When most people think of the Florida Keys, they conjure up images of peace and relaxation in a tropical paradise. But the Keys of the 1830’s were the exact opposite. Not only were these isolated rocky islands difficult to scratch a living off of, tensions were growing between the encroaching settlers and the Native Floridians.
After the 2nd Seminole War began in 1835 and the New River Massacre occurred in 1836, most of the Keys were abandoned, except for Key West, Key Vaca, and Indian Key. Despite fears of attack and sightings of Natives in the area, the inhabitants of Indian Key remained to protect their property and to be close to any shipwrecks near the Keys.
Among its notable residents was Dr. Henry Perrine, a physician and horticulturist who introduced and cultivated many tropical plants to Florida—most significantly the Key lime. On August 7, 1840, the Perrines were awoken by gunfire and shouts. A large party of Spanish-speaking Seminoles, led by Chief Chekika, had descended upon Indian Key.
Dr. Perrine herded his family into the crawlspace under the house and then covered the door with a chest. His wife, Ann, and three children escaped through the turtle kraal behind the house. They were able to find a boat and headed for the United States Navy base on nearby Tea Table Key, chased by two Seminoles in a canoe, but were rescued by sailors in a whaling boat.nMost of the 50 to 70 people living on the island were able to escape, but 13 were killed, including Dr. Perrine, who stayed behind believing he could reason with the Seminoles.
As a physician, he thought he could command the traditional respect that Natives paid to medicine men. Speaking to them in Spanish, he was able to convince them to leave for a while. However, they allegedly returned drunk, broke through the windows and doors, and began smashing furniture. Dr. Perrine pulled out his rifle but realized too late that his son had used all the bullets on a hunting trip the day before, leaving him defenseless. He was killed, and his home looted and burned along with all the other buildings on Indian Key. His charred bones were buried on Lower Matecumbe Key.
The Perrines were not the primary target of the attack, however. The Seminole’s motivation was to exact revenge on Captain Jacob Housman, the wealthy wrecker who developed Indian Key. Housman had recently written a proposal to the federal government which would allow him to collect $200 for every Native Floridian he captured or killed.
When news of this reached Chief Chekika, he began making plans to attack Housman’s island domain. Chekika was a fierce and physically imposing war leader—said to be the the tallest and strongest of the Seminole nation, and may have been one of the last remaining descendants of Florida’s lost Calusa tribe.
Avowed to never be conquered by or surrender to the white man, Chekika had already made bold and vicious exploits during the 2nd Seminole War, such as the raid at the Caloosahatchee Trading Post. He may have also been involved in the attacks on New River & the Cape Florida Lighthouse. Housman’s Indian bounty-hunting proposal was a further provocation to violence.
Under the cover of darkness, Chekika’s band silently paddled towards Indian Key & fanned out as they reached its shores, descending straight upon the Housman’s residence first. However, he and his wife Elizabeth were able to escape by running barefoot across the sharp coral rock to a boat, which they rowed to safety at the schooner “Medium,” anchored at nearby Tea Table Key.
Smoking a cigar as he gazed at the burning island, Housman said bitterly, “There goes $200,000.” The Seminoles had failed to kill Housman, but they had ruined him.
A year later, while attempting a salvage operation in heavy seas, he was caught between two ships and crushed to death. He was buried on Indian Key, and his wife ordered a gravestone with the inscription: “To his friends, he was sincere, to his enemies kind, and to all men faithful.” History suggests otherwise.
Indian Key never recovered after the massacre. A few of its residents returned, but by the end of the 19th century was uninhabited. In 1972, it was listed on the National Register of Historic Places and is now a State Park only accessible by boat, located between Islamorada and Lower Matecumbe Key.
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