Civil War Spies: Allan Pinkerton

Allan Pinkerton fell into detective work when he discovered a gang of counterfeiters in Illinois. In 1861, he helped thwart a plot to assassinate Abraham Lincoln, which may have led Lincoln to later tap Pinkerton to organize the first Union espionage.

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Episode Transcript

Speaker 1 (00:00):
Welcome to Stuff you missed in History Class from how
Stuff Works dot com. Hello, and welcome to the podcast.
I'm to bling a chalk reboarding and I'm out. And
a couple of months ago, we put out a call
for Civil War podcast ideas since it is the one

(00:22):
and fiftieth anniversary of the Civil War and all, and
listeners have actually sent us some really cool suggestions. Yeah,
we have quite a list going, and we don't want
you guys to think that we haven't looked at them.
We're looking at them and just trying to figure out
the best way to sort of organize them and approach
them in a way that makes sense. But luckily, the
observance of this anniversary is going on for the next

(00:43):
four years or so, so we'll have plenty of time
to sift through them and address some of those requests
as we go along. In the meantime, though, we wanted
to go ahead and take a look at some interesting
characters who participated in a side of the Civil War
that we are particularly fascinated by, and that's espionage. Who
isn't fascinated by espionage? Yeah, it was actually something of

(01:04):
an evolving art during the Civil War, but it became
invaluable for for political and military strategy at the time. Yeah,
at the time, though, espionage wasn't something that was taught
at military academies like West Point, I mean, obviously if
it was evolving, So spying was mostly left up to civilians.
Like this episode subject Alan Pinkerton, and he essentially organized

(01:26):
the first Union espionage. So he's a really interesting character
in that sense. But his work around this time was
essentially the foundation for the U. S Secret Service as well,
So he's got a dual role going already. And if
you haven't heard of him because of his connections to
the Civil War, you might have heard of his work
as a private detective. Some people call him the world's

(01:47):
first private eye. That's probably a bit of an exaggeration, um,
but there were definitely private detectives before. Still, though Pinkerton
did have a unique style, he certainly helped develop the
art of being a private eye. He did, and he
also founded the country's first national detective agency, Pinkerton's National
Detective Agency, which became quite successful and famous, and its

(02:11):
organizational structure was actually used as a model for the
Federal Bureau of Investigation the FBI, So several of the
agency's assignments catching outlaws of the wild West and some
strike breaking cases as well, would make great podcast topics,
but here, for time's sake, we're just going to focus
on his involvement with the war. But first, how did

(02:32):
he become a spy in the first place? He literally
stumbled into it, as as we're going to find out.
So we have one version of Pinkerton's early years that's
generally accepted, even though not everyone goes along with that.
For instance, Bruce Jurry, who edited an anthology of Pinkerton's
autobiographical writings, said, quote, Pinkerton conflated stories and contradicted himself

(02:54):
all the time, So it makes him an interesting guy,
but it also makes it sort of tough to to
try him. Yeah, that's true, and so some of these
details might be embellished, but here are some of the
basics that most sources accept as fact. Pickerton was born
in Glasgow, Scotland, on August eighteen nineteen. His father was
a police sergeant who died when Alan was young, leaving

(03:16):
the family in a pretty bad position money wise. So
Alan was apprenticed to a cooper or a barrel maker
by age fifteen and that's how he made a living.
So just an aside here, just to show you how
sources can differ and why some people aren't really sure
if he embellished or not. Some sources say that his
father lived till eighteen forty one, so that wouldn't have

(03:36):
supporting family exactly, and was a weaver instead of a
police sergeant, so some details may have been changed here,
But regardless, Pinkerton became involved with a militant labor group
known as the Chartists, who sought political and social reform.
His involvement in Chartism actually led the authorities to issue
a warrant for his arrest, so he ended up having
to escape to American in eighteen forty two along with

(03:59):
his new wife Joe and Carfrey. And this was supposedly
on the very day that of their wedding that they
had to do this, that they had to flee. So
pretty dramatic honeymoon. Yeah, dramatic and also maybe a little
bit exaggerated. Um. So, the first US city that Pinkerton
lived in was Chicago, and the next year he moved
to a town called Dundee, Illinois. It's about forty miles away,

(04:21):
and he set up a successful Cooper business. There a shop,
and one day in around eighteen forty eighteen forty seven,
he was out chopping wood on a deserted island on
a nearby river. So obviously, if you're making barrels, you
need wood to make them with. And some people said
that Pinkerton was was thrifty and he didn't want to
pay for wood for barrel staves, so he went chopped

(04:44):
at town himself. But regardless, he's out on this island
and while he's there, he discovered a gang of counterfeiters
and they didn't see him, so he went back to
town and he got the sheriff. The sheriff was able
to catch the gang red handed, and after that, the
sheriff offered him a job. Good discovery, I guess yeah.

(05:05):
He was offered the position of deputy Sheriff of Kane County,
so it was sort of a side gig for him.
He still had his Cooper business um, although after a
few more successful cases, he was able to sell that
business and moved to Chicago to pursue a career. It's
a full time private detective. Sounds like a movie beginning, right,
It really does, But initially most of Pinkerton's clients where

(05:27):
government agencies, so it's not like glamorous as you're you're thinking, right.
For example, one of his clients was the U. S.
Treasury Department. They hired him to find other counterfeitter gangs.
They figured, hey, he's good at this, let's let's put
him on the case. Um. The US Post Office also
had him looking into mail theft, and the Sheriff of
Cook County enlisted his help in some of his toughest cases,

(05:48):
so he eventually also appointed him Deputy Sheriff of Cook County. Um.
He still did private work on side as well too, though,
so we've got a lot of different gigs going on.
But by eighteen fifty five, Pingerton left the police Force
to start the Northwest Police Agency, which was a private
detective agency that was really the first of its kind.
It had a sign with a wide open eye on

(06:11):
it that became its symbol, So are a real private
eye kind of deal. And you can google it symbol.
I mean, you can look it up and see it
and you'll probably be like, oh, yeah, I've seen that
before definitely, And I mean the company's slogan to you've
probably heard that. It's we never sleep, So he's this
this is sort of laying the foundations for for what
we think of as private detectives for sure. Yeah, so

(06:32):
he is a detective at this point and also a
sort of businessman. He's growing into that role as well.
And at first it was just Pinkerton and about three
to five other employees, and they were specialized in railway
theft cases in Illinois specifically at that time, most of
the state's railroads ran through the countryside where the police
really couldn't protect them or prevent employee theft, so they

(06:55):
could be held up, or or somebody working on board
the train could steal, yeah, could take some of whatever
they were shipping, you know, in their freight cars, or
you know, pill for ticket money. As we'll see, the
detectives they did their work disguised as passengers, since many
of the trains did have both passenger and freight cars.
And right away they caught a conductor who was pocketing

(07:17):
money as we mentioned, and railroad employees unloading merchandise in
the middle of nowhere. So that's how they would steal
stuff without people detecting them. That's the equivalent of it
dropped off the back of the track right, So railroad
workers obviously hated them, but owners began to rely on them,
and by eighteen sixty one, Pinkerton and his men had
been employed to police railroads and other states too. Yeah,

(07:38):
and it was while he was out on one of
those out of state jobs, investigating threats by satners against
a Northern railroad company in Philadelphia, that Pinkerton overheard a
piece of information that eventually led to his involvement in
the Civil War. Or did he the crux of the
matter here, Yeah, because it's still for to be whether

(08:00):
Pinkerton's story was actually true. But in January eighteen sixty one,
he claimed that he heard rumors of a plot to
assassinate President elect Abraham Lincoln. Supposedly a group of young
Southern slave owners calling themselves the Knights of the Golden Circle,
planned to shoot Lincoln in February eighteen sixty one as
he passed through Baltimore on his way to Washington, d C.

(08:22):
The existence of that plot, though, has never been proven. Yeah,
and it really proved to be uh kind of an embarrassment.
As we're going to find out that Pinkerton convinced Lincoln's
advisors to have Lincoln change his plans and travel Incongnito
on a different train in the middle of the night
and Pinkerton Road shotgun in the caboose, and he had

(08:42):
agents placed at all the bridges and the major crossings,
and they'd give him all clear signals with lanterns, so
too long flashes, a pause, and then two more flashes,
and the train did arrive safely in Washington. But people
weren't really impressed, or at least not everyone was impressed,
and a lot of people saw Lincoln's actions as cowardly,

(09:03):
just kind of silly, and just when they wanted to
have a courageous, dignified leader, they have this guy traveling
in disguise, and of course, you know, we don't. We
don't think anything of something like this. Now, of course
you would, you would try to protect the candidate, and
you would recognize any threat, even if you don't know
what's necessarily behind it, but not at this time. Yeah,

(09:24):
people made fun of them. And it's unclear whether he
I don't know if he was actually traveling in disguise,
but newspapers reported that he was because he showed up
in a soft wool hat instead of a stovepipe when
he got off at Washington got off the train, and
so people when people saw this, they spread the story
that he was wearing a Scotch cap and a plaid shawl.
And Pinkerton's code message back to Harrisburg was pretty laughable

(09:47):
too at the time. It said, quote plums delivered nuts safely,
Pinkerton being the plums and Lincoln being the nuts. So
it's still pretty laughable. The worst code ever, I think, yeah,
it doesn't really go along with a serious covert operation.
But it also didn't help that they weren't able to
prove that there was a real threat. The mayor of Baltimore,

(10:08):
for example, had the rumors investigated and said that they
were baseless. So what really happened here? Somethink that Pinkerton
just made the whole thing up to get a little
bit of glory. Still, others, however, including Dorothea Dix and
some detectives from New York City who came down to
investigate the situation, thought that Lincoln was really wise to
do what he did. I mean, whether, yeah, whether the

(10:31):
threats are serious enough, it's better to stay on the
safe side. But Lincoln was still pretty embarrassed by the
whole thing, maybe especially the information about the Shawl, even
if that was made up, But he didn't take it
out on Pinkerton. You'd think maybe he just wouldn't trust
that guy anymore, and instead he gave the detective another opportunity,
in fact, a much grander opportunity. Yeah. So that April,

(10:53):
after the attack on Fort Sumter, Lincoln asked Pinkerton to
organize a federal secret service, which was basically a network
of spies that could have inform on Southern sympathizers around Washington.
And they were really good at us. For example, Pinkerton
caught a Southern spy and socialite named Rose O'Neill greenhow
who had been gleaning vital information from her suitor at

(11:15):
the time, Senator Henry Wilson of the Military Affairs Committee.
When it came to military work, though, Pinkerton's secret Service
was a much less effective. He directed intelligence operations for
General George B. McClellan, who I'm sure all of you
guys have heard of. After McClellan assumed command of the
Army of the Potomac. Yeah, and McClellan had already known Pinkerton.

(11:36):
He knew him from his role as a railroad executive
before the Civil War, but he didn't get such a
great reputation as a commander McClellan. That is, a lot
of people thought that he was overly cautious. You know,
he had built this great grand army and he kind
of just wanted to keep it together and not go
out and use it. He was also judged for always

(11:57):
seeming to be running away from the n ME instead
of running toward them and engaging them. Yeah, he seemed anxious.
I mean, others who commented thought that he almost was
looking for any reason not to confront the enemy. And um,
it seems like Pinkerton kind of gave it to him,
So it probably wasn't entirely his fault. He had asked
for these reports from Pinkerton's secret service so that so

(12:19):
that McClellan would know the size of the approaching Confederate armies,
and according to an article by Lloyd Lewis and the
Journal of the Illinois State Historical Society, the statements Pinkerton
turned in usually overestimated the enemy's strength by about a
hundred percent. For example, on June, Pinkerton estimated the enemy
at two hundred thousand men, when actually it was only

(12:40):
like eighty thousand. Yeah, so that makes you reconsider McClellan's
cautious reputation a little bit. He's getting numbers like that,
so we have to wonder why did Pinkerton mess up
so badly? However, those numbers so far off, and Lloyd
theorizes that it's because Pinkerton was inexperienced in war, and
he also hadn't yet established the organizational system that would

(13:02):
become the true hallmark of his agency. And eventually that
organization system was used by all military intelligence operations, and
it had to do with assembling a lot of small
details which, put together, could solve a mystery people. I mean,
this is later, but Pinkerton's people would send in reports
every single day from the field, and those reports were

(13:24):
written out and filed systematically by clerks, you know, putting
every single little piece together. So the inside of his
agency almost looked like it was a big mail order,
how stacked high with all of these papers and all
of his filing going on. But he wasn't to that
point during the time he was working for McClellan. Yeah. Well,
either that or he just didn't apply this method to

(13:47):
his work. In the war. We're not sure, but either way,
Lincoln dismissed McClellan in eighteen sixty two and Pinkerton was replaced.
He did a few things for the government during the
war after that, but it was more about catching profiteers
that sort of work. After this, Pinkerton mostly put his
energies back into his agency, which he renamed Pinkerton's National

(14:07):
Detective Agency. Okay, so his work in the war wasn't
a complete success, but Pinkerton's detective business was very successful,
especially when it came to protecting property and money, which
is sort of how he started out in the first
place with that counterfeiting gang. And we mentioned his work
in the West earlier. His agents, who became widely known

(14:29):
as the Pinkerton's hunted down wild West outlaws like Jesse
James and Butch Cassidy and the Sundance Kids, so you know,
really big names and their work or the Pinkerton's work
out there really helped curb that post war epidemic of
train robbers too. So the law general lawlessness that was
going on in the United States at the time. Yeah,

(14:50):
and as America started industrializing, which was also what was
going on at the time, Pinkerton's agents also started working
for company bosses and against labor unions as strikebreakers. And
this is kind of ironic because of Pinkerton's background as
a chartist, But Pinkerton at this stage of the game
saw strikes and riots as a threat to society. Yeah.

(15:12):
Obviously an older man too, and in a different place
in his life than he was back in Scotland. Yeah,
his whole thing was about catching people who were doing
things counter to society, you know, people he saw his enemies,
bad guys, and to him, people who were striking, and
a lot of times in those days strikings left to riots.
I mean, obviously they were considered enemies to him. Yeah,

(15:33):
And if we sort of consider his legacy as a
whole to despite some of his choices and those questions
about the validity of the Lincoln assassination threat, most considered
Pinkerton to be really amazing at what he did and
honest and diligent at his work too. He guaranteed to
turn down any reward, he worked only for an agreed

(15:55):
upon flat feet. So it reminded me a little of
Eliot and Nass or someone you know can be bought
and he didn't accept divorce cases because, according to Derry,
he didn't want to quote go down into the sewers
of humanity or quote have his men crawling around in
the undergrowth like peeping tom. So he's certainly maybe even

(16:15):
from a Civil war experience, he knew what he was
good at and in the direction he was he was
going to go. Yeah, and he also pioneered certain strategies
that are now classic detective moves, like covert surveillance, which
was referred to as shadowing, and the assumption of false identities,
which now we know is working undercover. He also published

(16:36):
eighteen books of memoir and he once wrote, quote the
detective should be hearty, tough, and capable of laboring unknown
to those about him. I shall not give up the
fight with criminals to the bitter end. And Debiliana, you
and I were talking about these memoirs earlier, and while
Pinkerton has a reputation as being one of the first
private eyes, he said he also has sort of a

(16:56):
reputation as helping start detective book too. Yeah, that was
the gist of this interview that I read with a jury,
and he said, I think the way he put it
was that Pinkerton can be considered not just the father
of the detective, the detective, I should say, the modern detective.
He can also be considered the father of the modern

(17:17):
detective novel or detective memoirs. Yes, absolutely, Speaking of detective fiction,
Pinkerton's agents have been featured over the years in various works,
and for example, in a Sherlock Holmes story called The
Valley of Fear. I know we have a lot of
Sherlock Holmes fans since we did the Who Was the
Real Sherlock Holmes podcast a few months ago. Uh, And

(17:38):
in later James Bond novels as well, there's a character
called Felix Liter who works for Pinkerton's so it makes
its appearance here and there. Yeah, And we were talking
to you about how how different he is from the
Sherlock Holmes inspiration. You know, he's not the intuitive type
of detective. He's the smart kind of detective who sort
of figures out these new methods like covert surveill and

(18:00):
the assumption of false identities. You know, a different, different
kind of man. Yeah. Well, I think since he, as
you mentioned earlier, since he fell into his work, his
line of work quite literally we don't have as much
information about how he developed these skills of his. He
just sort of became a detective and then he developed Yeah,

(18:21):
it was just job one day, and then he developed
these methods which were so unique at the time but
have become so core to what we think of as
the iconic detective. Yeah, for sure. So he died July one,
eighty four, but his company is still around today. It's
a subsidiary of Secure Toss, although now they are more
of a of a security company, so not quite as

(18:44):
detective sparring as as he might like to think. Yeah, well,
now we have the FBI and the Secret Service and
all these other agencies, so we don't have a need
really for all the private eyes. Yeah, for an agency
as Pinkerton's was originally, But it's just another way that
you might have heard Pinkerton's name if you haven't read
about him in history books or read about him in novels.
I think that's all the time we have for today

(19:06):
to talk about Pinkerton, although I'm sure we'll get a
chance to talk about them down the road. I mean
the wild West stuff, especially my votes, my votes in
that camp, Sarah's votes for the wild West stuff. I
don't want to talk about the Molly McGuire's a secret
society of coal miners, the Pinkerton's Men in full Traded
and everything that went on with that, So definitely more

(19:28):
material to delve into there. But if you have anything
to contribute to this story that we talked about today,
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want to learn a little bit more about the Federal
Bureau of Investigation, which we mentioned in close connection to

(19:49):
Pinkerton and it's it's a history and it's operations today,
you can look for it on our home page by
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(20:11):
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