The Second Seminole War by John T. Biggs

THINGS HAD BEEN GOING well for Indian Agent Wiley Thompson since he’d been assigned to Florida. His mission was to get all the Seminole bands of Florida to agree to President Andrew Jackson’s plan to transport them to Indian Territory. If he could persuade Principal Chief Micanopy to go along, the chiefs of the smaller bands would follow suit, and Micanopy was an aging, pliable leader.

Agent Thompson called a meeting of influential members of the tribe, to show them the major details for their removal. He spread an official looking document on a table for everyone to see even though none of the Seminole could read. Success seemed to be within the agent’s reach unless something totally unexpected happened. Naturally, it did.

A charismatic young warrior pushed his way to the front of the crowd, drew a knife, and plunged the blade into the agent’s table, some say through the document. He declared, “The only treaty I will ever execute will be with this.”

The rebellious young man’s name was Osceola. Everyone would remember it after the spectacle in Wiley Thompson’s office. Osceola had no official standing within the tribe. He’d been born into a faction of the Muscogee Creek Nation that had rebelled against white rule and were defeated by Andrew Jackson in the Red Stick War. But his friendship with Micanopy had grown strong over the years, and lately he’d become a close advisor.

Many Red Sticks had been assimilated into the Seminole tribe. They spoke the same language, had similar customs, and shared a strong moral opposition to enslavement of free people. Even though Osceola had no hereditary claim on leadership, the faction of the tribe that didn’t want to leave Florida would listen to him. Relocation plans for the Seminole were put on hold.

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PRESIDENT ANDREW JACKSON HADN’T expected much resistance from the Seminole when he signed the Indian Removal Act of 1830 into law. As a general, he had crushed their fighting forces when their British allies pulled out of Florida after the War of 1812. U.S. troops had forced the natives into the swampiest part of Florida where they could hardly survive without government rations.

White settlers had already seized all the Seminole’s productive land and had designs on their Everglades reservation. Jackson would have left the native population alone if they hadn’t opened their villages to runaway slaves. Plantation owners demanded the elimination of the tribe as a refuge for their enslaved workforce. And since the successful Haitian slave revolt of 1804, the thought of hundreds of armed, free blacks living among the Indians made white slave owners understandably nervous.

The Indian Removal Act promised to transport all the Seminole, including black Seminole tribal members—not including verifiable runaways—to Indian Territory. It didn’t sound like a bad arrangement. The U.S. government arranged for tribal representatives to visit the promised homeland to see for themselves it was better than the Florida swamps.

The trip did little to put the tribe’s mind at ease. Seven Chiefs and two black Seminole interpreters were taken under guard to Ft. Gibson in Indian Territory where the treaties were read to the tribe’s illiterate interpreters who then translated what they had been told to the chiefs. They were held for a month at Fort Gibson until they signed a treaty that not only committed them to removal of their tribe but agreed to merge the Seminole and Creek tribes.

Black Seminole were terrified of this arrangement since many of the Creek already in the territory owned slaves and functioned as slave catchers for white planters in southern Alabama and Northern Florida. There was every chance the Creek would assert ownership of the black tribe members if given the opportunity.

The Seminole might still have gone along with the removal if Osceola hadn’t shown them resistance was possible.

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THE TRIBE BEGAN BUYING ammunition in alarming quantities. Selling bullets, gunpowder, or even lead to blacks was already prohibited, but Wiley Thompson proposed expanding that rule to include native tribesmen.

Osceola made an uninvited appearance at an 1835 conference between Thompson, Seminole Chiefs, and black interpreters. The charismatic warrior announced in his typical larger than life fashion, “Am I a Negro? A slave? My skin is dark but not black. I will make the white man red with blood; and then blacken him in the sun and rain, where the wolf shall smell his bones and buzzards liven upon his flesh.”

OSCEOLA, A CHARISMATIC AND AGRESSIVE YOUNG WARRIOR WHO PLAYED A KEY ROLE IN THE SEMINOLE WARS.

His colorful threat ended the conference on what Agent Thompson must have considered a very sour note. Eight chiefs and eight subchiefs agreed to go to Indian Territory, but the rest—including Principal Chief Micanopy—flatly refused.

Osceola stalked Wiley Thompson. He interrupted the agent’s meetings. He insulted and even threatened him until Thompson ordered the warrior’s arrest. The Seminole firebrand put up no resistance when soldiers came for him. He went peacefully to jail and remained there only six days before he underwent a contrite transformation. Osceola apologized to Thompson. He meekly offered to emigrate to Indian Territory and volunteered to convince Seminole to do so, as well.

White men making false promises to natives was a well-known strategy by that time, but Thompson had total confidence in Osceola’s sincerity. As a show of good faith, the Indian Agent gave the warrior an extremely fine rifle and told him to be at Tampa Bay on January 8, 1836, with as many volunteers as he could muster.

Needless to say, Osceola didn’t keep his bargain. He used his new rifle to threaten Seminole who were selling off their livestock in preparation for leaving and even executed Charley Emathla, leader of the emigration faction. Osceola tossed the gold Emathla had received for his cattle in the dirt— “See! It is the price of your blood!”

The U.S. government took pro-emigration Seminole into their protection in Tampa while they awaited transportation to Indian Territory. They also sanctioned slave catcher raids on Seminole villages and permitted them to capture and sell mixed race Seminole who had never been slaves. Osceola got plenty of opportunity to use the rifle he’d tricked Wylie Thompson into giving him. Clashes sprang up with loss of life on both sides, and lines between the government and the resistance hardened.

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NEAR THE END OF December, 1835, the smoldering conflict burst into flame. Encouraged by Osceola and other outspoken members of the Seminole resistance, native and black warriors carried out carefully organized attacks on the region’s plantations. Local slaves swarmed to the Seminoles. Runaways painted their faces to demonstrate their new allegiance.

Osceola had already declared a war of sorts against Wiley Thompson, and it didn’t take long for the Indian Agent to become the focus of hatred for all the antiemigration natives and the runaway slaves as well.

An influential black Seminole warrior and interpreter named Abraham was called The Prophet by some members of the tribe because of his talent at divining the future. He predicted Wiley Thompson would be killed. Abraham’s prophesy wasn’t rich in details, but the prediction came true when Osceola and at least forty warriors ambushed Thompson and Lieutenant Constantine Smith while the two were taking an after-dinner walk. They riddled the men with bullets and scalped the corpses.

While Osceola was bringing Abraham’s prophesy to fruition, Major Francis Dade was joining his troops who were in route to defend Ft. King. Dade was in the company of a slave-guide who spoke Seminole and was in all probability passing information to the tribe. One hundred eighty natives and blacks led by Chief Micanopy hid at an ambush point with a plan to surprise the soldiers and kill off most if not all of their commissioned and non-commissioned officers. The Chief was so infirm he had to be carried onto the field of battle, but he fired the first shot, which hit Major Dade, and officially started the Second Seminole War.

The native warriors killed or wounded most of the officers within the first few minutes of the battle. They were picking off the remaining soldiers one by one until fifty black Seminole rode in armed with knives and axes to finish the job. Their battle cry was, “What have you got to sell?”—a question lounging soldiers often asked black tribe members when they visited military posts. Only three of the soldiers survived.

Major Dade’s guide could read and write, and in return for his captors’ leniency he translated dispatches and documents carried by the soldiers, giving the Seminole valuable strategic information.

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THE VERY NEXT DAY, Osceola got word from sympathetic local slaves that General Duncan L. Clinch was leading a column of soldiers toward Withlacoochee River. The general had no idea what had happened to Agent Wylie Thompson or Major Dade.

Indian guides led Clinch’s troops to a ford that was so deep the soldiers had to move their weapons across the river by canoe—a perfect point for a Seminole ambush. Many of the soldiers were swept off their horses by the current as they tried to cross, and others were occupied with keeping the boats carrying their arms from capsizing.

It looked like the Seminole would have a repeat of their quick victory against Major Dade, but Clinch’s troops vastly outnumbered the attackers and managed to organize a strong resistance in spite of sustaining heavy losses. In the ensuing gunfight, Osceola was hit in the arm with a musket ball and was forced to withdraw. It was a costly battle for the army, but a government victory none the less.

Osceola dictated a terse letter to a translator and sent it to General Clinch: “You have guns and so do we. You have powder and lead and so do we. Your men will fight and so will ours, until the last drop of Seminole blood has moistened the dust of this hunting ground.”

After the battle with General Clinch, the Withlacoochee River became a boundary of sorts. General Edmund Gaines tried to cross it with a large number of solders on Feb. 27, 1835, but like General Clinch, he had to rely on black and Indian guides who gave him bad advice and passed his location on to the Seminole. Osceola and other war leaders pinned the general down until March 5 with constant sniping and guerilla attacks, until the soldiers were reduced to eating their horses. The warriors then sued for peace on the condition that they would be allowed to withdraw unmolested and Gaines would do the same.

IN EARLY 1836, BREVET GENERAL WINFIELD SCOTT WASORDERED TO ENCIRCLE OSCEOLA’S WARRIORS AND CRUSH THEM. HE WAS UNSUCCESSFUL.

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THE SEMINOLE—BLACK AND native—were experts at guerilla tactics. Rather than try and hold positions against government troops, they attacked, then engaged in fighting retreats and disappeared into the swamps, leaving surviving government forces wounded, sick, and demoralized.

On January 21, 1836, Brevet General Winfield Scott was sent with three divisions (4,800 soldiers) operating out of Fort Alabama, a hastily built garrison with timber palisades on the Withlacoochee River. His orders were to encircle Osceola’s warriors in the Cove of the Withlacoochee and crush them. It was estimated the renegade fighting force did not exceed 1,200 men.

In spite of bad intelligence from local guides, and constant sniping and harassment from tribal warriors, General Scott managed to cross the Withlacoochee with 2,000 troops and artillery using flatboats. Osceola withdrew his warriors toward the cove so additional government forces could ford the river and move through the previous Seminole safe-haven burning villages that had been abandoned ahead of their attack.

A group of warriors approached the soldiers under a white flag and requested a meeting to discuss terms of surrender. General Scott quickly agreed and halted his advance thinking his rampage through the Withlacoochee Cove had convinced the natives they could not win. But instead of sending representatives to meet with Scott, the native and black Seminole used the time to move their families into the surrounding treacherous swamps. When the women and children were safe, the warriors opened fire on the soldiers’ camp and staged a fighting retreat as they vanished into the swamps to join their families. Casualties among the Americans were heavy, and the soldiers gave up pursuit.

As Scott ended his campaign, he ordered soldiers to abandon Ft. Alabama. They did so but left the magazine fully stocked with gunpowder and rigged a booby trap they called “The Infernal Machine.” About an hour after they left, it exploded. There were no reports on the numbers of Seminole killed or injured, but the American soldiers were ambushed later that day and took significant casualties before they managed to rally and disperse hostiles.

DRAMATIC PAINTING OF THE FIGHTING DURING THE BATTLE AT LAKE OKEECHOBEE,DURING THE SECOND SEMINOLE WAR.

Shortly after General Scott failed in his mission to crush Osceola’s warriors, he was recalled to Alabama to quell the resistance of a Creek faction that was also resisting Jackson’s Indian Removal Act. The Seminole responded to his withdrawal by attacking and occupying all the forts on Tampa Bay. Osceola set up temporary headquarters in Fort Drane, which had been built on a plantation owned by General Duncan Clinch.

Florida Territorial Governor Keith Call took over the campaign shortly after General Scott left. The Governor had served with Andrew Jackson in the first Seminole war and wasted no time in mustering troops for an attack. He set out with 1200 Tennessee Volunteers and 150 Florida conscripts to route Osceola from Ft. Drane.

The warriors learned from plantation slaves and Indian guides a large number of soldiers were on their way and once again retreated across the Withlacoochee River into the swamps. The river was swollen by seasonal rains and even more dangerous than usual. Soldiers attempted to cross while native and black Seminole sniped at them from the opposite shore. Several men and horses were drowned in the attempt, but the river was not crossed.

The Governor decided to wait until the river had receded and try again, this time after recruiting 750 Creek auxiliaries to join his force. The native soldiers belonged to a Creek faction (Lower Creek) that had supported Andrew Jackson during the Red Stick and First Seminole Wars. They wore white turbans to distinguish them from the hostiles and were to be paid in captured blacks rather than money.

The Seminole avoided the battle-hardened Creek as much as they could and concentrated their efforts on surprise attacks against the white soldiers. Eventually, they retreated into the swamp and gathered at a point where the attackers would have to cross an area that was so thick with black mud it looked impassable even though it was actually only three feet deep. The Creek mercenaries advised the army to cross and finish the enemy with a bayonet attack, but the white soldiers were exhausted and demoralized, and once again they withdrew.

THE PROPHET ABRAHAM, A HIGHLY-RESPECTED MYSTIC AMONGST THE SEMINOLE PEOPLE.

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IN LATE NOVEMBER, 1836, Brevet Major General Thomas Jesup was sent in to replace Governor Call. His strategy was different from all the military men before him. He set his sights on capturing women and children and used those hostages as leverage against native and black guides giving him false intelligence. In a short time, he was able to raid Osceola’s camp in the Withlacoochee Cove and send him running into the swamp with only his family and three warriors. The native and black Seminole warriors who fled from the camp were captured or killed by small cavalry detachments within the next few days.

Hidden villages in forests and swamps beyond the Withlacoochee Cove fell one after the other to American soldiers and Creek mercenaries. With every captive Jesup’s intelligence grew more accurate and his attacks more targeted, but still the Seminole did not sue for peace. Jesup was convinced the black Seminole were influencing the tribe to keep on fighting.

Jesup wrote to Secretary of War Lewis Cass: “Not a single first-rate warrior has been captured, and only two Indian men have surrendered. The warriors have fought as long as they had life, and such seems to me to be the determination of those who influence their councils—I mean the leading Negroes.” His plan was to dispatch a captive black Seminole to find someone who would hear and might accept his proposal. He managed to arrange a meeting with Abraham (The Prophet) who was respected as a mystic among the tribe partially because he had accurately predicted the death of Indian Agent Wylie Thompson. Abraham had been involved in war with the whites since the First Seminole War started in 1817. He was a respected elder, and both native and black Seminole would listen to him.

Things went as General Jesup had predicted. Once the influential black Seminole were on board, the tribe (including Principal Chief Micanopy) provisionally agreed to a treaty. The agreement guaranteed freedom in Indian Territory for black Seminole as well as runaway slaves who had been allied to the tribe throughout most of the Second Seminole war. Unfortunately for General Jesup, a new Secretary of War—Joel Roberts Poinsett— took office while the negotiations were in process, and he had no intention of agreeing to those terms.

Even before it became clear Washington wouldn’t support the treaty, critical terms had begun to slip. Under pressure from influential plantation owners Jesup backed away from his original promises and entered negotiations with Seminole bands to return at least some of their runaways to the plantations from which they escaped. This was totally unacceptable to Osceola. By fall, there was renewed fighting, but there was a significant faction of the tribe who were persuaded the war was unwinnable and were willing to agree to Jesup’s terms. Even some runaway slaves turned themselves in rather than continue the campaign.

The general lobbied Washington for authority to negotiate further, but by the time he had arranged another meeting with the tribe, his bosses ordered him to abandon diplomacy and pursue the war by whatever means necessary.

Osceola had already agreed to meet under a flag of truce to continue discussions. He rode with two warriors: Wild Cat, a legendary warrior who was the son of an important chief, and John Horse, a black Seminole warrior who was the brother-in-law of Principal Chief Micanopy. A number of other important band chiefs and black Seminole translators accompanied them. At a prearranged signal, two hundred Florida dragoons and militiamen surrounded the delegation forcing their surrender. Jesup quickly imprisoned them inside the five-foot thick stone walls of Ft. Marion in St. Augustine.

It didn’t take long for word to reach the international press that a general in the United States military had violated a flag of truce. Secretary of War Joel Roberts Poinsett gave Jesup full credit for the act of treachery even though it was he who forbade the general from continuing negotiations. The circumstances of Osceola’s capture became a stain on Jesup’s career he could never quite remove.

WILD CAT, A LEGENDARY WARRIOR AND CHARISMATIC LEADER OF THE SEMINOLES DURING THE WAR.

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THE MOST NOTORIOUS LEADERS of the Seminole insurgency were imprisoned collectively in an auditorium size cell with narrow barred loophole windows fifteen feet off the floor. Escape seemed impossible, but the tribe had been surviving against impossible odds since the Second Seminole War began in 1836. Within days they had worked out a plan.

They boosted a warrior to one of the windows and secured a rope braided from strips torn from the canvas bags they used as beds. They used a file smuggled in by a sympathetic slave to cut through one of the two bars that secured the window, which allowed them to crawl through an eight-inch wide, five-foot long passage and drop onto a marshy hillside some twelve feet below.

Osceola was sick, almost to the point of death with chronic malaria by then and did not attempt to escape. Band Chief King Phillip was too old and frail and stayed behind with Osceola, but his son, Wild Cat, and John Horse, escaped along with other members of the delegation. It was a legendary prison break that might have put John Horse and Wild Cat on equal footing with Osceola as new leaders of the resistance movement, but for most of the Seminole and their black allies, it was too late. Principal Chief Micanopy had met with John Ross, Princpal Chief of the already relocated Cherokee tribe, and had been persuaded to surrender. Many smaller bands followed suit. But Wild Cat and John Horse gathered four hundred black and native warriors and led them to Lake Okeechobee where they took up positions in a dense hummock across a nearly impassable swamp. Colonel (future president) Zachary Taylor pursued them with a thousand troops.

JOHN HORSE, A BLACK SEMINOLEWARRIOR AND BROTHER-IN-LAW TO PRINCIPAL CHIEF MICANOPY.

The tribe followed their tried and true battle plan of slowing down the troops with guerilla attacks while their sharpshooters selectively killed officers. The insurgents were so effective, every officer in the sixth infantry and most of the noncommissioned officers were killed or wounded, and in one company, only one in four soldiers remained uninjured.

Eventually the army’s superior numbers overwhelmed the Seminole, and one hundred sixty American troops reached the hummock. Again, the tribe resorted to their proven tactic of conducting a fighting retreat. This time, however, instead of disappearing into the swamps, they fled onto Lake Okeechobee in hidden canoes, and the soldiers could not follow. Zachary Taylor hailed the battle an American victory, even though seven of his own men were either killed or wounded for every Seminole casualty.

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GENERAL JESUP WASTED NO time in getting Osceola out of Florida. In mid-December 1837, he put the notorious renegade on a ship and transferred him to Fort Moultrie on the Sullivan Islands outside Charlotte, North Carolina. The government tried to keep the transfer quiet, but it didn’t take long for the story to get out. International journalists had taken up the story of Osceola’s capture under a white flag. Members of congress joined in criticism of General Jesup’s “treachery,” and Osceola became a captive hero. While in Fort Moultrie, nationally famous artists, George Catlin, W.M. Lanning, and Robert John Curtis painted his portrait from life. Curtis’s image of him inspired widely circulated prints and engravings and became the template for popular cigar store figures.

Perhaps Osceola’s notoriety would have led to a release in Indian Territory, but he was gravely ill from malaria now complicated with an acute case of tonsilitis. In a matter of weeks he developed a peritonsillar abscess that proved fatal on January 30, 1838. He was buried with military honors at Fort Moultrie.

Public rebukes from newspapers and the U.S. Congress had a devastating effect on the morale of General Jesup. He wrote to President Martin Van Buren: “In regard to the Seminoles, we have committed the error of attempting to remove them when their lands were not required for agricultural purposes; when they were not in the way of white inhabitants. My decided opinion is, that unless immediate emigration be abandoned, the war will continue for years to come, and at constantly accumulating expense.” Anticipating presidential approval, he used a black Seminole emissary to invite the chiefs who remained at large to another conference on Feb. 7, 1838.

Jesup was convinced that resistance would be eliminated if he separated the natives from blacks. He issued an order “that all the negroes [who are] the property of the Seminole Indians in Florida, who separated themselves from the Indians and delivered themselves up to the Commanding officer of the Troops should be free.” The black Seminole would not remain in Florida with the tribe but would be sent to a separate village in Indian Territory and be protected by the U.S. government. John Horse was not at the meeting but was specifically promised freedom in Indian Territory.

ZACHARY TAYLOR WON PROMOTION TO GENERAL ON THE STRENGTH OF HIS ACTIONS AT LAKE OKEECHOBEE.

Without a charismatic leader like Osceola, native and black Seminole did not have the will to continue fighting. They began turning themselves in immediately. A peaceful end to the conflict seemed in place, but once again, General Jesup was reminded of the limits of his authority. Secretary of War John Roberts Poinsett ordered the general to continue with the removal of the entire tribe to Indian Territory regardless of the difficulties.

Jesup decided to seize the insurgents with a plan almost identical to the one that had led to his disgrace with Osceola. He summoned the Seminoles to a council to be held on March 20, 1838, and ordered his troops to surround them starting at midnight, March 21. By violating a second flag of truce, he captured almost as many warriors as had been taken during the past fifteen months of fighting.

John Horse did not come to the council, but with the loss of so many warriors, he realized the war with the whites was unwinnable. He surrendered a few days later.

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ZACHARY TAYLOR WAS PROMOTED to the rank of Brigadier General on the strength of his questionable campaign at Lake Okeechobee and was assigned to replace Thomas Jesup. Taylor never forgave Wild Cat and John Horse for orchestrating the Seminole escape by water that turned what should have been a military victory into a fiasco. His strong objection was understandable when Major General Alexander Macomb hired John Horse as a guide and interpreter to help arrange the surrender of the remaining insurgents. Taylor argued, “I believe [John Horse] to be one of the most artful and faithless of his tribe.”

But the arrangements were made. John Horse shed his identity as a black Seminole warrior and quickly became a popular guide and translator for the officers. By 1840 he was destroying tribal crops and taking part in battles against insurgents.

Rumors abounded among the Seminole that Indian Territory was another white man’s lie. Many were convinced the U.S. Government was simply loading tribe members aboard ships and murdering them at sea. John Horse suggested the army bring Seminole chiefs from the Territory to put those speculations to rest. The strategy was successful. Two hundred twenty members of the Tallahassee band agreed to relocate peacefully. The wisdom of using a black Seminole as a negotiator was established.

John’s old friend Wild Cat was now the most influential chief still fighting the military. He couldn’t muster enough warriors for campaigns as legendary as Lake Okeechobee, but he caused a great deal of trouble for white settlers and businessmen. The army pursued him relentlessly, and although they couldn’t seem to catch him, they did capture his mother and his daughter.

John Horse got word to Wild Cat that his family was being held at Fort Gardner and invited him to meet with Colonel William J. Worth and negotiate for their release. Wild Cat had a flare for the dramatic. He and his warriors had recently attacked a company of actors near St. Augustine and plundered their wardrobe. When they came to meet with Colonel Worth, they were dressed as Shakespearian characters. The Chief himself took the role of Hamlet.

Wild Cat’s daughter ran to him when she heard his voice. She put her arms around him, offering him affection while sneaking him packets of musket balls and gunpowder she had stolen while a captive. Wild Cat broke down crying. He consented to remain in the camp, and after talking with the colonel and John Horse, he consented to emigration.

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IT TOOK SOME TIME for Wild Cat to become as committed to removal as John Horse. The tribal chief continued to steal weapons and ammunition for warriors he kept hidden in the swamps. But eventually John’s old friend threw his efforts behind the army and managed to convince all but a few hundred Seminole to emigrate to Indian Territory. John Horse, Wild Cat, and their families went with them. As promised, John was declared free.

The Second Seminole War ended on August 14, 1842. The conflict cost over twenty million dollars, four times what the United States paid Spain for Florida. It was the deadliest of the Indian wars, with more than 1,500 regular sailors and soldiers lost, and the longest—over seven years. It was, in fact, the longest lasting of any war America fought until the Vietnam conflict.

Hostilities ignited again in 1855 between the U.S. Government and the Seminole remaining in Florida— The Third Seminole War. Meanwhile, the rest of the tribe struggled for survival in Indian Territory.

—John T. Biggs is the author of six novels and hundreds of short stories and the winner of the Reader’s Digest Grand Prize. His writing is so full of Oklahoma that once you read it, you’ll never get the red dirt stains washed out of your mind. John lives in Oklahoma City with his wife, and they travel extensively throughout the world with their family.