Osceola Fights to Save the Seminole

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General Scott did finally attempt his three-pronged pincer attack, but Osceola skillfully maneuvered his people through the swamps and eluded all three enemy detachments. Scott’s campaign was an unmitigated failure, and the press called for him to resign his command, which he did. Gen. Richard Call, now the new governor of Florida, decided to personally lead the militia against the Seminoles.

In the summer of 1836, soldiers at Fort Drane began to contract malaria, a potentially deadly disease, and were ordered to move to Fort Defiance. Osceola and his men then occupied the vacated fort, making it their base of operations.

Governor Call was determined to destroy the Seminoles. In mid-November, he attacked two encampments, killing 45 tribe members. His men were low on rations, so Call withdrew, but he was satisfied that he had administered a damaging blow. Higher authorities disagreed, and Call was informed that he had been relieved of command. The new commander was yet another general, Thomas Jesup, a firm believer that “the end justifies the means.”

Among the United States public and in the press, the Seminole War was no longer a popular cause. Soldiers told stories about the horrible conditions they had endured—diseases, poisonous snakes, and marches through swamps in chest-deep water. Osceola was now regarded as an honorable warrior fighting for a righteous cause. People toasted his health: “To the still unconquered red man.”

General Jesup was not swayed. The fight would go on. He understood that small bands of Seminoles could attack his forces at will with few losses, so he changed his strategy, moving his troops through the territory like beaters in a pheasant hunt. Slowly but surely Jesup’s method reaped rewards. In the course of one month his troops killed dozens of warriors, destroyed camps, confiscated pony herds and supplies, and captured runaway slaves, who were shipped back to their masters or sold to defray the army’s expenses.

Part of Jesup’s success had to do with Osceola contracting malaria at Fort Drane. While he battled the disease, he exhorted his warriors to fight to the last man rather than leave Florida, and they renewed their attacks.

The stubbornness of the Seminoles, inspired by their leader, finally convinced Jesup that the solution for a quick end to the conflict was to negotiate a treaty. In March 1837 he persuaded several influential chiefs—who claimed to speak for Osceola—to meet with him. Jesup told them that if they would agree to migrate, he would allow their black brethren to accompany them. Most of the tribe agreed to the new treaty.

Osceola and his followers, however, had not given up. On the night of June 2, the leader and a party of warriors crept to the gates of the Tampa detention center. Without a shot being fired, they freed the 700 Seminoles held there—including several chiefs who had been taken away by force.

Osceola’s audacious act directly challenged Jesup’s authority, and the furious general now declared that the only course of action was to kill every Seminole in Florida. As an incentive, he told his troops that any fugitive slaves they captured would become their personal property.

Jesup’s right-hand man, Brig. Gen. Joseph Hernandez, swept through the territory with his militia, raiding the makeshift Seminole settlements. His forces killed and captured enough Seminoles to undermine Osceola’s ability to muster warriors.

By mid-October Osceola realized that his people could not fight much longer. And once again he decided to initiate treaty negotiations. He sent a message to 
General Hernandez.

On October 27 a white flag of truce was flying above Osceola’s camp when General Hernandez entered. Throughout the war, the white flag had been flown by both sides from time to time, and both sides had respected its meaning.

Hernandez asked the Seminole leader if he intended to cooperate with the government. Osceola did not have a chance to reply. Hernandez gave a prearranged signal, and his troops, who had silently encircled the camp, burst in and seized Osceola and his companions. The captives were marched away to the prison at Fort Marion in St. Augustine.

News of the capture of the famous Seminole enthralled the nation. The nature of his capture, under a flag of truce, sparked protests against the conduct of the war—and remains a controversial subject to this day.

Osceola was eventually transferred from Fort Marion to Fort Moultrie in Charleston, South Carolina. The repeated loss of his homelands combined with his bleak imprisonment and separation from his people in their continuing conflict broke Osceola’s spirit and affected his already weakened health.

On January 30, 1838, three months after his capture, the 34-year-old Osceola was dying. With great difficulty he stood up, dressed himself in his finest clothing, then lay back down on his prison bed. He crossed his arms on his chest, and a few minutes later, he was gone.

At the time of his death, Osceola was the most famous Native American in the country, and his demise was splashed across the front pages of newspapers worldwide.

The Seminoles continued to resist removal, but by mid-century as few as 100 members of the tribe remained in all of Florida. It was not until 1934 that the remnant tribe became the last Native American group to formally end hostilities with the United States.

Today Osceola is rarely mentioned in the same conversation as Geronimo, Sitting Bull, or Crazy Horse, but there is no doubt that his impact equaled that of any Native American leader who stood up to challenge the might of the United States government and army, seeking the rights of his people.