The First Seminole War

In 1812, US troops attacked the Seminoles and killed King Payne and engaged in battle. The US retreated after 8 days of battle. Hostilities continued, including the stealing of cattle from Seminoles, retaliation such as burning settlers homes, and Seminoles captured and sold as slaves. In 1808 the importation of African slaves became forbidden by an act of Congress, and the value of escaped slaves increased greatly. Slave catchers were constantly invading Seminole territory. Tensions kept escalating until it precipitated the First War in 1817.
Chief Neamathla had told soldiers that they could not trespass on his hunting ground. To put him in his place for issuing such a proclamation, 250 soldiers attempted to capture Neamathla’s village. The Seminoles resisted and nine days after this attack they retaliated and opened fire on a boat load of 40 soldiers most of whom were killed. The Secretary of War John C Calhoun commanded Major General Andrew Jackson to take 3,000 troops to attack the Seminoles. Jackson burned their towns, stole thousands of bushels of corn, took horses and hogs and thousands of heads of cattle, captured men, women and children, executed Indian leaders, scattered Seminoles deeper into the Florida peninsula, and the First Seminole War began.
Calhoun told Jackson, “Should you be of the opinion that your numbers are too small to beat the enemy, you will call on the Executives of adjacent states for such an additional milita force as you may deem requisite.”
General Andrew Jackson’s militia forced the Seminoles to move further south and his incursions into and seizing of Spanish Territory led to Spain ceding Florida formally to the United States.
The Second Seminole War

In 1832 the Seminoles were called to a meeting at Payne’s Landing. The Treaty negotiated with the US government called for Seminoles to move west if the land was found suitable. A delegation of seven chiefs toured the area for several months and signed in 1833 what they believed to be a statement that the land was suitable for consideration. Upon their return to Florida, however, there was disagreement as to the terms of the treaty. Many of the chiefs stated that they had not committed to move their people to the new territory and that they had been coerced, through force and misinterpretation into signing. Even some U.S. Army officers claimed that the chiefs had been misled regarding the agreement.

Micanopy (left) and five other sub-chiefs, during a truce conference, were made prisoners of war on December 14, 1837, while encamped near Fort Mellon. They were then sent on a steamer to St. Augustine, and later taken to Sullivan Island. Micanopy and 218 of their people were sent by steamer to New Orleans on February 22, 1838 and imprisoned there at the barracks of Fort Pike. Huithli Emathla (Jumper) died at the barracks April 18, 1838. The captors collected prisoners at the barracks until mid-May, when they sent 1,127 toward Fort Gibson in Indian Territory. Forty-seven of them died by the time they reached Vicksburgh, Mississippi. Micanopy’s party reached Fort Gibson in June of 1838.
Osceola (below) led the Seminole resistance to removal until he was captured on October 21, 1837, by deception, under a flag of truce, when he went to a site near Fort Peyton for peace talks. The United States first imprisoned him at Fort Marion in St. Augustine, then transported him to Ft. Moultrie in Charelston, South Carolina. He died there a few months later of causes reported as an internal infection or malaria.

The refusal of most Seminoles to relocate west of the Mississippi River led to what was known as the Second Seminole War. It formally began with Dade’s Massacre in December 1835. This started a conflict that would last until 1842 with many American commanders trying and failing to completely defeat and remove the Seminoles. The Seminole population steadily shrank as warriors were killed, and as groups were sent west through capture.
Under chiefs and warriors including Osceola, Jumper, Bowlegs, Micanopy, Arpeika, Halleck Tustenuggee, Coacoochee, and many others, the Seminoles never stopped resisting. The war was vicious and bloody. General Jesup captured many important Seminole leaders, including Osceola, Micanopy and Coacoochee, by seizing them while under a false white flag of truce.
At its conclusion in 1842, roughly 3,000 Seminoles had been removed to Indian Territory. Less than 500 remained in the Florida Everglades with Chief Billy Bowlegs and Arpeika. The Second Seminole War was the longest and most costly of all the wars of removal fought by the U. S. Government. Two thousand soldiers died, and $40 million dollars was spent. 1500 to 1600 Seminole warriors and 20,000 Americans fought over the 7 years of battle.
Seminole Voices from this period 1817-1842:
The Third Seminole War



Excerpts from Spessard Stone’s “Billy Bowlegs: Seminole Chief”
“During the Second Seminole War (1835-42), Micanopy was exiled west in 1838, thereby relinquishing his Florida chieftaincy; whereafter, in 1839, Billy Bowlegs was referred to as Holatter-Mico and awarded the title of Holata Micco, i.e., chief governor. On December 20, 1841, Major William G. Belknap engaged Billy Bowlegs and the Prophet’s bands in the Big Cypress in a campaign which, though initially indecisive, forced them to move into the Everglades and Alligator Swamp, west of Lake Okeechobee, and resulted in the surrender of two other bands. In early 1842, Billy Bowlegs achieved ascendancy by being named chief with Fuse-Hadjo as his sense-bearer. On August 5, 1842, Bowlegs and other Seminole leaders met with Colonel William J. Worth at Tampa, and Bowlegs accepted Worth’s peace terms. On August 14, 1842, Worth declared the war ended.
In 1843 General Worth estimated in Florida only a remnant of 300 Indians.
Of Bowlegs, Sprague observed: “In all respects (he) is qualified for supreme command, which he exercises with skill and judgment. He is about thirty five years of age, speaks English fluently, active, intelligent and brave…
Panic ensued in 1849 after two Indian attacks. At the Indian River settlement near Fort Pierce on July 12, four of a group of outlawed Indians killed one man and wounded another. Then on July 17 at the Kennedy-Darling trading post at now Paynes Creek, four Indians attacked and killed the manager and a clerk, wounded another clerk and his wife, and burned the store. Bowlegs, seeking to maintain the peace, averted war when he in October 1849 at Charlotte Harbor turned over to Major General David Twiggs three of the alleged murderers, the hand of a fourth, and reported a fifth had eluded capture.
On August 6, 1850, another crisis occurred when an eight-year-old orphan boy was killed by Indians in Marion County. An investigation by Capt. Casey resolved the situation in May 1851 with the arrest of three Indians, whom Bowlegs had surrendered.
On January 21, 1850 at Fort Chokonikla, General David E. Twiggs met with Bowlegs and four sub-chiefs for the purpose of arranging terms for emigration. On February 28, 1850, seventy-four Indians sailed from Fort Hamer to New Orleans, but most Seminoles, including the bands of Bowlegs, Sam Jones, and Chipco, who had initially indicated they would emigrate, made known to Capt. Casey their determination to stay.
Tragically, President Zachary Taylor, a few days before his death (July 9, 1850) told General Twiggs, “Gen. Twiggs, tell Bowlegs whenever you see him, from me, that if his people remain within their limits & behave themselves, they shall never be disturbed while I remain in office.”
A frequent U. S. ploy was taking delegations of Indians to northern cities to convince them that white power was so overwhelming that further resistance to emigration was futile. General Luther Blake, who replaced Capt. Casey as Seminole agent in Florida, so endeavored in 1852. Departing Fort Myers on August 31, General Blake escorted Bowlegs, six Indian chiefs, and an interpreter northward. At Washington, D. C., Bowlegs met with President Millard Fillmore, who awarded him a medal. On September 20, the chief and three others of the delegation signed a memorandum, in which they agreed to emigrate. On September 23, they arrived in New York City where they occupied two adjoining rooms on the fourth floor of the American Hotel along Broadway. At Niblo’s Garden, an entertainment center, they witnessed a ballet troupe in the “Barber of Seville.” They shopped at Grant and Barton dry goods, toured the New York Herald, visited Tiffany’s Jewelers, attended an evening performance of Christy’s Minstrels, toured Phineas T. Barnum’s American Museum, and finally at City Hall, Bowlegs met Mayor Ambrose Kingsland.
Leaving on September 25, they returned via the steamer Florida to Tampa Bay where Bowlegs in an interview with a New Orleans Delta correspondent stated: “I saw the Great White Father in the White House. I told him that no one would scare me from Florida; if I wanted to go, I would; if I did not, I would not.”
“I saw the Great White Father in the White House. I told him that no one would scare me from Florida; if I wanted to go, I would; if I did not, I would not.”
The reporter described him as “about five feet eight inches in height, rather stout, has a round face, and an expression one never forgets. He is said to be possessed of more cunning than any other Seminole Chief that ever lived.”
In 1854 another visit to New York and Washington, D.C. was arranged for Bowlegs and several other Seminole leaders, but the chief declared he would not leave Florida under any circumstances.
In May 1854, Jefferson Davis, the Secretary of War, resolved that only coercive measures would henceforth be used to induce the Florida Indians to emigrate. Talks and trade with them were directed to be stopped. Lands, previously withheld from settlement, were opened for homesteading in the fall of 1854. In August, Davis, in a letter to Senator Stephen Mallory, restated his stand, including force if the Seminoles did not consent to removal.
In 1855, the Army began to erect a new cordon of forts and roads and intensified patrols into the Everglades and Big Cypress Swamps. Lt. Hartsuff’s excursions into the Big Cypress resulted in his discovery of several Indian villages, including Bowlegs.’ The Indians protested to Capt. Casey, the Indian agent who had been reinstated in July 1853, that the incursions would inevitably lead to a renewal of hostilities.
On December 7, 1855, Lt. Hartsuff with six mounted men, two foot soldiers, and two teamsters left Fort Myers to resume exploration of the Big Cypress. Entering Bowlegs’ village on December 18, they discovered it had been uninhabited for some time and the garden unkempt. At about 5:00 A.M. on December 20 as the soldiers were breaking camp, a Seminole 40-man war party led by Billy Bowlegs opened fire and killed three. In the ensuing fire-fight, three of the privates were wounded, as was Lt. Hartsuff. After burning the wagons and killing the twelve mules and two of the horses and stealing the others, the war party, having thus commenced the Billy Bowlegs War, or Third Seminole War, withdrew.
In November 1857, the discovery and destruction of Bowlegs’ main stronghold near Royal Palm Hammock, including 30 dwellings and a 40-acre vegetable field, dealt a devastating blow.
On March 15, 1858, Bowlegs and Assinwah began negotiations with Elias Rector, superintendent of Indian affairs for the Southern Superintendency, and on March 27 the Seminoles in a council accepted the terms, which included $7,500 to Bowlegs, $1,000 to each of four other leaders, $500 to each warrior, and $100 to each woman and child, and exile west.
On May 4, 1858 at Fort Myers, 38 warriors and 85 women and children, including all of Assinwah’s band, 10 of Sam Jones’ band, and probably all of Bowlegs’ band boarded the steamer Grey Cloud enroute to exile. At Egmont Key, 41 more Seminoles who had been captured, boarded. On May 8, 1858, Col. Gustavus Loomis declared the war ended.
Via the steamer Quapaw, the exiles went up the Mississippi and Arkansas rivers to Fort Smith, Arkansas where they arrived on May 28, 1858. Then they continued overland by wagon on June 16 to the Little River in the Seminole Nation where Bowlegs was greeted ardently.”
The manifest of the US Steamer Grey Cloud which left Tampa Bay May 2, 1858 for the journey to Indian Territory with Billy Bowlegs and his band on board, and signed by the Superintendent of Indian Affairs Elias Rector is below. They traveled up the Mississippi River to the Arkansas River to Fort Smith and then by wagons and foot to the North Fork of the Canadian River in Creek territory.
In a letter written May 29, 1858 from the Supt. of Indian Affairs, Elias Rector to Charles Mix, Commissioner of Indian Affairs, writes, “I arrived here (Indian Territory) on the 26th of May by Steamer Quapaw with all the hostile Seminoles that left Florida with me. They are now encamped in the Choctaw Nation near here and will leave in wagons in four or five days. Agent Rutherford will accompany them to their country.- National Archives
Samuel Rutherford wrote Major Elias Rector on June 7, 1858 stating that he had arrived to Seminole Nation in Indian Territory with 125 Seminoles, “leaving Billy Bowlegs with 36 others near the North Fork on account of the extreme disposition of his young wife and two of his children. I made arrangements for teams to bring them. Four had died up until the time Billy stopped.”- National Archives.
Four of Billy Bowlegs’ children died during the journey. Sally Bowlegs, my third great-grandmother, age 13 in 1858 was one of the two children who survived.
Joseph R. Murrow, Baptist missionary wrote for the Index on April 2, 1859 “Billy Bowlegs, well known Seminole warrior of Florida notoriety, is dead. He died a few days since while on a visit to the “New Country” for the purpose of selecting a place to settle. A few of his followers were with him and buried him in the true old Seminole style: viz. with everything he had with him. They first killed his pony, and rifle, money, and everything else, were buried.”
In October 1859, Rector to Mix discusses the “impudent” Seminoles who were demanding monies promised as annuity payment and who threatened trouble if not received. “If any should occur I shall advise the malcontents be dealt with in the most summary and effectual manner. Bowlegs fortunately for his people , is dead, but others survive who are inclined to create difficulties and may need a salutary lesson.”
