Glorified

past two modern times. People have often revered the concept of rising up against oppression in tyranny as a hero or savior, so it's not surprising that tales of social banditories sparked the imaginations of those living in the American West during the eighteen hundreds. The written stories about robin Hood date back to the fourteen hundreds, and oral tellings probably stretched back a century before that. In these early tellings,

a corrupt abbot demands payment from a night. Robin Hood loans the night the money, and later robs the abbot. In the eighteen hundreds, in the American West, people romanticized outlaws and told stories suggesting that they might be doing something similar. One such example is the famous and infamous Jesse James. But before the outlaw became one of America's most hunted men. He and his brother served in the military,

fighting for the Confederate Army during the Civil War. It said that Jessie and his brother Frank took part in the Centralia massacre that killed twenty two Union soldiers. After the war, the brothers led a gang of outlaws specializing in robbing stage coaches, banks and trains. A word of the notorious James Gang spread across the nation, along with rumors that Jesse and Frank often robbed rich and gave

the poor. In one of the most enduring stories, the James Gang rode through Missouri to a string of successful and profitable robberies. They came across a farmhouse where a poor and elderly widow lived alone. With the law on their trail, the men asked the widow if they could stay and hide for a few days. She welcomed them and, in an act of kindness, shared her meager supplies and food. Jesse noticed the woman seemed distracted and upset and asked

what was troubling her. To a surprise, she broke down in tears. Aside from being recently widowed, her mortgage was due and she had no money to pay The widow explained that her lender was far from understanding or generous in the matter, and she had no place to go and no way to earn a living. Jesse asked the woman how much she needed to pay off her mortgage.

She told him she needed fifteen hundred dollars. Jesse promptly gave her the money and pulled her to get a receipt from the debt collector when he came for the money. Then he asked for the collector's description. The gang left shortly after, but instead of continuing their journey, they waited in the woods. The deck collector arrived, took the money, and handed the woman receipt. When he got back on his horse and rode away, Jesse and the gang followed.

They trailed the man for a while before robbing him. Jesse took back the fifteen hundred dollars and the gang rode away. Although this story is likely a myth, it's been widely accepted by the American imagination as fact. Like Robin Hood, stories about Jesse, James and his gang of merry men robbing the rich and giving to the poor have endured, making him seem like a noble Outlaw One. News of Jesse's death appeared in newspapers in April of

eighteen forty two. Rumors swirled that he was alive and well. Some believed that Jesse and fellow gang member Robert Ford had plotted to kill another man resembling Jesse, which allowed him time to escape. Since then, science and the marvels of DNA have proved that the body in Jesse's grave is indeed the Outlaw himself. But for many decades, Jesse's legacy of being the Great robin Hood of the American West lived on. I'm Lauren Vogelbaum. Welcome to American Shadows.

When we picture the life of American outlaws, we might think of the mid to late eighteen hundreds. We may envision the open Midwestern plains, rocky outcrops, and dusty trails. So we think of cowboys and wrestlers across Arizona Wyoming in California. But perhaps few would think of the early nineteen hundreds and Florida. Instead of dusty streets and tumbleweeds. The scenery in mid eighteen fifties, Florida looked a bit different.

South Florida was a wilderness of sawgrass marsh and mangrove forest. The mikatsuke In semin peoples shared the Everglades with a host of wading birds and Florida panthers. Water flowed down and across the state through the Kissimmee Basin and Lake Okeechobee, eventually reaching Biscayne Bay. Alligators, crocodiles, and other animals coexisted within the ecosystem. Early colonists thought the swampy, alligator infested

area was worthless. They dug out canals to drain the water from what they considered potentially valuable grazing and farmland. In eighteen sixty one, Florida seceded from the Union to join the Confederacy of Floridians depended on cattle, citrus, and other produce and feared that their economy would fall without the enslaved labor of indigenous peoples and Africans. In the coming decades, colonists dug more canals and drained more water away.

And while we might picture newcomers choosing to live on that open farmland, some families chose to live in the Everglades, and such was the life for the Ashley family. Julius Ashley, known simply as Joe, his wife Leuginia, and the couple's nine sons and two daughters, moved from Fort Myers to West Palm Beach, Florida in nineteen oh four. For a short time, Joe worked on the Flaggler Railroad and served

as a lawman. But Joe also made first rate moonshine, which conflicted with his career, and the family settled in a small town in the Everglades just north of Hobe Sound to hide the business. The Ashleys carved out a living distilling moonshine and living off the land. They knew the Everglades as well as anyone, and used their knowledge to hunt and trap animals, mostly alligators and otters. Occasionally, the Ashley boys teamed up with their seminal neighbors for

hunting or fishing expeditions. A Joe's son, John, became even more adept than the siblings in learning how to navigate the Everglades. At times, John disappeared down hunts for days, often with his friends and Desto Tiger, the son of a seminole leader. The friends went off hunting one day in December of nineteen eleven. Days later, John was spotted in town without DeSoto. For days, no one sawed Soto. Finally, on December twenty ninth, a crew dredging the New River

Canal near Fort Lauderdale found Soto's body. He had been shot in the back of the head. Naturally, John became the main suspect. The pair had last been seen transporting Otter Pelts in John's canoe. John then sold the pelts four twelve hundred dollars at a Miami trading post and pocketed the entire amount. With witnesses placing the two together. Then a strong motive for murder, Palm Beach Sheriff George

Baker ordered two deputies to arrest John. The men arrived at the Ashley camp, only to be confronted by John and his brother Bob. John told the deputies that he had let them live so they could deliver a message to the sheriff if Baker sent any more lawman to find him, that it hurt. The deputies left, but John figured they'd return with more men. Baker chose a different approach. Instead of sending men into the Everglades, they'd wait for John to come to them. At some point, John would

need to go into town. It didn't take long before nearly every post office in South Florida had a wanted poster of John Ashley on display, and there wasn't a town John could step foot in without being recognized. With a reward on his head, he decided to leave the state. Some say he headed toward New Orleans, others say he went to Seattle. Either way, John got homesick and returned in nineteen fourteen. He surrendered and was taken to jail to await trial, but John and his family had no

intention of giving up so easily. John Ashley's first trial in Palm Beach in July of nineteen fourteen ended in a trial Convinced of his guilt, the state prosecutor and Sheriff Baker were determined to see him hang for murder. After reevaluating the trial, the prosecutor determined that it had been a mistake to try John and Palm Beach, the county was full of friends, relatives, and customers of the Ashley family. When the prosecutor set a new trial date,

he also requested a new location, Miami. A judge granted the request, which didn't bode well for the Ashley's, but John managed to escape during transport, who climbing over a ten foot fence and disappearing into the everglades. Adding insult to injury, He'd escaped from Sheriff Baker's own son. The Ashley family had long been at odds with the law, and Joe had little problem encouraging his son's illegal actions. He helped his sons and their gang in an attempted

robbery of the Florida East Coast Railway. However, the gang's lack of a plan and a savvy poor foiled their attempt. In late February of nineteen fifteen, the Ashley Gang robbed a bank in Stuart. The group took in forty three hundred dollars about one hundred and twenty thousand dollars today. Though not everything went smoothly, kid Lowe, the gang's newest member, accidentally shot John in the jaw. The bullet's trajectory caused John to lose his eyesight. The group went into hiding

for a while. John's pain increased and he was forced to seek medical attention. A doctor removed one eye, replacing it with a glass eye and the patch. When he finished, Sheriff Baker and a posse arrested John and sent him to jail in Miami. It wasn't long before the Dade County jail guards heard rumors that the Ashley Gang had plans to break John out. A security increased, though that hardly deterred the Ashley's. Joe gathered his sons to make

detailed plans for John's escape. Bob grew impatient and decided to break John out in a blaze of glory by himself. On June second of nineteen fifteen, he went to the Miami Dade Deputy Sheriff's home next to the jail. Bob stood outside for a few minutes before knocking on the door. Deputy Wilbur Hendrickson answered. Bob raised his rifle and fired, shooting the deputy in the chest. While he took the deputy's jail house keys, Missus Hendrickson grabbed a rifle. She

pulled the trigger, but the rifle didn't fire. The shot had drawn the attention of nearby residence, forcing Bob to flee. In his hasty retreat, he dropped the keys. Bob carjacked delivery truck, though the driver had a gun to his head. He stole the truck to allow officer John Riblet to catch up in a vehicle behind him. When the officer demanded that he gave himself up, Bob shot him in the head. Incredibly, Officer Riblet returned fire, hitting Bob twice.

Both men were rushed to the hospital where Riblet died. The sheriff moved Bob Ashley to the jail, but he died upon arrival. John's second trial went better than expected. He managed to escape the death sentence for the murder of the Sodo Tiger. However, the court did sentence him to seventeen years for his part in the bank robbery. In March of nineteen eighteen, John Ashley got out of prison on good behavior and immediately returned to his former

life of crime. The Ashley Gang continued to rob trains and banks, but with prohibition, rum running and bootlegging proved easy money. The Ashley gang set up multiple stills around Palm Beach County. John, along with brothers Ed and Frank, made frequent moonlight trips to and from British liquor warehouses in the Bahamas to the Jupiter Inlet. The gang added a new member, John's girlfriend, Laura, up the grove Laura had had two children with her first husband and two

more with her second husband, Ernest. One day, she left Ernest and her children to join the Ashley Gang. Laura worked as a scout for the gang. She've also helped play in the bank robberies and often drove the getaway car. When members of the gang were arrested, Laura planned their escape. Though perhaps not a raving beauty, she still caught men's attention. She was tall, dark hair, dark eyed, and a notorious flirt.

By all accounts, she was a mean spirited woman who wore a thirty eight on our hip as She was as good a shot as any member of the gang, and like the Ashley's, Laura knew her way around the Everglades. By nineteen twenty, John didn't think life could get much better, but then he got word that his nemesis, Sheriff Baker, had died. John's elation didn't last though, a Sheriff Baker's son stepped in to take his father's place. He wasn't

about to give up on arresting the Ashley Boys. In nineteen twenty one, John was delivering liquor in Wachula when the new sheriff Baker arrested him. During the months that followed John's incarceration, his nephew, Hanford Mobley and gang member Roy Matthews ran the day to day operations. A brothers, Ed and Frank Ashley continued the run running operation without him, and they set out on a dark October night in nineteen twenty one for another trip across the Gulf Stream.

That was the last anyone saw of those two Ashley boys, But in the following years, the gang robbed the Bank of Stuart again and John escaped from prison, followed by the escape of two other gang members from a different prison. Reunited, the gang ramped up their crime spree to taunt Sheriff Baker. John began leaving a gun with a single bullet at every robbery. Infuriated, Baker swore that he would bring John to justice and carry his glass eye around like a

pocket watch. In the early morning hours of January ninth, nineteen twenty four, Baker gathered a large posse and surrounded a camp a couple of miles from the Ashley homestead. The two groups exchanged gunfire. One of the officers shot Joe in the head, killing him. John fatally shot Deputy Fred Baker, the sheriff's cousin, and during the exchange, Laura was also shot but survived. John Ashley vowed kill every deputy when given a chance. Then he and the gang

escaped into the Everglades the empty handed. The posse burned the camp and the homestead to the ground. The Ashleys had made a threat, and as far as the deputies were concerned, it was now them or the Ashley Gang. John and the gang robbed the Bank of Pompinow on September twelfth of nineteen twenty four. The heist netted the group five thousand dollars in cash and another eighteen thousand insecurities.

Was still angry over his father's death and Laura's injury, John wanted to humiliate Baker, so he handed the cashier and unspent bullet. He ordered the cashier to give the bullet to Sheriff Baker when he arrived, along with the message that he had another bullet waiting for the sheriff if he was man enough to come and get it. John moved the gang's camp nearly three hundred miles north to his sister's house. As some say he was headed

toward Jacksonville, where they were planning another bank robbery. Later, John's mother would insist her sons were trying to give up their life of crime. For a while. John took some delight that the press chastised Baker for his inability to capture the gang, but even the humiliation didn't quite quench his hatred for Baker. John wanted revenge for his father's death and vowed to assassinate Baker after the November elections. However, Sheriff Baker was already on to the Ashley's and their

new location. The Stuart police chief had been on the lookout and saw John's brother in law a loading an excessive amount of groceries into his car. A Baker called Saint Lucy County Sheriff J. R. Merritt, and the two men planned an ambush for the Ashleys. Merritt placed a roadblock on the Sebastian Bridge on November first of nineteen twenty four. Baker stayed behind, afraid that if he left Palm Beach, someone might tip off the Ashleys that he was onto them. Instead, Baker sent four men to meet

up with Merritt and to Saint Lucy. Deputies ten thirty that night, a car drove up and stopped a blockade. A second car carrying the Ashley gang, drove up behind the first. With the gang's interests centered on the car stopped in front of them, Merritt and the deputies took the Ashley gang by surprise, surrounding them and ordering them out of their vehicle with their hands up. What happened

next is still debated. Some say that the Ashley gang tried to escape and were shot, but the men in the first car claimed that the gang was already in handcuffs when they were asked to leave the scene. Ashley was known to carry a gun, and the deputies claimed they did not yet have the gang in handcuffs. John was ordered to keep his hands up and not make a move. They said he was shot when he lowered

his hands and stepped forward. The investigation ruled that the deputies shot and killed the rest of the gang when they attempted to flee, leaving some to speculate that Baker had ensured that justice would be served in one way or another. Laura up the Grove lived to tell the tale. She hadn't been there the night John was killed. Without John and the gang, she wandered around South Florida. Reportedly, Laura had told an informmant about John and the gang's

plans to travel north. She knew they would be traveling across the bridge that night. He had left her behind, and she had been angry. Or One night after the shooting, she fought with a friend over a bottle of moonshine. Angry and not paying attention, she grabbed a bottle that she thought was moonshine and drank deeply. Instead of alcohol, the bottle contained a strong disinfectant. Within minutes, she was dead. Rumors swirled that she had been the last to know

where the Ashley Gang had hidden their money. Locals speculated that the gang had stolen a large amount of cash that was unaccounted for and had buried it deep in the Everglades. It's estimated that the gang stole over a hundred thousand dollars, though only thirty two thousand was ever reclaimed. Some rumors say that Laura had some of the money buried with her. Others say that after John's death, she buried the money at a gas station. When the Great

Depression hit, the story of the Ashley Gang changed. They'd done some horrific things, but the new tale among many of the locals was that the gang gave food to the poor. To them, John became a modern day Robin Hood. People idolized the Ashley's, claiming the gang where missunderstood rebels rising up against a corrupt government and system designed to keep the poor impoverished. Others said that with the stolen money, the Ashley's were able to hire people in the community,

which helped them earn a living. Like the James Gang, It's unlikely that the Ashley Gang gave away their money to the needy. They most likely spent the money or gave some of its relatives. People have searched for their stash, including professional treasure hunter Robert Allison in nineteen seventy two. Reportedly, Allison found the treasure after his team used a front loader to scrape the top soil on the Ashley's property near Hope Sound, though this is also speculation and has

never been confirmed. One last detail for you. Remember how Sheriff Baker Wants swore that he would one day wear John Ashley's glass eye like a pocket watch. One of the deputies at the scene supposedly snatched the eye to give to Baker. Two stories follow. One account is that just after John's death, Laura walked into Sheriff Baker's office, leveled to forty five at his head, and demanded John's eye. After taking it from him, she told him that if he wanted it bad enough, he was welcome to come

and get it if he was a man enough. But the truth is more likely the second story. In an interview, the deputy who took the eye from John Ashley said he never ended up giving the eye to Baker. Instead, he was forced to return it to be married with Ashley. He stated that had he known John would get it back, he would have crushed the eye under the heel of his boot. There's more to this story. Stick around after

this brief sponsor break to hear all about it. Long before outlaws roamed the West, America feared a different villain, pirates, and while some treasure hunters still searched the Everglade for John Ashley's treasure, others looked the Florida Keys for buried gems and gold coins left behind by one of the state's most fearsome pirates in history. A little is known about Black Caesar. Legends tell us. He roamed the Caribbean Sea in the late seventeen hundreds, striking fear into the

hearts of sailors and merchants alike. Stories about him may actually be an amalgam of stories about different black men who were pirrating in the Caribbean at the time. Whatever the case, his real name was conveniently never known, and he adopted the pseudonym Black Caesar due to his dark skin and imposing stature. According to legend, he came from West Africa and was the son of a powerful chief.

He was rumored to be of enormous size and strength, and many enslavers tried to capture him, to no avail. It took betrayal to finally capture him. A business associate lured Black Caesar onto a boat, claiming there were many valuable and stolen goods that might be of use. Once aboard, Caesar was outmanned and subdued. His captors chained and shackled him, then transferred Caesar to a slave ship headed to the Caribbean. A sailor aboard the ship befriended him, and during a storm,

he freed Caesar. Together, the two managed to escape the ship before it smashed into the reefs, killing all those still aboard. Caesar and the sailor rowed a small boat, the Hurricane, and made it safely to a small island in the Florida Keys. There the friends began their pirrating scheme in earnest, laying wait for passing ships. The men would row out to sea and pretend to be lost

and in need of rescue. When the other ships offered help, the pirates took advantage of their kindness and plundered them. The scheme proved to be very profitable. Eventually, Caesar and the sailor added more men to their crew. Their partnership apparently ended when they captured a woman, and the sailor and Caesar both wanted her. Caesar killed his best friend over her. A black Caesar was known for his cunning

and intelligence, as well as for his immense wealth. He plundered countless ships over the years, amassing of fortune in gold, jewels, and other valuable goods. When he raided ships, he took men, women, in children captive and placed them in prisoner camps, hoping for ransoms. In Some stories say that escaped children created their own society on the islands as his wealth grew. It was said that Black Caesar kept his treasure in a secret location known only to him and a select

few of his most trusted crew members. According to legend, he buried the treasure off the Florida coast on Elliott Key, where he believed it would be safe. Caesar later joined Blackbeard's crew and was with him the day Lieutenant Robert Maynard killed him. As Caesar was arrested and later hanged in Williamsburg, Virginia, the rumors of Black Caesar's treasure spread like wildfire throughout the Caribbean. Many pirates and adventurers set out to find what they thought was a treasure of

unimaginable wealth. However, no treasure was ever found. As the years passed, the story of Black Caesar's treasure became the stuff of legend, and many said that the island was cursed and that anyone who'd tried to claim the treasure would suffer some terrible fate. Some even claimed that the island was haunted by the ghosts of those who had tried and failed to find it. The legend has it that Black Caesar's treasure is still out there and waiting

to be discovered. The skeptics say the treasure is nothing more than a myth and never really existed. Like the story of Robin Hood, taking from the rich and giving to the poor, legends of ill begotten treasure waiting to be found continue to capture the imagination of people all over the world. American Shadows as hosted by Lauren Vogelbaum. This episode was written by Michelle Muto, researched by Ali Steed, and produced by Miranda Hawkins and Trevor Young, with executive

producers Aaron Manky, Alex Williams, and Matt Frederick. To learn more about the show, visit grimanmil dot com. From more podcasts from iHeartRadio, visit the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.