Of what we know of the Spanish Indians, we only have the name of one of them, and that is Chekaika. We have no image except to know from written accounts that he was very large and tall.
His background and identity has always been speculated, and some people have even wondered if he was Calusa.
Below: Chekaika's hammock hideout where Harney tracked him down and killed him is visible from the Tamiamai Trail east of Miccosukee. It sits out there like a fortress, and the sawgrass makes an effective moat. We are pretty certain that this is the right place where it happened. The Miccosukee stay away from here.
According to Dr. Brent Wiseman who did a talk last month at the meeting of the Southwest Florida Archaeological Society, Dr. John Worth has discovered more information on Chekaika. Dr. Worth has investigated archives in Cuba and Spain about the Calusa Indians and Spanish-native relationships. According to what he has found, Dr. Worth says that Chekaika was also named Antonio, and had a ship. This would mean that Chekaika was a well established captain and leader among the Spanish Indians.
The Spanish Indians were not involved at the beginning of the Second Seminole War. But trouble was close behind. Their settlement on Charlotte Harbor was burned by the Seminoles and the customs official / tax collector was murdered. They fled to Tampa Bay. At first the government accepted them, but a change in leadership brought distrust, and they were rounded up for removal, even with a letter memorial from local residents, sent to the secretary of war protesting the removal. They insisted that they were Spanish, but marriages to the Seminoles made them no different than the rest of the Indians as far as the government was concerned.
150 Spanish Indians were sent to Oklahoma. When in New Orleans, seven of them would go no further, and were allowed to remain in the city and return to Florida when the war had ended. The Oklahoma Seminoles do claim some Spanish ancestry today, but we don't know what happened to the ones who stayed in New Orleans.
Whatever it was that set Chekaika on his effective campaign of destruction, a good bet is that it had to do with the unfair removal. And he conducted two bold raids during 1839 and 1840 that would see no equal during the war.
Chekaika's tactics were different than the rest of the Seminoles. That is a good sign that he was not totally from the Seminole Tribe. He conducted night attacks, which was unusual for most any other skirmish during the war. The raid on Harney's dragoon soldiers was bold and unexpected. The soldiers did not anticipate a direct attack, and it is the third deadliest skirmish of the war, behind Dade's Battle and the Battle of Okeechobee.
The destruction of the town on Indian Key was even more unexpected, and wiped out what was then the county seat for Dade County. The attackers had enough knowledge of naval artillery to fire a cannon to prevent the naval force from approaching the settlement. During the raid, the attackers were heard speaking in English, and not Muskogee or Mikasuki language.
So both these raids have different tactics and even a different feel from any other battles during the war.
Within a few months, Harney turned the tables and used a covert operation of his own, tracking down Chekaika with his men wearing Seminole clothing and travelling in dugout canoes. Harney's campaign of revenge was one of the first Special Forces operations.
What of the oral history among the Seminole / Miccosukee people? In the early 1950s, William Sturtevant went to south Florida to find out. The Miccosukee people that he interviewed nearby did not remember Chekaika's name, but their recollection of events was very much in agreement with the historical record. The big difference was that they had the time compressed between the Indian Key raid and Harney killing Chekaika, as a few days or weeks instead of four months.
The Miccosukee all agreed that Chekaika traveled down the Shark River, and that the soldiers hunted him down. Although they did not remember Chekaika's name, they all said that he was Indian, or one of them.
Sturtevant said that no remorse was felt by the Miccosukees interviewed about Chekaika's death. They felt that revenge fell upon him for raiding the Indian Key settlement, and was an expected response.
About six months after Chekaika's death, the Seminoles held a council during the Green Corn Dance, were Sam Jones / Abiaka had the people pledge to no surrender, and bring only war to the white man. Abiaka was furious over Chekaika's death, when he was killed offering a hand in surrender, and then hung like a dog. At that meeting, a remnant of the Spanish Indians were present, and were given shelter and adopted among the Miccosukee. It was probably just a small number that was left.
Finally when the war ended and Billy Bowlegs surrendered in 1858, he had an unusual comment. Bowlegs said that a dozen men and one boy were what remained of the "Boat People" and would willingly leave Florida if given the chance. These Boat People may have been among the last of the Spanish Indians, because their name denotes people that live a maritime life. History does not record what ever happened to these 12 men and their families.