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Located midway down the Florida Keys, between Upper and Lower Matecumbe, and barely a mile from the recently established U. S. Naval Station on Tea Table Key, Indian Key had seemed to be a snug harbor from the violence of the Indian War.
Here was located Captain Jacob Housman’s thrifty settlement, where he maintained a prosperous trading center which in former years had catered to the Indians. Now, because of the war, his trading was limited primarily to fishermen and the wreckers of the Florida Keys. Captain Housman had built his own reputation as a wrecker since he first came to the Keys in the early 1820s. His village was located some 30 miles offshore from the closest hostile Indians, thought to be near Cape Sable and in the Everglades to the north. As added insurance, Housman had erected a small fort complete with long guns, perhaps as much to impress his rival wreckers as the Indians.
The varied collection of small sailing ships sometimes called the "Florida Squadron” was frequently at anchor between the two small Keys as the ships took on fresh provisions and replacements and left their sick and wounded at the naval hospital. Lieutenant John T. McLaughlin was frequently at Tea Table Key in his flagship, the schooner Flirt. Other ships of the squadron regularly seen at the Tea Table Key anchorage were the schooners Wave, a former New York pilot boat, and Otsego, a former revenue cutter, and the barges
In August 1840, the fifth year of the Second Seminole War, virtually alt of the 600-man Florida Squadron was scattered from Cape Romano, upper left, to Key Biscayne, upper right, where the "Mosquito Fleet” was launching yet another raid into the Everglades. With only a handful of men to defend Indian Key, insert, its unsuspecting people and its bulging warehouses were at the mercy of the merciless Chekika.
Mayo and Harney. The officers and men from these ships and members of their Marine detachments were frequent visitors to Captain Housman’s Inn where they enjoyed respites from their frequent coastal patrols.
It was usually from the Tea Table anchorage that the ships of the squadron, with their crews of Indian- hunting sailors and Marines, set forth to raid Indian settlements along both coasts of South Florida. In recent months, by the skillful use of small boats built
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While Doctor Henry Perrine attempted to reason with Chekika, the doctor’s family huddled in the "bathing cellar,” from which they later escaped through the tunnel that led out under the wharf.
especially for this purpose, these raids had been carried into the heart of the Indians’ final refuge—the Everglades.
Apparently, Captain Housman’s fat storerooms, known to contain ample supplies of gunpowder, and his warehouse where he kept cargoes salvaged by him and other wreckers were sufficient temptation for the Indians to stage a raid of their own. The Indians had in former years been frequent visitors to the Key. They knew the salvage warehouse was likely to contain a sufficient supply of flour and rice which they badly needed, and cases of whiskey, rum, and wine, which they greatly desired. But, no war party, no matter how brave or foolhardy, would dare attack the settlement while the sailors and Marines were nearby. Thus, they had to wait for the moment when the ships were too far away to bring help, and when the garrison on Tea Table Key had been reduced to the point it could not rescue Indian Key.
This moment came in the pre-dawn hours of 7 August 1840. Earlier, the Otsego had gone to the small outpost on Key Biscayne where she was joined by Lieutenant McLaughlin in the Flirt. Here, near Cape
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Florida, the Americans were preparing for another raid into the Everglades in their small boats. Then, on 5 August, the Wave, Lieutenant John Rodgers commanding, departed Tea Table Key for Cape Romano, "carrying every man capable of doing service but five.”
Thus, Tea Table Key was left with five able-bodied men under command of Passed Midshipman Francis Key Murray, plus the sick and wounded in the hospital. Likewise, a number of Indian Key’s adult male residents had gone off on hunting and fishing trips. This, then, was the perfect moment probably long sought by Chekika, ruthless chief of the half-breed "Spanish Indians.” His canoes, each carrying from four to six warriors, moved silently and swiftly through the calm waters of Whitewater Bay on the night of 6 August. After stopping for a brief rest near the east end of Lower Matecumbe, and having made their final preparations for the attack, the war party struck across the narrow channel, probably landing along the southerly shore of Indian Key, the shore most remote from the village. They intended to make their way across the island and strike the village from the rear since, although they knew of Captain Housman’s fort, they did not know whether it was manned.
One of Captain Housman’s shipfitters, James Glass, could not sleep and was wandering along the beach when he discovered the Indians disembarking from their canoes. His shout of alarm and the discharge of his fowling piece gave the town’s inhabitants time to run from their houses, hide in cellars, under piers, in wells and cisterns. Some even swam for their lives.
The Indian Key Massacre 77
All who were found by the Indians were brutally beaten to death. One of the island’s most prominent residents, Dr. Henry Perrine, hid his family in his cellar while he attempted to dissuade the Indians from their murderous course. He spoke fluent Spanish and felt he might reason with them. He had occasionally met Indians during his botanical forays on the mainland and was known by many of them. After the raid, his bones were found in the ashes of his house. His family hid in the damp cellar until their burning house forced them to squirm through a small tidal opening leading to the turtle crawl under their wharf where live sea turtles were kept. Here they hid until the burning of the wharf forced them into the open where they happened on a small boat in which they escaped to the schooner Medium anchored in the harbor.
When Midshipman Murray became aware of the raid on Indian Key, he organized a relief force from his meager resources. He would later report:
". . . our force here consisted of five men, with whom joined to seven or eight of the sick, who volunteered readily, but were too weak to be of much service, I started for the Key—at first, with the intention of landing, which however was opposed by the enemy who had taken refuge in every house, and opened a heavy fire which fell thick around us, striking our boats, and wounding one
man severely . . . They appeared also in great numbers on the beach, yelling and firing, which firing was returned with three discharges of our four pounders in the Barges . . .”
Chekika’s party consisted of not less than 50 and possibly over 130 braves. They were all armed, had limitless gunpowder, and most were by now quite drunk. They were also quite resourceful as they manned the long guns of Captain Housman’s fort and commenced a heavy barrage of artillery fire on the approaching Navy boats, undoubtedly the only instance in history of American naval forces under fire from Indian artillery. Murray’s report continued:
". . . At the third discharge, being obliged to fire them athwartships, our guns rebounded overboard; being deprived of the means of cutting off their retreat, I returned to Tea Table Key, to make preparations for the attack which I think more than probably it is their intention to make upon us—
With Indian Key plundered and leveled, Chekika and his braves took refuge in the Everglades. But the waist-deep water, the tangled roots, and rotting stumps proved only to be a temporary hiding place.
ARTIST JOHN CLYMER. COURTESY OF MARINE CORPS GAZETTE
U. S. Naval Institute Proceedings, November 1074
being assured that our amount of force and means rendered us of no assistance to the inhabitants of Indian Key, if any survived, which is not to be supposed. . .
Midshipman Murray’s letter must have been written immediately upon his return to Tea Table Key where he thought the Indians would surely strike next. Chekika, however, was running out of time. His scouts had reported that two of the Navy’s ships, the Flirt and the Otsego, were at Cape Florida, 75 miles to the northeast, and the Wave he knew could be somewhere between Cape Sable and Cape Romano. He knew that the sailors and Marines in their small boats were becoming as skillful in the myriad waterways of the Everglades as were his braves. He could not risk being cut off in his retreat to the mainland. He knew that even now, in the mid-morning daylight of Indian Key, that messengers must surely be on their way both to Cape Florida and Cape Romano.
Having thus driven the frustrated rescuers back to Tea Table Key, the savages set about completing the ruin of the village. The houses, storebuildings, and warehouse were thoroughly plundered, their contents loaded in the Indian canoes and in six other boats taken at the Key. As the houses were looted they were set afire until the whole village—some 30 to 40 buildings— lay under a pall of smoke. As villagers were found they were dragged out and beaten to death.
Finally, the storerooms and warehouse stripped, and the village in flames, Chekika and his men departed, leaving only one building on the island standing—the home of Charles Howe, Collector of Customs for the town. Mr. and Mrs. Howe and their five children had escaped by small boat to Tea Table Key during the early moments of the raid.
The raid brought cries of outrage. Typical of the press reaction of the day was this comment from Niles National Register of 29 August 1840:
"Indian Key destroyed, and the inhabitants butchered by the Indians. Again it becomes our melancholy duty to record the cold blooded butchery of men, women, and children, by the sanguinary Semi- noles. Again, as the treacherous savages bathed their tomahawks and scalping knives deep in human blood, burning houses and destroying property, and been allowed deliberately to retire in security to their fortress, to prepare for another attack on the defenseless inhabitants of Florida, whenever a favorable opportunity shall offer. These scenes may, and probably will be reiterated time and again, unless some
more energetic measures are adopted to drive them from the territory, or the inhabitants flee from their homes and country, leaving the Indians in undisputed possession.”
Lieutenant Colonel William S. Harney, later one of this nation’s most celebrated Indian fighters, pledged to pursue Chekika to the death. Harney knew his man. Chekika and his savage band, not true Seminoles, had terrorized Southwest Florida during 1839 and 1840. It was Chekika who had led the attack on the trading post and garrison on the Caloosahatchee River and presided over the ensuing massacre from which Colonel Harney barely escaped with his life by dashing from his tent to the river clad in his underdrawers.
Colonel Harney organized and led a detachment of his 2nd Dragoons and the 3rd Artillery into the Everglades, where, traveling by canoe and dressed and painted like Indian warriors, they finally overtook Chekika’s band.
When the fighting was over, Chekika lay dead, a dragoon’s pistol ball through his head. The surviving six braves captured at that time were hanged on the spot. A contemporary account reported this summary execution:
"With sullen indifference they awaited their fate, asked for no mercy, but manifested, to the last moment, bitter contempt and malignity toward the white man.”
As a warning to those braves who had escaped, Chekika’s body was hanged in the tree with his braves who died there. His scalp was first "lifted” by one Private Hall, 2nd Dragoons, reputed to be the man who fired the last deadly shot.
Captain Housman, who had miraculously survived the Indian Key massacre, was soon to be returned to his ruined village. On 1 May 1841, while attempting to salvage a wrecked ship, he fell between his own ship and the wreck and was crushed to death. His body was returned to rest among the graves of the victims of the Indian Key massacre whose company he had managed to elude but a few brief months.
The Indian Key massacre of August 1840 and the resultant destruction of Chekika and much of his band early in December 1840 was a lesson to the wiser chiefs of the Seminoles that American military forces were now able to penetrate the Everglades. Although the Seminoles would fight on for more than a year, their fate was sealed; their secret places weren’t secret any more.