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Osceola: A Brief Account and Evaluation of His Life

by Collin J. Overby (MLRHR, MSW), Seminole descendent

Part I: Childhood and Youth
Part II: Military Career
Part III: Death and Remembrance

Military Strategy and Tactics

Osceola acquired many of his military skills by observing the soldiers at U. S. military facilities, particularly Forts Brooke and King. So great were his military skills that some soldiers believed him to be a West Point graduate. Many historians write of Osceola's military genius. His tactic of quick skirmish and retreat is frequently contrasted to the slow cumbersome tactic of the white soldier. McNeer summarizes one such Osceola skirmish as follows, " . . . Then a battle took place that spread the fantastic rumor the he (Osceola) was a West Point graduate . . . war broke out in one place after another . . . (it had been) nine months since the troops had met hostile Indians in actual combat... there soon became one of a quick foot attack from ambush and rapid disappearance into the forest or swamp. For troops, it was a march accompanied by baggage wagons, and laden with packs and then a failure to find the Indian marauders" (78).

During Osceola's imprisonment at Fort Moultrie, in conversations with his attending physician, Dr. Weedon, Osceola, in a playful and boastful manner, described military strategies employed by the Indian and the white man. McNeer describes Osceola during the conversations between the two as, " He arose and began to imitate the soldiers. First, he showed how the white man fights loading and firing. Then he showed how the Indian fought skirmishes and retreats."( 13 8).

Mark Boyd, as referenced by Hartley, offers accounts of Osceola's military genius and his effect in council on the chiefs. Hartley quotes, " . . . he (Osceola) became the master spirit of along and desperate war. Bold and decisive in action, deadly but consistent in hatred, dark in revenge, cool, subtle, and sagacious in council . . . In council, he spoke little; he made the other chiefs his instruments, an what they delivered in public was the secret suggestion of the invisible master" (248).

General Jesup, an U. S. officer who deceptively negotiated with Osceola believed, "An U. S. officer and his trained men should be able to defeat a ragged band of ex slaves and their slave allies. No U.S. officer should have to negotiate with such inferiors" (Katz, bl).

George Coe, however, according to Hartley, feels that the well earned fame of Osceola can be attributed to not only his true patriotism., but his determined effort against the combined armies of a great and powerful nation, in one of the most remarkable struggles known to history" (249).

The Hartleys in their cover jacket make the points that Osceola at no time led more than 1500 Seminole warriors to fight against 40,000 U. S. soldiers. In a war that cost the U.S. $40 million, and a white death toll greater than 1500 lives, Osceola successfully fought a slashing and harassing guerrilla type war which defeated the best officers of the U.S. Army including Generals Duncan Clinch, Winfield Scott, E.P. Gaines, and Thomas S. Jesup.


Even though Osceola had no specific standing in his tribe, he was able to become a great and successful leader of his people.

When Osceola was about 18 or 20 years old, he repeatedly made trips to Fort Brooke in Florida to watch the white troops drill. As he intently observed the soldiers, they also observed him. Louis, a Negro interpreter at the Fort, was sent by a captain to determine Osceola's identity. After speaking with Osceola, Louis reportedly said to the captain, "He is a Mickasukee a Red Stick and the best hunter, runner and fighter" (McNeer, 8).

Later when the Seminoles were forbidden to go to the coasts, Osceola had to stay away from Fort Brooke on Tampa Bay, so he went to live near Fort King. Here, he joined a band of Red Sticks in a village in the Wahoo Swamp, located 100 miles north of Tampa Bay. It was at this location that young warriors began to listen to Osceola, and he began to earn their respect and obedience.

The extent of Osceola's leadership ability was very evident over the years. He was a leader who frustrated U. S. generals in their attempts to carry out U. S. Indian removal policies, as in the case of General Thomas Wiley. Wiley aware of Osceola's growing influence as a leader, questioned Chief Charlie Amethla in November 183 5, as the chief was preparing to leave his village on the Withlacoochee River to join other Seminole Indians at Tampa Bay, regarding Osceola's (Powell's) intentions and influences. "Tell me, Charlie, what of that wild Indian Powell? Does Powell have much influence? Are the chiefs with him?" Charlie's reply to these questions was, "Osceola has many young braves with him. More chiefs are listening to his voice now" (McNeer, 52).

Osceola was also a leader who cast fear into the hearts of white soldiers. This is attested to by General Call, who had been dispatched by Washington, D.C. with an army of volunteers to protect settlers. When the commanding general, General Clinch, was planning strategy with Call for attacking the Seminole headquarters at the Cove of Withlacoochee, General Call said of his volunteer soldiers, "They are afraid of (Chiefs) Jumper, Alligator, and Osceola" (McNeer, 71).

As the year 1836 progressed and war flared across Florida, Osceola was not only the acknowledged "head war leader" known throughout the country for his boldness, energy and skill (McNeer, 77), but he was also known for his ethics. For example, when Osceola was leading a war party he granted no quarter (mercy) to his enemies, but no women or children were ever harmed. " I make war against white warriors," he said proudly, "for I am a warrior. I do not fight squaws and papooses" (McNeer, 77).

The Hartleys give a very detailed account and evaluation of Osceola as a leader. They describe him as a leader who, more than any other native American leader, personifies the spirit of Indian resistance to white domination. He is portrayed by the Hartleys as both the George Washington and Patrick Henry of the Seminoles. They also believe that Indian rituals, such as the Green Corn Dance, played an important part in developing his position as a leader. The Hartleys see him as figure of authority particularly among the young Seminoles who later followed him without question. Osceola, the leader, performed his duties with reverence, firmness and the diplomatic good humor that invited obedience (6I ).

Osceola, the leader, so deeply admired by his people, also had the unique ability to achieve the total involvement of his people. Uncharacteristically of his time, he could turn women into functioning communal commissariat, which as such supplied food and other support for warriors. So, even though women were often close to war parties, Osceola apparently had the ability to capitalize on this custom (Hartley, 161).

Osceola, the leader, also had periods of loneliness an doubt concerning his leadership ability. How did he question and evaluate his leadership abilities? On one occasion when he and his warriors were encamped at the Withlacoochee Swamp, Osceola stepped from the circle of fire, and stared at the evening, star. His people were all around him. There were women, children and warriors all being driven by the white man toward potential destruction. He reasoned (the story goes) that "none of it made any sense. The land was large enough for all. The Indians had never asked for anything more than to exist in peace." It is said, as he turned back toward his camp, he felt the loneliness of leadership. He thought how he had wanted to be a leader, even seized at leadership with passion. Now he was the main figure in a cruel war that might be wrong. He reasoned that among the Seminoles, no one had his influence. Their courage to fight came primarily from him; thus, he had to be a leader determined to win. He concluded, "we may die to win, but the children of my children will walk this land" (Hartley, 163).

Historians agree that Osceola as a leader had inspired his people, particularly the young, with a sense of tribal identity. His people had come to feel that they were a unified nation, rather than a conglomeration of weak bands or clans. He had given them a goal: the defense of their tribal rights to their homeland. Like many great American Revolutionary leaders, he may have been chauvinistic in leading his people toward this goal, but he was sincere. He thought it to be important that Indians be given back their humanity. Before Osceola's leadership, the Seminole warriors and their chiefs had cringed before the white man, accepting his support (food, money, etc.) and begging for his favor. Although Osceola could never entirely wipe out this dependency, he did reduce this dependency drastically (Hartley, 163).

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