Thomas Sidney Jesup and the Second Seminole War (Part Seven)

General Thomas Sidney Jesup commanded military operations against the Seminoles in Florida during the early stages of the conflict now known as the Second Seminole War (1835-1842). The Second Seminole War was the longest and costliest Indian War in American history. Jesup’s field diary, available on Florida Memory, contains his perspective on the war from October 1, 1836, to May 30, 1837. This series of blog posts places significant entries from the Jesup diary in the context of the Seminole Wars and the history of Anglo-American Indian-African relations in the American South. Below is the sixth post in the series.

On March 18, 1837, Micanopy agreed to the articles of capitulation negotiated by Jumper, Holatoochee, and Cloud.

“Met Micanopy to day in council—Read and explained the articles of the Capitulation. He stated that he had authorized the chiefs, Jumper, Holahtoochee & Yaholoachee to sign that instrument for him, he…”

“Met Micanopy to day in council—Read and explained the articles of the Capitulation. He stated that he had authorized the chiefs, Jumper, Holahtoochee & Yaholoachee to sign that instrument for him, he…”

“…agreed to every article, and formally ratified it. He, Aligator, and John Hopony a friendly chief, dined with Gen[era]l J[esup]. Had a talk with Aligator after dinner in relation to the movement of his people to Tampa & thence west.”

“…agreed to every article, and formally ratified it. He, Aligator, and John Hopony a friendly chief, dined with Gen[era]l J[esup]. Had a talk with Aligator after dinner in relation to the movement of his people to Tampa & thence west.”

After the initial military successes by the Seminoles in December 1835 and early 1836, the United States Army responded with search and destroy-style tactics in order to undermine the Seminole resistance. As noted in a previous entry not all Florida Indians shared the same politics, nor did they all agree on the issue of removal.


As noted in this entry, by March of 1837 several Seminole leaders had begun negotiations with General Thomas Sidney Jesup to end the war. Prior to the meeting of March 18, Micanopy’s advisor and interpreter, the Black Seminole Abraham, met with Jesup on several occasions to outline the leader’s position. Micanopy belonged to a line of hereditary leaders among the Alachua Seminoles. It appears that he was likely related to King Payne and the Cowkeeper, previous leaders of the Alachua Seminoles, through his mother’s family.

Like other southeastern Indians, Seminoles traced descent through the mother’s line. Anthropologists refer to this form of social organization as matrilineal. Hereditary leaders did not have absolute power. Their words probably carried more weight than any other single individual, but they ruled by persuasion rather than coercion. Other individuals such as war leaders, religious leaders, and advisors like the black Seminole Abraham also influenced decisions that impacted the Seminoles as a whole. Micanopy’s power, therefore, was somewhat more limited than Jesup likely understood. In reality, his authority extended probably no further than the boundaries of his own home village and its constituent parts.

During times of war the power structure changed. For all intents and purposes, Micanopy became the principal leader of certain bands of Seminoles during the Second Seminole War. Jesup considered his word binding on the Seminoles as a whole, even if the dispersed bands themselves thought otherwise.

The Articles of Capitulation agreed to by Micanopy on March 18 related to previous treaties between the Seminoles and the United States. When Florida became a U.S. territory in 1821, one of the primary concerns of the new government was what to do with Seminoles who occupied prime agricultural lands desired by planters. In 1823, several Seminole leaders agreed to the Treaty of Moultrie Creek. This treaty, among other things, created a large reservation in central Florida, provided rations and assistance for relocation therein, and required the Seminoles to prevent fugitive slaves from residing among them.

The Treaty of Moultrie Creek was supposed to be in effect for 20 years, at which time another agreement would be drafted. However, problems resulted from the treaty almost immediately. Since not all Seminoles were present at or party to the treaty, some refused to abide by its terms. The ill-defined boundaries of the Seminole reservation invited trespassing by whites seeking escaped slaves and cattle, and likewise, Seminoles in search of game and trade ventured beyond the bounds set at Moultrie Creek.

In 1830, the United States Congress passed the Indian Removal Act. This act required all Indians living east of the Mississippi River to emigrate to the Indian Territory. Each tribe had to arrange its own eventual departure with an Indian agent assigned by the U.S. government. In 1832, Indian Agent Wiley Thompson and a group of Seminole leaders agreed to what is known as the Treaty of Payne’s Landing. Before the treaty could take effect, a delegation of Seminoles would travel to the lands assigned to them in the west and thereby determine if they met the needs of the tribe.

What happened next is steeped in controversy and strikes to the very heart of the dishonorable history of U.S. Indian policy. The delegation did in fact visit the lands in question, at which point they were forced to sign another agreement, known as the Treaty of Fort Gibson. The Seminole people were informed that the delegation had already agreed to the terms of Payne’s Landing and that emigration would commence in 1835. This caused outrage among the various political factions of Florida Indians.

It became immediately apparent that the vast majority of Florida Indians had no intention of leaving the territory. Many were determined to fight to protect their lands. Several Seminoles emerged at this point and became nationally known figures. Perhaps the most famous was the warrior known as Osceola. Osceola was so enraged with what took place at Fort Gibson that he engaged in a verbal altercation with the Indian agent Wiley Thompson.

For his verbal threats towards the Indian agent, Thompson placed Osceola in chains. After being released Osceola vowed to avenge this humiliation. His anger set the stage for the beginning of the Second Seminole War (1835-1842). In late December 1835, Osceola attacked and killed Wiley Thompson near Fort King. He also led an assault against Charley Emathla the previous month, a member of the delegation to Fort Gibson. At about the same time as Thompson died at the hands of Osceola and his band, another group of warriors routed a column of troops under command of Major Francis Dade as they traveled north from Fort Brooke on the Fort King Road.

The Seminoles and their African allies then conducted a series of raids on plantations along the east coast in the first half of 1836. It was in the context of the early successes of the Seminoles that General Thomas Sidney Jesup was sent to Florida in October 1836.

Jesup’s strategy appeared to be working from his perspective. He thought the agreement reached with Micanopy on March 18, 1837, would finally end the war. Micanopy and other leaders had agreed to cease fighting. Many brought their people in to Fort Brooke and assembled for emigration. Despite these positive signs, as it turned out, Jesup was wrong.

The situation took a dramatic turn on the evening of June 2, 1837. Warriors led by Osceola and Sam Jones (Abieka) liberated several hundred Seminoles detained near Fort Brooke. This event convinced Jesup of the need for more brutal tactics against the Seminoles. He raised additional troops and again penetrated the interior of the peninsula in search of their camps. It was during this time that Jesup devised a strategy for ending the war that ended up defining the rest of his military career.

Under the commonly accepted rules of war, discussions taking place under a white flag of truce carried the expectation that all parties were free to leave. Jesup began using the white flag of truce to lure Indian leaders into talks from which he never intended their escape. Most infamously, Jesup captured Osceola using this tactic in October 1837. The famed warrior later died at Fort Moultrie in Charleston Harbor, South Carolina. Instantly, the press seized on the dubious circumstances of his apprehension, and held Jesup responsible. This tarnished an otherwise lengthy career in the U.S. military for the Army’s longest-serving Quartermaster.

Always at the forefront of Seminole-American negotiations was the status of Seminole property in the event of forced resettlement in the west. The issue of cattle was not easily solved, as the Seminoles depended on livestock for their livelihood.

Even more contentious was the issue of the Black Seminoles. Leaders such as Micanopy made it clear to Jesup that emigration was only possible if the Black Seminoles accompanied them to the west. Jesup had hoped to make this concession as a means towards ending the war, but met stiff resistance from southern planters and politicians. His opposition claimed that many of the blacks in Florida were seized during the war, and therefore, belonged to white plantation owners and not the Seminoles. The Seminoles maintained that this was not the case, and feared that their African allies would be taken immediately upon arriving in either Tampa, or New Orleans (the point of entry into the Mississippi River for the trek to the Indian Territory). These fears played out in the aftermath of the Battle of Loxahatchee in January 1838, when slave catchers re-enslaved many Black Seminoles despite previous agreements.

Another layer of drama resulted from the fact that the negotiations over the issue of the Black Seminoles had always involved African interpreters, such as Abraham and John Horse. Since Abraham helped council Micanopy and conduct the business of negotiating with the Americans, it can be assumed he did everything in his power to ensure a favorable outcome for the Black Seminoles.

Any conclusions Jesup felt had been reached by the March meetings quickly proved short-lived after the raid on Fort Brooke on the night of June 2, 1837, and in the ensuing five years of conflict.

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