Pogey Bill: The Last Frontier Lawman
I had the distinct—or dubious, depending on your outlook—privilege of growing up in the old Florida city of Okeechobee, situated at the northernmost point of Lake Okeechobee. Because of that, I often find myself caught in between worlds. I wasn’t sufficiently rugged to be accepted as a local cracker (no, that's not a racial slur)yet I spent enough time with them that I was seen as a redneck (It's only an insult if used by non-rednecks) by the city folks when my family moved away some time later. It’s put me on the fence, of sorts, and I like to think it’s provided me with a greater perspective of a way of life that’s both gone and underappreciated.
That way of life could best be summed up in the life of one man.
Walk up to any native Okeechobeelander and ask if they know who Pogey Bill is. They’re bound to say, “Sure.”
Ask them to tell you about Pogey Bill. They’re bound to just scratch their heads. The truth is that Bill fits somewhere between the factual yet larger-than-life exploits of famous frontier lawmen like Wyatt Earp and Wild Bill Hickock, and the tall tale superheroes of centuries past like Pecos Bill and Paul Bunyan.
His later life is haphazardly documented in the rather unimaginatively titled Okeechobee News but events prior to that, particularly those involving his life before appearing in Tantie (the old name for OkeechobeeCity prior to 1915, so named after schoolmistress Tantie Huckabee) in 1910 are notoriously sparse. This is partly due to the fact that he was an itinerant sailor, brawler, and drinker for the first thirty years of his life and partly due to the fact that any genuine records of him were likely destroyed in the great hurricane of 1928 which claimed the lives of more than 2,000 people living around Lake Okeechobee. I should add for the sake of people interested in Florida’s history that this incident is what led the southern shore of the lake to being dammed and has since caused so much trouble with the drying Everglades and the interruption of its ecosystem.
Pogey Bill’s story is one of a man who always made good on his word, despite being rough around the edges. There are dozens of versions of it. You see, with a lack of facts, all we have to work with are anecdotes of the people who knew him or grew up with him as their protector, all of whom have regrettably passed on as well.
So, despite its foibles and flaws, let’s look at the most comprehensive version of the stories of the last frontier lawmen of the US, High Sherriff of Okeechobee County William E. Collins, AKA Pogey Bill.
Bill was born in an unnamed cargo vessel May 24th, 1884 in Sydney Harbor, Australia. The ship was American, as were his parents, whose names have since been lost to time, making him an American citizen according to maritime law. Unfortunately, this story has several immediate flaws. Chief among them is the fact that no merchant vessel of the time period would employ a woman, least of all a pregnant one, begging the question of why she was aboard in the first place.
It’s possible she and her husband were passengers bound for Australia, but this makes little sense when you consider the fact that the next time there’s any mention of Bill it’s in South America. He spent most of his childhood and teens aboard one ship or other, making the long runs round the southern tip of South America with anything fit to be sold. The rigors of shipboard life are harsh for a full-grown adult. For a child, the hardships he must have faced are impossible to imagine, and may go a good way to explaining his hardiness later in life.
It was at this point he learned to, as he put it “Put my knuckles up and make a lil extra coin.” Given the lawless nature of the open sea, it would be unsurprising if he learned to fight in order to protect what meager possessions he called his own from other crewman who thought because of his youth he would be an easy target.
He proved them wrong, perhaps to his detriment. In his early twenties, he was a shade over six feet tall with short legs, a long trunk, and longer arms: the perfect boxer’s build. Tall but with a low center of gravity. Add into that he could reportedly drive a fist through an inch-thick oak plank thanks to his days loading cargo and nights pit fighting in the ship’s hold, and his decision to pull up anchor was probably not so driven by adventure as most Okeechobeelanders suppose. You see, it was around 1905 that he jumped ship at Buenos Aires and stowed away until he got to Tampa. A journey of several thousand miles over open water with the danger of being found out and thrown overboard isn’t simply made out of boredom.
I would be unsurprised if perhaps a pit fight weren’t taken a little too far and Bill had need to avoid the authorities or people looking for revenge.
Whatever the case, Bill arrived in Tampa, Florida, which was considered the gateway to the great untamed wilderness of South Florida at the time and the last bastion of civilization, however tentative. He quickly found work as a boilermaker, another point for suspicion. Given the incredible stress and heat which boilers were expected to contain, boilermakers were typically highly skilled and often Navy certified welders. Where Bill gained the necessary skills in a time when many cargo vessels weren’t possessed of iron-sheathed hulls is a question that goes unanswered, unless of course he was employed as an apprentice or gopher and simply chose to talk himself up a little in his old age, though this would go against his laconic, truthful nature.
The only reason Bill stayed in Tampa for as long as he did was because of the local politics. Labor unions were common at the time, though they bore no similarity to the labor unions we know now. In actual fact, they were gangs of menials and petty laborers who went about terrorizing people and influencing elected officials to suit the agenda of their parent company... Actually, nevermind. They sound just like the labor unions of the present. (Just kidding). As the boilermaker Bill worked for was simply one business of a larger group, he found himself caught up in the territorial disputes and brawls of the day, and loved every minute of it.
It is strange how gangs, when able to exist outside the law, end up self-governing. Though the local police were understaffed and often paid to look the other way, the violence that ensued in Tampa was typically kept low-key; a mugging of a key union member in an alleyway, an act of vandalism to a factory floor, that kind of thing. But when serious contention arose, they employed something that looks remarkably similar to a trial by combat.
Rival gangs would appoint champions, representatives in other words, and set them to fighting one another. The outcome would determine which gang got their way.
Bill quickly became a thorn in the side of the boilermaker’s enemies in that respect. No one could beat him in a fistfight. And based on pictures of him, he was such a consummate pugilist that his nose was never broken and his ears remained intact, which was practically unheard of for bareknuckle boxers.
It got to be such a point of contention that the rival gangs pooled their money and hired a professional prizefighter to face Bill. Bill knocked his opponent unconscious in the fifth round, further infuriating the other gangs.
Supposedly it is at this time, around 1910, that Bill decided to pick up stakes. He’d heard that Tantie was practically the ends of the earth. Plenty of adventure to be had and no one to tell you what to do; perfect for someone who had such a dislike for authority. The official story is that he’d become bored of Tampa politics and backbiting, and while that may be true, the timing is just too precise to be a coincidence. If you’d just enraged most of the gangs of an entire city and wasted more of their money than you’d make in ten years, would you expect them to play fair instead of just shooting you in the back next time you walked by a dark alley?
No. Though there’s no evidence to support or disprove it, it seems likely Bill headed for the shores of Lake Okeechobee at least in part because it was a good hiding place.
At the time, there wasn’t a great deal there: a movie theater, the school, six bars, three hotels, almost a dozen specialty stores, a canvas-sided Baptist church house, and one large department store owned by the well known Raulerson family. Mr. Flagler, the noted industrialist, hadn’t established the railroads connecting Tantie with the coastal towns to the east yet and there was no straight road to any of the other settlements along the lake’s shore. Dirt and shell were the only road materials if you were lucky, and most of the houses in Tantie were constructed of local cypress. The poorer buildings were just a framework with canvas and mosquito netting to shield the occupants from the constant humid swarms.
However, private companies had already dredged the canals and there was talk of draining the marshes, swamps, and bogs that made up most of South Florida. This caused a trickle of settlers to arrive from up north, people who’d heard of the amazingly fertile properties of Florida soil. In the mid-20s this would give way to a real estate craze unlike anything anyone had ever seen before. People were so hypnotized by the idea of owning the last of America’s untamed soil that they were showing up in droves at the door of anyone who supposedly owned real estate. They paid exorbitant prices for deeds to property no one actually owned or had ever surveyed. Often the same tract of land was sold to different people simultaneously, owing to the fact they wouldn’t realize what had happened until the con artist was well on his way out of town.
This all came to a screeching halt when the stock market crumbled. The government abandoned their plans to drain South Florida, and have never resumed them, meaning all those people bought deeds to lands that are still underwater.
Of course, when Bill arrived in Tantie, there was practically nothing. It was originally just a trading post. Then the Okeechobee Waterway was built by private landowners in 1908. Though it wasn’t officially finished until 1937, ocean-going vessels could use it to pass east-west straight from the Gulf of Mexico to the Atlantic Ocean without having to sail around the southern tip of the State, avoiding the headache of navigating the Florida Keys. It also punched straight through Lake Okeechobee.
This made Tantie a port of call for the smaller vessels, as well as a place to take on fresh provisions you might not find elsewhere. Most abundantly catfish.
A very clear pecking order was established in Tantie. Townies had precedence, what with owning anything you might be interested in buying, so you were polite as possible. They could be identified by wearing daydresses or slacks, and shoes that weren’t hand-me-downs. They also went unarmed, without whip, knife, gun, or machete, which was unusual.
Crackers were cattlemen that came down from Georgia during the Civil War. The swamps of Florida were heavily populated back then, yellowhammers, a breed brought to America by Conquistadors in the 1600s which were left to live feral after the local tribes slew most of the Spaniards who set foot on Florida’s shores. The crackers, who took their names from the bull hide whips they used to herd cattle, rounded up the yellowhammers and shipped them to Cuba once every year or so. Following the Spanish-American War, crackers were forced to keep the cattle rather than let them roam free to graze and subsequently introduced larger breeds like Brahmin and Herefordshire to increase the poundage, slaughtered them on site, and then shipped them up north using Henry Morrison Flagler’s railroads and refrigerated railcars. Because crackers normally worked for wealthy landowners, they were given a certain amount of leeway when coming into town to blow off steam.
Independent farmers tended to work the lands out east of Tanti, which were naturally drier and more what you think of when you imagine Miami Beach, sans the drunks, junkies, buildings, retirees, and hookers. They owned a few hundred acres each and usually came from up north, having sold what possessions they had in an attempt to start a new life. The land was not kind to many of them. They quickly learned that, though short, the winters could kill off orange trees in the course of a few hours. Thus the burgeoning citrus industry was moved down to Miami, which is one of the reasons why the city became so popular so early on. Though frostproof breeds of citrus were generated later on, early farmers were forced to make do with root vegetables.
They were discernable by their straw hats, heavy leggings wrapped around their denim pants to protect against snakebites, and cane machetes always carried in the crook of one elbow. What differentiated farmers from the lower-ranking sawmill workers was the possession of all their fingers and toes.
Central Florida has a wealth of a pine subspecies called slash pine. It makes up most of Florida’s scrubland and only grows in areas where the water table is lower than usual, that’s to say three feet or deeper. Scrub jays and many other species live in Florida pine scrub that you’ll find nowhere else. Unfortunately, pine scrub is prime land for real estate development, meaning it’s been cut down and flattened for the last century or so. Cheap pine was a major export of South Florida, and legions of sawmill workers used to live in tent towns outside the mill twenty miles north of Tantie, only able to come to town and see their families on the weekends.
And then there were the people at the bottom of the totem pole: the fishermen, who could be discerned by their bare feet and overalls rolled to the knees to keep from getting wet. Prior to the creation of the Okeechobee Waterway, they were just squatters who lived out in the swamps west of Lake Okeechobee as well as on the shores of the lake itself. With no wildlife laws in place and no one enforcing property laws, life was relatively easy. There were always plenty of birds and fish to eat, lots of cypress for boats and shacks, and you could probably cobble together a still from the town’s cast-offs and make “stump lightning” as it was called.
But then there was suddenly a high demand for fish. Huge ships were passing through, many of them willing to pay top dollar for a fresh catch. And what couldn’t be sold immediately was bought up by commercial game agents who would go from fishing camp to fishing camp on behalf of the railroads. In less than a year, catfishing became a boom industry and the squatters now had more money than they knew what to do with. Plus, they often had an axe to grind for old snubs by townies and folks a little better off than they were.
Imagine the sense of foreboding the townies felt when the catfishing fleets pulled up to dock on Friday nights, brimming with raucous hellraisers already half drunk with pockets full of cash and a burning need to get even. It became the norm for Tantie to be drunk dry by Saturday morning, for a couple bodies to be found in the middle of Flagler Park (sometimes still alive, sometimes not), and for the town to look like it had been hit by a hurricane.
They fought with sawmill workers, farmers, crackers, townies, and even each other when there was no one left standing, one fishing camp versus another. For those who owned houses and businesses on the main drag, it became popular to sit on the roofs and watch the battles rage. Betting on the outcomes was a common pastime and eagerly looked forward to throughout the week.
Bill couldn’t have been happier. He settled right in after a few hiccups, the most notorious earning him his nickname. After a particularly bad day’s fishing, he returned to camp to find a game agent waiting. Embarrassed over catching nothing, Bill tried to hand over his bait bag, hoping the agent wouldn’t check the contents. The agent did, and when he opened it proclaimed, “There ain’t nothin’ in here but pogies!”
A pogey, for those unfamiliar with the term, is a freshwater baitfish also referred to as a mossbunker or bunker fish, largely considered inedible to humans.
It quickly became a term of endearment, and Bill was well liked by most of Tantie, despite his quirks.
He liked fighting. He was never happier than when he’d had a few drinks and found himself in the middle of a swirling melee, throwing punches harder than most people can hurl bricks. More opponents just meant more to hit. And where many of his opponents took getting hit personally, he tended just to shrug it off. There was something about him that was always cheerful, whether staring down the barrel of a gun or knocking its owner’s teeth out, that same savage grin rarely left his face. The danger didn’t scare him; he’d grown up with it, after all. It was all in good fun, and if someone should lose their temper, then they needed to be taught a lesson in fair play.
Bill was a proponent of fair play to an extreme. So much so that, shortly after becoming the leader of his own fishing camp, he and his crew were invited to a more prosperous camps’ fishing house run by one Buck Tillmann, which had genuine cypress walls and cypress bark shingles on the roof. It was clear to Bill Buck and his boys were showing off, but he remained polite all through the dinner they took together. Finally, once the evening had worn on and all the liquor Bill had brought as a gift had been drunk, Buck refused to tap his personal still and told Bill and his men to leave.
Bill didn’t take kindly to that breach of etiquette. Bill had shared his liquor. It was only right that his hosts do the same. During the fight that broke out, Bill threw Buck and his crew through every wall and window of the new fishing house (solid cypress planks, mind you), leaving only once the roof remained, utterly useless in keeping the skeeters out.
Another quirk which might be attributed to his sense of fair play is that Bill never once used a weapon. Keep in mind that many brawls involving dozens of participants resulted in serious injuries or even deaths, and drawing a gun or knife was not uncommon. Later in his life, Bill was asked about this several times. Two answers have survived to this day. The first is, “Never pull a weapon the other feller can take from you,” which is sound advice, as carrying a weapon without knowing how to use it is more dangerous than going unarmed. The second goes, “If the other feller’s got a knife and you floor him with your bare hands, chances are it ain’t you’s goin’ to jail.” This suggests an excellent knowledge of the law, if not exactly an adherence to it.
You may be wondering what redeeming qualities Bill might’ve had, given that it seems all he was interested in was fighting and drinking. (Don’t forget the gambling.) But seriously, his sense of fair play extended to people he considered non-combatants. And though he went overboard from time to time, he was able to distinguish someone who was fair game from someone who was out of bounds when many of his peers could not or simply didn’t care.
One frequently told anecdote involves the local baker, one Albert Berka, who had moved from Vienna of all places. Herr Berka was woken from a dead sleep one night by the sound of wood splintering under hard fists. He ran downstairs to his shop to find eight drunken catfisherman had broken down his front door. They were hungry and demanded he start baking bread for them.
Terrified by the grizzled, heavily-armed men, Herr Berka darted into his back room and got to work. Seconds later, he nearly jumped out of his skin as the sounds of gunshots filled his front shop. To pass the time, the catfishermen had drawn their pistols and were taking potshots at the cans of fruit arrayed on shelves above the display case which the baker used in his desserts. The only thing separating the baker from the gunfire was a wall of cypress boards, and after several shots whizzed by his ears, he continued working while plastered to the floor.
A few minutes passed, syrup and pulp spattering the walls, before there was a quiet knock during a lull in the shooting. The catfishermen turned to find Bill standing in the doorway. One of their number was out cold on the ground, dropped without anyone noticing, his gun (a brand new Colt 1911) in pieces. Without looking away from them, Bill slowly laid the pistol’s return spring sideways in one open palm and pressed his other palm down on top of it. When he took his hand away, the spring was about the length of a pencil and flat as a pancake, crushed with no apparent effort.
The fishermen sheepishly holstered their weapons, aware of both Bill’s reputation as the undisputed king of brawlers on old Lake Okeechobee and just how uncharacteristically angry he was. Bill called the baker, who hurriedly appeared from the back, slapping a ball of dough from hand to hand.
“Twenty-five dollars a can sound about right to you?” Bill asked, to which Berka could only stare.
Bill waited while Berka finished baking. The catfishermen claimed their bread, offered murmured apologies for the trouble, and slunk out, leaving behind more than five-hundred dollars on the counter for roughly four dollars worth of fruit.
Such acts, part justice and part generosity, were endemic to Bill’s personality. He made more money on the lake than he could drink, there were only so many things a person could keep with him (he still maintained a drifter’s mindset), and he didn’t trust banks, so he tended to give his money away to anyone who was down on their luck. Likewise, he tended to police the town’s catfishermen by either forcing them to pay damages for their actions or covering such things from his own pocket.
It should be noted that Tantie did indeed have lawmen, just none that were effective. There was no police force at the time, and the post of town marshal was often vacant. One JW Raulerson, antecedent of the later line of Raulerson Sheriffs and a good friend of Bill’s later in life, held the post for a record-breaking four months. They were simply so outnumbered that little short of a murder committed within city limits was worth the time. OkeechobeeCounty did not exist until it was ratified by the state in 1917. Before then, Tantie was a part of St. Lucie County, the capital of which was Fort Pierce, a significant drive and far too distant for the sheriff, who was already overworked, to pay much attention to.
To that end, Bill filled in by taking the law into his own hands. However, things took a turn for the weird when his sense of mischief got the better of him around 1914. No one’s quite sure why he did it, but one day Bill got it into his head to make things official. Several men from his fishing camp had been arrested on minor charges of public drunkenness as a futile attempt at making an example to the rest of the population.
On his way to try the accused was Judge Henry H. Hancock, a well-regarded resident of the county who was being escorted by several marshals. It was somewhere around the outskirts of Tantie on Parrot Avenue, which bisects the city east-west, that Bill and the rest of his fishing camp ambushed His Surprised Honor. They disarmed the marshals, stripped Hancock of his robes, tied them all to cabbage palms (which are not at all comfortable, believe you me), piled into Hancock’s brand new Cadillac, and drove into town.
Bill arrived at the Okeechobee County Courthouse, AKA Darrow’s Drug Store, dressed in Hancock’s robes and with his gavel in hand. He jumped out of the car, took the judge’s seat across the table from the accused, heard their evidence, and found them guilty of public drunkenness, fining them all a quart of stump lightning from their personal stills each.
The kicker is that the accused all had enough alcohol on them, even though in chains, to pay the fine then and there!
Bill took the liquor, left half of it for Hancock and the marshals whenever someone untied them, and everyone skedaddled to Mr. Bryant’s Rough House Saloon on Taylor’s Creek to get thoroughly soused.
Of course, Hancock was furious and let it be known he would bring Bill to justice. Bill, safe in the swamps west of Okeechobee, said if Hancock came for him he’d be happy to throw him in the lake for the gators.
Months passed with Hancock calling in as many police officers, marshals, deputies, and lawmen he could get a hold of, all to no avail. Bill’s network of friends was so expansive and solid that he always knew where Hancock’s men would be looking for him, and so he was never there.
Things came to a head when Hancock offered an open bounty of his own money for Bill’s capture. The exact amount is not remembered, but something in the area of $50,000 dollars was paid out to all those who aided in the hunt. Thousands of people finally herded Bill into an impassable bog, and though he dropped dozens, he was eventually overwhelmed.
But that led to another problem. Hancock needed to assemble a jury, find advocates, and figure out what to charge Bill with. He’d been so focused on catching the man that he hadn’t thought ahead about what to do with him. In the meantime, there was no place to hold Bill. The local jail was too flimsy. Even wrapped in chains from shoulder to waist like he was wearing a straight-jacket, Bill was still kicking holes in the jail walls!
They settled for welding Bill into an abandoned cattle railcar in the railroad depot east of Tantie. You can imagine just how angry he was, tied up and cooking in a hot iron box under the blazing sun for over a week before being taken out at gunpoint and brought before the judge.
The trial took place in Darrow’s Drug Store, dozens of grim lawmen pointing guns at Bill’s head while he glowered across the table from Hancock. Hancock began the proceedings, but had forgotten the exact wording he was going to use, and so produced a large book of law which appeared a great deal like a magazine in order to look up a passage.
Bill, upon seeing Hancock leafing through the book, snarled, “I ain’t gonna be tried outta no damn Sears and Roebuck catalogue!” and drove his knees upward, upsetting the table as well as the large pitcher of water resting on it.
His Sodden Honor was so shocked that he forwent the trial and gave Bill ninety days in the Fort Pierce Prison for assault on a public official and contempt of court. Technically, Bill got off of charges of resisting arrest, grand theft auto, multiple assaults, and kidnapping, so getting Hancock that angry actually went in his favor, though Bill didn’t see it that way at the time.
It was roughly halfway through his sentence that several fires broke out in Tantie. The crime rate skyrocketed, and it became painfully clear to everyone involved that while the cat’s away the mice would play. Only then did Hancock realize that Bill had been keeping order in his own way, and without him around the town was descending into sheer pandemonium.
Here’s where things go kinda screwy. Hancock, with the aid of the local physician, one Doctor Anna Darrow, also known as “Doc Anner” and “the Squaw Doc” given she provided aid to local Seminole tribsepeople (She also had the distinction of earning the highest score of the state medical licensing exam at the time, as well as being the first woman to pass that exam), approached Bill while he was in prison. Somehow they got him to swear off brawling and gambling and put all his energy to the common good. This sort of overnight change just doesn’t happen in real life, but every story about Pogey Bill includes this miraculous transformation, so I’ll leave you to fill in the blanks here.
Bill agreed to become the town marshal, and in return Hancock pardoned him immediately.
He made good on his word. He policed the town, breaking up fights he normally would’ve joined in and jailing drunks he normally would’ve numbered amongst. There were some more reluctant to accept his new status than others, the most notable resulting incident being when he found a number of moonshiners raiding the local livery for corn feed to use in their mash. He knew them all personally and had probably helped them in mash raids before, but this time he told them to either pay for what they were taking or head to jail.
The fight that broke out is not well documented, save that one of the shiners had Bill’s left thumb between his teeth near the end of it and was threatening to bite it off unless Bill let him go. Bill refused immediately and parted ways with the digit without a second thought.
No one was under the illusion he was joking about his new duties after that.
Of course, what no one asks is why Bill would have his thumb in someone else’s mouth unless he was intent on ripping out their cheek. It’s called fish hooking, and the result is extremely gruesome.
His rise through the ranks was near meteoric. Thanks to his results—and inside knowledge of the local criminals, what with having been one—the state allocated the funds to construct a local police station. Bill was hired as Chief of Police not long after, and also became one of the first “squatters” to own a Ford Model T. He began courting a young woman named Merle Dupree, one of 8 children of Rebecca and Horace Dupree, lifelong residents of Florida. Merle was a native of Fort Myers and attended schools in Fort Myers and Okeechobee City.
In 1917, OkeechobeeCounty was officially formed, the sheriff being Smith J. Drawdy, a minor businessman whose family hailed from Savannah and had moved to Tantie from PolkCounty some years earlier, acknowledging the wealth of potential the land possessed. He was instrumental in funding the draft of the bill sent to the Capitol, and though not to belittle the man, did not have the martial presence necessary to command the respect of the county’s criminal element. Thus, when Bill ran for sheriff in the 1918 elections, he won by a landslide. Supposedly not even Drawdy objected, but that could be just a rumor.
Bill quickly began a series of public works programs worthy of a film montage. He regularly visited the elderly and sick, bringing groceries whether they asked or not, often just leaving them on people’s doorsteps so they wouldn’t feel obligated to express gratitude. Though his own religious denomination is unknown, he contributed to the construction of the Sacred Heart Catholic Church, an edifice which still stands in Okeechobee today. Also, he worked with the local priest to establish a boy’s boxing league, in which he sought to impart his years of experience to youths who would hopefully use it more judiciously than he. The first Boy Scout troop in Tantie was formed in 1927 and he became the scoutmaster within the year.
The reason he’s remembered as much as he is is because he liked children so much, and they him. He commonly took the local children on daytrips to Fort Pierce or West Palm for ice cream, learning to swim at the beach, or to take in a baseball game. This is likely transference given the fact that his wife was barren and Bill never did have any children of his own.
Perhaps one of the most commonly referenced stories about him is his love of baseball. Given his arm strength, he made an excellent pitcher. But more than that, he felt it was an ideal and safe outlet for rivalry and the need to fight. To that end, he purchased a small tract of land in Tantie’s west end and built a baseball diamond on it which still stands to this day, sandwiched between the community college and middle school. He also paid for the uniforms and equipment, creating two teams: Okeechobee North and Okeechobee South.
There was never any shortage of players. Bill had a wholly unique method of recruitment. Any man who moved into town would receive a knock at their door. Bill would be there in his suit, and promptly tell the newcomer that they could either join one of the baseball teams or go to jail. No, there’s no record of anyone refusing, so we haven’t a clue as to whether or not he was bluffing. Personally, I think he meant you could either find a constructive way to work off your aggression or end up crossing the law eventually. Then again, I don’t think I would’ve called him on it. At that point, he tended to officiate games rather than play, sometimes being asked to throw in the first ball of the game.
As the ‘20s wore on, Bill was forced to hire a number of deputies, chief among them Mr. Charles Lee: a retired Texas Ranger little is known about aside from the fact that grown men supposedly quaked wherever he passed.
It was a time of booming business. New roads were built. The Conner Highway was formed by “Fingey” Conner, the owner of a series of successful Chevy dealerships along the East coast who moved to Tantie because of his love for fishing. The highway opened up Tantie to Central Florida and heralded a wealth of new settlers that transformed the sleepy little burg and nearly quadrupled the population within just five years.
Conner was quoted about his highway as saying, “I’ve been doing damn fool things all my life. People’ve told me building this road would be the foolest. Be a damn shame to stop now.”
With the new business and byways came unwanted attention. Prohibition was in full swing at the time, and Bill was known to personally disagree. He felt that a person should be able to take a drink if he wanted, and was notoriously lenient with moonshiners. It was around this time, just prior to the Great Depression, that Bill was approached by representatives of Al Capone. They wanted to know if he might be interested in looking the other way for a fee while they set up a distillery. The Capone mob already had distilleries in Tampa and Fort Pierce, meaning it would not be difficult to ship liquor out from Tantie.
Bill made it quite clear that such large operations were not welcome and they would be arrested if he saw them again.
Ultimately, I believe this to have been Bill’s downfall. The hurricane of 1928 came soon after. And with it a certain amount of Bill’s spirit was dampened. He was called upon to identify more than 2,000 corpses around the lake. He knew all of them, and considered the majority to be friends. Those who survived had lost a great deal, and he hadn’t the funds to help them all rebuild. So he made a few concessions he wouldn’t have in better times. You see, in 1929 he was found by federal agents in the Tantie railyard with several subordinates. They were aiding moonshiners load liquor jugs into a series of hollowed out cypress logs on a lumber car by guarding the road into the railyard.
Bill was no proponent of Prohibition. He proclaimed, “It’s the bunk,” many times and complained that he spent most of his time just keeping people from selling booze in the post office. But up to that point, he’d never actively abused his position. Though not proven, the fact that federal agents were tipped off to Bill’s activities suggests this was subtle revenge wrought by Capone’s gang. No one in Tantie served to gain anything by Bill being reported for his actions.
He was tried twice, both times in Miami, a known getaway and neutral ground for mobsters in the ‘20s, particularly Capone, who was supposedly in town during both trials. The first resulted in a hung jury. The second time he received a six-year sentence which was reduced to probation immediately upon his appeal.
He willingly resigned his position as sheriff, but according to him it was only to save Governor Doyle Carlton the embarrassment of requesting his resignation, what with ninety percent of OkeechobeeCounty’s citizens petitioning the governor, demanding he not remove Bill from his post.
Owing to Bill’s funds being seized by the state on suspicion of it being liquor-money, he didn’t have enough money to campaign for the 1932 elections. He lost by three votes and shortly thereafter was offered the position of Frostproof’s chief of police. Located in the adjacent Polk County, the city of Frostproof is an agricultural community, the name an early advertising gimmick to suggest to possible settlers that they had never had a hard frost, thus growing citrus there was safe.
This was almost certainly a drastic step down from the position Bill was used to holding in terms of responsibility, citizens under his care, pay, and, most of all, adventure. With less than 1,000 people in Frostproof and very few troublemakers, Bill took to working with the volunteer fire brigade whenever possible. Whilst responding to a fire one day, Bill was hanging onto the side of a fire engine as it passed through Frostproof’s main drag. The engine took a hard turn, and it had been raining hard earlier that afternoon. The fire engine rolled, crushing Bill beneath it.
Miraculously, he survived, though most of his ribcage had been crushed. However, due to his infirmity and the fact that he was given total bed rest, he was not strong enough to fight off the fluid and pneumonia that brewed in his lungs several days later. He died February 14, 1935.
Because of the depression, he was buried in an unmarked grave. Because of his sheer popularity, they had to hold three funerals so everybody who wished it could attend.
Some years later, JW Raulerson, one of Bill’s deputies, was elected to the post of Sherriff of Okeechobee County. He won on the platform that he would run things the way Bill would’ve wanted, and the first thing he did was have Bill exhumed and placed under the shade of an oak tree in the Okeechobee County Cemetery.
That’s his story. He’s made up of blurbs here and there and tall tales aplenty, given form and substance by the Boy Scout troop he nurtured, the baseball diamond and church he helped build, the diner he took his breakfast at every morning, and graves that remain in a town and state that’s changed so very much he probably wouldn’t recognize it.
Surprisingly little for someone who did so much, isn’t it?
But, then again, maybe you don’t need a skyscraper with your name on it to proclaim your accomplishments. Bill was human, but he was also what a lot of people needed. He and people like him fought to forge some semblance of order so that we can enjoy a relatively peaceful life, and though right wasn’t always on the same side as the law, he had the strength of character to know the difference. And that, I think, is the defining quality of the iconic frontier lawman. When the law fails, do what’s right. Words to live by.
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