First Battle of Withlacoochee
After the Battle of Black Point, the almost total elimination of Major Dade’s column, and the killing of General Wiley Thompson, there was no doubt but that Florida was now engulfed in a war. It eventually became known as the Second Seminole War, although the combatants included Creeks as well as Seminoles. In fact, the most prominent figure on the Indian side in this conflict with the United States was the Creek Osceola.
By far the best known of the Indians who took up arms to oppose migration, Osceola was soon being credited for almost every military action taken by the Indians of Florida, whether or not he actually participated in them. For the U. S. military, he became the face of the enemy, even after his health began to decline, limiting his effectiveness as a warrior and reducing his involvement as a leader of the resistance.
The first major battle of the Second Seminole War occurred on December 31, 1835, along the Withlacoochee River southwest of Fort King, not far from Osceola’s village. Osceola led about 220 warriors and some 30 blacks. During the battle, Osceola suffered an apparently minor wound to an arm or hand,
Although rumors circulated that he had been badly injured or even killed in the battle. Osceola was reported to be wearing a U. S. army coat during the engagement, perhaps a gift from Wiley Thompson.8
Early in the morning of the final day of the year, General Duncan Clinch and a force consisting of about 250 regulars and 500 Florida volunteers reached the north bank of the Withlacoochee. Finding no feasible ford across the river, Clinch used an old Indian canoe left at the river to ferry the regulars across, seven or eight at a time, with the soldiers steadily bailing out the canoe to keep the leaky vessel from sinking. The canoe may have been left at Osceola’s direction to induce a crossing that would limit the number of soldiers who would be able to make it across the Withlacoochee and at the same time to set up an ambush. After crossing, Clinch took his men about 400 yards south of the river and stopped to rest.
At that moment, Osceola’s warriors began shooting. Caught in a serious trap with the volunteers still north of the river, Clinch finally ordered bayonet charges to repel the attackers. Meantime, most of the volunteers would not cross the river, probably because their period of enlistment was up the following day and they did not want to put themselves in jeopardy so close to the end of their service. Ultimately, between 30 and 60 volunteers did cross. The regulars then retreated toward the volunteers and took up a defensive position, thereby preventing the Indians from separating them from the river.
Osceola directed the firing, urging his men to try to shoot the officers. He may also have taken part in the shooting, although that remains uncertain. General Clinch had his horse shot out from under him, and there were reports that a musket ball went through his hat.
Realizing that he had inflicted significant damage on the military but that he could not encircle them, Osceola called for a withdrawal. Clinch took advantage of his opponents’ departure by constructing a wooden bridge and taking his men back across the river. There were not a high number of fatalities in the battle (which had lasted about 90 minutes)—3 Indians and 4 U. S. soldiers—but the military suffered many more wounded than did the Indians, 50 to 5.9
The outcome was not a clear victory for either side, but it certainly convinced both parties that the Indians could more than hold their own against the U. S. military. They had gained confidence by stopping the advancing army, and Osceola had demonstrated his ability as a war leader. From this point on, U. S. officials would identify Osceola as their prime enemy, and defeating him would become tantamount in their minds to winning the war. That, of course, was a simplistic overstatement of Osceola’s role and a serious reductionist assessment of the opposition, but understanding the complexity of Indian life in any of its dimensions was something that U. S. political and military officials were seldom very good at doing.
Additional Battles
The war continued through 1836 with the U. S. military trying unsuccessfully to capture Osceola (still usually referred to as Powell by his adversaries).
In late February, troops under General Edmund Gaines were locked for days in a precarious position by surrounding Indian forces in a second battle along the Withlacoochee. Then came a ceasefire on March 6 and a parley, with Osceola, Jumper, and Alligator representing the Seminoles and Creeks. Osceola remained adamant about not leaving Florida, but he and his associates agreed to accept the Withlacoochee River as a boundary line between U. S. and Indian lands. Gaines responded that he lacked the authority to make such an arrangement but stated that he would relay the offer to government officials; he suggested that Osceola stay south of the river until an answer was forthcoming. Regardless of whether the talks had any chance of success, the arrival of a relief column under General Clinch, which immediately began to shoot, ended the discussion and the Indians withdrew. In the battle Gaines lost 5 men, with an additional 46 being wounded, and two of his own teeth were knocked out by a bullet.
Additional battles during the year included an attack on U. S. forces on July 19 at the Battle of Welika Pond and a November attempt to capture Osceola’s stronghold, known as the Battle of Wahoo Swamp. The former was an engagement at the north-central settlement of Micanopy, named after the pro-emigration leader. Osceola attacked a wagon train escorted by 60 men. Five soldiers were killed and six wounded before troops from Fort Defiance (one of several U. S. forts by that name) came to the train’s rescue.
In November, forces under Lieutenant Colonel Benjamin Pierce (recently promoted from major at the recommendation of General Richard Call) joined Call’s troops near the scene of Major Dade’s earlier defeat. Also present was a group of Creek volunteers who were prepared to fight for the United States. Call had been harassing Osceola, burning three of his deserted villages and inflicting moderate casualties, including approximately 45 fatalities. The great prize remained Osceola’s stronghold.
Osceola was prepared when the joint forces approached in the morning of November 21. Osceola and his men fired but soon began to pull back, firing from tree to tree, with the pursuers floundering after them through the swamp. Call’s forces finally struggled to reach a stream and again engaged the Indians in a gun battle. The time was about 3:30 p. m. Fearing that the dark water was deep, and realizing that the day was rapidly coming to an end and that his soldiers were tired, Call decided not to attempt a crossing. That decision was a stroke of luck for Osceola: The stream was actually only three feet deep, affording a potentially easy crossing that would have put Call within easy striking distance of Osceola’s stronghold.
As the war continued through 1837, Osceola’s active participation and leadership role declined, to a considerable extent apparently because of his health problems. Osceola was not alone in falling ill amid the inhospitable topography and climate exacerbated by serious shortages of food. In fact, illness was common among the U. S. troops, seriously undermining military efforts. Nonetheless, U. S. soldiers methodically destroyed whatever they could find that might assist their adversaries, including their crops.
General Thomas Jesup
Brevet Major General Thomas S. Jesup replaced General Call as commander of the Florida forces on December 9, 1836. Jesup brought to his new post a determination to achieve what no one else had been able to manage—the capture of Osceola, who remained in the military imagination both the will and the backbone of Indian opposition.
The experienced Jesup had served with distinction in the War of 1812. By 1818, he was a quartermaster general with the rank of brigadier. In 1828, he earned a promotion to major general. Jesup proved to be a formidable opponent for Osceola, one who would earn lasting fame and infamy for the manner in which he finally brought down his opponent.
On the Run
As rumors of Osceola’s declining health (apparently recurring fever occasioned by malaria) circulated during the spring of 1837, troops again approached his stronghold, forcing Osceola to remain steadily on the move. Jesup had established a circle of forts around the Withlacoochee area, and Osceola understood that his people would have to spread out in smaller groups to avoid the potentially large-scale disaster that likely would occur if Jesup attacked Osceola’s primary village—“Powell’s town” as the military referred to it.
Osceola moved to the Panasoffke Swamp on the Withlacoochee to take up residence at a village of former slaves. (Today Lake Panasoffke lies west of Leesburg.) At least part of Osceola’s motivation was to defend the runaways, many of whom fought bravely alongside him in the war. East of the village was Fort Mellon, commanded by Lieutenant Colonel William Harney. Osceola spent the night of May 7 as the guest of Colonel Harney, to whom he spoke of bringing the war to a close. Harney apparently believed that Osceola was sincere, but the visit likely was intended to slow down military efforts with a strategically misleading suggestion of peace.
Adding to the pressure on Osceola was the capitulation of several prominent leaders to the U. S. forces on March 6, including Micanopy and Jumper. Jesup tried to entice Indians to yield by agreeing that they would be permitted to take with them to the west any blacks to whom they had rightful ownership. In the face of considerable opposition claiming that he was permitting the property of white slave owners to escape, Jesup later modified the provision to exclude runaway slaves and ordered the Indians to turn over all runaway slaves. Using a variety of carrot-and-stick methods, Jesup sent a message to Osceola warning him that he was importing bloodhounds from Cuba to hunt Osceola down for hanging.
Still Resisting
Osceola’s bouts with fever during 1837 seriously hindered his military activities and reduced the number of warriors around him, a natural development
Given that a leader who was unable to fight would be unlikely to have a large group of able-bodied men waiting beside him when they could be productive elsewhere. Yet despite his health problems, Osceola remained unwilling to surrender. In May 1837, he attempted to unify his allies and improve their morale by arranging a ball game at Fort Mellon. In an attempt to divert U. S. authorities from his true purpose, Osceola led them to believe that the game was designed to encourage Indians to come together with the intention of emigrating to Indian Territory.
Osceola later reported to Colonel Harney that he could not keep his own appointment to report for emigration in early June because he had hurt his foot in the game. The report of the injury may have been true, but in any case it offered a useful excuse not to appear. Instead, Osceola and Abiiiki gathered a force of some 200 warriors and traveled to Fort Brooke (where the city of Tampa would eventually arise). There Micanopy, Alligator, and Jumper, among a group of about 700, had gathered prior to emigration. The three men, from Osceola’s perspective, had betrayed the cause and led many others astray.
During the night of June 2, Osceola and his party went about awakening those who had gathered at the fort, urging many to abandon the emigration, threatening some, and leading the contingent out of Fort Brooke, from where they eventually scattered to various sites. Micanopy was stripped of his leadership role after again proving that he could not be trusted to resist efforts to remove the Florida Indians, and his place was taken by Abiiiki. The successful removal of the 700 people from Fort Brooke led General Jesup to request that he be relieved of his command. That request was denied, leaving Jesup to decide that victory could never come while Osceola remained at large.
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