The Unconquered Tribe | Part 2: Osceola vs the USA

March 13, 2023

The Unconquered Tribe | Part 2: Osceola vs the USA
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‘A man that with the feeblest means, produced the most terrible effects'

‘A man that with the feeblest means, produced the most terrible effects'


Today we explore the rise and fall of Osceola, a charismatic and determined leader of the Seminole people

Osceola's courage in his wars with the United States government was legendary, and his leadership during the Seminole Wars marked a turning point in the struggle for Native American sovereignty. 


We also delve into his deep-seated hatred of President Andrew Jackson and his administration, which drove much of his resistance against the US government's attempts to remove the Seminoles from their ancestral lands.


From his cunning ambush of US troops in the Battle of Withlacoochee to his dramatic capture by American forces under false pretenses, Osceola's story is one of perseverance in the face of overwhelming odds. 


Join us as we explore the life of a truly remarkable figure in American history.




  • The Seminole by Liz Sonneborn
  • A Native American Encyclopedia: History, Culture, and Pritzker, Barry
  • Great North American Indians : profiles in life and leadership by Frederick J Dockstader
  • A Seminole legend : the life of Betty Mae Tiger Jumper by Jumper, Betty Mae
  • Unconquered people : Florida's Seminole and Miccosukee Indians By Brent Richards Weisman
  • Osceola's legacy by Wickman, Patricia R.
  • The Seminole wars : America's longest Indian conflict by Missall, John
  • The Scott massacre of 1817. A Seminole War battle in Gadsden County, Florida by Dale Cox
  • Indian removal Act 1830
  • Treaty of Paynes Landing
  • The Seminoles of Florida by James Corvington
  • History of the Third Seminole War, 1849-1858 Co-authored with Dr. Joe Knetsch.
  • The Black Seminoles by Kenneth W. Porter
  • Red Patriots: The Story of the Seminoles by Charles Coe


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  • All images are public domain unless stated otherwise.
  • Paid license for 'Anthology Of Heroes Podcast' utilised for numerous sounds/music
  • 'The Ice Giants' by Kevin MacLeod is licensed under Creative Commons



It's December 28th, 1835, outside a U.S. Army fortification in North Florida.
Lieutenant Constantine and his commanding officer, Wiley Thompson, take a stroll on
the dying light of the afternoon.
It had been a tense few months since Andrew Jackson declared war on the Seminole tribe
their little outpost had been attacked several times.
But Thompson was optimistic.
He had befriended a man of great influence within the Seminole tribe named Osceola.
The flamboyant outspoken Indian was a regular face at the fort.
And Thompson was sure that with enough gifts, his cooperation could be bought.
After all, what Indian couldn't be.
In fact, he was so sure of this that he had broken the law and gifted his friend a shiny
new rifle.
Unbeknownst to Thompson, that very rifle was now being levelled at him from across the
field he was strolling through.
As a pace of the two men slowed, Osceola took aim at the commander.
He would show the United States that the Seminole's could not be bought for a few
cheap trinkets.
Breathing in, he pulled the trigger.
And the lifeless body of Wiley Thompson dropped to the ground.
The most expensive Indian war in the history of the United States had just begun.
It's Tom Cole, my friends.
That's a hello in Seminole Creek, well at least I hope it is.
Welcome back to Anthology of Heroes, the podcast sharing stories of defiance and heroism from
across the ages.
You've just dropped into part two of our episode about the incredible story of Osceola
and his tribe, the so-called unconquered people, the Seminole's.
In part one, we traced the origins of the tribe as they broke away from another group
and migrated south into Florida.
We talked about the things that made them Seminole's, ceremonies like the black drink
ritual and the green corn dance.
We walked through the first few conflicts that involved the United States and the surrender
of the state of Florida from the Spanish Empire to the USA.
We talked about the growing number of black slaves and freedmen who lived amongst the
Seminole's and the growing concern of plantation owners about a slave uprising.
We saw the Seminole's lose the first Seminole war and saw the tribes confined to a reservation
in central Florida.
The episode finished with President Jackson penning the Indian Remover Act, leading to
the forced migration of several tribes from their ancestral lands to present-day Oklahoma,
a migration that would see many, many Native Americans die through disease, murder or exposure
as they trekked across all corners of the United States, remembered today as the Trail
of Tears.
Part one was the prologue, the opening salvos of the war, you could call it.
There was no specific character that was followed like our usual episodes, it was a little more
fact-heavy and you could probably get away with skipping it if you were pushed for time.
But to help understand the motivations of our main characters, I'd recommend listening
to it first.
So now is as good as any time to reintroduce our cast.
First and foremost, General, and soon to be President, Andrew Jackson.
Nicknamed Sharpknife by his Indian foes and Old Hickory by his own soldiers, Jackson was
a rising star in the United States.
As polarizing then as he is now, he was a vocal supporter of slavery and had little
care for the desires of Native Americans, who he saw as little more than a speed hump
in peating the progress of the new empire of the United States.
Jackson was a no-nonsense, no-compromise kind of guy.
If you weren't with him, you were against him.
Our second character, stepping up onto the main stage going forward, is Osceola.
Osceola was a young, up-and-coming seminal warrior.
In his youth, he had been a bit of a wanderer, but inspired by his distant uncle's resistance
to the United States Army, he was beginning to make his feelings hurt amongst the tribe.
Passionate and charismatic, you could disagree with Osceola.
You could hate Osceola, but you couldn't ignore Osceola.
Tall, handsome, and dripping with jewels and beads, the young man enjoyed eyes being on
him, being the center of attention, but that didn't mean his passion for the cause was
any less genuine.
So far, Osceola has been a background character for our story, as he's been too young to
participate in politics or war, but that's about to change.
These two, as well as two other Indian chiefs I'll introduce later, will make up our main
cast for these episodes, so keep that in mind if names start to get a bit overwhelming.
The swamps of Florida are about to boil, so let's raise the rifle and get into it.
The Unconquered Seminoles Part 2, Osceola.
It's the year 1829.
In their large reservation in Central Florida, the Seminole tribe had begun to settle down
in their new home.
All the different bands had more or less come to terms with the loss of their territory
to General Jackson.
The soil on their new reservation wasn't as good, but as in the past, a steady stream
of experienced black slaves and freedmen fleeing life on plantations kept their society afloat.
Weapons were harder to come by, and raids continued sporadically, but by all accounts
a shaky peace had been achieved.
The preference of the United States government was still that these people should emigrate
to Oklahoma, but if any government agent nudged the chiefs to consider moving, they
were told bluntly, no.
John Hicks, a Seminole chief, said, quote, The land we occupy, we expect will be considered
our own property, to remain as such forever.
We have already said we do not intend to move again, end quote.
As far as the Seminole nation was concerned, they had lost a war and paid the price.
This was then new land, and no one should or could pull it out from under them.
All that changed on March the 4th, 1829, the day that Andrew Jackson was inaugurated as
the seventh president of the United States of America.
Jackson's battle for the presidency had been a bitter one.
So bitter it had destroyed the Democratic Republican Party, which had been founded by
none other than Thomas Jefferson.
Jackson, with his famously vindictive personality, had a few grudges to settle, but none more
than with the Seminole people.
He hated them for two reasons, one because he thought there were just a bunch of runaways
from another tribe he had defeated earlier, squatting on land that was never theirs in
the first place, and two because the tribe was a safe haven for black runaways.
As a man who made his fortune from slavery, President Jackson was very sympathetic to the
complaints of plantation owners who wanted his government's help in recovering their
labor force.
Standing in front of Congress, the new president addressed the nation.
He spoke boldly of defending the borders, of respecting the limits of his presidency,
and then, if there were any doubts, made his policy on Native Americans crystal clear.
It has long been the policy of government to introduce among them, meaning the Native
Americans, the arts of civilisation in hope of gradually reclaiming them from a wandering
This policy, however, has been coupled with another, wholly incompatible with its success.
Professing a desire to civilise and settle them, we have at the same time lost no opportunity
to purchase their lands and thrust them further into the wilderness, and he then goes on to
say, quote.
As a means of effecting this end, I suggest for your consideration the proprietary of setting
apart an ample district west of the Mississippi and without the limits of any state or territory
now formed, end quote.
Let's think about this, this is a pretty incredible admission when you think about
He's effectively said, the Native Americans are upset because we've stolen their land
and forced them into the wilderness.
But rather than stop stealing their land, we're going to continue doing it, but now
we're going to ship them out some more west.
Probably then they'll be grateful and soon they'll become like us.
So from this day forward, removing Native Americans from their ancestral land was now
official government policy.
Sharpknife had just shone a spotlight on the Seminoles, he was coming for them.
Barely after he'd stepped off the inauguration podium, Jackson drafted his Indian Remover
Act, which Congress passed into law with a wafer-thin majority of 101A to 97NA.
What's interesting about this bill is it doesn't mention anything about using force
on the tribes, it just talks about an exchange of land.
The wording makes it seem like the tribe was just swapping their plot of land for an
identical plot on the other side of the country.
But the land wasn't identical.
Putting aside the native spiritual attachment to the lands, Oklahoma had dry and barren
soil compared to the fertile swampy islands of Florida.
So now, barely eight years after being forced onto their reservation in central Florida,
the Seminoles were asked, told they needed to move again.
This time, halfway across the country to a place they'd never even set foot in.
To try and grease the gears and get the ball rolling, a delegate from the Jackson government
arranged a tour of the new territory, a number of high-profile chiefs were coaxed into attending.
Hey, we'll take you out west, you'll have a look around, talk to some of the Indians
living there already, and if you don't like it, no problem, we'll try something else.
Though there were seven chiefs that went along for the tour, I want to focus on the two that
will be our final main two characters in this story.
Halada Miko, better known by his American name, Billy Bowlegs, was a spirited and cluey
chieftain probably in his late 20s.
Squat and flat-faced, he was probably a distant relation of cowkeeper, the founder of the
Seminole Nation, and that pedigree inspired both him and his followers.
Confident having served in several battles already, Bowlegs was a voice of moderation
among his people.
He has seen the enormous arsenal and manpower the United States could call upon in wartime,
and with this in mind he helped temper the passions of young warriors who pushed for
war at all costs.
This was not to say the man was any kind of coward, he was not moving to Oklahoma, and
if sharp knife would force him to decide between that or war, then he'd choose war.
On the battlefield he was known to be cunning and patient, traits that weren't usually
acknowledged in native leaders who preferred to go in with all guns blazing.
In battle, Bowlegs would quiet his rowdy men and wait for the perfect ambush, and once
he saw it he'd be head first in.
The other man who I've been fascinated about since I learned about him was Abiyaka.
Often spelt many different ways, but I'll be pronouncing it as A-B-I-A-K-A, Abiyaka.
Also known by his American name, Sam Jones.
Abiyaka was an ancient, almost mystical figure among his people.
There's different thoughts as to whether Abiyaka and his band identified as Seminole
or Mikasuki, a different tribe, but regardless his plight was interwoven with the Seminoles.
Early in his 80s at this point, Abiyaka had seen it all, hell he'd been alive for almost
as long as the tribe itself.
Every wrinkle on the Octogenarian's face was a lesson learnt at battle fought or ritual
He'd seen the Spanish rise and fall, he'd seen powerful chiefs come and go, and through
it all he was there, a constant.
His tribe believed that he was an Elector, a kind of shaman that had the power to heal
through communications with the spirits.
And how did this revered figure spend his days?
Perhaps a top of mountain peak waiting for visitors who could consult him once a decade?
Selling fish to US troops.
An elderly Indian shambling through camp and selling off his latest catch, well who was
going to look twice at him, right?
So dragging around his net of fish he drifted in and out of barracks, mess halls and training
grounds, and everything he heard he took back to his followers.
Abhiaka barely spoke, but when his croaking voice filled the long halls of the Indian
villages everyone listened.
To the US delegates showing the chief around, they must have wondered why this mute old
man had come to tour the New Province, they had no idea how much influence he held.
And they definitely didn't know that this shriveled old man would be the most unwavering
blocker to the resettlement out of all the Seminoles they would encounter.
Like Billy Bowlegs, Abhiaka had already decided he would fight the US until the bitter end
before he left Florida.
As the seven chieftains were escorted through the barren, still forming Indian villages
of Oklahoma, few were impressed with what they saw.
Some of the inhabitants had positive things to say about their new home, but the reality
was a few scattered wigwams and a couple of crates of food weren't about to convince
them to leave their ancestral homes.
At the end of the tour, the delegates pressured the chiefs into placing their mark on a treaty
that said they were satisfied and that they agreed to move.
Concerned that they might not return home unless they did so, most did.
Once they returned to Florida though, they renounced their approval, saying that only
signed on the duress.
It was more than just trading good land for bad land, part of the treaty said that they
needed to surrender all black people that lived amongst them.
Slave or freedman, Jackson saw no difference and neither did the plantation owners.
And to make things even worse, fitting with Jackson's lack of recognition for their tribe,
their plot of land was to be governed by the Creek people, their tribal enemies.
The whole process was pretty shady, though virtually no real witnesses and even US troops
remarked that the chiefs quote, had been weedled and bullied into signing end quote.
But to Andrew Jackson, none of that mattered.
It didn't matter that only a couple of chiefs had signed and the ones that did signed on
the duress.
In his mind, the tribe had now agreed to migrate.
Anyone who refused was a vagrant and would face a full might of the United States military.
When it became clear the Seminoles weren't budging, President Jackson sent in a buddy
of his to get the ball rolling.
His name was Wiley Thompson.
Thompson was an old friend of Jackson's and he knew as well as anyone that old Hickory
had little patience for delays or excuses.
He had a job to do and he'd better do it quickly.
Thompson set up shop in Fort King, a large frontier guard post near modern day Gainesville,
north central Florida.
Over the weeks he watched the daily comings and goings of the fort and was particularly
intrigued by the friendship between a Lieutenant Graham and an audaciously dressed Indian man
named Osceola.
Despite the cultural differences and the impossible to ignore friction between the two nations,
the two men met up regularly and went for long strolls together.
With curiosity Wiley Thompson watched the two laughing and chatting as they strolled
through the plains.
Who knows what they talked about but they caught up regularly by all accounts they
were just good friends.
He watched with fascination as Osceola's face lit up after the Lieutenant gifted him
a western style frock for his young daughter and on the next occasion Osceola bought his
daughter on one of their walks dressed in a costume.
To show his appreciation the Indian gave his friend a little white talisman he'd made
telling him that it would protect him in battle.
This friendship between two men whose cultures were on the brink of war might seem strange
to us but this was fairly typical of Osceola.
He always seemed to be able to compartmentalise situations separating his friendship with
a man from the cause he represented.
Even as things began to sour between the two nations these two maintained a strong bond.
Osceola became a familiar face around Fort King.
The tall, attractive Indian dripping with baleen and beads was hard to miss.
He was friendly and chatty, he laughed loudly and spoke freely on all manner of things but
his demeanour changed quickly if anyone mentioned migration.
He firmly told anyone he spoke with the Seminoles would not be leaving Florida.
This is a lot about this guy that he was able to come and go as he pleased through
this fort, striking up friendships and conversations with soldiers who were at that very moment
mobilising for a war against him.
All the while he was saying to them, hey, you're a good guy, I like you a lot, but
you know, we won't leave, yeah?
Wiley Thompson reckoned that if he could get Osceola to agree to migration, others like
him would follow.
But Osceola was no fool.
Whenever Thompson mentioned anything about incursions or expedition through Seminole country,
the Indian flew into a rage, telling Thompson exactly what he could expect if he tried to
take more land from him.
Thompson continued to underestimate him, he was sure that with the right amount of leverage
and time he could break the man and get him to agree to migrate.
He was so sure of this in fact that he gifted Osceola a state of the art rifle.
Under frontier law it was illegal to provide the Seminoles with rifles, but Thompson felt
that with this rifle he had bought the friendship of this influential young man.
It was a mistake he lived to regret, the Seminole tribe could not be bought.
As Wiley Thompson played politics with Osceola, the rest of the frontier was heating up, raids
had become increasingly violent.
Seminole chiefs now openly defied the boundaries of the previous treaty.
I mean, what was the incentive to stay on their reservation if the government was just
going to evict them anyway?
Under pressure from the scared frontier families, Thompson decided to outlaw selling Indians,
weapons and ammunition.
Prior to this, under US law, the only person who couldn't carry a weapon was a slave.
And many Seminoles felt that this is what the government had reduced them to, slaves.
The Florida Reservation boiled with anti-US settlement, well-armed, angry young men from
a warrior society who felt that their rights were being infringed upon.
During a heated meeting, as the other elders spoke of peace, young Osceola took to the
platform and supposedly told his countrymen, quote,
�The white man shall not make me black, I will make the white man red with blood and
then blacken him in the sun and raid, and the buzzard shall feast upon his flesh,�
end quote.
Fist in the air, his nation roared back in approval.
Wiley Thompson was losing whatever control he thought he had.
Cracking down on the Seminole rights had made the situation even more volatile, and President
Jackson's patience was wearing thin.
So far, he had only made things worse.
If he couldn't turn Osceola, he'd need to find others who would be more pliable.
Things were made with Seminole chiefs who had influence, and, with the promise of the
most choice land in Oklahoma, several gave in.
Through bribery, tricks, or deceit, the migrations began.
Little communities emerged from the interior of Florida.
The children wide-eyed and scared as they clutched their mother's skirts.
The men wary and cautious, and the chief trusting.
Trusting in the word of the United States government.
Some would survive the journey to Oklahoma, some would not, but none of them would ever
see their ancestral homes again.
All throughout this, Osceola still swaggered around Fort King like he owned the place.
His attitude now irritated Thompson, and everything came to head in a now famous scene.
Osceola and several chiefs were summoned by Thompson.
The frustrated governor sat them down and lectured them with the same tied-out script
he always did.
He said, �Listen, your chiefs came to Oklahoma and agreed to migrate.
They made their mark on the page.
I don�t care if you don�t like it, you are bound by that.
Your tribe must leave Florida.�
Different chiefs spoke back in protest, and Thompson talked them down one by one.
And when it began to look like they were wavering, Thompson pressured them, one man at a time.
He began to harangue them, telling them to stand up, �Come over here, take the pen,
and put their mark on the parchment.�
Osceola, from the back of the room, stands up and walks purposely through this crowd
of �much more senior� seminal figures, and without breaking eye contact with Thompson,
he says to him something like, �You want my signature?
Here it is.�
He pulls out a knife and stabs the treaty, and leaves the knife just sticking out of
the page.
All eyes in the room stared intently at the knife, and Thompson just stood, speechless.
This is a great story, and it�s popular in books, paintings, and even statues, but
truthfully it probably didn�t occur at least like this.
It�s more likely that instead, Osceola waved a knife around and discouraged other
chieftains from signing.
This seemed much more fitting with his character.
However it happened, Thompson finally felt he could take no more, and had Osceola locked
away for the night until he calmed down.
All throughout the night, Osceola raged, pacing up and down to the cell and yelling about
the injustice of the whole affair.
But by the morning, after yelling himself �horse�, he�d calmed down, and when
Thompson approached the cell, he found Osceola patiently waiting for it.
Perhaps he hadn�t been intending to let him out so quickly, but Osceola made him an
offer that was too tempting to refuse.
He said that if he freed him now, he�d agree to migrate.
Not only that, but he�d gather up as many of his followers as he could, and they too
would migrate.
Thompson�s heart must have skipped a beat as he fumbled with the keys.
But one of his colleagues warned him.
He told him, �To an Indian, being locked up is something incredibly humiliating.
You�ve offended his honour, and if you let this man go, you�ll regret it.�
But Thompson brushed him off.
Osceola thanked him, and assured him that he would return soon with his followers.
As the Seminole man exited Fort King and disappeared into the dark Cyprus swamps, Thompson felt
that finally, this whole ordeal was coming to an end.
Soon he�d be back in Washington, perhaps with a promotion or a commendation from Old
He would not live to see the end of the year.
From the moment Thompson had clapped irons on him, Osceola had made up his mind that
war was inevitable.
Not only that, but Wiley Thompson must die first.
The arrogance of the man infuriated the proud Seminole man.
Who was he to meddle in tribal affairs?
Who was he to imprison him?
Back at the Florida Reservation, Osceola had no difficulty swaying most others into war.
Many other chieftains had already learnt that they gained nothing from compliance with the
United States.
The ancient medicine man Abiyaka would never leave Florida, and the usually moderate Billy
Bolegs had given up trying to tow the line.
Over the coming weeks, the Seminoles managed to get their hands on a stack of powder and
rifles, and Thompson�s letters to Washington became increasingly desperate.
�I feel it as an imperious duty to urge the necessity of a strong reinforcement of
this post, and the location of a strong force at Tampa Bay�.
Something was building.
He didn�t know when they would strike, but he knew he wasn�t ready.
While another commander in Florida was particularly concerned about the number of angry slaves
and freedmen who could supplement the strength of the Seminoles, his own letter to Washington
begged for more man, quote �If a sufficient military force to overall them is not sent
into the nation, they will not be removed, and the whole frontier may be laid waste by
a combination of Indians, Indian Negroes and the Negroes on the plantations, it is useless
to mince this question,� end quote.
Nothing was sent.
Truth be told, the US Army was stretched thin.
Defending multiple borders from multiple hostile nations, the President had all manners of letters
on his desk, just like these ones.
The US Army wasn�t a standing army like today.
At this point the country wasn�t even 100 years old.
The Army was made up of a permanent force of regular troops, supplemented by militia.
Men of limited military experience who would join the regular troops for a set period of
time, save two months.
This meant that long drawn out expeditions were near impossible, the militia would just
leave once their service was up.
For the Seminoles, what they needed above all else was unity.
The United States had chipped away at other tribes when different opinions rose from
within, for them to have any chance they needed to speak and fight the United States with
one voice.
By this point Wiley Thompson had chipped away any of the fence-sitters, everyone who now
remained had to be 100% behind their cause.
But one man wasn�t.
Charlie Amanthala was a middle-aged Seminole chief who had been swayed by Thompson�s
promises of an easy life out west.
His presence on the reservation could help turn others, he had to go.
Having sold much of his livestock to raise money for the migration of his followers,
Charlie was on his way back from the cattle market when he turned onto an off-road and
found Osceola standing in the middle of the road.
We don�t know what went down, but an hour later, chief Charlie Amanthala was dead.
His belongings stolen as caravan set alight.
One source says that Osceola picked up the purse of coins the chief had sold his cattle
Turning the bag upside down, the gold coins clinked as they hit the ground, and Osceola
told the others with him, quote, �See, this is the price of your blood,� end quote.
The message was clear as day.
The Seminole of Florida were at war, and any chief that collaborated with the whites was
a traitor.
Was around this point that Osceola at the height of his fame made a speech to his followers.
I struggled to verify the source of this speech, but even if he never spoke these exact words,
they very much captured the spirit of his rebellion, quote.
My brothers, the white people got some of our chiefs to sign a paper to give our lands
to them, but our chiefs did not do as we told them to do.
They done wrong, we must do right.
The agent, meaning Wally Thompson, tells us we must go away from the lands which we live
on, our homes and the graves of our fathers, and go over the big river among the bad Indians.
When the agent tells me to go from my home, I hate him, because I love my home and will
not go from it.
My brothers, when the great spirit tells me to go with the white man, I go, but he tells
me not to go.
The white man says I shall go, and he will send people to make me go, but I have a rifle
and I have some powder and some lead.
I say we must not leave our homes and lands.
If any of our people want to go west, we won't let them, and I will tell them they are our
enemies and we will treat them so, for the great spirit will protect us," end quote.
Osceola was no chief, but man he could get the crowd riled up.
White settlements that were set up on disputed Seminole lands were in a state of panic.
A witness says, quote, it is truly distressing to witness the panics and sufferings of white
frontier inhabitants.
Men, women and children are seen flying in every direction, and leaving everything behind
them save a few articles of clothing, end quote.
Those that didn't leave slept with one eye open, and a loaded rifle by the bed.
Witnesses refused to leave their homestead, which made forming a militia to patrol the
countryside more difficult.
The only one who didn't seem panicked by the recent attacks was Indian agent Wally
Thompson, the man who had imprisoned Osceola.
As the most superior officer in the isolated Fort King, he should have known better than
to wander far outside the safety of the fort.
But Thompson knew reinforcements were being sent his way.
In the past, the presence of a large western army, with its discipline and rifles, had
helped break the spirit of Indian resistance, so Thompson figured it was just a matter of
time until it worked for the Seminole.
Wanting to stretch his legs outside the cramped quarters of Fort King, he and a junior officer
went for a stroll outside the walls.
Osceola and a small band of warriors laid in wait, ready to confront the man that had
imprisoned him.
As the two walked, they heard what was described as a shrill and peculiar war cry, and before
he had time to turn around, Wally Thompson was shot dead, then, for good measure, shot
another 13 times, then scalped.
The symbolism of Osceola shooting Thompson with a rifle that he had given to him to try
and buy his loyalty was never lost on the American public and helped feed into his legend.
With Thompson dead, the Seminoles launched into all-out war.
The reinforcements Thompson was waiting for were indeed coming, a group of about 110 men
marched as quick as they could through hostile territory.
They knew the Indians were watching them, they could hear them.
All throughout the night, they were hooting and yelling, trying to intimidate them.
But when the spooked troops fired into the tree lines, no one was there.
The sentries kept watch from dusk to dawn, but no attack came.
Tension grew over the days, as the Seminoles were sighted on one side of the camp before
disappearing and being seen on the other.
Many troops no doubt wished the attack would come and they could just get it over and done
But, unbeknownst to them, the men in the woods were waiting on word from Osceola that Thompson
was dead.
As the swampy overgrowth began to give way to flatlands, the troops felt that finally
they could relax.
The worst of the march was now behind them and in a couple of days they would be safe
within the confines of Fort King.
There was a feeling of relief.
If the Indians wished to face them, they could no longer spring from the forests.
The leader of the expedition, Major Francis Dade, was so confident that he had not even
bothered to send out scouts ahead.
In the cold morning air, the expedition trudged in double file through the flat plains.
The troops shivered, their great coats were buttoned up and, crucially, their ammo boxes
were stored away inside their jacket pockets.
As the columns shivered by them, the Seminoles could wait no longer.
The chief leading them was still hesitant.
Crouching in the long grass, he waited desperately for news that Osceola had done what he said
he would.
The warriors with him were getting restless though, and soon his brother and lord told
him sternly that he'd better right now decide if he was with them or not, because in a few
hours these men would be inside Fort King.
This was their opportunity and it was slipping through their fingers at this very moment.
The chief, perhaps remembering what happened to Charlie Amunthala, relented.
We have an eyewitness of this battle from a Seminole warrior and chief named Alligator
that I'm going to work into this, quoting Alligator.
About nine o'clock in the morning, the command approached.
So soon as all the soldiers were opposite, Jumper gave the whoop.
Meconopy, the chief, fired the first rifle.
The signal agreed upon when every Indian arose and fired, end quote.
A lone grey horse was pushed from the tall grass into the pathway of the army.
Meconopy took aim at major day and fired.
As a bullet hit him in the chest, he slumped forward into the saddle and gurgled out, my
god, as he died.
The field exploded with noise, from the tall grasses the young Seminole warriors charged
in, while from the treeline the oldest sharpshooters picked off the US troops one by one.
The troopers tore open their jackets and grabbed desperately for their bullet boxes.
Under a hail of gunfire they dropped their knees, scrambling for their ramrods, looking
in vain for a spot to fire back at.
Shots seemed to be coming from every direction and men were dropping by the dozen with each
Logs and trees were dragged into place to try and give them a bit of protection, but the
Seminole's had picked their position well, and Dade's men were completely surrounded.
The artillery cannon boomed back at the Indians, scaring some of them backwards, but the veteran
warriors coached their men to wait and count the time between each shot and time their
counter-fire in between.
Laughter was heard from the Seminole positions after cannonballs sailed over their heads
and crashed into the trees.
Soon, the US troops were low on ammunition, an alligator tells us quote.
As we approached, we saw six men behind two logs placed one above another, with the cannon
a short distance off.
We soon came near as the bullets went over us.
They had guns, but no powder.
We looked in the boxes afterwards and found that they were empty.
The firing had ceased and all was quiet when we returned to the swamp about noon end quote.
Out of the 110 men sent to relieve Fort King, one made it there.
Two other survivors ran back the way they came, both suffering severe injuries.
One man was so badly injured, he lay amongst the rest of the corpses until a Negro Seminole
ally came across him and decided to let him be, stating quote, he's dead enough.
The Seminole's had killed them almost to a man.
Retreating back to their swamp in victory, the Seminole's held a scalp dance.
To the beat of the drum, warriors danced in a circle, brandishing the bloody scalps of
those they had killed in battle.
Once the Ola arrived to a cheering crowd, all of them now very drunk, the scalpel Wiley
Thompson was hoisted on the tallest pole and placed in the middle of the circle.
The black warriors from the tribe, who spoke the most English, did impressions of Thompson's
Wiggling their fingers at the crowd, they repeated as lectures and threats about leaving
Florida for Oklahoma.
The crowd roared with laughter and applause, and the party carried on until the fires died
out and the warriors passed out from exhaustion.
The Dade Battle, or the Dade Massacre, as some called it, made headlines all throughout
the US.
Newspapers embellished the heroic last stand against savagery.
The New York Herald told of how 100 brave American heroes stood against 3,600 Indians,
when in reality the number was probably around 200.
One of the three survivors horrified and infuriated the public as he told of how Negro Seminole's
had picked and desecrated the corpses of US soldiers.
Slave holders, particularly, were in uproar.
Pointing out, see, it's already started, the Negroes are forming an army.
They began to petition the government to take the war more seriously and appropriate more
funds for it.
While up in the White House, Old Hickory realised he may have underestimated these people.
The Dade Massacre was a turning point for the Florida Wars.
Joseola was thrust into the limelight of the United States press.
It's easy to see why, he was the spurned savage who had his land stolen, right?
With little factual information about his early life, the press spun stories out of
thin air, like one that said his wife was forcibly abducted by Wiley Thompson himself,
or the more famous one about him stabbing the treaty like we mentioned earlier.
The event was also a bit of a wake-up call for the government.
The Florida Governor, its Indian Affairs Officer and its commanding generals had all requested
more money in men and had been virtually ignored.
For Andrew Jackson, he began to clue in that this affair would be harder than the removal
of other tribes.
For one thing, the swamps of Florida were unmapped.
I mean, they had rough maps of the coast, but the interior was really just one big question
mark on a page.
A general would later exasperate, quote,
We have as little knowledge of the interior of Florida as of the interior of China, end
And the Seminole's didn't need maps, they'd lived there for a millennia and knew every
bit of it.
But it wasn't just this that inspired resistance.
Unlike other tribes that were having their territory nibbled away on all sides, the
Seminole's had only the northern border that they needed to defend, and they had an entire
unmapped state they could run back into when things got rough.
The makeup of the army, as we mentioned before, was causing problems too.
The militia company that augmented the regular troops were sometimes as difficult to manage
as the Indians themselves.
Historian George Bittle gives us a bit of light on how these groups usually formed.
He tells us that it was usually just a bunch of blokes ending up at a tavern together and
after a few ails, they all of a sudden decided, hey, why don't we make a militia?
With names like the Mosquito Roars, many of them sounded and acted more like college football
teams than the United States Army.
For those that had lived in frontier towns that had previously enjoyed peace with the
Seminole's, they hated having to host these companies.
To them, they'd swapped out a fairly peaceful neighbour for a rowdy bunch of soldiers that
they also needed to feed and house.
You can see why.
Have a listen to this entry from a man in one of the militia companies, writing about
the reception he expected when he arrived in one of these towns.
What was our disappointment in penetrating the town and finding ourselves unnoticed?
No governor came to meet us, no crowded population thronged to salute us, no beautiful females
from windows, porticoes and balconies with their fairy hands waved white handkerchiefs
to bid us welcome.
The man tasked with keeping these guys' egos in check was General Edmund Gaines.
Gaines was a soldier shaped by the frontier.
He liked to get into the thick of things quickly.
He based decisions on soldiers' instinct and hated wasting time with complicated manoeuvres.
Good discipline and good firepower, that was how you win a war.
But Gaines had a problem, and it wasn't the Seminoles.
He had to share command with another general, Winfield Scott.
And wouldn't you know it, the two men hated each other.
Scott was the polar opposite to Gaines in every way.
Born into sophistication, he obsessed upon how Napoleon had taken Europe, the cavalry
charges, the intricate manoeuvring and ah, the artillery, moi.
To him, the best way to defeat these Indians was through multi-pronged attacks with many
Scott believed himself the best educated man in the new world on military tactics, and
he flat out refused to share the battlefield with Gaines, who he saw as something of a
quaint country yokel.
All across the frontier, the Seminoles raided again and again.
General Gaines saw minor successes, catching a raiding party out here and there, but for
every party he caught, many others slipped past him.
Salmon and sugar plantations were the top targets, and the Seminoles always hit them
at harvest season, when the planters had the most to lose.
The more financial damage they could do, the more inclined the whites would be to leave
them alone.
At least, that was the idea.
Soon almost all of the east coast Florida was in the hands of the Seminoles.
Though maps were lacking, it was well known that the Seminole power base was centred around
the Cave of the Widlokuchi, a dark, twisting swamp west of modern-day Orlando, so a subordinate
general named Duncan Clinch was sent in.
He marched his men in and searched around until he found an old Indian canoe on the
side of a riverbank.
Deciding that he was on the right track, he slowly ferried his company back and forth
across the river, one boatload at a time.
After the first few groups crossed with that incident, they relaxed a little.
But just as they did, a shrill, peculiar war cry cut through the air.
From behind the gnarled trees, Osceola and his men surged forward.
One report says that during the battle, the war leader wore a United States Army uniform,
either to mock his enemies or because he believed it offered him a kind of magical protection.
Clinch, who was crossing the river, yelled to his men to hunker down and hold their position.
They were all almost across.
Follies were exchanged back and forth, but in the heat of battle, Osceola saw his old
friend, Lieutenant Graham.
Risking everything, Osceola directed his men to avoid firing on his old friend, and some
of the US troops noticed this and began to stick close to Graham throughout the fight.
Clinch urged his men forward, and the militia waited into the river.
The pressure was high, but Osceola didn't budge.
Noticing his men pulling dead bodies from the river, he ordered them, quote, take away
the wounded, never mind the dead, end quote.
As the US trooper surged up the banks, Osceola was shot through the bicep.
Cradling his arm, he ordered a fighting retreat.
General Clinch, who was in no position to follow any deeper into the swamps, also retreated.
For the next few months, the general would attempt a few more probing attacks on the
with the Kuchy, and each time he would be stopped.
For the time being, Osceola and the US army were neck and neck, and with a touch of arrogance,
he wrote to the general, quote, you have guns and so of wee.
You have powder and lead and so of wee.
Your men will fight and so will ours, till the last drop of the Seminole's blood has
moistened the dust of his hunting ground, end quote.
Slowly, the top brass of the US army began to realise, one report at a time, that this
was not going to be an easy fight.
One of the many letters that landed at the desk of the War Ministry was from an Indian
agent, who concluded his own opinions on the Seminole wars with, quote, the truth is, the
Indians have been underrated and held in most unwise contempt by those who insist on knowing
Some of them have paid the forfeit of their folly, end quote.
The next year, General Gaines had his window again.
This time, he wouldn't let Osceola catch him out.
He had more troops, more guides and more artillery.
There was only one problem.
The part of Florida he was heading into was under the command of his rival, General Scott.
Ignoring his rival's order, Gaines set off to relieve General Clinch, who was struggling
under a siege from a Seminole bunch near Tampa.
The march got off to an ominous start.
As they veered off the main path, the army soon came across a field of rotting corpses
in US Army uniforms.
They'd stumbled across the infamous Dade massacre site from the year before.
It was a bad omen, and should have been a reminder to the men that the Seminoles were
a serious threat.
Gaines had the bodies buried and continued along the very same path towards the isolated
Fort King.
Once he got there, he found a skeleton crew of staff and almost no food.
As was a problem, Dade had expected a well-stocked fort he could use as a base to launch raids
Instead, he found an under-supplied outpost in the middle of hostile territory.
He was in a tough position.
He could retreat and face a second round of ridicule from his rival, or he could push onwards
to relieve Clinch.
In the end, he chose retreat, but he thought if he took a different route back, he could
disguise the retreat, you know, make it look like a scouting expedition or something.
Although the company with little food and little supplies ventured deeper into the swamps
of Florida.
Soon, the telltale signs of Indians watching them started to appear.
Branches snapping in the distance, charred wood from campfires.
If they didn't get out soon, they'd end up like the Dade expedition.
The Indian Guides, employed by Gaines, were also unsure of exactly where they were.
They'd never planned to be this deep in the swamps.
As they scratched the heads, the Seminoles opened fire.
Gaines had with him a huge force, so the Indians dared not attack head-on, but picked
off stragglers here and there.
With no real idea of where he was, Gaines ordered a makeshift fort built from logs.
Safe for the night, but aware that the Seminoles could be on them soon, Gaines sent a message
to Clinch, the man he was actually there to relieve, telling him that he needed supplies
and he needed them, you know, right now.
Little did he know, though, Osceola was closer than he thought.
Knowing the best places to ford the river, Osceola's band had crept in overnight and
surrounded the half-built fort.
Hitted in the tallest trees and scrubs, the Seminoles waited through the night.
At dawn, the bugle sounded, and the worn-out soldiers rubbed the sleep out of their eyes
and grabbed a pot of whatever watery soup had been prepared for them.
After breakfast, they made their way into the forest and set about logging trees for
the camp.
When the sentries were at their fewest back at the fort, Osceola's high-pitched war cry
once again filled the air.
The tranquility of the camp dissipated instantly as the war chief pressured those inside the
half-built fort.
A surgeon inside gives an account of the ceaseless pressure Osceola kept them under, quote.
They fired their guns by hundreds at our blockhouse and succeeded in taking our only means of escape,
our boat, which they took down river and destroyed after the battle.
He then goes on to say, quote, they displayed their ingenuity by shooting fire arrows upon
the roof which destroyed the roof and left us exposed to the inculmency of the weather,
end quote.
General Gaines, however, was not about to be humiliated by the Seminoles again.
As he directed fire back into the tree line, a stray bullet caught him in the lip, knocking
two of his teeth out.
Spitting out chunks of teeth and blood, the leathery veteran was reported to have laughed
and told his troops, quote, it is mean of the redskins to knock out my teeth when I
have so few, end quote.
Regardless of the demeanour he maintained for his troops, the general and all those
that were inside his half-constructed fort were in big trouble, effectively under siege
from Osceola.
When the ammo began to run low, Osceola waited for the cover of smoke before giving the signal
to retreat.
Gaines and his men had survived the first attack, but Osceola would be back.
We're not sure if General Scott knew of just how dire his rival's position was, but if
he did, he did nothing to address it.
The man was busy.
He was putting the finishing touches on his own plant to defeat the Seminoles.
Plant, well, masterpiece really, one that would ensure he'd be remembered for generations.
After this expedition, the Napoleon of America, that's what they'd call him.
In three tight columns, Scott marched into the swamps of Florida, taking with him his
library, his furniture, and of course, his marching band.
The plan was a master stroke.
Well, it would have been, if his supplies arrived on time, which they didn't, if his
troops were as well trained as the Napoleons, which they weren't, if Florida was as dry
and solid as Europe, which it wasn't, and most importantly, if the Seminoles formed
up for battle like a European army, which they didn't.
For all his love of military history, Scott forgot the number one rule of warfare, know
your enemy.
While Scott was not fighting a settled European people with a capital to protect, he was fighting
determined nomadic warriors who lived off the land and stayed away from set-piece battles.
Each of his three columns were to take a different route towards the location.
Along the way, they were commanded to destroy any Indian villages they came across.
But with no maps, almost as soon as the group split apart, they immediately lost coordination
and direction.
But for General Gaines and his boys, things were much worse.
Despite having virtually no experience in siege warfare, Osceola had ensured the camp
was completely cut off.
This was very unusual, Native Americans didn't besiege US forts, that just wasn't how they
conducted warfare.
Late one night, a few troopers and Allied Indians snuck past Osceola's siege lines.
On the edge of the Seminole camp, they heard the unmistakable shrill voice of the war
Their Indian scouts translated for the troopers, telling them that Osceola was trying to convince
the other chiefs to maintain the siege.
He faced steep opposition from senior chiefs who were concerned of white reinforcements.
But as usual, Osceola was the one that had the last word.
The siege would continue.
Many of the soldiers were now starving.
Corn was gone, horse meat was gone, and a quarter pound of dog meat was selling for
five dollars.
In a few more days, a head on assault by Osceola would be enough to overwhelm them.
General clinch was General Gaines' only hope, but he had been ordered directly by General
Scott not to leave his post.
As time dragged on, clinch made the decision to disregard the order and marched out to
relieve Gaines.
At that very moment, Osceola was parlaying with General Gaines.
Initially, the proud old veteran refused all attempts at diplomacy with the man he'd
earlier called a red skin, but now with his troops days away from death, he had no choice.
General Gaines must have ground his few remaining teeth as he agreed to a peace treaty, denoting
the Withlakuchi Cove and anything below it as Seminole territory.
But like something out of a movie, in the final moments of negotiation, gunfire was
heard in the distance.
General clinch's long-awaited reinforcements had arrived, and unaware of any negotiation,
they'd opened fire as soon as they sighted the Seminoles.
He nervous and jumpy, the Indians bolted.
If they hadn't arrived at this very moment, perhaps we'd be talking about the clinch
massacre right now.
General clinch and his men arrived to find the half-built camp full of quote, living
Over the next few days, they were fed and nursed back to health before travelling back.
Interestingly enough, there were no more attacks while they recovered, despite the fact that
Osceola's men were still definitely in the area.
American historian Kenneth Wiggins Porter believes that Osceola may have assumed that
the deal still stood, even though it was broken off at the last second.
By the end of the campaign season, little progress had been achieved.
The Withlakuchi River had become the de facto border between the two states.
Despite general gains stating that the Seminoles had been quote, met, beaten and forced to
sue for peace, those in Congress were not fooled.
They could see the debt piling up.
For over a year and a half, they had sent their best and brightest into the swamps of
Florida and had nothing to show for it.
As President Jackson sat in the Oval Office, shuffling through the various letters on his
desk, he came across one that caught his eye.
It was from an old friend of his, Richard Call.
In another life, Jackson had been something of a mentor to Call, and now his old protege
was reaching out to offer assistance.
Richard Call was not a general, he was a governor, but as the letter said, he'd heard of General
Scott floundering through the swamps and how Gaines's ego had almost lost an entire company.
He lamented that a war so easily won was being led by such foolish men.
There was nothing particularly innovative about what Call was suggesting, it was more or less
a direct attack on the Withlakuchi Cove, the Seminole Heartland.
But old Hickory was always more impressed with loyalty as opposed to talent, and he knew
his old friend shared his contempt of the Indians and the blacks.
So Jackson gave the plan a green light, while he and his supporters in Congress shifted the
narrative and the blame onto the generals.
The failure of the recent expeditions were attributed to General Gaines, General Clinch
and General Scott's collective incompetence rather than the capability of the Seminoles.
As one congressman quipped, quote, there are no people on Earth so easy to deal with as
our half-civilized Indians, end quote.
More Call's plan was rubber-stamped, and just like that, another $5 million of taxpayers'
money was approved for another campaigning season.
Osceola's strategy of peace or total war was working.
His end goal was to prove that there could be peace between the United States and the
Seminole people, but if the United States government continued to insist on relocation,
they would fight them till he had no breath left in his body.
But living rough had taken its toll, not just on Osceola but on all of the Seminole communities.
It was hard work securing ammunition, planning, ambushing and retreating.
There had women and children that needed to be taken care of, and the probing raids of
the US Army had the warriors sending their family further and further south.
Osceola was running himself into the ground, and may have already been suffering from malaria.
But there was no slowing down.
He was the spirit behind the war in both the eyes of his people and the whites.
It was now a matter of who would break first.
Governor Call's campaign got off to a slow start.
Railroads were in the infancy at this time, and Florida was an isolated backwater.
Supplies, men, munitions, all of them had to be shipped from other states.
When he finally departed, his plan to raid the Widdler Coochie was already in shambles.
The delays with his supplies had lost him his window of opportunity, and the river he
planned to ford was now flooded.
But he did have one advantage – 750 Creek Warriors.
These were the same men that fought with Andrew Jackson in his Red Stick Wars, the same people
that Osceola's mentor Billy Powell had spoke about with such hatred.
The Seminole Indians despised the creeks, but the Black Seminoles more so, because Jackson
had promised them any slaves that they captured during the expedition.
Nevertheless, it was a new challenge that the Seminoles needed to deal with.
These men were more like them – they could live off the land and were used to longer
Low on supplies and late in the camp season, Call pushes men south at speed, crossing the
ever-challenging Widdler Coochie proved easy when Indian scouts located a crest where the
river was shallow.
Outnumbered and without their moat, the Seminoles were vulnerable, so at the last minute they
abandoned the ever-reliable safety of the Widdler Coochie.
But Governor Call knew where they were headed.
The remote Wahoo Swamp was a familiar, retreating location that many raiders fell back to after
torching white settlements.
This was the last line of the Seminole defences – if they lost this, they had nowhere to
As the white settlers followed them in, they struggled against the environment.
Up to their chest in thick, dark sludge, their feet snagged all number of roots and plants
as they waded through the swamp.
In the soupy, dark morass, vicious hand-to-hand fighting took place.
The battle raged for an hour and a half as the Seminoles fired from the tree lines and
the US troop has charged up the hills.
Some of the officers, still mounted on horseback, directed fire, trying to dislodge the Seminoles
from their cover.
Casualties began to mount, but the Indians refused to budge.
General Call himself makes note of a black commander and says, quote,
A Negro, the property of a Florida planter, was one of the most distinguished leaders,
end quote.
Families of the Seminole warriors waded anxiously on the edge of the swamp.
Their meagre belongings gathered with them ready to disappear into the jungle should their
men lose.
Then from the slopes charged the creek auxiliaries.
Howling, they reached the edge of the riverbank as they traded shots with their old enemies.
With his troops on one side of the river and the Seminoles on the other, Governor Call
had no way of knowing how deep it was.
There was only one way to find out.
One volunteer agreed to test the depth of it, but as he reached the middle, the Seminoles
peppered in with bullets.
With that, Governor Call, who was now low on supplies and ammunition, decided to call
it a day and let his exhausted men back to the safety of their nearest fort.
If he had of advance, we could be telling a very different story, because the river
was just three feet deep.
Governor Call wrote about the battle, quote,
A brilliant day, redounding to the honour of our arms, and calculated to bring the war
to a speedy termination, end quote.
But President Jackson wasn't fooled.
He had told his old mentor that he could get the Seminoles to agree to migrate, and to
that end he'd achieved nothing, though he had pushed them out of the width of the kuchi.
Call had failed, just like Gaines, Scott and clinch had.
The Seminoles, though bruised, were still there.
Lord Hickory bitterly disappointed in his protégé stripped Call of his position and never forgave
him for his failure, and the two men went on to become political rivals.
The United States Army was running out of generals.
Scott, Gaines, Call and clinch had been experienced high-ranking generals, and Osiola and other
chieftains had chewed them up and spat them back out.
The position had become something of a poison chalice, as if the Florida Swamps was where
the reputations of seasoned generals went to die.
General clinch was requested to return, but he responded with a polite, yeah, thanks but
no thanks.
There was really only one man left.
His name was Thomas Jessup.
Now, Jessup is going to be around for a while, so let's introduce him properly.
Thomas Sidney Jessup was a Virginian quartermaster.
With a clinched bottom jaw, long nose and heavy brow, he looked something like the actor
Patrick Stewart.
He was in his late 40s and had served with distinction in numerous conflicts.
A quartermaster's job was to keep the army fed, watered and supplied.
Even though logistics are kind of boring, they're extremely important for an army to
function, and in case you hadn't noticed, they were usually the root cause of almost
every failed expedition up to this point.
Today in the US Army, Jessup is sometimes referred to as the father of the modern quartermaster
He was extremely good at his job and took great care and attention in sourcing, arming
and feeding his troops.
Jessup had served under the pompous General Scott in the past and had been partially responsible
for a few of his successes, but when things went badly for Scott, he tried to blame it
on his subordinate.
Jessup's curt defence of his reputation as well as his rapport with junior officers
had earned him President Jackson's respect, and now with little other options, quartermaster
Jessup got his summons and clearly not afraid of a challenge, excepted the assignment.
One of the first things that Jessup did was create a kind of primitive coast guard to
patrol the Florida coast and keep out Spanish traders and smugglers who were supplying the
Women and children who were captured in raids were promptly sent west, demoralising their
men who were fighting in the warbands.
His idea was to wear the Seminoles down and make life so unbearable that they would agree
to migrate.
But to do that, he needed men, lots of men.
Luckily for Jessup, he had an advantage his predecessors didn't.
President Jackson now appreciated that this was not an easy task and started dropping
some serious cash on the expeditions.
The General also cleverly played on the fears of Southerners, telling them to remember,
quote, this is a Negro war, not an Indian war, gaining even more troops and cash from
The war was now pulling men and resources from all corners of the US.
From Maine to Missouri, the defiance of this tiny little tribe made news and the portraits
of the steely-eyed Osceola graced the front pages of newspapers across the country.
Remember, there were tons of other Seminole leaders, actual chiefs, unlike Osceola.
But after he'd killed Wiley Thompson with the very same gun that he'd given him as
a token of friendship, well, you know how tabloid papers are, right?
It's a good story.
Osceola had become something of a fascination for the press, and the public sentiment began
to shift to one of sympathy for him.
Jessup began the reconstruction, or regarison, of a number of forts bordered the Seminole
He achieved no quick victories, instead he delivered slow, incremental results.
His raids were simple and weren't dependent on precise timing and complex maneuvering.
He sent out constant patrols from the forts which made it impossible for the Seminole's
to plant their corn.
With their food supplies dwindling, some Seminole chiefs and prestigious ones at that began
to surrender.
The linchpin of the surrender deal seemed to hinge upon black members of the tribe being
allowed to travel west.
The fate of black slaves and freedmen had always been touchy, but seeing that the Seminole
would not give an inch on this condition, Jessup made concessions, allowing them to migrate
with the rest of the tribe.
But when slaveholders from Alabama and Georgia heard that bands of Negroes were assembling
for transportation, they began to arrive en masse.
Despite Jessup's deal with the Seminole's, they pressured him to hand over any slaves
that they recognized as runaways from their plantations.
The deal was supposed to only cover people that were explicitly slaves, that is those
who would run away to Seminole country to escape enslavement.
But if you're black, how do you prove that you aren't a slave?
It quickly turned into a plantation known as Word against that of a black person, and you
can imagine whose word carried more weight.
To the Seminole's, Jessup had now broken his word, and Osciola, who had previously
been at least entertaining discussion about surrender, broke away.
He and the ancient medicine man, Abiaka, half abducted, half rescued the crowd of two hundred
or so and retreated into the swamps.
It was a heroic move, but the Seminole's knew they couldn't go on like this.
Their food supplies were dwindling and their families were starving.
They were always low on ammunition and many of them were run down and sick.
Lice was rampant amongst them, as was malaria and all kinds of other tropical diseases.
A council was called, and in a rare event representatives from the Seminole bands all
across Florida assembled.
From dusk until dawn, an influential chief named Wildcat gave a long, impassioned speech
about how they had given everything they had and how they just couldn't endure another
season, especially with Jessup's patrols closing in on them.
Simon Osciola, who now looked worn out, thin and sick, said nothing in protest as the speech
But rising up from his seat came the ancient Abiaka, the eighty-something-year-old medicine
man rebuffed the chief, who was his own son-in-law.
This extract is based on Titus, a black informant who lived among the Seminole's.
He, Abiaka, would not give up as long as he had a single ball and a single charge of
powder, that when he could no longer shoot game, he would live on fish.
When his lines are worn out, he will make others out of horsehair.
When his hooks are broken, he will cut up his old tin pans and make others.
He concluded by saying that he had seven hundred warriors and that he would fight as long as
they would stand by him, and that if every other Indian should leave Florida, he would
retreat among the islands of the Everglades, remote from the face of white or red men.
Wildcat, a son-in-law of old Abiaka, advised contrary measure, but Abiaka became exceedingly
enraged, demanded back his daughter and actually drove him from the camp, end quote.
How's that for powerful, this ancient old man shouting down everyone else, telling them
all that he'd cut up old tin pans to make hooks and live alone in complete squalor rather
than leave.
Osceola was torn, he had given his life to this war and he was a symbol of it, but he
knew he just couldn't go on.
He needed medicine and he needed rest.
So while he had a good track record of victories, he approached General Jezeb under the flag
of Truce.
The idea was to negotiate from a position of strength and hopefully retain a reservation
for Florida for him and his followers.
Historian Tom Hatch describes what follows as quote, one of the most disgraceful acts
in American military history, end quote.
Under the white flag of Truce, Osceola, 71 warriors, six women, and four black allies
came to meet General Jezeb.
As soon as all the Seminoles were accounted for, 250 armed US soldiers surrounded the
sick Indians.
The Seminoles were told to surrender at once, when a few protested a scuffle broke out,
but soon it became obvious that Jezeb had double crossed them.
This is the length that the US military had to resort to.
When the Florida paper, The Niles Register, got wind of this set up, they wrote quote,
we disclaim all participation in the, and they put this word in quotations, glory of
this achievement of American generalship, which if practiced towards a civilized foe
would be characterized as a violation of all that is noble and generous in war, end quote.
But fellow military men who had been outfoxed by Osceola again and again, wrote in defense
of Jezeb quote, there was too much sympathy extended upon these treacherous murderous savages.
General Jezeb was dealing with the very individuals who had repeatedly and treacherously trifled
with the flag of truce, and he goes on to say, public opinion ought not only to justify
but commend him for this transaction, end quote.
While some would try and justify the capture, the kidnapping of Osceola would haunt Jezeb
for the rest of his career, becoming a stain on an otherwise very impressive track record.
For Osceola though, it was finally over, and the exhausted warrior breathed the sigh of relief.
For the next few weeks, the imprisoned Indians languished in Fort Marion.
The cell they found themselves in was the most secure space in all of Florida.
Escape was impossible.
Or was it?
Over the weeks, several chieftains refused food and consumed just enough nutrients to
stay alive, their ribs protruded from their bodies and their clothes hung on their frames
like old rags.
Their jailers must have assumed that this was some sort of strange Indian ritual or maybe
they were starving themselves out of protest, but they weren't.
On the roof of their cell was a narrow opening for light and air, a tiny square gate with
two iron bars bolted across.
Every night once their jailers had gone to bed, a captive would jam his knife into the
mortar between the bricks and vault up to the ceiling.
Hanging from the roof, they would use the knife to chip away at the mortar for hours
on end, until one night, the bar gave way.
Using a rope braided from old cloth, a couple of the emaciated Indian chiefs shimmied up
and forced their bodies through the tiny opening.
The sharp coral that lined the bars cut deep into their skin, but they thought only of
freedom as they pushed through the pain.
Bleeding, thin, and almost naked, they fled back into the swamps.
When the morning light shone through the broken bars, the jailers found that only a few older
chieftains were sitting in the cell, along with Osceola.
What I wouldn't give to know what these men talked about during that night, and what
caused a spirit like Osceola not to jump at the opportunity to escape.
It was sick, we know that.
By all indications he was just done, but the Seminoles were not, and the starved chieftains
returned back to the swamps in triumph.
To Jezeb, the Seminoles had again broken their word and spat on his generous peace terms.
To the Seminoles, Jezeb had deceived them, he'd violated the internationally recognised
flag of truce.
Furious and humiliated, Jezeb ordered the mobilisation of the largest force yet put
together in Florida.
Meanwhile, Osceola wavered between bouts of sickness and health.
Firmly established in custody and making no efforts to escape, scores of reporters and
painters drifted in from across the country, eager to meet the man who had frustrated the
efforts of President Jackson for the last two years.
Many of our best eyewitnesses' accounts about his mannerisms, his habits and his behaviour
come from these reporters.
And the picture that's painted as a man resigned to his fate.
Though he still wished to remain in Florida, he was slowly coming around to the notion
that Andrew Jackson was just never going to let that happen.
He became particularly close with one painter called George Katelyn, and the two frequently
chatted to the early hours of the morning as he painted the warrior's likeness.
Unlike most others in captivity, Osceola completely refused both whiskey and cigarettes.
He joked around regularly with his captors.
One time one of his jailers served him some eggs and Osceola took the plate before grinning
and handing it back to him, telling the man that it was better that he didn't get his
strength up because otherwise he'd come after him.
The jailer shoved him playfully and Osceola laughed as he pushed him back.
Though Osceola's condition was intermittent, it was worsening.
A recent examination of a lock of his hair found a bunch of egg casings for head lice.
Excess scratching of lice can result in a skin infection that leaves the victim debilitated
for a week with fever and chills as it might attach before recovering and the cycle repeating
as the lice breed.
It's likely we'll never know what exactly Osceola was suffering from, but it was getting
By the 26th of January, 1838, he was on his deathbed.
His list of infections, old battle injuries and a nasty bout of tonsillitis had pushed
him over the edge.
He looked back on his life and, looking through his possessions, one time a visitor got him
talking and with a tearful smile he showed the man the items that he still had with
Thumbing through them, he told him, quote,
It was always my pride to fight with the big generals.
I wore this plume when I whipped general gains.
He spurs as I drove back general clinch and these moccasins when I flogged general call,
end quote.
In the last few hours of his life, the man's defiance burned bright one last time as he
proclaimed firmly that his people had done nothing wrong except murdering Wiley Thompson
and he begged his physician to promise that his bones would be buried in Florida no matter
what President Jackson decreed.
He lamented bitterly how their country had been stolen by Jackson and other white men
and in his last moment declared that if he lived longer, he would do it all again and
right all the wrongs that had been done to the Seminole people.
At 6.20pm on Tuesday evening, the 30th of January, 1838, Osceola died, surrounded by
several of his wives and many of his children.
It was about 33 years old.
The Florida paper, the Niles Register, gave the best summary of his life I think I've
ever come across, quote.
We shall not write his epita or his funeral orations, yet there is something in his character
not unworthy of the respect of the world.
From a vagabond child, he became the master spirit of a long and desperate war.
He made himself, no man owed less to accident, bold and decisive in action, deadly but consistent
in hatred, dark in revenge, cool, subtle and sagacious in counsel.
He made the other chiefs his instruments and what they delivered in public was the secret
suggestion of the invisible master.
Such was Osceola, who will long be remembered as a man that with the feeblest means produced
the most terrible effects, end quote.
And that is where we pull the handbrake for this week.
As Osceola's last breath left his body, over half the standing army of the United States
had been summoned to Florida.
Men flocked from all corners of the country with the goal of eradicating or removing
a people who could not field an army of more than 500 at any given time.
But Florida was big, and as Abiyaka said, as long as he had a ball of lead and a single
charge of powder, there would be no surrender.
Nothing had changed, and if the United States would give no quarter, neither would they.
Osceola may have been gone, but the war would go on.
This has been Anthology of Heroes.
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Seth, Lisa and Tom.
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