Peter McQueen was the son of a White father and Indian mother. He considered himself Creek and affiliated with the Redsticks who favored preserving the old ways. While bringing supplies to his band, he was attacked by local militia at Burnt Corn Creek in the battle that touched off the Creek War. The tide turned against the Redsticks and McQueen lead his people into Florida and joined the Seminoles. McQueen passed away in 1818 but his band of warriors would fight with Osceola in the Second Seminole War.
Osceola claimed both his parents were Creek, and his mother later married James McQueen. More likely James McQueen was his father. He was the grand nephew of Peter McQueen. He most likely was of mixed race, including some Black. He was too young to fight in the Creek War. However he was caught in the migration south. He and his mother were separated demo James McQueen, and became a part of e Seminole People. Osceola participated in the First Seminole War. He was captured but Andrew Jackson let him go because he was so young. Osceola was not an hereditary chief, nor an elected one. He was vehemently opposed to e Seminole removal to the West. He had a seething conflict with the local Indian agent Wiley Thompson. Reportedly Thompson sold out Osceola's mulatto wife the slave hunters. At a council held by Thompson he insisted on abiding to the original treaty with Indian removal. Osceola put a knife through the papers. Osceola killed a chief who supported emigration. He later killed Thompson. He and his men attacked a baggage train. His men attacked a column of 100 troops, killing all but three. Osceola and his men attacked another party of regulars in the First Battle of the Withlacoochee and killed many. Osceola was wounded in the engagement. This began the Second Seminole War which raged for seven years. Osceola was the main focus of federal efforts until his capture. Osceola's warrior included many escaped slaves and he fought to protect them. Osceola was able to free 700 Indians held in detention. Osceola suffered from malaria, and accept an invitation to talk under truce. This lead to his capture. He was transferred to Fort Moultrie and died from his declining health. Depression contributed to his health issues of malaria, toncillitis and abscesses.
Micanopy was a Seminole leader by birthright and the closest to a chief during the Second Seminole War. He had considerable holdings of land and slaves. He refused to sign the Treaty of Payne's Landing. He supported Osceola and Wildcat, young people who could resist Seminole removal. He and Osceola lead the group that attacked Major Francis Dade's men, leaving only three alive. He had his doubts about the cause and surrendered. He was kidnapped back by Osceola but hen retaken when Osceola was captured under flag of truce. He went West and found the Seminole were part of the Creek aRea. This caused friction. After several years he negotiated a Seminole area in Indian Territory.
Wildcat was the most aggressive of the Seminole warriors, fighting in the Second Seminole War. He was the nephew of Micanopy. He was captured and jailed. He escaped through a small window 15 feet above the floor. Four years later he was recaptured and sent West. He lived with the Cherokee, fearing reprisals from the Creek. He and his people went to Mexico where they were granted land.
Billy Bowlegs was the primary leader in the last Seminole War 1855-58. By this time most of the Seminole had already been removed to Indian Territory, except those who lived deep in the Everglades. In 1832 he signed the Treaty of Payne's Landing. He fought in the Second Seminole War even after Osceola was captured. This included attacking a trading post and killing most of the garrison. He finally surrendered in 1842. He did not leave Florida however. In 1850 government official began to pressure him to leave and offered money. He still resisted. In 1853 all remaining Indians in Florida were declared outlaw. In 1855 government surveyors and soldiers penetrated the area where Bowlegs and his people lived. Bowlegs lead the attack on the intruders, and three years of guerrilla warfare followed. In 1858 Bowlegs finally accepted a large financial settlement to move to Oklahoma. During the Civil War he resisted the call to serve with the Confederacy and instead went to Kansas to enroll with the Federals. This was not expected as he was a slaveholder. He died of smallpox during the war while serving in the army.
Arpeika was the only Seminole leader to avoid premature death or removal to the West. He fought in the Second Seminole War despite his advanced age. He warned Osceola and other leaders against trusting the Americans and their flag of truce. They did not head his warning. While most Seminole were removed, he stayed and fought in the Third Seminole War alongside Billy Bowlegs. He was not only a warrior but also a medicine man. He hung on in the Everglades and died at about 100 years of age close to Lake Okeechobee in 1860.