February 23, 2023 • 26 mins
When we think of American outlaws, we often think of cowboys and dusty trails in the Wild West. Meet the Ashley Gang who operated out of the Florida Everglades.
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Speaker 1 (00:02):
You're listening to American Shadows, a production of iHeartRadio and
Grim and Mild from Aaron Mankey. The mythical figure of
robin Hood has endured for centuries. This classic tale of
(00:23):
the anti hero who stole from the rich and gave
to the poor has been retold countless times in books, movies,
and folklore. Variations are found in multiple cultures from centuries
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
(00:46):
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.
(01:09):
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
(01:32):
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
(01:54):
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,
(02:15):
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
(02:39):
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
(03:00):
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
(03:24):
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.
(03:48):
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
(04:10):
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
(04:32):
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.
(04:53):
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
(05:16):
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
(05:39):
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,
(06:00):
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,
(06:22):
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,
(06:44):
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
(07:05):
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
(07:25):
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
(07:48):
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.
(08:08):
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.
(08:30):
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
(08:56):
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
(09:18):
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
(09:38):
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.
(10:02):
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
(10:25):
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
(10:47):
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
(11:09):
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.
(11:32):
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.
(11:53):
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.
(12:15):
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,
(12:37):
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
(13:00):
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
(13:22):
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
(13:57):
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,
(14:20):
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
(14:43):
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,
(15:06):
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
(15:31):
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
(15:54):
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
(16:15):
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
(16:38):
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
(17:00):
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
(17:21):
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
(17:44):
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
(18:06):
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.
(18:37):
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.
(19:00):
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
(19:21):
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
(19:41):
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
(20:03):
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,
(20:25):
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
(20:45):
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.
(21:07):
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.
(21:28):
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
(21:51):
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
(22:12):
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
(22:34):
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
(22:56):
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
(23:19):
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,
(23:43):
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
(24:05):
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
(24:25):
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
(24:47):
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
(25:12):
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
(25:33):
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.
(26:03):
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
(26:24):
wherever you get your podcasts.
You're listening to American Shadows, a production of iHeartRadio and
Grim and Mild from Aaron Mankey. The mythical figure of
robin Hood has endured for centuries. This classic tale of
(00:23):
the anti hero who stole from the rich and gave
to the poor has been retold countless times in books, movies,
and folklore. Variations are found in multiple cultures from centuries
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
(00:46):
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.
(01:09):
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
(01:32):
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
(01:54):
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,
(02:15):
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
(02:39):
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
(03:00):
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
(03:24):
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.
(03:48):
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
(04:10):
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
(04:32):
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.
(04:53):
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
(05:16):
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
(05:39):
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,
(06:00):
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,
(06:22):
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,
(06:44):
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
(07:05):
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
(07:25):
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
(07:48):
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.
(08:08):
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.
(08:30):
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
(08:56):
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
(09:18):
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
(09:38):
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.
(10:02):
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
(10:25):
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
(10:47):
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
(11:09):
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.
(11:32):
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.
(11:53):
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.
(12:15):
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,
(12:37):
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
(13:00):
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
(13:22):
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
(13:57):
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,
(14:20):
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
(14:43):
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,
(15:06):
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
(15:31):
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
(15:54):
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
(16:15):
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
(16:38):
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
(17:00):
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
(17:21):
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
(17:44):
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
(18:06):
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.
(18:37):
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.
(19:00):
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
(19:21):
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
(19:41):
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
(20:03):
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,
(20:25):
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
(20:45):
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.
(21:07):
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.
(21:28):
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
(21:51):
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
(22:12):
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
(22:34):
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
(22:56):
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
(23:19):
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,
(23:43):
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
(24:05):
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
(24:25):
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
(24:47):
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
(25:12):
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
(25:33):
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.
(26:03):
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
(26:24):
wherever you get your podcasts.
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