Skip to content Second Seminole War (1835-1842)

As the realization that the Seminoles would resist relocation sank in, Florida began preparing for war. Settlers fled to safety as Seminoles attacked plantations and a militia wagon train. Two companies, totalling 108 men under the command of Major Francis L. Dade, were sent from Fort Brooke to reinforce Fort King. On December 28, 1835, Seminoles ambushed the soldiers and wiped out the command. Only two soldiers made it back to Fort Brooke, and one died of his wounds a few days later. Over the next few months Generals Clinch, Gaines and Winfield Scott, as well as territorial governor Richard Keith Call, led large numbers of troops in futile pursuits of the Seminoles. In the meantime the Seminoles struck throughout the state, attacking isolated farms, settlements, plantations and Army forts, even burning the Cape Florida lighthouse. Supply problems and a high rate of illness during the summer caused the Army to abandon several forts.

Andrew Jackson wasn’t the only American growing tired of the war. Major Ethan Allen Hitchcock was among those who found the remains of the Dade party in February. In his journal he wrote a haunting account of the discovery, then vented his bitter discontent with the conflict: “The government is in the wrong, and this is the chief cause of the persevering opposition of the Indians, who have nobly defended their country against our attempt to enforce a fraudulent treaty. The natives used every means to avoid a war, but were forced into it by the tyranny of our government.”

On November 21, 1836 at the Battle of Wahoo Swamp, the Seminole fought against American forces, killing David Moniac, the first Native American graduate of West Point. This key skirmish restored much confidence and proved their ability to hold their ground in the Florida wilds against their old enemies the Creeks and white settlers. Late in 1836, Major General Thomas Jesup was placed in command of the war. Jesup brought a new approach to the war. Instead of sending large columns out to try to force the Seminoles into a set-piece battle, he concentrated on wearing the Seminoles down. This required a large military presence in Florida, and Jesup eventually had a force of more than 9,000 men under his command. About half of the force were volunteers and militia. It also included a brigade of marines, and Navy and Revenue-Marine personnel patrolling the coast and inland rivers and streams.

In January 1837, there was a change in the war. In various actions, numerous Seminoles and Black Seminoles were killed or captured. At the end of January, some Seminole chiefs sent messengers to Jesup, and a truce was arranged. In March a “Capitulation” was signed by several chiefs, including Micanopy, stipulating that the Seminoles could be accompanied by their allies and “their negroes, their bona fide property,” in their relocation to the West. By the end of May, many chiefs, including Micanopy, had surrendered. Two important leaders, Osceola and Sam Jones (a.k.a. Abiaca, Ar-pi-uck-i, Opoica, Arpeika, Aripeka, Aripeika), had not surrendered, however, and were known to be vehemently opposed to relocation. On June 2 these two leaders with about 200 followers entered the poorly guarded holding camp at Fort Brooke and led away the 700 Seminoles there who had surrendered. The war was on again, and Jesup would never again trust the word of an Indian. On Jesup’s orders, Brigadier General Joseph Marion Hernández commanded the expedition that captured several Indian leaders, including Coacooche (Wildcat), Osceola and Micanopy when they appeared for conferences under a white flag of truce. Coacoochee and a number of other captives were able to escape their cell at Fort Marion in St. Augustine, but Osceola did not go with them. He died in prison, probably of malaria.

Jesup organized a sweep down the peninsula with multiple columns, pushing the Seminoles further south. On Christmas Day, 1837, Colonel Zachary Taylor‘s column of 800 men encountered a body of about 400 Seminoles on the north shore of Lake Okeechobee. The Seminoles, were led by Sam Jones, Alligator and the recently escaped Coacoochee, and were well positioned in a hammock surrounded by saw grass. Taylor’s army came up to a large hammock with half a mile of swamp in front of it. On the far side of the hammock was Lake Okeechobee. Here the saw grass stood five feet high. The mud and water were three feet deep. Horses would be of no use. It was plain that the Seminole meant this to be the battleground. They had sliced the grass to provide an open field of fire and had notched the trees to steady their rifles. Their scouts were perched in the treetops to follow every movement of the troops coming up. At about half past noon, the sun shining directly overhead and the air still and quiet, Taylor moved his troops squarely into the centre of the swamp. His plan was to make a direct attack rather than encircle the Indians. All his men were on foot. In the first line were the Missouri volunteers. As soon as they came within range, the Indians opened with heavy fire. The volunteers broke, and their commander, Colonel Gentry, fatally wounded, was unable to rally them. They fled back across the swamp. The fighting in the saw grass was deadliest for five companies of the Sixth Infantry; every officer but one, and most of their non-coms were killed or wounded. When that part of the regiment retired a short distance to re-form, they found only four men of these companies unharmed. The Seminoles were eventually driven from the hammock, escaping across the lake. Taylor lost 26 killed and 112 wounded, while the Seminole casualties were eleven dead and fourteen wounded. Nevertheless, the Battle of Lake Okeechobee was hailed as a great victory for Taylor and the Army.

At the end of January, Jesup’s troops caught up with a large body of Seminoles to the east of Lake Okeechobee. The Seminoles were originally positioned in a hammock, but cannon and rocket fire drove them back across a wide stream, where they made another stand. The Seminoles eventually just faded away, having caused more casualties than they received, and the Battle of Loxahatchee was over. In February 1838, Seminole chiefs Tuskegee and Halleck Hadjo approached Jesup with the proposition that they would stop fighting if they were allowed to stay south of Lake Okeechobee. Jesup favoured the idea but had to write to Washington for approval. The chiefs and their followers camped near the Army while awaiting the reply. When the secretary of war rejected the idea, Jesup seized the 500 Indians in the camp, sending them west.

In May, Jesup’s request to be relieved of command was granted, and Zachary Taylor assumed command of the Army forces in Florida. With reduced forces in Florida, Taylor concentrated on keeping the Seminoles out of northern Florida by building many small posts at twenty-mile (30 km) intervals across northern Florida, connected by a grid of roads. The winter season was fairly quiet. While incidents and skirmishes continued, there were no major actions. In Washington and around the country, support for the war was eroding. Many people were beginning to think that the Seminoles had earned a right to stay in Florida. The war was far from over and had become very costly. President Martin Van Buren sent the Commanding General of the Army, Alexander Macomb, to negotiate a new treaty with the Seminoles. On May 19, 1839, Macomb announced that an agreement had been reached with the Seminoles. The Seminoles were to stop fighting in exchange for a reservation in southern Florida.

As the summer passed, the agreement seemed to be holding. On July 23, some 150 Indians attacked a trading post on the Caloosahatchee River that was guarded by a detachment of 23 soldiers, under the command of Colonel William S. Harney. Some of the soldiers, including Colonel Harney, were able to reach the river and find boats to escape in, but most of the soldiers, as well as several civilians in the trading post, were killed. Many blamed the “Spanish” Indians, led by Chakaika, for the attack, but others suspected Sam Jones, whose band of Mikasukis had been the ones to actually reach agreement with Macomb. Sam Jones promised to turn the men responsible for the attack over to Harney in 33 days. Before that time was up, two soldiers visiting Sam Jones’ camp were killed.

Trying new tactics, the Army turned to bloodhounds to track the Indians, with poor results. Taylor’s blockhouse and patrol system in northern Florida kept the Seminoles on the move but could not clear them from the area. In May 1839, Zachary Taylor, having served longer than any preceding commander in the Florida war, was granted his request for a transfer and replaced by Brig. Gen. Walker Keith Armistead. Armistead immediately went on the offensive, actively campaigning during the summer. The Army was seeking the hidden camps of the Seminoles, burning fields and driving off horses, cattle and pigs. By the middle of the summer, the Army had destroyed 500 acres (2.0 km2) of Seminole crops.

The Navy was taking a larger role in the war, with sailors and marines pushing up rivers and streams, and into the Everglades. In late 1839 Navy Lt. John T. McLaughlin was given command of a joint Army-Navy amphibious force to operate in Florida. McLaughlin established his base at Tea Table Key in the upper Florida Keys. Travelling from December 1840 to the middle of January 1841, McLaughlin’s force crossed the Everglades from east to west in dugout canoes, the first group of whites to complete a crossing.

i- Indian Key
Indian Key is a small island in the upper Florida Keys. In 1840, it was the county seat of the newly created Dade County, and a wrecking port. Early in the morning of August 7, 1840, a large party of “Spanish” Indians sneaked onto Indian Key. By chance, one man was up and raised the alarm after spotting the Indians. Of about fifty people living on the island, forty were able to escape. The dead included Dr. Henry Perrine, former United States Consul in Campeche, Mexico, who was waiting at Indian Key until it was safe to take up a 36 square mile (93 km²) grant on the mainland that Congress had awarded to him.

The naval base on Tea Table Key was manned by only a doctor, his patients, and five sailors under a midshipman to look after them. This small contingent mounted a couple of cannon on barges and tried to attack the Indians on Indian Key. The Indians fired back at the sailors with musket balls loaded in cannon on the shore. The recoil of the cannon broke them loose from the barges, sending them into the water, and the sailors had to retreat. The Indians burned the buildings on Indian Key after thoroughly looting it. In December 1840, Col. Harney at the head of ninety men found Chakaika’s camp deep in the Everglades. Chakaika was killed, and some of the men in his band were hanged.

Ii- War winds down
Armistead had US$55,000 to use for bribing chiefs to surrender. Echo Emathla, a Tallahassee chief, surrendered, but most of the Tallahassee, under Tiger Tail, did not. Coosa Tustenuggee finally accepted US$5,000 for bringing in his sixty people. Lesser chiefs received US$200, and every warrior got US$30 and a rifle. By the spring of 1841, Armistead had sent 450 Seminoles west. Another 236 were at Fort Brooke awaiting transportation. Armistead estimated that 120 warriors had been shipped west during his tenure and that there were no more than 300 warriors left in Florida.

In May 1841, Armistead was replaced by Col. William Jenkins Worth as commander of Army forces in Florida. Because the war was unpopular with the nation and in Congress, Worth had to cut back. Nearly 1,000 civilian employees of the Army were released, and smaller commands were consolidated. Worth then ordered his men out on “search and destroy” missions during the summer, which effectively drove the Seminoles out of much of the rest of northern Florida.

The continuing pressure applied by the Army was having an effect. Some groups of Seminoles surrendered to avoid starvation. Others were seized when they came in to negotiate surrender, including, for the second time, Coacoochee. A large bribe secured Coacoochee’s cooperation in persuading others to surrender.

After Colonel Worth recommended early in 1842 that the remaining Seminoles be left in peace, he received authorization to leave the remaining Seminoles on an informal reservation in southwestern Florida and to declare an end to the war, which he did on August 14, 1842. In the same month, Congress passed the Armed Occupation Act, which provided free land to settlers who improved the land and were prepared to defend themselves from Indians. At the end of 1842, the remaining Indians in Florida living outside the reservation in southwest Florida were rounded up and shipped west. By April 1843, the Army presence in Florida had been reduced to one regiment. By November 1843, Worth reported that the only Indians left in Florida were about 95 men and some 200 women and children living on the reservation, and that they were no longer a threat.

iii- Aftermath
The Second Seminole War may have cost as much as $40,000,000. More than 40,000 regular U.S. military, militiamen and volunteers served in the war. This Indian war cost the lives of 1,500 soldiers, mostly from disease, plus many Indian lives and homes. It is estimated that more than 300 regular U.S. Army, Navy and Marine Corps personnel were killed in action, along with 55 volunteers. There is no record of the number of Seminoles killed in action. A great many Seminoles died of disease or starvation in Florida, on the journey west, and even after they reached Indian Territory. An unknown but apparently substantial number of white civilians were killed by Seminoles during the war.

iv- Second Interbellum
Peace had come to Florida. The Indians were mostly staying on the reservation. Groups of ten or so men would visit Tampa to trade. Squatters were moving closer to the reservation, however, and in 1845 President James Polk established a 20-mile (30 km) wide buffer zone around the reservation. No land could be claimed within the buffer zone, no title would be issued for land there, and the U.S. Marshal would remove squatters from the buffer zone upon request. In 1845, Thomas P. Kennedy, who operated a store at Fort Brooke, converted his fishing station on Pine Island into a trading post for the Indians. The post did not do well, however, because whites who sold whiskey to the Indians told them that they would be seized and sent west if they went to Kennedy’s store.

The Florida authorities continued to press for removal of all Indians from Florida. The Indians for their part tried to limit their contacts with whites as much as possible. In 1846, Captain John T. Sprague was placed in charge of Indian affairs in Florida. He had great difficulty in getting the chiefs to meet with him. They were very distrustful of the Army since it had often seized chiefs while under a flag of truce. He did manage to meet with all of the chiefs in 1847, while investigating a report of a raid on a farm. He reported that the Indians in Florida then consisted of 120 warriors, including seventy Seminoles in Billy Bowlegs’ band, thirty Mikasukis in Sam Jones’ band, twelve Creeks (Muscogee speakers) in Chipco’s band, 4 Yuchis and 4 Choctaws. He also estimated that there were 100 women and 140 children.

v- Indian attacks
The trading post on Pine Island had burned down in 1848, and in 1849 Thomas Kennedy and his new partner, John Darling, were given permission to open a trading post on what is now Paynes Creek, a tributary of the Peace River. One band of Indians was living outside the reservation at this time. Called “outsiders”, it consisted of twenty warriors under the leadership of Chipco, and included five Muscogees, seven Mikasukis, six Seminoles, one Creek and one Yuchi. On July 12, 1849 four members of this band attacked a farm on the Indian River just north of Fort Pierce, killing one man and wounding another man and a woman. The news of this raid caused much of the population of the east coast of Florida to flee to St. Augustine. On July 17, four of the “outsiders” who had attacked the farm on the Indian River, plus a fifth man who had not been at Indian River, attacked the Kennedy and Darling store. Two workers at the store, including a Captain Payne, were killed, and another worker and his wife were wounded as they escorted their child into hiding.

The U.S. Army was not prepared to engage the Indians. It had few men stationed in Florida and no means to move them quickly to where they could protect the white settlers and capture the Indians. The War Department began a new build-up in Florida, placing Major General David E. Twiggs in command, and the state called up two companies of mounted volunteers to guard settlements. Captain John Casey, who was in charge of the effort to move the Indians west, was able to arrange a meeting between General Twiggs and several of the Indian leaders at Charlotte Harbour. At that meeting, Billy Bowlegs promised, with the approval of other leaders, to deliver the five men responsible for the attacks to the Army within thirty days. On October 18, Bowlegs delivered three of the men to Twiggs, along with the severed hand of another who had been killed while trying escape. The fifth man had been captured but had escaped.

After Bowlegs had delivered the three murderers, General Twiggs told the Indians, much to their dismay, that he had been ordered to remove them from Florida. The government would apply three tactics to carry out the removal. The Army in Florida was increased to 1,500 men. One hundred thousand dollars was appropriated for bribing Indians to move. Finally, a delegation of Seminole chiefs was brought from the Indian Territory to negotiate with their counterparts in Florida. Eventually a Mikasuki sub-chief, Kapiktoosootse, agreed to lead his people west. In February 1850, 74 Indians boarded ship for New Orleans. They were paid a total of US$15,953 in bribes and compensation for property left behind in Florida. There were a couple of incidents that soured relations after that. A Muskogee and a Mikasuki who had gone in to trade at the same time as Kapiktoosootse and his band were surrendering were involuntarily shipped off to New Orleans with them. Then, in March a mounted detachment of the Seventh Infantry penetrated far in the reservation. As a result, the other Indians broke off contact with the negotiators. By April, Twiggs was reporting to Washington that there was no hope of convincing any more Indians to move.

In August 1850, an orphan boy living on a farm in north central Florida was apparently killed by Indians. Eventually enough complaints about the incident had reached Washington to cause the secretary of war to order the surrender of the Indians responsible, or the president would hold the whole tribe responsible. Captain Casey was able to get word to Bowlegs and arrange a meeting in April. Bowlegs promised to deliver the men responsible, although they apparently were members of Chipco’s band, over whom Bowlegs had no authority. Chipco decided to surrender three men as the possible killers, and they were arrested when they showed up to trade in Fort Myers. Once in custody, the three protested their innocence, saying that Chipco did not like them and that other men in Chipco’s band were the actual killers, and Captain Casey believed them. The three men tried to escape from the jail in Tampa but were caught and chained up in their cell. They were later found hanging from the bars in their cell. One was still alive when found but was not cut down until the next day, after he had died. It was noted in the community that the constable who had chained the three men in their cell was the father-in-law of a brother of one of the men killed at the Kennedy and Darling store in 1849 (the Paynes Creek Massacre).

vi- Further Indian removal
In 1851, General Luther Blake was appointed by the secretary of the interior to move the Indians west. He had successfully removed the Cherokees from Georgia and was presumably up to the job of removing the Seminoles. He had funding to pay every adult male $800 and every woman and child $450. He went to the Indian Territory to find interpreters and returned to Florida in March 1852. He went far into the field to meet with all of the Indian leaders and by July had sixteen Indians to send west. Finding Billy Bowlegs insistent on staying in Florida, Blake took Bowlegs and several other chiefs to Washington. President Millard Fillmore presented Bowlegs with a medal, and he and three other chiefs were persuaded to sign an agreement promising to leave Florida. The chiefs were then taken on a tour that included Baltimore, Philadelphia and New York City. Upon returning to Florida, the chiefs repudiated the agreement they had signed in Washington. Blake was fired in 1853, and Captain Casey was put back in charge of Indian removal.

In January 1851, the Florida Legislature had created the position of commander of the Florida Militia, and Governor Thomas Brown appointed Benjamin Hopkins to it. Over the next two years, the Florida Militia pursued Indians that were outside the reservation boundaries. During this period the militia captured one man and a few women, and 140 hogs. One old Indian woman had committed suicide while being held by the militia, after the rest of her family had escaped. The whole operation had cost the state US$40,000.

Pressure from Florida officials once more pushed the federal government to take action. Captain Casey continued to try to persuade the Seminoles to move west but had no luck. He sent Billy Bowlegs and others to Washington again, but the chiefs refused to agree to move. In August 1854, Secretary of War Jefferson Davis initiated a program to force the Seminoles into a final conflict. The plan included a trade embargo with the Indians, the survey and sale of land in southern Florida, and a stronger Army presence to protect the new settlers. Davis said that if the Indians did not agree to leave, the Army would use force.

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