The first notice by Europeans came when a group of anonymous Conquistadores came back and published a map of their exploits in 1516. There, at the bottom of Biscayne Bay where the Florida Keys popped out of the water like turtles, was a spot on the mainland. A little symbol indicating a spring of fresh water was all that was notable in the area, but it was very important. Wandering minds dulled by days at sea might dream of gold and other riches, but the tongues always thirsted for fresh water first.
The land had been known to the Tequesta, a rough group of natives who like their island cousins the Taino led an easy life. They weren’t a people who built large permanent settlements but instead preferred to roam up and down the ridge of coral that was 10 feet higher than the sea and no more than a mile wide. It stretched more than 60 miles down the Florida coast, a thin strip between the Everglades and the bay, an island of its own. The Tequesta had little need for the swamps, and the sea was little more than a source of fresh meat. When the Conquistadores asked them questions about the riches of their land, it certainly must have been puzzling; to Tequesta, the land was riches enough. They grew and hunted whatever they thought they needed all year.
What the Tequesta didn’t know was that the lack of valuables like gold wasn’t enough to save them. In time, the paler people would learn the value of this land.
For the time being, however, the lack of anything valuable kept life pretty simple. The next time this spot on the map shows up in history books is around 1690, the waning days of piracy in the Caribbean. That is when Black Caesar, an escaped African slave started operations in this corner of the world where no one would bother looking.
Black Caesar himself was said to be impressive, a huge man who spoke little and acted easily and violently. He came to the area after escaping, drawn by the stories of fresh water and the promise of an easy life. His crew was assembled in time, drawn mostly from other slaves escaping from Jamaica and Haiti. From their base they preyed on whoever started out riding the Gulf Stream from its creation in the Straits of Florida and on home to Europe. All the ships of the Caribbean passed this way, so it was only a matter of picking the easy targets. The riches of Florida that had eluded the pale people were discovered by a black man who was primarily looking for freedom; those riches were what the whites brought to the area, not from it.
What Black Caesar got from Cutler, however, was more valuable than gold. It was freedom.
The stories become a bit murky, as any good legend must. Supposedly Black Caesar had a harem and an army to protect them on Elliot Key, housed in great stone buildings. They were unchallenged as long as they stayed there, with no navy willing to risk running aground on the 3-5 foot deep waters of Biscayne Bay. There are two problems with this story, however – there are no remnants of stone buildings on Elliot Key, and there is no fresh water there, either. It is more likely that Black Caesar bragged about the size of his band of free men and lied about their location in order to keep everything secure.
Black Caesar is the Founding Father of Cutler in the sense that not only did he create the first settlement but also the mythology of the place. The strip of land between swamp and bay is a place of great freedom for people who find that not caring about the finer details of life suits them well. The sea provides both food and easy marks full of treasure if you are as patient as a fisherman.
Eventually, Black Caesar and his men joined up with Blackbeard and sailed north to Virginia. There, they were eventually caught and hanged. Up there, freedom is a little tougher – and the color of your skin matters just a bit more.
The land went back to being ignored for a long time afterward, which suited the natives well enough. It was little more than a watering stop for wayward ships.
In the 1820s, the Creek Indians of the Carolinas were forced to relocate westward in what would be known as the “Trail of Tears”. Some of them refused to go, and broke off to form their own band known as “Seminole” – the Creek word for “Renegade” or “Runaway”. They chose to fight. Eventually, the forces of Andrew Jackson beat them back in the First Seminole War, and they escaped into the swamps of the Everglades. No one was willing to follow them, so they were allowed to live in peace. The Seminole were very welcoming, and a number of escaped slaves and even a few whites chose to join their band. Most of the Tequesta joined up as well. The Seminole didn’t just live in southern Florida, they became it.
In 1832, the US Government tried to force them out. Taking the arrival of Haley’s Comet as a sign, the Seminole attacked. On of their first acts was to take a fort and kill everyone there, including the commander Francis Langhorn Dade – for whom Dade County is named. When their chief, Osceola came under a flag of truce to negotiate, he was captured and ultimately hanged. The war become more fierce as the Seminole demanded revenge.
Dr. Henry Perrine had been granted a piece of land in the area, originally on Cape Sable at the end of the Everglades. He was a botanist who wanted to find out what productive plants could grow in the area, with a special interest in quinine that was used to fight malaria. Having spent time as the US Console in Merida, Mexico, he knew the value of tropical plants and the riches they could provide.
Perrine was hoping that the land could provide more than a quiet subsistence living that Florida promised, but his plans were in disarray. He waited out the war on Indian Key, hoping he could get in and explore his grant. But the war continued on into 1840, a stalemate between the guerilla tactics of the Seminole and the heavy forces of US soldiers unsuited to the swamps. Perrine transferred his claim to the shores of Biscayne Bay, including the area of Cutler, where the high ground appeared safer. Just after he did this, however, he was killed when Indian Key was stormed.
In 1840 he newly renamed Dade County then stretched from Lake Okechobee south to the keys, but had only 18 free white men – that is, people who could legally vote – left living in it. It was Seminole territory. The Seminole to this day remain the only native nation that has never signed a peace treaty with the US, and proudly call themselves “unconquered”.
The US gradually lost interest in the Seminole, especially when the Civil War broke out. The people of Key West learned that Florida had seceded from the Union when the Navy sailed in and told them they were under military occupation. This became the center of operations of the Blockade, an attempt to seal off Florida from all trade that would help the rebel cause. More than a few rebels fled northward, and found that the place with fresh water at the bottom of the Bay was an excellent place to conduct a blockade running operation. Like Black Caesar before them, they lived as they could off of the gentle land, smuggling in guns and food and whatever was valuable on their side of the wall of Navy ships.
Their settlement grew to include over 400 houses, each one tied to the operations that brought war material over to the rebel lines. It was a perfect place to operate as a smuggle, just as it had been perfect for piracy. The shallow bay prevented deep water ships from coming in too close, and the nearby islands of Soldier Key and Elliot Key made for perfect clandestine rendezvous. All it took was a shallow pram steered by the moon and the gentle breezes off the bay to get out to the deep landing and back.
After the war, Henry Perrine Jr. became interested in reclaiming the land he felt he had inherited. It wasn’t until 1876 that he asserted his rights to the area, and by then the squatters camp that had started as a smuggler’s haven had grown considerably. In the case to have them all evicted, the squatters came to be defended in court by a mysterious Floridian known as Dr. William Cutler, who is the stuff of legends himself. One story has him running away from his family in Ohio to seek his own way, and one story has him the son of rebel blockade runners. Whatever the cause, the squatters won the case and incorporated as a town – duly named Cutler for the man who defended them. Civilization had finally come to this part of the world, for better or worse.
From this time forward the history is well documented and preserved. But in these misty swamps, there is always room for a romantic mind to forget a few details and elaborate a few others. What we do know is that in 1896 Henry Flagler built his Florida East Coast railroad down to Miami, and the city was founded. In 1902 a road was built south to Cutler along the coral ridge that is still known as Old Cutler Road. The details of how people made a living in this part of the world are murky, but legends of smuggling and even a little piracy persisted well into the 1920s. At that time, the cheap rum of the Caribbean suddenly became valuable through Prohibition, giving Cutler another good source of income. When the restaurant Black Caesar’s Forge was built, it was said to be a favorite stop of Al Capone and other mobsters who were seeking to get away from their own speakeasy in Miami, Tobacco Road.
The most important change in the area came in 1926 when Charles Deering, the an inheritor of the International Harvester fortune, bought up much of the land and walled it off with coral rock. His estate was south of his brother’s more elaborate Viscaya, and much less prominent. But the landing that was the soul of Cutler was taken away in this process, leaving only a small dock at the north often called the “Tomato Dock” by locals. Supposedly, the produce that had come to dominate the area was shipped north to Miami in shallow draft boats from this location. Cutler was pacified. The spring that had made the Spanish maps was privatized on the Deering Estate.
Since having its heart taken, Cutler fell on hard times. In 1962 Canal C-100 drained this corner of the swamp to the bay, exiting just south of Cutler. The spring dried up with the pressure from the fresh water behind the coral ridge. The land to the west gradually became farms and then suburbs. Much of the history still left was washed away when a 30 foot tall wall of water came in with Hurricane Andrew in 1992, the worst of the storm known to hit Cutler. In 2002 it was re-incorporated along with the suburbs as Palmetto Bay, a generic name that speaks to realtors more than real pirates.
Today, there is little to mark Cutler. The Old Cutler Inn is a dive bar on the site of Black Caesar’s Forge. The Deering Estate is open to the public as a park, making it a lot less fun to sneak into. The legends of pirates and smugglers remain, but are known only to the older people who like to tell the stories while relaxed on a lawn chair.
The spring that put it on the maps as long as 500 years ago has finally been conquered. The land proved valuable to the pale people not as a way station for passing ships or as a home that brought an easy life. The riches that the Conquistadores were seeking were finally found in real estate. In a sense, the Tequesta were right all along – it was the land itself that mattered.