The attack on the Dragoons on the Caloosahatchee River trading post before dawn on July 23rd, 1839 is one of the most costly attacks for the Army. It has never received as much attention as it should.
In May of 1839 General Macomb made the Fort King Treaty with a couple of the Miccosukee leaders. There wasn't much to it, except both parties agreed to end hostilities. The Seminoles would agree to stay in south Florida, and a trading post would be established for them. Problem was that the whole Florida Indians never agreed to this agreement, only two Miccosukee leaders. So the United States made the mistake once again, that one person spoke for all the different bands roaming around.
A trading post was established about 20 miles up river on the Caloosahatchee, probably around where Fort Myers is today. Several years ago there was private property that was being excavated, which recovered a huge amount of beads. It was called Fort Bead, and the beads were sold on the internet in little packages. You may still see a few of these on ebay.
Anyway, a company of Dragoons had come to help establish the trading post. Actually it was less than 30 soldiers, so it really wasn't anywhere close to full company strength. Col. William S. Harney was leading the command with no other officers. I wonder why Harney went, unless it was a special detachment. Usually this size a detachment would have no more than a captain, and not a colonel.
One of the things that makes this attack significant, was that the soldiers were elite Dragoons. And at that time in the Army, the 2nd Regiment of Dragoons under Harney was considered the best there was; elite fighting troops. They were armed with different weapons, the Colt rifles, which were the most advanced weapons of the day. Harney himself was in top physical condition, stood at a commanding height of 6'3", and had a temper to be feared. He was one of the most feared and respected commanders in the Army.
Early in the morning a large Seminole / Miccosukee / Spanish Indian force attacked the Dragoons. The attack was so swift and unexpected that many soldiers did not even get to their rifles in time. Some were killed laying in their mosquito nets. One fatal flaw was that the soldiers did not have a guard mount organized, so there was no warning.
Indians involved in the attack were bands under the leadership of Chekika with the Spanish Indians, and Miccosukees under Hospetarke and Billy Bowlegs. They seized many trade goods and made off with the Dragoon's Colt breech-loading rifles. There was no warning of the attack, and the soldiers had previously talked talked peaceably with the Indians who came in to visit.
So the motivation behind the sudden attack will probably remain a mystery. Judging from the ferocity of the attack and the manner in which the soldiers were killed, the Indians obviously had a score to settle.
Col. Harney escaped because he had bedded down separate from the rest of the soldiers, and was not attacked when the killing started. He fled to the boat landing where he was met by a lone sergeant. Most of the men were killed and a few others escaped into the river.
Harney was the wrong person to become the enemy of the Seminoles. The next year he made it his mission to track down and kill those responsible for the attack, which he did in an unprecedented manner, going where the Army had not penetrated before, into the deepest Everglades. He found Chekika at his own camp and had him shot and hung like a dog. Hospetarke was captured two years later, but went willingly because he was very advanced in age. Billy Bowlegs was forced to surrender and leave home twenty years later, to end the 3rd Seminole War. For the rest of his military career until he retired on the shores of Lake Eola in downtown Orlando, Harney had the reputation of a brutal and unyielding Indian fighter on the level of Phil Sheridan.
(Below: Harney enjoying retirement on the shores of Lake Eola after the Civil War.)