The Legend of Chokoloskee Island
Tracking the Notorious Epic of Edgar “Bloody” Watson through Florida’s Ten Thousand Islands
“Sea birds are aloft again, a tattered few. The white terns look dirtied in the somber light and they fly stiffly, feeling out an element they no longer trust. Unable to locate the storm-lost minnows, they wander the thick waters with sad muted cries, hunting seamarks that might return them to the order of the world.
In the wake of hurricane, the coast lies broken, stunned. Day after day, a brooding wind nags at the mangroves, hurrying the unruly tides that hunt through the flooded islands and dark labyrinthine creeks of the Ten Thousand Islands. Brown spume and matted salt grass, driftwood; a far gray sun picks up dead glints from the windrows of rotted mullet at highwater line.
From the small settlement on the Indian shell mound called Chokoloskee, a baleful sky out toward the Gulf looks ragged as a ghost, unsettled, wandering. The sky is low, withholding rain. Vultures on black-fingered wings tilt back and forth over the broken trees. At the channel edge, where docks and pilings, stove-in boats, uprooted shacks litter the shore, odd pieces torn away from their old places hang askew, strained from the flood by mangrove limbs twisted down into the tide. Thatched roofs are spun onto their poles like old straw brooms; sheds and cabins sag. In the dank air, a sharp fish stink is infused with the corruption of dead animals and overflowed pits from which the privy shacks have washed away. Pots, kettles, crockery, a butter churn, tin tubs, buckets, blackened vegetables, salt slimed boots, soaked horsehair mattresses, a ravished doll are strewn across bare salt-killed ground.
A lone gull picks at reddened mullet cast on shore, a dog barks without heart at so much silence.
A figure in mud-fringed calico stoops to retrieve a Bible. Wiping grime from its caked cover with dulled fingers, she straightens, turns, and stares toward the south. The fingers pause. From the black mangrove forest down the Bay, a boat motor, softened by distance, comes and goes and comes again, bound east through Rabbit Key Pass from the Gulf of Mexico.
“Oh Lord no,” she whispers, half-aloud. “Oh please no, Mister Watson.”
Along toward twilight, Postmaster Smallwood, on his knees under his store, is raking out the last of his drowned chickens. Hearing the oncoming boat, he groans in the putrid heat. Soon one pair of bare feet, then another, pass in silence on their way down to the landing. More men follow. He knows his neighbors by their gait and britches.
Over low voices comes the pot-pot of the motor. Three days before, when that boat had headed south, every last man on the island watched it go, but the postmaster had been the only man to wave. He, too, had prayed that this would be the end of it, that the broad figure at the helm, sinking below the tree line into darkness at the far end of the Bay, would disappear forever from the Islands. Said D. D. House that day, “He will be back.”
That old man’s Sunday boots descend the Indian mound, then the bare feet of his three sandy, slow-eyed sons. The oldest, Bill House, climbs the steps and enters the store and post office, calling to Smallwood’s wife, his sister Mamie. Bill House’s feet creak on the pine floor overhead.
In the steaming heat, in an onset of malaria, Smallwood feels sickly weak. When his rump emerges from beneath his house and he attempts to stand, he staggers and bangs heavily against the outside wall, causing Mamie to cry out in the room above. He thinks, This dark day has been coming down forever.”
-Prologue, Shadow Country
There is something about prevailing history that’s fascinating. I say “prevailing” because we all grow up getting the version of history our schools and families want us to know. We take those institutions and our families at their word because we ask, “Why would they intentionally or negligently misinform us?” It isn’t until we are much older we can begin to question whether those accounts are accurate. Whether it’s an agenda by the purveyor or an innocent inaccuracy, the result is the same.
And if you’re a student of history, the deeper you look, the more you learn that history is simply a story handed down over the generations. We were not there. We did not witness it. We are left to rely on the accounts of others, most of whom we don’t know. Some of it is better documented and thus not subject to much debate. And yet, other stories begin to resemble legend more than truth. And it’s the legends that hold a mysterious, undefinable allure.
To visit the site of one of Florida’s most notorious frontier legends, one has to drive backroads, no matter the starting point. The route heads southwest on Interstate 4 for a few miles before it turns onto U.S. 27 south; just west of Lake Okeechobee, it changes to state highway 29, crossing I-75 near the northern border of Big Cypress National Preserve, and finally into Everglades City. Highway 29 becomes a road called Copeland Avenue, and before the driver realizes it, the route heads across the earthen causeway onto Chokoloskee Island, now all built up and developed.
The route terminates at the scene of one of the most notorious frontier legends in American history — if not one of the most well-known — behind the Smallwood Store, which still sits — preserved for posterity — at the southern edge of the island and looks out over one of the few remaining undeveloped areas left in the continental 48, the “Ten Thousand Islands.”
Few outside these relatively insular acres would even know the place existed if Peter Matthiessen had not put it on the map in his novel, Shadow Country, winner of the 2008 National Book Award for fiction. It’s not as if it’s on the way to somewhere, or a crossroads, or even well-known as the site of some epic military battle. Rather, it sits at the edge of something, and always has. And due its location alongside the Everglades, it probably will sit along that edge forever; out on the fringe. A border of sorts, but not between countries or nations, but more like an old military fort out on the border between the settled land and undeveloped wilderness territory. Step off into that wilderness, and you’re essentially stepping back into the past. How far back into the past you go depends only on how much risk you’re willing to take, because there are areas in the Everglades that have remained unchanged for millennia. The “shadow country” can indeed be ruthless and unforgiving.
Out of this ancient wilderness legends emanated, similar in many respects to the tales of settling the American west. And it wasn’t just the land and the creatures that inhabited it that could kill you, but like the West, the unfriendly people you might run into as well. But out here in deep southwestern Florida, along the Gulf Coast, legends with their own unique kinds of drama unfolded. It was just a different kind, where federal marshals and other lawmen were scarce and people were left in most ways to police themselves. And as history tells us, those types of arrangements are volatile and usually don’t work out too well.
“In a shift of wind, the pot-pot-pot of the oncoming boat comes hard as a pulse. A frantic young woman runs out of the store — “Oh dear God!” She hurries down the steps, calling her little boy.
Near the shore, Henry Short leans his old lever-action .30–30 into the split in the big fish-fuddle tree that the hurricane has felled across the clearing. The rifle is hidden when he turns, arms folded tight in sign that he is here against his will, that none of this is any of his doing.
The men are gathering. Charlie T. Boggess, ankle twisted in the hurricane, limps past the store. He turns and shouts back at a woman calling, “All right, all right!” To Smallwood he complains nervously, “Ain’t you the one said he was gone for good?”
“Not me! I knowed he would be back!” Isaac Yeomans, fiery with drink, acts cheered by what the others dread. “His kind don’t like to be run off. You recall Sam Lewis, Ted? At Lemon City?”
Smallwood nods. “They lynched Sam Lewis, too.”
“This ain’t no lynching,” Bill House calls.
“Don’t think so, Bill? What if he’s just coming to pick up his family, keep on going?”
The men stare away toward the south as the oncoming boat comes into view, a dark burr on the pewter water. Most have worn the same clothes since the hurricane, they are rank as dogs and scared and cranky, they are anxious to enlist Ted Smallwood because the participation of the postmaster might afford some dim official sanction.
If nobody is innocent, who can be guilty?
“No hanging back!” shouts Old Dan House, glaring at Smallwood.
Isaac Yeomans breaks his shotgun and sights down the barrels, pops a shell in, sets his felt hat. “Best throw in with us, Ted,” he urges his old friend. “We don’t care for this no more’n you do.”
“He always pays his bills, plays fair with me. I ain’t got no fight with him and you fellers don’t neither.”
“Hell, Ted, this fight ain’t nothin to be scared of! Not with his one against more’n a dozen.”
“Maybe I ain’t scared the way you think. Maybe I’m scared of murder in cold blood.”
“He ain’t scared of cold blood, Ted. Colder the better.”
The twilight gathers. Hurricane refugees from the gulf coast have gathered by the store, fifty yards back of the men down by the water. “You fellers fixin to gun him down?” one hollers. “Thought you was aimin to arrest him.”
“Arrest Watson? They tried that the other day.”
Edgar “Bloody” Watson (1855–1910) was a native South Carolinian who moved to Florida in the 1880s. He arrived amidst a cloud of rumors that he was on the run from lawmen in Arkansas, Oklahoma, and even the northern part of Florida. While still a youth, he allegedly stabbed and killed a man in a fight in northern Florida, and fled to the Oklahoma Territory. While there he allegedly killed Belle Starr, herself a notorious outlaw. But Watson was acquitted of her murder by a jury.
Suspected of other killings in Oklahoma and Arkansas, he returned to Florida in or around 1891. Seeking to avoid the authorities up north, he popped up in the town of Arcadia just east of modern-day Sarasota, and was again suspected of killing a man, this time in self-defense. Again, a jury acquitted him. Watson then moved to the Ten Thousand Islands area, where he bought a claim on the Chatham Bend River in Monroe County and started holding himself out to the locals as a gentleman farmer. But soon enough, his past would prove difficult to escape.
On a trip south through the keys, Watson got into a well-documented argument in a saloon with a fellow businessman and cut his throat in the fight that followed. The man survived, but was so terrified by the incident he refused to participate in a prosecution against Watson. Watson later purchased another parcel on the Lost Man’s River, in Monroe County. He soon discovered someone squatting on his property, and the man was eventually found dead. Again suspicion fell on Watson, but as with so many prior episodes, nothing came of it.
After Watson returned to his sugar cane farm in Chatham Bend, things appeared to settle down around him, for a while. He began hiring several farmhands that lived and worked on his property. But after a while, new speculation started to drift back to Chokoloskee that strange things were happening on the Watson plantation. Watson was said to be employing some outlaws, one of whom was suspected of killing a policeman and burning down a factory.
Another account had it that Watson and some of his outlaw workers had killed two people last seen in the vicinity of his property. The body of one of the missing people was later found nearby. And still, other stories began to come out of Chatham Bend that Watson, rather than pay many of his seasonal laborers, would kill them instead, once he no longer needed them to harvest the sugarcane crop. Local legend has it that over the past century, scores of skeletal remains have been found in the area that used to be the Watson plantation. But none of them have ever been positively linked to him.
“The postmaster can no longer make out faces under the old and broken hats. Too tense to slap at the mosquitoes, the figures wait, anonymous as outlaws. Behind the men skulk ragged boys with slingshots and singleshot .22s. Shouted at, they retreat and circle back, stealthy as coons. In his old leaf-colored clothes, in cryptic shadow, Henry Short sifts in against the tree bark like a chuck-will’s-widow, shuffling soft wings. Dead still, he is all but invisible.
Not slowing, the oncoming boat winds in among the oyster bars. Her white bow wave glimmers where the dark hull parts the surface, her rifle-fire potpot-pot too loud and louder. The boatman’s broad hat rises in slow silhouette above the line of black horizon to the south.
The wind-stripped trees are hushed, the last birds mute. A razorback grunts abruptly, once. Mosquitoes keen, drawing the silence tight. Behind the rusted screen of Smallwood’s door, pale figures loom. Surely, the postmaster thinks, the boatman feels so much suspense, so much hard pounding of so many hearts. The day is late. A life runs swiftly to its end.
In the last light Ted Smallwood sees the missing child crouched in the sea grape, spying on all the grown-up men with guns. In urgent undertones he calls; the amorphous body of armed men turns toward him. He does not call again. He runs and grabs the little boy.
Hurrying the child indoors, he bangs his lantern. His wife raises a finger to her lips as if the man coming might hear. Does she fear denunciation of her husband for attempting to alert the boat? Hadn’t they learned that, warned or not, this man would come in anyway? Mamie whispers, “Is Daddy the one behind this, Ted? Bill and Young Dan, too?” He squeezes a mosquito, lifts his fingertips, winces at the blood. “Light that smudge,” he tells his little girl, pointing at the mangrove charcoal in the bucket. He says, “They’re all behind it.” He cannot stop yawning. “They want an end to it.”
The motor dies in a long wash of silence. His daughter whimpers. The postmaster, queerly out of breath, sends her to her mother. He joins the young woman on the porch. “Please, Edna,” he entreats her, “go back inside.” In the onshore wind out of the south, the boat glides toward a point just west of where the store landing had been lost to storm. Like a shadow, Henry Short crosses behind the men and positions himself off the right hand of Bill House, who waves him farther forward, into knee-deep shallows. Smallwood’s heart kicks as the bow wave slaps ashore: a wash and suck as the wood stem strikes with a violent crunch! of dead shell bottom.
Bearing his shotgun, the man on the boat runs forward and leaps. A moan rises with the rising guns.
The earth turns. Time resumes. The reckoning has been deferred but the postmaster’s relief is without elation. An exchange of voices as a few men drift forward. Starting down the slope toward the water, Mamie Smallwood and her friend are overtaken by the little boy, who runs to meet his father.
The shift toward death is hard and sudden. Rising voices are scattered by the whip crack of a shot, two shots together. There is time for an echo, time for a shriek, before the last evening of the old days in the Islands flies apart in a volley of staccato fire and dogs barking.
The young woman stands formally as for a picture, brown dress darkened by the dusk, face pale as salt. Though Mamie Smallwood drags her back, it was Mamie who shrieked and the young woman who takes the sobbing Mamie to her bosom; she regards the postmaster over his wife’s shoulder without the mercy of a single blink. He stumbles toward them, stunned and weak, but his wife twists away from him, mouth ugly. In a low, shuddering voice she says, “I am going, Mr. Smallwood. I am leaving this godforsaken place.”
The young woman goes to her little boy, who has tripped and fallen in his wailing flight. Patches of hurricane mud daub his small knees. She pulls the child away from the churning men, who in the dusk are milling on the shore like one great shapeless animal. In a moment, she will crawl under the house, dragging her brood into the chicken slime and darkness. “No, Lord,” she whispers as the terror overtakes her.
“No, please, no,” she moans.
“Oh Lord God,” she cries. “They are killing Mister Watson!”
Things finally came to a flashpoint in late 1910, when a woman named Hannah Smith was killed. Circumstantial evidence pointed at Watson, but he blamed one of his foremen for the killing, a man named Leslie Cox. In the midst of this, a massive hurricane struck the area, destroying many of the rough-hewn homesteads and killing most of the livestock. This ratcheted up the intensity of the situation and put everyone on edge.
When Watson made the mistake of showing up only a few days into the wake of this destruction, a group of local men had had enough and confronted Watson at the Smallwood store on the southern bank of Chokoloskee Island. But on that day, Watson somehow wriggled out of it by pledging to hunt down Cox and bring him back “dead or alive.”
As Watson left Chokoloskee in his motorized schooner Warrior, the group of men who had confronted him stood watching as his boat slowly disappeared over the horizon. “If he knows what’s best, he won’t come back,” uttered one. Another observed, “He’ll be back. He always has to have the last word.” “Well, if he does, I’m gonna be ready,” said another man ominously.
A few days later, they were going about their business when they heard the distinctive sound of the Warrior’s motor in the distance. They could scarcely believe their ears. Most accounts say that a group of about 30 local men gathered quickly near the Smallwood store, most of them armed with rifles, shotguns, or pistols. When Watson docked, tied up, and walked onto the dock, he was wearing a pistol in a concealed shoulder hoster and was carrying a shotgun. “Where’s Cox?” somebody shouted. Watson said he had shot Cox after trying to apprehend him, but had misplaced his body.
At this point, the stories differ, but accepted lore has it that someone ordered Watson to put down his shotgun, but Watson raised it toward the crowd. A volley of shots rang out, dropping Watson. A few of the men walked in at point blank range and finished the job. Some of them towed the body out to one of the islands and buried it under coral and sand. When the body was found by authorities later, thirty-three bullets were recovered from the body.
When law enforcement finally made their way down to Chokoloskee to investigate, nobody seemed to know who fired the shots that killed Watson. Although reports have it that over 50 people were present when Watson was gunned down, there were mysteriously no good eyewitnesses to the incident.
No one ever spent a day in jail over the killing of Edgar “Bloody” Watson. It was as if the men who shot him — instead of having committed a crime — had performed a public service to the residents of Chokoloskee and the Ten Thousand Islands.
Was Watson a victim of frontier mob-justice? Or was he one of the worst killers in Florida history? Or was it both?
Shadow Country and the other books that explore the Watson legend have spawned a small tourism industry, and when a visitor rolls into town he can see several small businesses with signs proclaiming some kind of product tied to the legend. The books can be found at almost any business catering to the industry, either in Everglades City or at the Smallwood Store itself, the former trading post and now museum where it all happened, still run by the Smallwood family.
Until just recently, there were reenactments of the Watson shooting staged out back of the museum in the area believed to be the scene of where it all went down, complete down to the participants wearing 1910 Florida frontier garb and using replicas of the firearms carried by the actual posse.
There’s something enchanting about the place. It’s the kind of charm created by any place untamed or unexplored; places that despite our efforts to harness and overpower them, have still managed to throw us off and spit us out. Inhospitable is not quite the word for it, but the overall take away is that it’s one of those areas out on the edge. Like the mountains, the desert, or any other kind of wilderness; you can’t take things for granted.
Cross over too far into nature unprepared, and nature will kill you. It’s overused sometimes, but indisputable; the place has a strange vibe. Although the weather may be clear one day, things can rapidly change in a region routinely savaged by storms coming in off the south Atlantic. Anyone who has grown up or spent time along the gulf coast knows this.
The Ten Thousand Islands area is a collection of low-slung islands and reefs, pounded incessantly by tides and storms, ever-changing; islands here today might be underwater tomorrow, and then reappear again in a different shape or location. Channels that were navigable for decades can suddenly fill up with sediment after storms, creating new landmasses. It has been this way long before humankind arrived on the scene. As the Park Service maps and signs in the vicinity warn, “Area subject to constant change.”
One tries to picture what it must’ve been like for early settlers, trying to hack out homesteads in the steamy, alligator and mosquito-infested Everglades or out along the coral-infested coast along the labyrinth of islands that stretch for twenty miles north and west toward Marco Island.
In the opposite direction out toward Watson’s old properties, the going gets only more difficult; the land becomes more and more primal as it goes deeper and deeper into the Everglades. How would that have been in 1890, before we started draining the Glades, hunting out all its species, and encroaching on what must’ve been the most primordial land in our part of North America? How could a human being in the 19th century survive in that environment, let alone thrive? Storm clouds both real and metaphorical were bound to form up up like harbingers of doom over people already living hard lives.
Outside Everglades City and Chokoloskee, one searches for insight by trying to get out into the Glades, but there are still very few public roads leading anywhere untrammeled. In fact, there are no roads heading south into the area of so many legendary tales. U.S. Highway 41 north of town runs east toward Miami, but it passes through Big Cypress National Preserve, and any effort to get off the beaten path there requires park service permission and a back country permit.
What really happened? The initial take away is a vision from an old western movie with a common premise: A town of otherwise good citizens is controlled, perhaps even terrorized, by some kind of bully. The bully might be some gunfighter, or he might be a bigger and more sinister version of Ed Watson: the rich landowner who does whatever he wants until a hero (or anti-hero) rides into town to save everyone. How do most of these stories or movies end? The outlaw bully eventually gets his comeuppance in one way or another. Eventually, Ed Watson got his, even though the how and why of it remains shrouded in mystery over a century later.
Indeed, the search for the truth in the Watson legend is just like this primeval back country of mangrove roots, rivers, canals, streams, creeks, and little branches of each that twist and turn in all directions in an impossibly complex web: It makes you want to go in a thousand different directions at once.
Glen Hines is the author of six books, including the recently published Welcome to the Machine, all available at Amazon.com and Barnes and Noble. His writing on sports, the outdoors, military service, and the bright and dark sides of American culture has been featured in Sports Illustrated, The Concussion Legacy Foundation, Task and Purpose, The Human Development Project, Kirkus Book Reviews, and elsewhere. Kirkus recently called Welcome to the Machine “An often-compelling examination of a sport’s sins from a man with an insider’s view.” He was inducted into the Authors Guild in 2022.
