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Collier County and the Seminole Wars Part 6 Chekaika

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I am posting my talk from a recent program I gave at the Marco Island Historical Society. Several people who could not attend wanted to hear it, so I am posting the entire talk here.


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.

Dr. John 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.

Whatever it was that set Chekaika on his effective campaign of warfare and destruction, a good bet is that it had to do with the unfair removal. 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. He conducted night attacks in the pre-dawn hours, which was unusual 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 Major Dade's Battle and the Battle of Okeechobee.

Attack on Harney on the Caloosahatchee

On the night of July 23rd, 1839, warriors under Chakaika & Hospetarke attacked the trading post that was being established on the Caloosahatchee River. Many soldiers with the 2nd Dragoon regiment were encamped there, but were killed before they can even get out of bed, and Colonel William S. Harney escapes in his nightclothes. Many of the goods were looted, and the last that was seen of Chakaika was escaping up Henderson Creek into what is today Rookery Bay on route to his Big Cypress hideaway. Harney turned out to be the worst foe that Chakaika could have chosen.

[Below: Harney late in life. When he retired, he moved to Orlando and lived on the shore of Lake Eola, now downtown.]

Attack on Indian Key

About a year later in August 1840, Chakaika led a bold raid against the town on Indian Key. This island town was the first county seat for Dade County, and was a community whose main industry was salvaging shipwrecks.

The attackers of Indian Key waited until nearby Naval forces had left. During the raid, the attackers were heard speaking in English, and not Muskogee or Mikasuki language. The objective of the attackers appears to be the looting of the general store, where they made off with many goods including gunpowder, and at least a half dozen more boats to carry their stash. Thirteen people were killed, including the most prominent island resident, Dr. Henry Perrine. His wife and children fled through a crawl space below the floor of the building, to a small row boat, and were later rescued by a small naval vessel. Many of the buildings burned, and today Indian Key remains a deserted island that is maintained as a state park. A nearby ship tried to help the fleeing settlers, but was prevent from approaching when the attackers found an artillery piece in the settlement and started to fire upon the ship. This was the only instance in the war where the Indians fired a cannon.

[Below: Indian Key today.]

Harney Hunts Down Chekiaka

Within a few months, Col. Harney of the 2nd Dragoon Regiment turned the tables and used a covert operation of his own, tracking down Chekaika and his warriors by wearing Seminole clothing and traveling in dugout canoes. Commander of the forces in Florida at that time was General Walker K. Armistead (the father of Lew Armistead of Gettysburg fame), and he reprimanded Harney for not wearing proper uniform on the expeditions, but Harney was successful.
The soldiers tracked Chekaika to his hideout, using a captured slave who had been among the Seminoles in the Everglades previous, and were able to approach the village undetected.

Chekaika’s village was in a large hammock that is today visible from the Tamiami Trail and has the appearance of a tree fortress. (Past the Miccosukee Reservation.) They took it completely by surprise and surrounded Chekaika. He knew that he was captured, and as he extended his hand as if to greet the soldiers, he was shot through the head and died immediately. Harney had Chekaika’s body hung from a large tree on the island, and even today the local Miccosukee avoid this place.

[Below: Chekaika's hammock is in the distance; in the background on the right, about a mile to mile and a half away. Rising like a tree fortress on a sea of sharp sawgrass.]

What of the oral history among the Seminole / Miccosukee people? In the early 1950s, William Sturtevant came to this area to find out. The Miccosukee people that he interviewed 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 compressed time 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 in what is today Everglades National Park, and that the soldiers later hunted him down. Although they did not remember Chekaika's name, they all said that he was Indian, and one of them.
From the interview, it was found that no remorse was felt by the Miccosukees for 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, the legendary Seminole medicine maker, had the people pledge to no surrender, and bring only war to the white man. Abiaka was furious over Chekaika's death. 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 of Spanish Indians that were left.
Current Location:
Royal Palm Hammock
Current Music:
Kate Ryan
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