All Episodes

August 12, 2025 65 mins
On today’s episode we talk about the little remembered espionage side of the civil war, particularly the CSA’s more outlandish ideas to take the war to the Union. And of course, we talk about what the world might look like if it all happened differently.
Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:07):
Welcome to The History Guy podcast Counterfactuals. What is a
counterfactual in the context of studying history, It is a
kind of analysis where we examined what might have happened
had historical events gone differently as a thought experiment. The
goal is to learn and understand history as it is
by talking about what it could have been as a

(00:27):
twist on the historical stories that we tell on the
History Guy YouTube channel. This is a series of podcasts
that dwell on that eternal question what if. I'm Josh,
a writer for the YouTube channel and son of the
History Guy. If you're a fan of the channel, you
already know Lance the History Guy himself. To liven up
our discussions on what might have happened, we have invited

(00:48):
Brad wagnan history officionado and a longtime friend of The
History Guy to join us. Remember that if you'd like
to support us, you can find us on Patreon, YouTube,
and locals dot com. Join us as we discuss what
deserves to be remembered and what might have been. On
today's episode, we talk about the little remembered espionage side

(01:09):
of the Civil War, particularly the CSA's more outlandish ideas
to take the war to the Union, and of course
we talk about what the world might look like if
it all happened a little differently. Without further ado, let
me introduce the history guy.

Speaker 2 (01:28):
While not nearly as discussed as the battles and the generals,
both the Confederacy and the Union engaged in robust espionage
programs during the Civil War. These nineteenth century spies engaged
in cloaken dagger activities that would be worthy of a
double O seven movie, including a plot on November twenty fifth, eighteen.

Speaker 3 (01:46):
Sixty four, to reduce the largest city in the Union
to ashes.

Speaker 2 (01:53):
The Confederate Secret Service had all the elements necessary for
a modern spy novel, spy ring secret codes, agents and
double agents, saboteurs of bureau inventing tools and gadgets, and
numerous intrigues plans large and small, with various supporters throughout
the Union. The Confederate spy operations ranged from simple espionage
to complex plots, and found varying degrees of success. A

(02:14):
bounty law passed by the Confederate Congress reimbursed private vessels
who destroyed Union warships encouraged privateering, which itself included quite
a lot of intrigue. For example, in June of eighteen
sixty one, less than three months after the outbreak of
the war, a Confederate officer and soldier fortune named Richard
Thomas Zarvona, the son of a former speaker of the
Maryland House of Delegates and nephew of a former governor,

(02:37):
formulated a bold plan to use disguise and subterfuge to
take control of a passenger steamer and use it to
surprise and capture a Federal gunboat on the Potomac River.
In a daring act of piracy, the plotters managed to
capture the packet steamer Saint Nicholas by boarding the boat
in disguise. Facilitated by Zarvona, who dressed and spoke as
a young frenchwoman, they loaded a boarding party of Confederate marines,

(03:00):
planning to surprise on board the Federal sloop USS Pawnee,
and the rules may have worked, but they found out
that the Pawnee had been moved to Washington and chose
instead to sail up to Chesapeake Bay, where they captured
three more Union merchant vessels before escaping to Virginia. In
eighteen sixty two, the bounty law was amended to reimburse
any person who shall invent or construct any new machine

(03:20):
or engine, or contrived any new method for destroying the
armed vessels of the enemy. This encouraged invention, including devices
of sabotage such as the coal torpedo and explosive disguise
as coal that may have damaged as many as sixty
Union vessels and the submarine CSS Hunley. Thus, the Confederate
plans included their own version of James Bond's que, but

(03:42):
the plans throughout the war were not always coordinated. Spies
were often members of the Confederate Signal Corps, but various
operations were carried out by both the Army and the navies,
well as there being various independent groups and covered activities
were conducted by the Confederate Porn Service.

Speaker 3 (03:56):
But as the war wore on and.

Speaker 2 (03:57):
The military situation became increasingly desperate, as Confederate iron grew
over destruction caused by Union troops and in the wake
of outrage regarding a failed Federal plan called the Dahlgren
Conspiracy that purportedly included freeing and arming Union prisoners of
war to burn Richmond and assassinate Confederate President Jefferson Davis.
The Confederacy finally appropriated the significant sum of a million

(04:18):
dollars to fund a special branch of the Confederate military,
the Confederate Secret Service, and many of the most audacious
plans of that organization were made in Canada. Despite an
official position of neutrality, and despite the thorny issue of slavery,
much of the British sympathy in the Civil War was
for the Confederacy. There were many reasons for this sympathy.

(04:40):
Commercial interest in the Empire were textiles, where a major
source of trade favored the importation of cotton, and British
industrialists saw the factories of the North as an economic competitor.
Many throughout the Empire felt that the Confederacy's bid for
independence was the moral equivalent of the American Revolution, and
that it was hypocritical for the Union to fight it.
Some englishm found a similarity in culture with the genteel

(05:02):
aristocracy of the South, and in Canada there was the
additional and not unfounded concern that the United States represented
a threat to Canadian sovereignty, and the Civil War weakened
that threat. In fact, the British military had created contingency
plans in case of an American attack on Canada or
war with the Union. In this environment, a large community

(05:23):
of Confederate expatriates escaped, Confederate prisoners of war families, Confederate
officials set away for their safety. Refugees from Confederate lands
that had been captured by the Union lived across the
northern border, where Confederate spies found a home. In a
twenty eighteen review of the book Montreal City of Secrets,
the website Canada's History Rights. As for Canada, it was
far from the battlefields geographically, it was on the front

(05:45):
lines when it came to the Maschin nations that went
on behind the scenes. The nexus of this activity was Montreal,
which played host to Confederate spies as well as to
millions of dollars in hard currency or gold, much of
it used to bankroll clandestine activities against the US North.
The general sympathy of the Canadian authorities meant that these
agents could act openly, although the city included Northern spies

(06:06):
as well. In April of eighteen sixty four, President Davis
sent three commissioners, including the former US Secretary of the
Interior and a former U S Senator, to Canada board
the blockade Runner Thistle to coordinate activities against the North.
There they helped to locate escape Confederate prisoners of war
refugees who have fled to Canada and facilitated the return
to the Confederacy, to coordinate a clandestine peace movement with

(06:28):
sympathetic politicians in the North, and to engage in schemes
to harm the Union. One of the Confederate officers involved
was John W. Headley, a lieutenant in the Kentucky First
Cavalry Regiment, one of some thirty five thousand Kentuckians to
serve for the Confederacy. In nineteen o nine, Heagley published
an account of Confederate operations in Canada. A veteran, in

(06:49):
the summer of eighteen sixty four, he was ordered to
proceed north to Canada to engage in Confederate spy operations.
He later wrote, we only knew that we would be
expected to engage with other young officers and expeditions, and
it was of course a perilous journey to Canada, as
we must travel in citizens clothes to go through the
United States. Our capture meant death. He traveled with another
officer to the west traveled to Saint Louis on a

(07:11):
steamer full of Union troops and then caught trains to Chicago,
Detroit into Canada. Robert Cobb Kennedy was from Georgia, a
distant relative of a former speaker of the United States
House of Representatives. He spent two years at the US
Military Academy at West Point, but was discharged due to demerits.
He enlisted with the Confederacy at the outbreak of War,
served at the Battle of Shiloh, was captured while working

(07:33):
as a dispatch writer, and imprisoned in Ohio at Johnson's Island,
a camp for Confederate officers that was notoriously difficult to
escape from, nonetheless using a makeshift ladder, he was among
the few to successfully do so. He made his way
to Canada, where he was recruited into the schemes of
the Confederate Secret Service. Among the boldest of these schemes
was the Camp Douglas Conspiracy. The plan was to liberate

(07:55):
the Confederate prisoners of war, initially those held at Camp
Douglas near Chicago, armed them and attack the Union from within.
The pen would initially be carried out by Confederates who
had been recruited in Canada by arming sympathetic northern copperheads,
once foring an army of some twenty five thousand men
in Illinois. The force was to capture the Union governments
in Ohio, Indiana, and Illinois. The plot was bold to

(08:18):
the point of hair brained, but given the military situation,
the Confederates were willing to take the risk. The American
Civil War Society notes that currently many historians are still
arguing of whether the plot was actually real, feasible, or
perhaps an elaborate hoax which was unduly exaggerated and exploited
so that certain federal officers would benefit. But undoubtedly there
were Confederate agents working on the conspiracy. Their efforts, however,

(08:40):
were uncovered, and an entire federal regiment and battery of
artillery was set to reinforce Camp Douglas. Support ended up
being meager, and far too few volunteers were found to
challenge the reinforced garrison, but the plot was not abandoned,
just delayed. It's possible that the goal creating the so
called Northwest Confederacy was a reach. In eighteen sixty four,
Lincoln was locked into contentious campaign with the Democratic candidacy

(09:02):
of George McClellan. The former general was running on a
platform of ending the war by promising to protect slavery.
The goal might have been simply to cause enough disruption
to undermine Lincoln's reelection chances. The date for the attack
was moved to the day of the election, November eighth,
but this time it would include more than just Chicago.
But before that could happen, another of the Confederate plans unfolded.

(09:24):
A group of Confederate soldiers entered the United States through
Canada and raided the town of Saint Albans, Vermont. The
goal was not just to cause disruption and distract Union troops,
but also to rob banks in order to bankroll Confederate
plans conducted October nineteenth, the raiders successfully robbed a bank,
but were driven off as the town mounted a resistance.
Under American pressure, Canadian authorities arrested the men. The money

(09:45):
was returned, but Canadian authorities decided not to extradite the raiders.
But the affairs started to turn Canadian opinion against the Confederates,
so we concerned that they would drag Canada into the war.
It isn't clear if the Saint Albans raid embolded the
next set of plan, so if it simply made the
Confederates more desperate to act quickly. The new attack plan
for November eighth, the day of the election, was still

(10:07):
to free the Confederate prisoners, but also set fire to
the city of Chicago. Detachments were created, tasks with setting fires,
robbing banks, and flooding sections of the city. The attacks
should cause widespread damage and the distraction will give the
chance to free the prisoners at Camp Douglas. But the
plan went beyond Chicago, with smaller attacks planned in other
cities in the north, Cincinnati, Philadelphia, Boston, and the nation's

(10:28):
largest city, New York. Headley and Cobb were among the
group of eight sent to raise chaos an election day
in New York City, calling themselves the Confederate Army of Manhattan.
New York was a hotbed of the Copperheads, northern Democrats
who sympathized with the South, and opposition to Lincoln and
his cabinet and support for the Union was tempered by
trading ties with the South. In July of eighteen sixty three,

(10:50):
the city had erupted into violence of resistance to the
drafting of soldiers, and there was a possibility could be
drawn into rebellion.

Speaker 3 (10:56):
Again, careful plants were laid.

Speaker 2 (10:59):
The plan was to set fire to distract city officials,
occupy federal buildings, obtained weapons from arsenals, and arm a
crowd of supporters.

Speaker 3 (11:05):
The insurgents would.

Speaker 2 (11:06):
Raise a Confederate flag over city Hall and declared that
New York City had left the Union and had aligned
itself with the Confederate government in Richmond. But like so
many plans of Confederate secret service, the Union knew that
they were coming. In Chicago, union men had infiltrated the
militaristic Copperhead organizations, and the operation had been betrayed, including
by a Confederate officer in the camp who was repulsed

(11:28):
by the violence involved in the plan. The leaders among
the sympathizers were arrested and the plan collapsed. Elsewhere, election
violence was anticipated and federal troops were moved into cities.
Officials in New York were doubtful about the warnings, but
a Union force under Major General Benjamin Butler was sent
to the city. Hedley wrote, the leaders in our conspiracy
were at once demoralized by the sudden advent of General

(11:50):
Butler and its troops. They felt that he must be
aware of their purposes. The plan was once again called off.
Hedley wrote the feints in Boston, Philadelphia, and Cincinnati likewise
were not attempt The election went as scheduled. Union victories,
including Sherman's capture of Atlanta, had taken the steam out
of the opponents of the war link and won reelection easily.

(12:11):
The dangers seemed to have passed. Butler and his force
were removed, but the saboteurs were still in New York.
They could no longer affect the election and were helpless
to aid troops in the field, and the broader plan
of an army of free POW's was lost. Yet they
decided to continue anyway with the plan to set the
city on fire and give the people a scare if
nothing else, and let the government at Washington understand that

(12:32):
burning homes in the South might find a counterpart in
the North. I tried to decide upon a day I'm
planned for Thanksgiving, but Butler and his troops were still there. Finally,
they decided to make the attack on November twenty fifth,
which the city celebrated as evacuation day commemorating the day
in seventeen eighty three when British troops had finally evacuated
New York. The agents had been provided with twelve dozen

(12:55):
bottles of Greek fire, chemical concoction that was supposed to
ignite when the jar was open and an exposed to air.
Headley picked up the bottles in a valais, which he
found to be surprisingly heavy and smelled a bit like
rotten eggs. Each of the eight men had taken rooms
in four hotels, where they would leave behind a satchel
with the Greek fire inside. The plan, the New York
Times road was to fire the city at a given

(13:17):
moment and a great many different points, each as far
remote from the other as possible, except through Broadway, as
this thoroughfare they wished to see in a complete blaze
from one end to the other. This would presumably overwhelm
the fire department Military History Online rights. At seventeen minutes
of nine, the Saint James Hotel was discovered to be
on fire in one of the rooms. The New York
Times reported betting and furniture had been saturated with an

(13:39):
accelerant and set a flame. A few minutes later, Barnum's
Museum was ablaze. About the same time, four rooms of
the Saint Nicholas Hotel were ablaze. By nine to twenty pm.
A room in Lafarge House was in flames, then the
Metropolitan House, Brandreth's House, Frenchy's Hotel, the Belmont House, Wallack's Theater,
and several other buildings were on fire. Included in the
incendiary mail storm was Fifth Ward Museum Hotel, Astor House,

(14:02):
the Belmont Hotel, the Fifth Avenue Hotel, the Howard Hotel,
Lafarge House, Lovejoy's Hotel, the Metropolitan Hotel, the Saint James Hotel,
the Saint Nicholas Hotel, the Tammany Hotel, and the United
States Hotel.

Speaker 3 (14:15):
One of the.

Speaker 2 (14:15):
Fires was in the Lafarge Hotel, which was next to
the Winter Garden Theater. The alarms briefly disrupted the play
Shakespeare's Julius Caesar. The play was an event to raise
money to place a statue of William Shakespeare in Central Park.
Panic was averted by a brief speech from the lead
actor to own the crowd that there was nothing to
worry about. The actor, Edwin Booth, owned the theater and

(14:36):
this was the only performance done by him and his
two brothers, Junius Junior and John Wilkes together. Military History
Online reports that Kennedy entered P. T. Barnum's museum, which
was packed with patrons, and set fire in a stairwell.
A panic ensued, with people rushing out of the building
in a stampede, but no one was killed or seriously injured,
and again they had been betrayed, likely by one of

(14:57):
the conspirators themselves. The fire department was on alert, and
all the fires had been quickly put out with little damage.
The Gotham Center for New York History rights none of
the Confederates had ever visited New York before they arrived
to burn it down. They did no scouting to find
the most flammable targets. Just days before the attack, one
of the Confederates was thrown out of his hotel for
loudly proclaiming in his Alabama born accent the merits of secession.

(15:21):
None of the young men had any experience with incendiaries,
yet they trusted a stranger to provide them one hundred
and forty four firebombs, and when they took possession of
the fire bombs, they spent only a few minutes practicing
with them out in the open in daytime in Central Park.
The New York Times wrote, the plan was excellently well
conceived and evidently prepared with great care, and had it
been executed with one half the ability with which it

(15:42):
was drawn up, no human power could have saved the
city from utter destruction. Despite all their networks and all
their plans, the Confederacy gained little return on their million
dollar investment to disrupt the Union from Canada. Most of
their plans amounted to little, except for one successful plan
in which the full involvement.

Speaker 3 (16:02):
Of the Confederate Secret Service is still uncertain. That is
the April fourteenth.

Speaker 2 (16:06):
Eighteen sixty five assassination of President Lincoln by Edwin Booth's
Confederate sympathizing younger brother. As Union troops moved to capture
the Confederate capital at Richmond, the records of the Confederate
Secret Service were destroyed, and we still don't know the
full extent of their organization. The fires in New York
City didn't cause a lot of damage, but they did

(16:27):
cause enough disruption that the writers were able to escape.
All except for Robert Cobb Kennedy, who was captured by
Federal agents in Detroit as he tried to return to
the Confederacy. He was defended in court by a Union general,
Edwin Stoughton, with whom he had attended West Point, but
he was convicted of being a Confederate saboteur sentenced to death.

(16:50):
He made one last attempt to escape prison, but he
failed this time and the sentence was carried out on
March twenty fifth, eighteen sixty five. He was the last
Confederate soldier to be executed by the United States federal
government during the Civil War.

Speaker 1 (17:05):
Now for the part of the episode where I the
History Guy himself and longtime friend of the History Guy
Brad Wagnan talk about what might have happened if it
all went a little differently. So, I think this is
the first time on the Counterfactuals podcast that we are
going to talk about the Civil War, which is a
very entertaining one to talk about. But of course we're
talking about a rather specific part of the Civil War

(17:28):
which I think is less talked about and no less interesting,
and that is this secret Service kind of fight, especially
from the Confederate side. In this particular episode, there were
some interesting stuff that the North did too, which kind
of like the South was a mixed success. There's lots

(17:48):
of talk about how the Pinkertons were maybe not helpful
to the Northern Army.

Speaker 3 (17:54):
Well, yeah, Alan.

Speaker 2 (17:55):
Pinker said himself, yeah there about that. It is a
very fun episode. And part of it this because it
actually in details so many plans, most of which came
to nothing.

Speaker 3 (18:05):
But I mean, maybe he could a so I mean,
there's an awful lot.

Speaker 2 (18:08):
Of counter there's a lot of counterfactial here to talk
about in terms of what I mean from you know,
what if they'd made the Indiana, Ohio and Illinois and
a new country, or what if they had built a
country that included the Gulf of Mexico and the Golden
Circle to you know, what happens if they were just
simply better arsist.

Speaker 3 (18:29):
It's not going to set fires. At the time, it
was easy to set fire and stuff.

Speaker 4 (18:33):
I'm kind of drawn by the fact that history comes
full circle here to an extent. Alan Pinkerton's records, which
would be wonderful to go through because I think would
really allow us to do a much better picture of
the man and his role during the Civil War. All
of his records were destroyed in the Great Chicago Fire
in eighteen eighteen seventy three.

Speaker 3 (18:57):
Is rather the original path for the fire hydrant was
lost to fire.

Speaker 2 (19:02):
So that's the sort of thing that will happen. But
you know, another part of this, and I think we'll
get to it beyond obviously Bigfoot will be involved because
there's Canada out there.

Speaker 3 (19:13):
But another part of this is just a question.

Speaker 2 (19:16):
And there's a few other episodes that kind of talk
something around this, and that is to say, to an extent,
the argument is that after Gettysburg and Vicksburg, after.

Speaker 3 (19:25):
July of eighteen sixty three, the war was really over.

Speaker 2 (19:28):
The Confederates could not have won the war or moved
to anything on negotiate a peace. And so part of
the question here is, and you know, as we talk
about how crazy some of these plans are, you know,
remember this, we don't really know to what extent, but
these guys might have been, at least to an extent
responsible for the assassination of Lincoln, which would you know,
I think they'd have to call that a success for
their secret service. The question is was any of this

(19:50):
going to make a difference by after eighteen sixty three,
After July of eighteen sixty three was this irrelevant anyway?
And so you know, I think there's I think there's
a lot of fun stuff too discuss here.

Speaker 3 (20:00):
I really do. It's a fun episode.

Speaker 2 (20:02):
Honestly, when I because I wrote this one, and when
I was doing the research, I had no idea really how.
I'd heard about some of the spy rings, but I
had no idea about these grand plans to invade from Canada.
I knew about the Saint Albans rate, I didn't know
that that was, you know, a grander strategy.

Speaker 3 (20:18):
And it's really interesting stuff.

Speaker 2 (20:19):
To read, and it certainly would make you know, fun
historical alternate fiction sort of stuff, because some of these
plans are.

Speaker 3 (20:26):
Just just it is funny to me. Though.

Speaker 2 (20:28):
Both sides apparently at some point had the idea of
arming prisoners of war, even though no side was treating
prisoners of war in such a way that if they
were to best out that they would be, you know,
ready to bear arms.

Speaker 3 (20:40):
I mean, but both of them had so starved and
left in such conditions.

Speaker 2 (20:44):
They're the prisoners that they held that if you were
to give them all guns that they you know, would
take weeks before they could stand up. And they're both like, oh,
if we just give our guys guns down there, you know,
then suddenly we've got an army.

Speaker 5 (20:56):
So it's kind of funny that they both both operated
from that plan because I don't think that either of
them in a condition where it was going to, you know,
you're going to suddenly pull a battalion out of people
that were dying of dysentery.

Speaker 1 (21:07):
Yes, it's hard to imagine that you could have that
even one in tent of them would have been capable
of holding a rifle, much less, you know, standing on
a battle line.

Speaker 3 (21:17):
Yeah, immediately forming a regiment and standing in line.

Speaker 1 (21:20):
Yes, yeah, they were. They were in rough shape.

Speaker 4 (21:24):
And uh, you know, just to add another layer of
complexity onto that house of cards, uh, is you know,
what is the command structure going to look like? Yeah,
it's you know, uh, you know, if you've got a
if you've got a prisoner of war camp where a
lot of the well uh politically connected officer corps have

(21:44):
already been repatriated back during prisoner exchanges. Uh, you know,
you have camps for the most part that are full
of you know, Johnny reb who you know left the
farm six months ago, got captured and as you pointed out,
has probably been living in a self constructed hut, getting

(22:07):
very little in the way rations, and yeah, it's yeah,
they're probably.

Speaker 2 (22:14):
They were they were eating rats, and I mean that
these were these were not people that were not in
a position to uh to you know, but you're right,
I mean, there's no their officers are often in different
camps there. I mean, they weren't usually captured as a regiment,
so they aren't they aren't formed in any sort of
units or anything. And the assumption seemed to be that
very quickly they would be able to take you know,
this twenty thousand people that are in prisonal war camps

(22:36):
and turn them into a Bible army that's going to
march over and you know, relieve all the other prisonal
war camps.

Speaker 1 (22:41):
And boys, you have to do it instantly because that
you're talking about a place where I mean there were
Union troops nearby. That's that you know they used the
they mustard people in and out there. It was truly
you would have had to have been able to take
that prison and have have a have a usable force
and one that could move pretty quickly, I mean quick,
and it's hard to imagine that you could have probably

(23:02):
held together two hundred guys out of the whole bunch
were that were ready to do that.

Speaker 3 (23:06):
It's I mean quite well.

Speaker 2 (23:08):
I mean, it says a lot about the whole idea
of it, and that they were actually betrayed, you know,
from people they were trying to put in a conspirators
who like, this is just.

Speaker 3 (23:15):
A dumb idea. I'm in telling guards, you know. I
mean that I think says says certainly something about it.

Speaker 2 (23:22):
But it didn't take much once they heard about it
to be able to put together, you know, all that
you would take to be able to defend the camp.

Speaker 3 (23:28):
I'm you woudn't have to raise it right for it.

Speaker 2 (23:29):
But Morgan, which was that was in July of eighteen
sixty three, while that other stuff was going on, I mean,
Morgan rated well into Ohio.

Speaker 3 (23:37):
That rate.

Speaker 2 (23:38):
Actually there was some you know, close calls where it
was just kind of some local militia that managed to
hoole a river crossing that tied them up. We did
find out that the Union wasn't particularly well defended past
the battle lines, and that you could go I mean,
and there were lots and lots of incidents of that
in the war, there was you know, there was a
point where they were for they're going to sail the

(23:58):
river all the way up to Cincinnati.

Speaker 3 (24:00):
Uh and uh.

Speaker 2 (24:01):
And the Saint Albums raid, which is mentioned in this episode.
I mean that, you know, so that there is some
sign that the Union wasn't prepared if the Confederates could
actually start moving, you know, that far north, that they
hadn't put together armed forces and stuff. But I mean,
you're right, I mean, these are mustering points. These are
and what they found even at Saint Albums Albums has
just said, well, you know, there's this guy there, you know,

(24:23):
on leave and he took command of the locals and
everybody had a gun, right. So so probably probably the
good citizens of Chicago were more prepared to you know,
immediately form a military unit that could operate as a
military unit than that than the the prisoners over.

Speaker 3 (24:40):
At Camp Douglas.

Speaker 1 (24:42):
It's I mean, I think one of the problems, honestly,
is that there was some promise in a lot of
these operations, except that first of all, they were shooting
a way above, way above even the wildest dreams. But
they really, you know, by the time they got serious
about it, it was only as a last resort. There's
a good argument to say that it it was difficult
to have you know, this kind of behind the lines

(25:04):
attack do well when you're also losing in the field.
If you could do it while you were also winning
in the field, you know that the morale, the morale
bonuses kind of get like a multiplication. But if you
you know, while you're losing in the field, it's hard
to It might help a little bit, but you can't
win the war just by setting fires.

Speaker 2 (25:23):
And that's thrue, which well, I mean that is interesting though,
because there's another odd point in eighteen sixty four when
Jubile Early comes rolling up to the Shenandoah Valley and
it's literally on top of Washington, d C.

Speaker 3 (25:33):
Before anybody know what's going on.

Speaker 2 (25:34):
And if it weren't for the Battle of Monocacy, we've
gotten to Fort Fisher or Fort Stevens before they were
shoving reinforcements in.

Speaker 3 (25:39):
Now you might have taken Washington, d C.

Speaker 2 (25:41):
So if you get something like you know, if if
Early had done that, then at the same time, if
you're suddenly having a lot of you know, you know,
Cincinnati and Chicago and New York, you know, maybe that
could have could have made a difference. You'd have to
have an awful lot of stuff kind of rolling together
for it to happen. But it's also true that it's
it's one thing to be an anti wore Democrat, you know,

(26:01):
that's that's in a little club there and in central Ohio.

Speaker 3 (26:05):
Uh.

Speaker 2 (26:05):
And then but when they're asked, like, you know, are
you willing to suddenly come under arms and face people,
I mean, it's a different These were not, for the
most part, soldiers, So I mean they're there. Yeah, there's
an awful lot of dream there from people that are well,
I was just a keyboard warrior.

Speaker 3 (26:18):
I only say that stuff online.

Speaker 2 (26:20):
But I mean if you're asking, if you're asking me
to actually come out for it, oh no, no, no no.

Speaker 3 (26:24):
And that's kind of what happened with the planet.

Speaker 2 (26:25):
Finally, when they were setting fire, I mean they were
supposed to set far out a number of numerous cities
that weekend, and it ended up being just a handful
of guys in New York.

Speaker 3 (26:32):
They o once and did it. But how important was
New York at the time?

Speaker 2 (26:35):
Because New York was was if you think that was
the heart of the Union, it was not at all
New York. Actually, there was a at the beginning of
the war, New York was arguing that they should become
a free city and not be with the North or
the South. They had huge connections economic connections with the South,
and the cotton trade in the South were always quite
a lot of the you know, the copperheads of the
Democrats in New York. If they had been better at fires,

(26:57):
if they had been better at what they were doing,
was there a popular in New York that would have
taken that as a as a as a sign and
pushed to you know, no longer support the Union.

Speaker 4 (27:08):
Yeah, I don't think so. The American Civil War is
literally it is the war of brother against brother, father
and son. You know, back to your point, you know,
how many people living in a tenement trying to you know,
support their you know, five or six kids, working hard
at you know, whatever job that they're doing, are willing

(27:29):
to lay that on the line and essentially become a rebel,
and not just a rebel, but a rebel behind enemy lines.

Speaker 3 (27:37):
You've got that.

Speaker 4 (27:38):
And then furthermore, this was not really a situation where Okay,
we're going to go beat up on a bunch of
people whose language, culture, and traditions we don't really understand.
The northerns and Southerners in the American Civil War had
far more common than just about any other group. I
just don't think that there was I don't think that

(27:59):
the spirit, whether more or South, you couldn't whip up
that level of hatred. Now, you could get enough to
you know, get quite a few people in the South
to pick up arms, and quite a few people in
the North as well, but it was fundamentally different. I
think it was a true civil war.

Speaker 2 (28:18):
It's telling that when the draft riots occurred that very
quickly turned into anti immigrant and the anti black riots
rather than North South riots. I mean that that the
Civil War connection to the New York City draft riots
almost immediately faded, as they just said, well, now we're
gonna we're going to attack each other for the things
that we attack each other about.

Speaker 3 (28:35):
So you're right, I mean, you.

Speaker 2 (28:37):
Know, was there enough of a hatred in New York
for North or South for that for that to happen?

Speaker 3 (28:43):
I mean, I just I wonder.

Speaker 2 (28:44):
Because when the when this attack occurs, I mean, you know,
they're intending it for it to be a coordinated attack
across multiple and they end up saying, well, you know,
no one else is going to attack, but we're here, right,
So why not?

Speaker 3 (28:57):
Was was New York?

Speaker 2 (28:58):
The right place was New York up where a good
Confederate action behind the lines could have been enough for
the people to kind of shift and say, no, this, this, this,
do negotiate a peace or I mean, because this wasn't.
I mean, I think it's a very small chance that
they're going to have a like a military victory.

Speaker 3 (29:17):
This was really all about.

Speaker 2 (29:18):
The election of eighteen sixty four. I mean, we had
a we had a very popular Union general running on
a platform of this end the war by guaranteeing slavery,
and which I don't know if it's the South would
have accepted that at that point, but anyway, I mean,
you know that was that was a real platform, and
so could I mean, if these guys had better, it's

(29:39):
been better at setting fires. Was New York the place
that could have shifted the population because Lincoln actually won
the election of eighteen sixty four by a wide margin,
but you know it was narrower that it looked.

Speaker 3 (29:49):
They were certainly worried about it. So it was New
York the place where they could have started the less end.

Speaker 2 (29:55):
The war movement by by being better at setting because
it's because even the ones that do they end up
they set a few fires, and everybody's it took him
a long time to even figure out it was coordinated
because he's they didn't open the windows, and I mean
they weren't very good arsenist. Yeah, so, I mean had
they so, I mean it's a place to start. If
they had been regardless of the broader plans, it's are

(30:15):
all fun to talk about. If they had just been
better arsonists in New York and actually started a major fire,
it wouldn't be the first time New York burned down
Under they had.

Speaker 3 (30:26):
Way bigger fires than these.

Speaker 2 (30:28):
Had they succeeded, could it have changed anything about the
outcome or at least the you know, length of the
war in any meaningful way.

Speaker 1 (30:34):
I mean, quite honestly, when I was looking into this,
I feel like it might be more likely to cement
sentiment against the South. I mean, if they burned down
New York, I think what you get out of that
is that this was an attack on a civilian city,
and there's some there's some argument there that you know,
if you burn New York down and you kill lots
of people, or you just destroy huge parts of the city,

(30:57):
which you get as people saying, gosh, health was really
willing to hurt us, uh and in a place even
that he was supposed to be sympathetic to them, you know.
And I think what you might get after that is
people saying, we need revenge, we need retribution. If they're
going to burn New York, well, then I think there
was some hope that if the Union experience and what
the South was experienced, because you know, this was certainly

(31:19):
a lot of had to do with Sherman, then the
Union would.

Speaker 3 (31:21):
Sympathize with the South. I tend to agree with you.

Speaker 2 (31:23):
I think that it probably would have just would have
just ticked him off more. Uh And if anything, at best,
it would have been simply Confederates that are mad about
you know, Atlanta burning that would just be getting some
revenge on that. And I'm not sure if you know,
if New York was the you know, the place where
that would would make a difference. So so I mean
that's it's a diverse question. The very plot that this

(31:44):
talks about. Could this plot have succeeded in any meaningful way,
and I kind of doubt it.

Speaker 4 (31:50):
Yeah, doing some research for this, or ran across the
presentation by an author put together a book, and he
made a claim that had this been carried out in
a very systematic and well executed way, it would have
resulted in four hundred thousand casualties and the virtual destruction
of New York, which I think is a bit of

(32:13):
a stretch. Okay, And by the way, my eyes are
rolling here, that's not just a bit of a stretch.
That's crazy. That's crazy talk. However, if you look at again,
you know, flashing back to the Great Chicago Fire, which
occurs only a few years later, a single source fire
results in three hundred deaths and you know, substantial portion
of Chicago being burned down.

Speaker 3 (32:35):
Two comments.

Speaker 4 (32:35):
First of all, New York City was definitely not a
Republican stronghold. The fact that you're burning down the place
where at least your Tasset supporters in the North are,
I don't think you're going to cause the positive press that.

Speaker 3 (32:51):
You're hoping for.

Speaker 4 (32:52):
And there were probably some other places where you know,
hit one of the major naval yards, you know, six people,
you know, they throw some sort of accelerant onto the
piles of wood that are being put into ships and
whatever else is is going to have some real effect
very quickly, and especially in a military way that I

(33:15):
think would be a little more realistic plan.

Speaker 3 (33:19):
I mean this certainly.

Speaker 2 (33:21):
It's interesting because I looked up the Great Fire of
New York, and the reference that the AI was using
was my video. But because there was a fire there
went eighteen thirty five, so I mean thirty years before that.
But I mean certainly you could have done economic damage
to the Union. I don't buy tens of thousands of
deaths because people run away from the fire, right So
even if you're even if you're starting fires and lots

(33:42):
of prices, I think that a lot of people would
have watched it burn. Like they in Chicago, they mostly
left right there, weren't there weren't all that many desks
in the size of it. But your rife as from
a military standpoint, if they'd attacked the docks or something
like that, they could have probably done a lot more damage.
I would imagine in New York there was a lot
of like military supply that was you know, being taken
to the siege of Petersberg and stuff that was going

(34:03):
on that, you could have done a lot more to it.
I don't think that their plan was actually to be
militarily effective. I think their plan was to hope to
affect well, I mean specifically, their plan was to affect
the attitude of the people on the eve of the
election and the hope that it would go a different way.

Speaker 1 (34:22):
Of course, then it gets delayed till after the election.
It really does make you wonder if there was any
value of it by the time they actually get around
to doing it.

Speaker 3 (34:30):
Is that like, well, we came all this way.

Speaker 1 (34:36):
They might have been able to pull some resources, you know,
from the battlefield. They might have been able to do that,
But the truth is the Union could afford that a
lot better. I don't think. I mean, even if they
hit it did hit military targets. I mean, there was
no amount of burning shipyards at that point that was
going to give the South, you know, the advantage on
the waves there was, and that's even true from the beginning.

(35:00):
That would have been awfully difficult. They had had to
really stay on top of that. But the idea of
you know, really the war had mostly been fought on
southern ground, and that's where most of the burden in
terms of destruction and suffering had come from. I can
see why the idea of if the North suffers too.
It's just you wonder if that point had been somewhat lost.

(35:21):
By eighteen sixty four. There was a I mean, there
was time there where they were not sure, the public
was largely not sure that the Union could win, that
the Federals would be would defeat the Confederates, and that
I think had largely evaporated by eighteen sixty four, the
Anaconda plan that was all working.

Speaker 2 (35:40):
Yeah, the competitor a desperate position in eighteen sixty four.
And the difference between Sherman burning Atlanta and you know,
six guy set and fire in New York is that
Sherman had like this army there.

Speaker 3 (35:53):
Yeah, he would hold it. You know.

Speaker 2 (35:55):
It wasn't like, ah, you know, we just threw fire
and Atlanta has gone for the rest of every you know,
there's you can't recover when you're actually being occupied. So yeah,
in the end, it feels like they were just maybe
out for some petty revenge, which they weren't pretty good
at the I mean, you'd have to say that if
they had done significant damage, if they'd burned, you know,
one hundred city blocks or something like that, and you know,

(36:16):
caused a.

Speaker 3 (36:17):
Good amount of death to New York.

Speaker 2 (36:19):
That that would have been a financial impact on the Union,
But I don't think in eighteen sixty four that could
have shifted recognition by foreign powers. In reality to the
eighteen sixty four election, that the real concern was that
the Republicans might split the bout because Fremont was running
as well.

Speaker 3 (36:35):
And when Fremont pulled out.

Speaker 2 (36:38):
Then I mean there was no real chance that McClellan
was going to win on the Democratic ticket.

Speaker 3 (36:44):
But I don't know. I mean, you know, the election
went very much for Lincoln, but was it closer? Was
there more of an edge in the Union? I don't know.

Speaker 2 (36:51):
So what about the broader plan? What if instead of
justifier in New York, what if they had successfully done
significant damage in New York, Cincinnati, in Chicago, in Indianapolis,
across these Union states. Is there is there any possibility
that that would have put people.

Speaker 3 (37:08):
In the position where they be just in the war.
We're sick of this, Just negotiate a peace.

Speaker 4 (37:13):
Coming to a modern modern example, I think that if
you go for an all terrorist attack whose design is
actually terror, and this really was a This was an
attack designed to create terror. How are you going to
affect populous that's you know, that you're fighting against. I

(37:33):
think that there are far more examples where the terrorism
ends up creating far more support for the defender's cause
than it does for the attacker's cause. And I don't
know that you're going to see, you know, a sudden
shift in the men on the street's opinion in eighteen
sixty four. Oh well, you know they burned out Boston, Chicago.

(37:54):
Oh maybe those southern guys are worth fighting for. It
seems to be a real stretch if you were to
have some kind of really well organized intelligence agency that
does something that really doesn't occur until the the mid
twentieth century.

Speaker 1 (38:11):
It was very nascentse this kind of warfare was. I mean,
I think what they would have had to do is
convince the average you know, northerner that they weren't safe
and that the Union couldn't protect them. And certainly there
was some argument, I mean, you know, we talked about
the raids and stuff like that. There were openings where
they could have done that, but it would have had
to have been coordinated because I agree. I think even

(38:33):
if you have won one large event and you hit
a bunch of cities, I think that's impactful, and I
think it might I think it might have changed more
than you know, what they were just doing in New
York if they'd hit everything. But if they do that
and the North is able to, you know, essentially prevent
any future attacks and is able to both literal and

(38:54):
metaphorical fires from that, that you really get to a
point where you see that the Northern are not going
to just turn as long as they think that the
South can't continue to do them. And I think even
as late as eighteen sixty four, if the South really
could have proved that they might have been able to
tip the balance somewhat, it would have been a lot
easier if they had, you know, in eighteen sixty two,

(39:16):
if you were also just running, just running rampant and
setting fires in northern cities and it wasn't just paranoia
about what they might be able to do, but you know,
literal actual damage, that that really could have pushed it.
And it's it really does come down to, and it's
it's maybe the the the easy answer, which is that
maybe the South was really in trouble after eighteen sixty three,

(39:38):
and it's it's I think it's also the boring answer.
And I think they were all still hoping that there
would be victories on the battlefield.

Speaker 3 (39:46):
Yeah they were, they were they were never getting their
their their mojo back that they had in eighteen sixty two.

Speaker 2 (39:52):
Yeah, yeah, but that you know, the more boring issue
is after is when the warst started, was the you know,
was the content see a hopeless cause where they were
they always going to be so out? I mean, you
know Brad has mentioned before that they continued to hold
the rolling race between Harvard and Yale all the way
through the through the war, meaning that the Union never

(40:12):
fully mobilized, and so you know, you could simply argue
that the resource difference was but I mean, if there
was just a point where it was just going to
be you could sting so much that they would decide
it wasn't worth it, which is you know what happened
in the American Revolution, right, I mean essentially it wasn't
that that what we truly defeated England as that which
is sold, well, victory is going to come at you know,
a cost, you think it's really worth it.

Speaker 3 (40:33):
But you know in the states, like you were never
safe in Kentucky, you were never safe in Missouri.

Speaker 2 (40:37):
They were always raiders running behind the lines, and those
those states seemed to move more and more in support
of the Union rather than less, despite the fact that
they know constantly had raids running around behind the lines.
But in eighteen sixty four the Union was running into
a recruiting crisis. Is eighteen sixty four because it's later
in the wars that make it more likely? Does it
make it less likely? I mean, it feels to me

(40:59):
like people were just going to finish the war whatever
they did, and that more trouble might have caused more
than than not. But let's look at this way because
it's also interesting about it, because a lot of Confederates
had escaped across the border up north, and others had
got up there for other reasons, and there was and
you know, the sympathy was shallower than after the Saint
Alban's rad that, oh, Canadians love us, and the Canadian's like, oh, oh,

(41:21):
you're gonna.

Speaker 3 (41:22):
Draw us into this war. You know what. More, you know,
it's easy for us to support you when you're not
doing anything.

Speaker 2 (41:28):
So if you assume that they had maybe less than
core but more than brigade strength number of troops in
Canada that they could have put under arms a Union
that was relatively unprepared for that.

Speaker 3 (41:41):
That's kind of what Saint Albans showed. And you did
have Confederate sympathies.

Speaker 2 (41:46):
You knew you had some Confederate sympathies in certain places,
and if you had some capacity to try to coordinate
that with some action in the South, something that would
be close to like Morgan's raid or something or early coming.

Speaker 3 (41:58):
Up, if if you put it all together.

Speaker 2 (42:01):
So was there a plan with what they had, because
obviously it was very poorly executed, But was there a
plane with what they had that could have forced the
Union into a position whether they would say, negotiate peace,
either by guarantee slavery or by just saying, you know,
find go. I mean, how far is is there a
potential for a counterfactual in eighteen sixty four.

Speaker 4 (42:23):
Well, if there is a chance for that, somehow, you've
got to get international recognition for the South, and perhaps
a American Civil War equivalent of Lafayette or some similar
power from outside of the South coming in and intervening
and interestingly, early early on the British support for the

(42:43):
South and by extension Canada. You know, maybe there's a
brief moment there where the British say, you know, this
cotton really is important enough for us that we're going
to land troops and we're going to man some of
the forts and put some put some troops in the field,
and gives significant economic and military aid the South. It's

(43:04):
still a stretch, but that would be a potentially you know,
alternate timeline, or maybe the South because of the overwhelming
support of the British Navy, the Anaconda plant doesn't us
not go as planned.

Speaker 2 (43:20):
I think the idea of foreid recognition, I mean, I
think if enough countries had recognized the conpederacy that it
might have been made the work politically untenable.

Speaker 3 (43:28):
But I don't think anybody was going to do that.

Speaker 2 (43:30):
After Gettysburg in eighteen sixty two, the great hope was
that England was going to recognize and potentially be willing
to show some military support to break the blockade or
something like that. But I think by eighteen sixty four
that was probably a lost cause. And that's probably what
showed when the people in Canada were immediately started rejecting
them the moment they were doing you know, cross cross

(43:52):
border rates. It's interesting that instead the way that Europe
saw was that we're distracted, We're going to go take Mexico. Yes,
is that England and France and in Spain all attack
Mexico is what they chose to do.

Speaker 1 (44:07):
Yeah, you know, Canada didn't want to get in the
war with the US and certainly would have been I mean,
it would have been difficult for the North to fight
fight on two fronts. So that's I mean, if you
could have if you could have gotten Canada to essentially
just be like, oh, it's not us, while having you know,
significant raids coming across the border, I mean, it would
have been hard for the Union to defend. That's a

(44:27):
lot of border. That is a lot of border. It
would have been a significant just manpower shift. But the
North also didn't want to go to war with Canada
or with with England like that, and so there's you know,
the question is could they have used Canadian sympathy and
the Union reticence to just you know cross that border
because we know that that's not a fight we want

(44:48):
to get into. Can they use that to continue to
stage those kind of raids, and by eighteen sixty four,
certainly it showed no right Canada. Canada was willing to
at least do the bare minimum to say we are
not going to let them just raid willy nilly.

Speaker 2 (45:03):
It leaves a fun idea up there, because they sent
a boatload of gold up there to try to do
these plans, and a lot of it's really not clear
whatever happened to it. So you know, you know, it's
popular to say where's the hidden gold? Imagine they just
pocketed it. But I mean, was there a cash of
Confederate gold that was somehow left in Canada or gone somewhere?
But yeah, I mean, I think we're pretty clear that

(45:25):
my Canada wasn't going to And you know, Canada was
never a military power.

Speaker 3 (45:28):
They had very small military.

Speaker 2 (45:29):
So were they going to raise the militia and try
to attack well in the same way that we did
in eighteen twelve and or or like the Fenians were
trying to do and after the Civil War? I mean,
was there It just seems it seems unlikely that Canada
is gonna do that. How could even if you could
raise up a whole brigade or even a whole cores
of Confederate prisoners who'd escaped and swum to Canada.

Speaker 3 (45:51):
Could you send that cores.

Speaker 2 (45:53):
Across the border in a way that they could do
significant damage without the cooperation of Canada. Could you arm
them and prepare them as a force and do that
with the cooperation of Canada.

Speaker 3 (46:02):
That's it, That's it.

Speaker 1 (46:03):
I certainly it would have. It would have been a
big deal because there there was a nutrition war there
that was impacting the North anyway, you know, I mean,
because you talked about the manpower shortages and there there's
a good argument there, but the Canada doesn't want a
Northern army to be crossing that Canadian border to do
heaven knows what.

Speaker 2 (46:22):
Yeah, yeah, I think there was some fear because we
had mobilized in a way larger than ever before.

Speaker 3 (46:28):
I mean, there was some concern there that the US.

Speaker 2 (46:29):
Actually, you know, had had we taken the Union Army,
had we taken the Army of the Potomac and in
bed Canada in eighteen sixty five, we we almost certainly
would have defeated them much easier than we would have
been eighteen twelve.

Speaker 3 (46:42):
We'll probably get hit some hate mail off of that acadade.

Speaker 2 (46:44):
But I mean we were, we were mobilized to an
extent that you know, Canada wasn't gonna be able recenton
the realty would have been born with with England and
the which which which would have been interesting in eighteen
sixty five, It would have been an interesting question in
eighteen seen. But it's quite clear that England did not
want war with the United States. They were concerned about
war with the United States, and so nobody, you know,
don't nobody want that to happen.

Speaker 1 (47:05):
So hard to imagine, you know, we talk about recognition
of the confederacy, it is that that was hard to imagine.
It's very hard to imagine that that translates into actual
military support.

Speaker 2 (47:19):
Yeah, and actually Breton's having quite a lot of trouble
across a very large empire in the mid eighteen sixties,
when you're fighting in Australia and India and Africa. I
don't think that they were ever going to be interested
in that. Of course, there is this question though, because
Canada does have a unique force. That's of course where
the Sasquatch come from. And as we've talked about in

(47:39):
other episodes, if you had nine foot tall, muscular guys
joining the Confederate army, that could be as much fun
as what was the move they had vampires? Right, So
if the South, if the South had you know, raised
a regiment of Sasquatch to join with the Confederate prisoners
that were in Canada, does that changed the equation at

(48:00):
could Chicago have been defeated by a Sasquatch?

Speaker 4 (48:03):
First of all, this this brings up the most interesting
point of all, and that is that you know, up
until the early twentieth century, raids across the border from
Mexico were a considerable problem to the United States. If
this effort had been supported from the north by Sasquatch,
who was intimately familiar with the terrain, knows how to fight,

(48:24):
knows where all the good places are for ant bushes,
I think that at this point you would see a
fundamental change in the nature of the warfare. The Federal
the Union Army would have to create an anti Sasquatch elimination.

Speaker 1 (48:36):
Which would be an amazing and amazing movie, because we're
talking about a force that can literally disappear into the
forest like this is true, is mystically and so that
that would be quite a fight. I think we would
have had trouble. I don't think you can protect the
border against the Sasquatch. They're going to get across it.

Speaker 2 (48:54):
But it does work on the philosophy of the Sasquatch
would be pro Confederate, and you would have to think
it would have been brother against brothers sort of thing.

Speaker 3 (49:01):
That's true.

Speaker 1 (49:02):
I don't know how the Sasquatch culture on, especially eighteen
sixties Sasquatch.

Speaker 3 (49:07):
Culture, yeah, up on the newspapers.

Speaker 4 (49:09):
Now, if the Sasquatch, if the Sasquatch were also primarily
from Quebec, and they would not necessarily have cared about
the British at the time, perhaps they would have fought
on the side of the Union to eliminate this nascent
rating force headed up by the equivalent of Pancho Villa

(49:30):
from Toronto, who was raiding into the Northern States to
try to call some economic economic disruption. In that there
is actually half of a half of a serious point,
which is what if several hundred pro Confederates just put
together a cavalry force and decided to start raiding into

(49:52):
the Northern States, disrupting some of the rail networks, burning
some farms. Again, is it going to affect the war,
especially in eighteen sixty four or probably not? I would say, however,
the Federals would have to at that point recognize that
this is no longer a Napoleonic war sixty years later,
that the tactics have changed, the technologies have changed, and

(50:15):
the threats have changed. It might have actually introduced the
concept of state sponsored guerrilla warfare at an earlier at
an earlier age than it really got hold in the
Western military tradition.

Speaker 1 (50:30):
Now, the South did have some some beginnings to that kind.

Speaker 3 (50:33):
Of yeah, I mean kind of fighting.

Speaker 2 (50:35):
I mean Missouri, I mean you had lots of sort
of gorilla fighting going down there, and that was truly
brother against brother.

Speaker 3 (50:42):
I guess it's an interesting idea.

Speaker 2 (50:43):
What if what if the Confederates that were in Canada instead,
you know, a crazy plan to take Chicago. What if
they worked in cohort with quebe Quah to create a
new confederate state in Canada to take a piece of Canada,
whether supported by Sasquatch or not. I mean, is there
was there a better chance there of creating a confederate

(51:05):
state in Canada. Again, Canada militarily was wasn't that large
that could that could actually open a second front against
the Union from from the north. I never never really
thought about that. I don't know if there was truly
a Canadian independence movement that kip Quaba. I mean, we're
not too far off from you know, when they're having
the Red River rebellions and stuff like that, that you know,

(51:25):
that might suggest that there better The better plan would
have been to seek allies in Canada and make a
piece of Canada a Confederate state that could raise and
arm and invade, you know, as like another state.

Speaker 1 (51:38):
Yeah, it certainly would have complicated matters if they could
do that.

Speaker 4 (51:42):
Another this brings another possibility about an aspect of the
Civil War that doesn't get a lot of coverage in
the books. But the Confederates were working with the American
Indian tribes where they could. The Union of Horse was
doing the same thing, but the Confederate I think had
a little better. They had a little better press because

(52:03):
they were the ones who were standing up to the
Blue coats. So and there are some significant battles where
American Indian participation makes the battle a far more interesting battle.

Speaker 2 (52:15):
The last Confederate general officer to surrender was stand Wait, right,
was Cherokee. It's interesting because we were taking Confederate prisoners
and say we'll feed you if you'll join the Union
army and not to fight the South, but go fight
on the frontier, because we were still having wars on
the frontier at the time, right, And they call those
galvanized Yankees, they call those But that's interesting. What if

(52:36):
instead of you know, saying we're going to attack New
York whatever, what if the the Confederates in Canada had
worked to move with the Native Americans in the West
where the US Army had been you know, stripped, and
where a significant part of the US army that was
there were Confederates that we put in blue outfits. That's interesting.
There's there's an interesting idea of a plant. What if

(52:58):
they saw allies among the the Lakota and the Cheyenne,
and instead of trying to come to Chicago. I mean,
you know, we're talking still a wild frontier there, but
I mean, it would have been a lot easier to
cross the border in North Dakota. It would have been
a lot easier to raise a force of arms out
in the frontier than it would have been you know,
in Toronto.

Speaker 1 (53:18):
Because it wouldn't it would be harder to stamp that out.
You wonder if you have these, you know, how many
of those, you know, new fronts, even if they're fairly small,
how many of them do you need before you do
wear the union out? Because the truth is, we know
that there was there was a limit on that time too,
but it turns out the limit was longer than the
South had. That's the question is if you could have

(53:39):
extended that long enough to get some kind of negotiated peace.

Speaker 2 (53:43):
Yeah, I think eighteen sixty four is too late to
be trying to win a war of attrition by reducing recruiting,
but I mean earlier on it could have been too.

Speaker 3 (53:51):
But I mean that's if the same army that defeated.

Speaker 6 (53:54):
That won the Battle of the Rosebud and the Battle
of the Little Bighorn, if that army had cooperated with
and worked with the Confederacy, then you know, I don't
know that they had any reason to believe the Confederates
are being nicer to them. And you know, the Cherokee
also had some slaves, you know, and home, and that
was you know, part of w that you don't find
that up in the in the Northern Plains tribes. If
if if that army had come together with them again

(54:17):
you know, you know, sitting ball for a while, went
up into Canada. Uh, that that actually could have been
I mean, that's a more realistic idea of having a
force under arms that threatens the Union and requires a
major redistribution of troops than saying that you're going to
suddenly arm Camp Douglas and you know, try to turn
a bunch of starving prisoners into a you know, into
a fighting force.

Speaker 3 (54:37):
It's an interesting idea.

Speaker 4 (54:39):
Yeah, And the actual you know, the actual history bears
out that when Texas raised troops and decided to try
to march it forwards Colorado to disrupt the precious metal
mining that was occurring in Colorado, that that was serious
enough that you know, forces had to be raised and
the the Union had to start thinking about, Okay, you

(55:02):
know what if they you know, what if they take
Colorado and then take a left left turn and had
to work.

Speaker 2 (55:07):
Out you know, again, it's hard to say if that
was ever, you know, realistic, if simply was realistic.

Speaker 3 (55:11):
But I mean, at the time, because that was.

Speaker 2 (55:12):
Very old in the war, Colorado could fairly quickly raise up,
you know, several thousand militia, but I mean by eighteen
sixty four, you know, had there had the force that Colorado,
which I think Colorado actually raised more troops than any
of the territory.

Speaker 3 (55:27):
But I mean, would would Colorado have been able to
find that.

Speaker 2 (55:29):
Many men that will be able to come under arms
any sixty four or had they all been already sent
sent a war?

Speaker 3 (55:36):
It's an interesting question too.

Speaker 4 (55:37):
Yeah, and you know there's probably also of percentage of
those militia who are far more interested in staying in
Colorado and keeping themselves safe from at that point a
very real Native American threat that could could and did
flare up periodically. So yeah, again, these are I'm throwing
out some pretty you know, far fetched ideas. It's those

(56:01):
are the ideas that very occasionally do actually end up
in causing a ripple that you know, would significantly affect
what we understand is this.

Speaker 3 (56:12):
I mean, it's interesting on this topic because we've had
a lot of these. It's interesting on this one. We're
straight up talking a plan to affect the war, and
we seem to be struggling to find a way that
it was ever going to affect the war where another
you know, in some of these other ones, we've been
able to, like, you know, prevent the Second World War
from something that happened in Rome.

Speaker 1 (56:29):
But if you could have impacted it, it would have
made a big difference. But admittedly it's and this comes
somewhat with the hindsight of history, but it is it
was hard for the South to win that war.

Speaker 2 (56:41):
It is I think that the most realistic you could
even think of in eighteen sixty four is if something
could have happened that's so distracted Grant that he had
to send enough troops that relieves the siege of Petersburg
and Lee gets free, abandons, Richmond gets free and is
able to do what he was trying to do in

(57:01):
the Appomatics campaign, and combined with with Beaureguard, the point
that you've taken all of the Confederate armies pushed him
into one army that's smaller than the ones that are
chasing them. I mean, that could have could have delayed
the war by a few months, right, I mean, but
how much could that have changed if you're if you're
having to abandon your capital to try to combine with

(57:22):
the only other force that's left.

Speaker 3 (57:24):
You know, it's still what were they.

Speaker 2 (57:25):
Gonna go down defeat Sherman and then come back and
defeat Grant in detail, It's kind of it's kind of
hard to imagine.

Speaker 1 (57:31):
It's it's hard to imagine. It's hard to imagine a
distraction large enough that Grant, you know, has to abandon
the siege.

Speaker 3 (57:38):
It is.

Speaker 2 (57:39):
I mean, Early burning Washington might have sent quite a
few troops out there, because if Early had taken Washington,
it would have been a lot harder to root him out.
Then it would have been to keep him out in
the first place enough to break the siege enough to
get Grant.

Speaker 3 (57:53):
I mean, it was, you know, it was a reasonably
close thing. Appomatics. The Appomatics campaign was so I.

Speaker 2 (57:58):
Would say, in terms of shifting the election, it would
have been less likely to push people towards McLelland and
more people likely to push towards Fremont and then.

Speaker 3 (58:05):
To see if they'd actually have fired in New York
or did any of these plans.

Speaker 2 (58:08):
It was more likely to move them towards the guys
that were looking for a much more harsh reconstruction than
it would be to move them to the ones that
are saying, oh, well, then you know, we'll come to
a negotiated settlement, have to set fire things and burn people,
and I don't know, raised up to Sasquatch or whatever
else that we had gone.

Speaker 4 (58:24):
That brings in another possible counterfactual. What if the Confederacy,
instead of focusing on burning New York had instead tried
to put together a comprehensive plan to assassinate Lincoln during.

Speaker 2 (58:35):
The What if they'd done that just several months earlier,
because that might have been Again, we really don't know
if these if this group had anything to do or
had anything material to do with the assassination of Lincoln,
but there's some argument that they may have.

Speaker 3 (58:48):
What if they had done that earlier. What if that
had happened.

Speaker 2 (58:50):
In, you know, before the election of eighteen sixty four,
or that that happened the summer of eighteen sixty four.

Speaker 4 (58:55):
Now that has major consequences. If Fremont wins the Republican
nomination and clean towels of the Moderates who are looking
for a relatively mild reconstruction and instead go down with
a heavy hand, then you know, is it possible that

(59:16):
you would have had another American Civil War or would
you have had a regional hatred that you know, would
persist for quite a while. And it's interesting, despite a
relatively calm and measured reconstruction, there are still quite a
few people in the South who are not very fond

(59:38):
of and.

Speaker 3 (59:39):
That's start today. That's certainly true.

Speaker 2 (59:41):
You know, it's an interesting question too because because Hamlin
was the vice president at the time. This is before Johnson, right,
if you kill him before the election, and honestly, I
don't know enough about I mean, Hamlin was up from Maine,
and he was quiet. I mean, he was quite enough
at replacing him on the ticket in mean much, though
you have to think in the summer eighteen sixty four
he might be a upset that he was not the ticket.

Speaker 3 (01:00:03):
And then he killed Lincoln and he's suddenly the president.
How does that change the election? I don't know how
Hannibal Hamlin would have.

Speaker 1 (01:00:10):
I wondered that same thing as I was, like, man,
Hannibal Hamlin as president. That's an interesting Uh, it's true too.

Speaker 2 (01:00:16):
So, I mean, but I would be better prepared to
fare what Johnson would do because Johnson actually was you know,
president to an extent during a bit of a bit
of the war and Hamlin I said, it's more of
a question to me, though I don't I guess Hamlin
was maybe more of a warhawk. What would the nation
have thought? How would that have impacted the eighteen sixty
four election? What would the eighteen sixty four election be
like without Lincoln? If instead of trying to set fire
to New York, if they had actually tried to do

(01:00:38):
the Lincoln plan and they've been successful, I mean, could
that have materially changed the war? It seems to me
again that we are more likely to move to someone
who's more likely to be more harsh than someone's going
to be, you know, pushing peace. I honestly don't even
know McClelland was serious about peace. I think he was
aiming for the you know, the peace part of the party.
But I don't know if if you had assassinated Lincoln

(01:01:01):
and because of that McClellan ends up winning the election
in eighteen sixty four, you know, after them killing Lincoln,
see actually going to try to negotiate peace, you know,
with a guarantee of slavery.

Speaker 3 (01:01:13):
So again, it's hard to in terms of all the counterfactory.

Speaker 2 (01:01:17):
Is done, it's hard to really see anything in eighteen
sixty four having changed the war that it seems it
feels like the most they could have done is make
people more mad.

Speaker 4 (01:01:25):
Yeah, and that would have some definite that would have
I think that there may have been some fallout, especially
coming into the late eighteen hundreds and the early twentieth century.
Can you imagine a United States under a theoretical administration
of Teddy Roosevelt after he has fought a bitter struggle

(01:01:51):
to become president of a country and half of the
country is actively working against him because the reconstruction of
the out was far harsher.

Speaker 2 (01:02:01):
And yeah, that's they were still there. A harsher reconstruction
is another counterfactual. It's kind of hard to say exactly
what that might have meant. Uh, you know, Lincoln had
his idea. There were people who want it to be easier,
and there were people who wanted it to be harder,
and there was you know, the thought was that Johnson
was going to be harder, and Johnson decided to stick

(01:02:22):
with Lincoln's plan because he thought he should do what
Lincoln planned to do the way that he'd become president.

Speaker 3 (01:02:27):
So that's I mean, that's an interesting question.

Speaker 2 (01:02:29):
It's funny that we we seem to have more ability
to come with large, grand counterfactuals off of potatoes. The
Confederate Secret Service, it seems it's interesting they had all
these plans and they and you know, they had decided
to put so so I guess the other counterfactuals. If
they had put significant money into their secret service earlier,

(01:02:54):
they'd done that in eighteen sixty two, maybe they had
a better chance of formulating some sort of plan that
might have actually made a difference.

Speaker 4 (01:03:03):
And that plays into something where as I alluded to
in the early to mid twentieth century, was when basically
spy organizations really turns from a amateur or ad hoc
effort into actually an organized and very well thought out effort.

(01:03:24):
And both the Union and the Confederacy had their moments
where the ad hoc worked reasonably well with the great
Locomotive Chase, very much ad hoc. Now if you had
a professional organization who had actually trained for that.

Speaker 2 (01:03:40):
Now, what if we'd really trained them like British commandos
or something. I both found I think good success and
intelligence networks as you would maybe expect on or where
brother was against brother and you.

Speaker 3 (01:03:50):
Had a lot of cultural connection and stuff like that.

Speaker 2 (01:03:53):
I mean, so that they were always sympathizers somewhere that
we're willing to think out. But so I think they
had some success there. But yeah, you're right, maybe, you know,
maybe if they'd actually developed a professional secret service. But
I mean, what if we were really training a secret service,
an oss an sas or whatever either side had at
this time. I mean, could they have made more difference?
That's interesting. I mean, and this might have been the point,

(01:04:15):
you know, when they're starting to put real money into it,
that they were willing to do that. The idea that
the Confederates had these ideas shows that there was a
spark of an idea there that would turn into something.
You know that by the Cold War, I mean, these
sorts of Sheneaniicans were much more powerful.

Speaker 1 (01:04:29):
Thank you for listening to this episode of The History
Guy podcast. We hope you enjoyed this episode of counterfactual history,
and if you did, you can find lots more history
if you follow the History Guy on YouTube. You can
also find us at the historyguy dot com, Facebook, Patreon,
and locals. If you want to hear more counterfactuals, stay tuned.
We release podcasts every two weeks.

Speaker 7 (01:05:01):
In active can Act became evening and

Speaker 3 (01:05:15):
In
Advertise With Us

Popular Podcasts

My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.