Battle of the Caloosahatchee

On July 23, 1839, the Second Seminole War saw one of its more brutal clashes along the Caloosahatchee River, an engagement later remembered by some as a massacre. Near what is today North Fort Myers, a sizable and mixed coalition of Native American fighters descended on a trading post and an adjoining Army camp. Stationed there were troops from the 2nd Cavalry Regiment, led by Lieutenant Colonel William Harney. Those who struck the post drew from multiple Miccosukee, Muscogee, Seminole, and Spanish Indian bands.

Behind the assault lay a sense of betrayal: word had reached the natives that the United States planned to break the Macomb Treaty, an accord they had struck with General Alexander Macomb only shortly before, one meant to secure their continued presence in Florida. When the warriors swept through the encampment and trading post, they cut down the majority of the soldiers and the civilian traders stationed there. Harney himself, along with a handful of his men, narrowly slipped away before it was too late. What followed was a return to open conflict, dragging the war onward for another three years.

Background

When William Harney and Abiaka met for a parley at Fort Lauderdale in May 1839, Harney urged the Seminole leader to pursue a peace settlement with the United States. Abiaka accepted the idea and chose one of his warriors, Chitto Tustenuggee, known as Snake Warrior, to represent him in the coming negotiations. Harney then brought the warrior to Fort King, the site chosen for the discussions. Once there, Chitto Tustenuggee met with General Alexander Macomb of the U.S. Army, and the two sides worked out an agreement. Under its terms, the various allied bands known collectively as the Seminole could remain in Florida provided they stayed south of the Peace River. The arrangement also called for the Army to establish a trading post along the Caloosahatchee River where the natives could exchange and purchase goods. Harney and his men were given the job of constructing this post, situated roughly fifteen miles up the river's north shore from its mouth. This settlement became known as the Macomb Treaty.

Its provisions infuriated the newly arrived American settlers across Territorial Florida. These white residents sought the complete expulsion of every native inhabitant, viewing their continued presence as a danger to public safety. Hoping to soothe these anxieties, Secretary of War Joel Poinsett issued a letter explaining that the Macomb Treaty was meant only as a temporary measure and that the government still planned to remove the Seminoles at a later time. Copies of this letter circulated widely across Florida, and word of its contents eventually reached the Seminoles themselves. Feeling betrayed once they realized the peace had never been intended to last, the Seminoles denounced the treaty as a sham. They resolved to renew their resistance, and Abiaka ordered that Harney's troops and the post on the Caloosahatchee be attacked.

Battle

Fifteen miles upriver from where the Caloosahatchee met the sea, the army had set up camp on the northern bank, situating itself roughly 400 yards from a trading post that stood unguarded when the fighting broke out. Not long before the assault, Harney left the area altogether, crossing to Sanibel Island in search of wild hogs. With him gone, command of the camp fell to Sergeant John Bigelow, who failed to station sentries and also neglected to distribute ammunition for the men's new Colt rifles. By the time Harney made his way back, exhaustion from the hunting expedition sent him straight to bed, and like Bigelow before him, he set no watch over the camp.

At daybreak on July 23, 1839, the attackers struck. They split into two parties, sending one against the trading post and the other against the military encampment. Caught entirely off guard, the soldiers were still asleep and lacked any ammunition for their weapons. Most of the men, Bigelow among them, were quickly killed, and every civilian working at the trading post died as well. Harney, dressed in nothing but his underwear, threw himself out of bed and into the Caloosahatchee, managing to escape the slaughter. A handful of other soldiers likewise fled into the water and later found their way back to him. As they hid from their attackers, a sloop arriving from Tampa Bay found and rescued Harney's group. Meanwhile, the natives stripped the trading post of silver coin, liquor, gunpowder, and various other supplies. Among their spoils were thirty Colt ring lever rifles taken from Harney's men, weapons that represented the finest firearms technology the army possessed at that time.

Aftermath

The clash effectively tore up the Macomb Treaty, the most serious peace effort attempted during the conflict, and pushed the Second Seminole War toward further bloodshed. That treaty's collapse meant the fighting dragged on for three more years, finally ending in 1842 not through any signed agreement but because Colonel William Worth simply ordered every U.S. soldier in Florida to halt operations. Harney stayed in the fight after this engagement, eventually tracking down and killing Chekaika, one of the native leaders who had joined forces at Caloosahatchee. He never managed the same success with Abiaka, though, despite repeated efforts to locate him deep in the Everglades.

Among those the Seminoles captured during the Caloosahatchee fight were two Black Seminole men, Sampson Forrester and Sandy Perryman, both marched off into the Big Cypress Swamp. At the war's outset these two had stood with the Seminole tribe, but they eventually switched sides to join the United States, drawn by the promise of living as Free Blacks. Because of their years spent among the Seminole, the Army put both men to work as scouts and interpreters. Perryman held the particularly close role of Harney's own interpreter, and he had also served as lead interpreter when the Macomb Treaty was hammered out at Fort King. It was this very involvement that turned the native tribes against him. They held him responsible for talking them into accepting what proved to be a fraudulent agreement, and Abiaka gave the order for his death. His execution was brutal: the natives bound him to a pine tree, drove splinters of fatwood into his flesh, and set them ablaze, leaving him to die in agony over the course of several hours.

Sampson Forrester faced the same sentence, but Holata Micco, also called Billy Bowlegs, spoke up for him, arguing that Forrester deserved to live because of his past friendship with Osceola. The native leaders relented and let him live, though they kept him prisoner for two years before he finally broke free and made his way back to the U.S. Army in 1841. Once free, Forrester disclosed that the attack at Caloosahatchee had been ordered by Chief Abiaka himself.