Osceola Fights to Save the Seminole

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Thompson instantly ordered his guards to seize Osceola and place him in irons in the fort’s prison. Osceola knew that he could be of no help to his people while confined. The next morning, he promised Thompson he would sign the paper if he were released. 
As a reward for his apparent cooperation, the influential young leader received a gift from Thompson of a silver-plated Spanish rifle, a superior firearm at the time. Osceola, however, had not abandoned the cause.

In November 1835 Chief Charley Emathla, Thompson’s most important ally in the tribe, was preparing for his departure to the West when Osceola confronted him. The two men argued, and Osceola, who considered Emathla a traitor, shot him dead. Osceola continued his violent protest of the Payne’s Landing treaty by leading his band on a series of raids against white settlements, resulting in casualties on both sides.

On December 23, a column of 110 officers and men led by Maj. Francis Dade marched out of Fort Brooke on its way to Fort King, following a trail recently hacked out of central Florida’s dense scrub. A group of Seminoles under the overall command of Osceola, but being led by a warrior named Alligator, shadowed the column. Osceola had pushed ahead to Fort King, where he waited in concealment near the main gate. When Wiley Thompson walked through the gate, a bullet struck and killed him. It came from Osceola’s Spanish rifle.

In effect, Osceola had declared war. He now hurried to join Alligator’s force of some 200 warriors hidden among the palmettos on one side of the road. As the army column approached, marching two by two, over-coats buttoned over their muskets to protect them from a cold drizzle, Alligator attacked, before Osceola had time to reach them. The screaming warriors fired into the surprised troops at point-blank range. The entire left side of the column—half of the total force, including Maj. Dade—fell dead in the initial volley. By nightfall all the soldiers were dead except for one, who managed to crawl through the swamps and make it back to the fort to tell the tale.

Osceola was far from finished.

A few days later a force of 250 regulars under Gen. Duncan L. Clinch, along with 500 Florida volunteers led by Gen. Richard K. Call, marched out of Fort Drane with the intention of invading the Seminole settlements along the Withlacoochee River. On the afternoon of New Year’s Eve, the column crossed the river, halting to rest about 400 feet inland in a horseshoe-shaped clearing flanked by thick hammock.

Osceola, who wore a blue army officer’s jacket as a show of contempt, had assembled about 250 warriors. They moved into position in the underbrush on two sides of the unsuspecting soldiers. He gave the order—a loud war-whoop—and the warriors commenced firing on the unsuspecting troops. The soldiers panicked, but Clinch managed to form them into ranks, and they returned fire.

During the fight, a bullet struck Osceola in the arm. Although the wound was relatively minor, it greatly disturbed the warriors to see their leader injured. The battle seemed to be a stalemate, and Osceola ordered his men to melt back into the palmettos. The Battle of the Withlacoochee was, in fact, another victory for Osceola. The soldiers had suffered four dead and scores wounded, compared with three dead and five wounded for the Seminoles. 
More importantly, the tribe had repulsed an invasion of its homeland.

Public outrage over the Florida losses elicited a swift response from Congress. In January 1836 a hero of the War of 1812 and future presidential candidate Gen. Winfield Scott—the most highly regarded officer in the U.S. Army—assumed command in the Florida Territory. Scott arrived vowing to crush the uprising in a few months. He devised a three-pronged pincer movement to catch the warriors in their camp and destroy them.

Scott was unaware that Gen. Edmund Gaines, commander of forces in Louisiana Territory, had led about 1,000 troops into Florida in response to the Dade Massacre. On February 26 Gaines and his men reached the fording place on the Withlacoochee that had been the site of Osceola’s ambush of generals Clinch and Call.

Gaines was met at the ford by sustained rifle fire from the Seminoles, the first shot killing Lt. James Izard. Osceola’s men kept the soldiers pinned down the entire day. The troops managed to build a breastwork of logs to hide behind, christened Fort Izard for their fallen lieutenant, and Gaines dispatched a messenger through the lines to seek help. At dawn, Osceola resumed the attack. For eight days the siege of Fort Izard continued;32 soldiers were wounded, many of them severely.

Osceola held the overall advantage in the war and certainly in this siege, but he wanted to end the bloodshed. He knew that the army could withstand a long war far more easily than his people could. They were already feeling the effects of hunger and illness. He requested a parley with General Gaines, who with several officers met with the Seminoles outside the breastwork. Osceola offered to cease fighting if the general would promise that the Seminoles could remain in their homeland.

Gaines was in a quandary. He did not possess the authority to arrange such a treaty. Yet, if he refused the terms, he and his men would likely be slaughtered.

At that moment, to everyone’s astonishment, General Clinch marched into the clearing with a company of reinforcements and began firing on the warriors. Osceola ordered his men to fall back. The cease-fire—and the siege—were over. Osceola’s first attempt at a negotiated peace had ended in a hail of gunfire.