I want you to imagine a founding father whose
resume reads less like a traditional American
history book and more like an absolutely unhinged
Hollywood script. Yeah, it really does read like
a movie. Right. Like we are talking about a man
whose life includes nighttime bayonet charges,
massive political scandals, being actively betrayed
by his own second in command. Who happened to
be a Spanish spy, by the way. Exactly. A Spanish
spy. Yeah. And ultimately. having his own corpse
boiled down in a kettle by his son. So welcome
to today's deep dive. It is quite the list of
credentials. And looking through the historical
documents, it is all completely true. Every bit
of it. Yeah. We are looking at a figure who fundamentally
shaped the geographical and military trajectory
of the early United States. Yet his personal
life was essentially a masterclass in chaos.
Our single source for this deep dive is a comprehensive
Wikipedia article on Anthony Wayne, who lived
from 1745 to 1796. And the mission for us today
is to unpack the complicated, highly contradictory
and honestly deeply fascinating life of the man
known to history as Mad Anthony. And the stakes
here for American military history are remarkably
high. I mean, Wayne is celebrated as a brilliant
tactical commander. He's the namesake of countless
American towns, counties, a national forest.
And even a very famous fictional billionaire.
Right, exactly. But his legacy is also heavily
scrutinized today. The overarching theme you
will notice as we go through this material is
that extreme tension, the friction between his
unquestionable military brilliance and his utterly
disastrous civilian life. It is a wild ride.
And if you're looking to truly understand the
messy reality of the American Revolution and
the early days of the Republic, this is the story
you need to hear. OK, let's unpack this, starting
with the making of the man himself. Right. Going
back to the beginning. Yeah. Wayne was born in
1745 in Chester County, Pennsylvania, to a Protestant
Anglo -Irish family. But from the very beginning,
he was not exactly the compliant son, was he?
Far from it. His father, Isaac Wayne, owned a
large estate and naturally wanted his son to
follow in his footsteps and become a farmer.
Which didn't go over well. Not at all. Wayne
fiercely clashed with him over this. He had grown
up listening to his father's stories as a captain
in the French and Indian War. And the historical
accounts show Wayne would actively mimic those
battles as a kid. Organizing the local boys into
mock military units and everything. Exactly.
He clearly had absolutely no interest in agriculture.
Instead, he went to his uncle's academy and the
College of Philadelphia to become a surveyor.
And he was remarkably good at it. So good that
in 1765, when Wayne is just 20 years old, none
other than Benjamin Franklin sends him and some
associates up to Nova Scotia. That's a huge deal
for a 20 -year -old. It is. Wayne is tasked with
surveying a staggering... 100 ,000 acres of land
up there to help start a settlement. That is
a massive logistical undertaking for a young
guy. It really is. And it shows his early capacity
for enduring grueling conditions and managing
complex logistics. But as we know, the American
Revolution was brewing and Wayne eventually found
his true calling in the military, completely
discarding the conventional rule book along the
way. So how exactly did he operate on the battlefield?
Because my understanding is that 18th century
warfare was incredible. It was. What's fascinating
here is Wayne's specific military philosophy.
In the 18th century, conventional warfare was
all about rigid lines of infantry marching across
open fields and exchanging volleys of fire. Just
standing there and shooting at each other. Pretty
much. But Wayne rejected that entirely. He famously
stated, and this is a direct quote, That's a
great line. It is. He focused intensely on maneuver
warfare, speed, utilizing the terrain, and maintaining
strict, unflinching discipline among his men.
But that... aggressive, unconventional approach
didn't always work out for him. We have to look
at the trauma of the Battle of Paoli in 1777.
Wayne's camp gets attacked at night by British
General Charles Gray. Yes. And from what the
text describes, the mechanics of this attack
were absolutely terrifying. They really were.
The British commander, Gray, actually earned
the nickname General Flint because of the specific
orders he gave his men that night. He ordered
his troops to remove the flints from their muskets.
Which means they literally couldn't fire their
weapons even if they wanted to. Exactly. In the
heat of a night battle, a soldier might panic
and pull the trigger. A musket flash in the dark
would instantly give away their position and
rumin the element of surprise. So it's forced
discipline. Precisely. So by removing the flints,
Gray ensured his men would attack Wayne's camp
in the dead of night using only their bayonets.
It was a complete disaster for Wayne. He suffered
significant losses, his men were routed, and
his reputation was severely tarnished. It was
a huge embarrassment. Huge. The public backlash
was so intense that Wayne actually demanded a
formal military inquiry just to try and clear
his own name. But then... and this is arguably
the most cinematic moment of his military career,
comes the redemption. Two years later, in 1779,
at the Battle of Stony Point, Wayne is tasked
with taking a British cliffside fortification
on the Hudson River. A nearly impossible target.
Right. The geography alone makes it a nightmare
to assault. So how does he pull it off? He perfectly
replicates the exact same tactic that was used
against him at Paoli. It's brilliant. It is a
brilliant and highly risky psychological play.
Wayne personally leads a nighttime bayonet attack
against the British fort. He commands his light
infantry to storm the fortifications with unloaded
weapons, relying entirely on speed and the bayonet.
The coordination required for that must have
been immense. It was. The assault lasts only
30 minutes. Wow. Yeah. The result is stunning.
Wayne's forces capture about 550 British prisoners
while suffering fewer than 100 casualties themselves.
And Wayne himself is literally leading from the
front. He took a British musket ball to the head
during the charge. A deep gash to the scalp.
But he refuses to stop. Talk about adrenaline.
Yeah. He has his men carry him forward so he
can keep commanding. The Continental Congress
ended up awarding him a gold medal for the victory.
It was a massive morale boost for an American
army that had been suffering a string of brutal
defeats. And it certainly contributed to his
legendary nickname, Matt Anthony. Though the
historical record notes there is some debate
about where that moniker actually originated.
Right. Some historians say it came from his incredibly
aggressive, fiery battlefield tactics, like at
the Battle of Greenspring. There, His men were
suddenly trapped by a massive, overwhelming British
force, and Wayne ordered a borderline suicidal
bayonet charge straight into the British lines
just to shock them long enough for his men to
escape. Which is definitely a mad tactic. Totally.
But others claim the nickname came from his notoriously
quick temper and his off -color language. Specifically,
there was a well -documented incident where he
severely punished a highly skilled local informant
simply because the man showed up drunk. Either
way, both explanations add to the mythos of a
man of intense extremes. He demanded absolute
perfection and aggression, which brings us to
the period after the Revolutionary War. Here's
where it gets really interesting. Because the
man who could command an entire battlefield with
brilliant precision was an absolute, unmitigated
disaster in his private life. Total train wreck.
The war ends. Wayne tries to transition to being
a regular civilian in Pennsylvania, gets involved
in politics, tries his hand at business. And
it just completely falls apart. It really does.
The friction between his military self and his
civilian self is glaring. To set the stage, his
marriage completely fractures. His wife, Mary,
ultimately abandons him. And there was a lot
of drama there. Oh, yeah. This estrangement happens
amid rampant rumors spreading that Wayne was
having an affair with Catherine Green, the wife
of his fellow general Nathaniel Green. Wayne
already had a history of romantic relationships
with other women, so the marriage was incredibly
strained long before the breaking point. On top
of his family life imploding, he ends up completely
bankrupt. And his political career is a total
embarrassment. He gets elected to the U .S. House
of Representatives representing Georgia in 1790.
But his opponent... A man named James Jackson
contests the election, accusing Wayne's campaign
manager, Judge Thomas Givens, of blatant electoral
fraud. And the House committee investigated and
actually agreed. They found that significant
fraud had indeed been committed, and Wayne was
formally kicked out of Congress. Kicked out entirely.
Yeah. Now, the records implicate local magistrates
rather than Wayne personally organizing the fraud.
But regardless, he lost the seat and was later
disqualified from even running again due to residency
issues. Which brings up the question of why a
guy from Pennsylvania was running for Congress
in Georgia in the first place. And this leads
us to his plantations. When looking at Wayne's
post -war life, the historical record presents
a deeply complicated and messy picture regarding
his involvement with slavery. It does. And we
should be clear that we are maintaining strict
impartiality here, simply reporting the historical
facts from the source material without taking
sides on modern political debates. Absolutely.
Just looking at what the documents say. Right.
So during his brief private career, Wayne was
an active slave owner. He initially inherited
a 40 year old man named Toby in Pennsylvania
who was registered under the law as a slave for
life. Later, the state of Georgia actually purchased
a massive slave plantation for 4000 guineas and
rewarded it to Wayne for his military service
in negotiating peace treaties in the region.
Just to put that in perspective for you, 4 ,000
guineas at that time was an astronomical sum
of wealth. It was a gift meant to instantly establish
him as a wealthy aristocratic planter. Exactly.
And to run this massive new enterprise, Wayne
took on massive loans from Dutch bankers and
purchased 47 enslaved people. But the documents
highlight profound contradictions between his
internal views and his outward actions. It's
very jarring. It is. Initially, like many American
planters at the time, Wayne supported the institution
of slavery. However, However, much like George
Washington, his personal letters show he gradually
grew to oppose the practice. The contrast is
stark. You have a man taking out loans to buy
enslaved people. But at the same time, his letters
express deep concern regarding the harsh, brutal
punishments inflicted upon them. He's actually
documented providing refuge for slaves fleeing
punishment from other plantations in Georgia.
And even earlier during the Revolutionary War,
while traveling between military camps, Wayne
wrote letters expressing how horrified he was
by the treatment of slaves he witnessed. He even
formally urged the governor of Georgia to recruit
black soldiers to fight for the patriots, advocating
for their arming and inclusion in the military
effort. So how did this guy? With no agricultural
interest and massive internal conflicts about
the labor he was using, actually managed these
plantations. Spectacularly poorly. His attempt
at running these Georgia plantations, named Richmond
and Kew, was a total failure. The historical
record shows he severely neglected his business.
He just wasn't cut out for it. No, he was constantly
traveling, attending political events, partying,
or hanging out with former soldiers. He and his
overseer were criticized by contemporaries for
having a relaxed hand with the plantation management.
Meaning they just weren't running it effectively?
Exactly. Because of this neglect, his complete
lack of business acumen, and his penchant for
wild spending, he acquired massive debt. He actually
had to beg acquaintances for financial help before
finally - selling the properties at a loss. So
let's look at the scoreboard by the early 1790s.
Anthony Wayne is totally bankrupt. His wife has
left him. His plantations have failed. He's been
booted from Congress in a fraud scandal. And
physically, he is a disgraced, sick man suffering
from recurring, debilitating bouts of malaria
he caught down in Georgia. A complete ruin. His
civilian life is practically non -existent, but
then the 18th century equivalent of the phone
rings. If we connect this to the bigger picture,
it was President George Washington calling. And
Washington was facing a crisis of existential
proportions for the young nation. This is the
Northwest Indian War. The United States was desperately
trying to secure the Northwest Territory from
a powerful alliance of Native American tribes
known as the Northwestern Confederacy. And the
U .S. military had just suffered a catastrophic
loss. Catastrophic almost feels like an understatement.
In 1791, an American force led by General Arthur
St. Clair was ambushed and practically wiped
off the map. The historical accounts put the
casualty rate at an astonishing 97%. 97%. It
remains the most decisive defeat in the entire
history of the American military and the largest
defeat the U .S. ever suffered at the hands of
Native Americans. The American public was outraged,
and the young nation's ability to defend itself
was entirely in question. So how do you even
begin to rebuild an army after a 97 % casualty
rate? Washington was actually under congressional
investigation because of this defeat. He needed
someone who could rebuild the military from literal
scratch and deliver a decisive, undeniable victory.
Washington reviewed his options. And despite
Wayne's recent shameful personal and political
status, Washington knew Wayne was, in his words,
active and enterprising. He understood Wayne's
uncompromising demand for discipline. So Washington
calls a swollen -legged, malaria -ridden Anthony
Wayne out of his ruined retirement to become
the senior officer of the army. And Washington
didn't just give him a fancy title. He handed
him the keys to the treasury. Washington allotted
an extraordinary budget of $1 million for Wayne
to completely rebuild and triple the size of
the army. Which was an insane amount of money.
To understand the scale of that, $1 million represented
about 83 % of the entire federal budget at the
time. Could you imagine one general getting 83
% of the national budget today just to build
an army from scratch? It shows you exactly how
desperate the political and military situation
was. Wayne immediately accepted the command and
set about creating a brand new military force,
the Legion of the United States. And this raises
an important question. How do you prevent another
complete disaster like St. Clair's defeat? Wayne's
answer was rigorous, formalized and unrelenting
instruction. He basically invents U .S. Army
basic training, doesn't he? He does. Wayne quickly
realizes that trying to recruit and train men
in Pittsburgh is a logistical nightmare because
the troops keep getting distracted by the taverns
and the local vices. Wayne literally refers to
the area as a frontier Gomorrah. That's a great
description. It paints a picture. So he marches
them out into the wilderness and builds Legionville.
It is the very first facility established expressly
for the purpose of basic training for regular
army recruits. He structures this new army into
sub -legions, which are basically the historical
forerunners of today's modern brigade combat
teams. And he relies on the training manuals
written by the Prussian officer von Steuben,
the same von Steuben who famously whipped George
Washington's starving troops into a professional
fighting force at Valley Forge years earlier.
And the discipline Wayne enforces at Legionville
is incredibly severe. He was an absolute hardliner.
The historical documents note that he executed
several troops for severe offenses, including
putting two soldiers to death simply for falling
asleep at their guard posts. But there's that
duality of command we talked about earlier. He
executes guys for sleeping, but at the same time,
he builds this immense, almost cult -like loyalty
among the ranks. He was in the trenches with
them. Literally. He shared all the brutal winter
hardships with his men out in the freezing wilderness.
He obsessively managed the supply lines to make
sure they had proper gear. And he instituted
a policy of giving the troops a half gill of
whiskey, which is roughly a strong two -ounce
shot. every single day and an extra shot to the
best marksman. It was a brutal but highly effective
method of team building. By 1794, the Legion
of the United States was a highly disciplined,
well -oiled machine, and they began marching
north into Ohio, building a series of strategic
forts along the way. This brings us to the climax
of the campaign, the Battle of Fallen Timbers
on August 20, 1794. Wayne mounts a massive assault
on the Indian Confederacy near modern -day Maumee,
Ohio, and it is a decisive overwhelming victory
for the U .S. forces. It essentially breaks the
alliance and ends the war, leading to the Treaty
of Greenville the following year. Yes, a treaty
where Wayne promised the remaining land to the
West would remain Native American forever, a
promise that, as the history books show, was
quickly broken as settlers continued pushing
westward after his death. Now, regarding his
tactical operations following the Battle of Fallen
Timbers, the historical record details that,
under the direct policies of President Washington,
Wayne engaged in severe scorched earth tactics.
Right. And again, keeping strict impartiality
here, we're just reporting the historical reality.
The goal was to ensure the Confederacy couldn't
regroup or survive the winter. Exactly. As winter
approached, the U .S. military systematically
destroyed the fields, food stocks, and homes
of the Native Americans across the region. Wayne
reported on this progress back to the capital,
noting grimly that their future prospects must
naturally be gloomy and unpleasant. It is a harsh
and brutal reality of the frontier campaigns.
But intertwined with that brutality is this incredible,
almost cinematic standoff right after the battle.
The fleeing Native American forces tried to take
refuge inside the nearby British Fort Miami.
But the British commander, Major William Campbell,
locked the doors. He refused to let them in because
he didn't want to accidentally start a war with
the United States. Wayne then deliberately sets
up his camp right in sight of the British fort.
He proceeds to destroy crops and burn villages
right in front of the British garrison, clearly
trying to provoke a response. Just daring them
to do something. Yes. When Commander Campbell
sends a message asking what exactly Wayne thinks
he's doing operating so close to a British fort,
Wayne replies that his answer had already been
given by the sound of American muskets. And then
the very next day, Wayne takes it a step further.
He rides his horse entirely alone right up to
the exterior walls of the British fort. He slowly
conducts an inspection of their defenses, basically
daring the British soldiers to shoot him. It's
wildly bold. The British garrison actually debated
firing upon him, but they didn't have explicit
orders, and Britain was already tied up fighting
France, so they held their fire. Two commanders
staring each other down, neither willing to be
the one to start a global conflict. It is the
absolute epitome of his character. But while
Wayne was staring down the British Empire, he
was completely blind to the massive threat sitting
right next to him. And this is perhaps the most
shocking political drama in the entire narrative.
Throughout this grueling campaign, Wayne's own
second -in -command, General James Wilkinson,
was actively trying to destroy him. Wait, how
does a U .S. general act as an enemy agent without
getting caught? Because Wilkinson was secretly
a Spanish spy. It is an incredible betrayal.
Wilkinson was actually serving as a paid Spanish
officer known as Agent 13, all while wearing
a U .S. military uniform. That's insane. Wilkinson
would smile to Wayne's face, but behind his back,
he was orchestrating a massive shadow campaign.
He wrote anonymous smear pieces to local newspapers,
and he constantly sent highly critical negative
letters to politicians back in D .C. trying to
get Wayne relieved of command. But it wasn't
just office politics and bad press. He actively
sabotaged the Army's logistics. In December 1794,
Wilkinson secretly instructed the military suppliers
to delay the troops' rations. He wanted them
to send just barely enough food to keep the Army
alive, intentionally trying to starve his own
men just to prevent Wayne from making any further
military progress. Yes, Wilkinson's goal was
to create enough disaster and mutiny that he
could step in and take Wayne's job. Finally,
Secretary of War Henry Knox gets suspicious and
tips Wayne off about Wilkinson's activities.
Wayne quietly starts his own investigation, and
his men actually intercept Spanish couriers carrying
hidden gold payments meant for Wilkinson. So
Wayne finally has the hard evidence. He intercepts
the gold, he uncovers the treason, and he is
getting ready to court -martial his traitorous
second -in -command. But he never gets a chance
to swing the trap. In a sudden, almost anticlimactic
turn of events, on a return trip from Detroit
in December 1796, Wayne develops a severe complication
from gout and a stomach ulcer, and he dies at
the age of 51. Just like that. Just like that.
There has been historical speculation over the
centuries, though it has never been definitively
proven, that Wilkinson actually had Wayne poisoned.
After all, Wilkinson benefited immensely from
Wayne's sudden death. With Wayne gone, the impending
court -martial completely vanished, and Wilkinson
actually replaced Wayne as the senior officer
of the army, where he continued to pass U .S.
intelligence to Spain in exchange for gold for
years. So the Hollywood villain actually wins
in the end. But the bizarre story of Anthony
Wayne doesn't actually end with his death. We
promised you a boiled corpse at the very beginning
of this deep dive and we deliver. Wayne was originally
buried at Fort Presque Isle in Erie, Pennsylvania.
But years later, in 1809, his son Isaac decides
he wants to move his father's remains across
the state to the family plot in Radnor, Pennsylvania.
Yes, the logistics of moving a body in the early
19th century were quite grim, and Isaac opted
for a highly unusual method. He disinterred his
father's body, but instead of moving the entire
heavy casket, he hires a doctor to boil the corpse
in a large iron kettle to separate the remaining
flesh from the bones. then packs his father's
clean bones into two saddlebags for the long
horseback journey home. And he leaves the boiled
flesh, the water, and the burial tools right
there in the original grave. So today, man Anthony
Wayne famously has two distinct grave sites on
opposite sides of Pennsylvania. So what does
this all mean? How do you synthesize a legacy
like this? Synthesizing Wayne's legacy requires
acknowledging how these two completely different
versions of the man existed simultaneously. Professionally,
he is the undisputed founder of modern U .S.
Army basic training. He was a brilliant, relentlessly
aggressive tactician whose victories secured
the Northwest Territory for the young United
States. He took 83 % of the federal budget and
completely rebuilt an army from the ashes of
the nation's worst military defeat. Yet personally,
he was a deeply flawed civilian, a man who failed
at business, failed at managing his plantations,
failed at politics, and alienated his family.
And that is exactly why you should care about
this story. Because history is messy, and it
is rarely made by perfect, one -dimensional people.
Wayne's story is a masterclass in how someone
can be an absolute disaster in their personal
life, totally incapable of running a farm or
maintaining a marriage, yet entirely reshape
the military and geographical trajectory of an
entire nation when they are called upon in a
crisis. It highlights the chaotic, unpredictable
nature of history. and his influence reaches
much further into our modern culture than you
might initially think. We mentioned a famous
billionaire earlier. Yes, the ultimate pop culture
Easter egg. Comic book writer Bill Finger literally
named Bruce Wayne Batman after Anthony Wayne.
Later comic writers even officially established
in the lore that Bruce Wayne is a fictional,
direct descendant of Matt Anthony, which honestly
makes perfect sense when you think about a guy
who uses fear, theatricality, and nighttime attacks
to fight his enemies. It's a fitting cultural
tribute to a man whose real life was often larger
and stranger than fiction. It really is. We've
covered the midnight bayonets, the Spanish spy
betrayals, and the boiled bones, but I want to
leave you with a final lingering question to
mull over on your own. When you look at a figure
like this, where their professional brilliance
is tied directly to the exact same obsessive,
erratic, and uncompromising traits that completely
ruin their personal life, Oh wait, I mean, they
completely ruined their personal life. Can you
ever truly separate the madness from the genius?
Think about it. Thanks for joining us on this
deep dive.