him twice before, they refused to attend. He then sent out troops to round up all Seminoles in the vicinity, seizing some 500 Indians and 165 black Seminoles.

The Army viewed the black Seminoles as “more bloodthirsty, active and revengeful” than the Indians, and Jesup decided if he was to put an end to the war, he would have to separate the Seminoles from the blacks. To accomplish this, he did a remarkable thing. Anticipating Abraham Lincoln by nearly three decades, he issued the nation’s first emancipation proclamation, declaring all black Seminoles willing to surrender and emigrate west to be free. Jesup hoped the impending loss of their black allies would dishearten the Indians, and indeed, the proclamation prompted the immediate surrender of some 1,200 Seminoles and blacks.

But by the spring of 1838 Jesup had had enough. After less than two years at the helm he asked to be relieved, and Brig. Gen. Taylor took over command of Army forces in Florida. Predictably, Taylor was no more able to bring the war to a rapid close than his predecessors. At one point he brought in bloodhounds to track down the enemy—an act that further outraged an American public still angry over Osceola’s betrayal and death.

The Seminoles struggled on another four years. But as the Army continued to chip away at the Indians’ power base —burning their fields and running off or killing their stock—the war became one of attrition, with raids and skirmishes but no major battles. The Army had killed or captured most of the Seminole leaders and warriors, and its duty became less a matter of confronting a united foe than of tracking small, desperate bands to their hideouts deep in the Florida swamps.

After the expenditure of tens of millions of dollars and the senseless loss of lives on both sides, it would have been a simple thing merely to declare the war over, as Jesup had urged. But no one did. Gradually, nearly all the Seminoles— harried past the point of endurance and concerned for the welfare of their families—gave up and were sent to Arkansas.

Florida, described by one disgusted Army officer as “the poorest country that ever two people quarreled for,” went to the victors.

For further reading Ron Soodalter recommends America’s Hundred Years’ War: U.S. Expansion to the Gulf Coast and the Fate of the Seminole, 1763–1858, by William S. Belko; The Seminole Wars: America’s Longest Indian Conflict, by John Missall; and In Bitterness and in Tears: Andrew Jackson’s Destruction of the Creeks and Seminoles, by Sean Michael O’Brien.

Originally published in the July 2012 issue of Military History.