February 14, 2011 • 28 mins
During Prohibition, the US was awash in booze-fueled crime. Gangsters feuded savagely to control their turf, especially in Chicago. On Feb. 14th, 1929, these rivalries culminated in one of America's most notorious unsolved crimes. Tune in to learn more.
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Episode Transcript
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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 Sarah Dowdy and I'm Deblina Charko Boardy, and we
have a Valentine's story that may kind of change the
way you think about Valentine's Day. Valentine's Day, of course,
(00:23):
usually conjures up images of hearts, flowers and pretty lace
trimmed cards, but if you're from Chicago or you're a
true crime buff then it may have very different connotations.
And that's because it was February fourteenth nine that the
Valentine's Day massacre, which was one of the most famous
unsolved crimes in US history, went down in the Windy City.
(00:44):
It was obviously a terribly brutal crime, and it incorporated
a lot of the unsavory elements in Chicago, all the
stuff that was going down at the same time, gangsters, bootlegging,
dirty cops, and we don't want to leave out the
top guns stuff. Lena and I were talking about it earlier.
I liked you said, the Tommy guns are pretty much
another character, and there an extra person almost in this.
(01:08):
But but we didn't get a chance to go too
much into that that they do. That you play a
part here, but it all actually starts with something that
was intended to make life a little more virtuous, and
that was prohibition. And that's kind of like the irony
of the whole thing is that prohibition is what sort
of instigated this whole kind of wave of events that
(01:29):
is going to happen here. But we have a whole
podcast about prohibition. But the general just was that in
January n the eighteenth Amendment to the Constitution went into effect,
and this prohibited the manufacturer, the sale, the export, the import,
the transportation, all that having to do with alcoholic beverages.
It didn't ban personal possession and consumption though, so that
(01:50):
was kind of sort of an extra side note to it.
You could you could drink it if you had it,
so if you had your own personal stash, you could
consume it. You just couldn't buy it. They were just
to see ming that if you procured any you'd be
breaking laws anyways. Um, So prohibition almost immediately started a
new wave of organized crime, which was centered around bootlegging.
(02:11):
I mean, it really did start immediately. Some sources described
whiskey trucks in freight cars in Chicago being hijacked just
an hour after prohibition went into effect, and um Katie
and I did an episode on the molasses explosion. That's
another sort of immediate effect of prohibition, or leading up
to it, at least people people reacted quickly. Yeah. I've
(02:35):
even seen prohibition described as the engine that drove the
gangster era. So again sort of seeing the irony here
of wanting to do something good but having it all
sort of terribly ironic, terribly wrong immediately. So we should
give a little background to this though. There were gangs
before this, but they were mostly weren't too things like
(02:56):
muggings and robberies, and as far as business interests went,
they controlled gambling and prostitution type establishments to make money.
So with bootlegging, though, gangster saw the opportunity to really
turn crime into more of a business, into up their
profits considerably. Along with that, though, came the inevitable jostling
for territory between rival gangs, you know, I mean turf wars.
(03:19):
That's basically how we think of gangs today too, definitely,
and in Chicago is most notorious for that, right, It
was notorious, I guess for the outright gang on gang warfare.
The gangs there, they didn't even really try to hide
it or conceal it at all. The gangs attacks on
each other were often really horrible and gory, but it
was mostly just gang on gang violence. They generally avoided
(03:40):
attacking just your normal, average citizen on the street. Um
also avoided attacking cops, so I guess as a citizen
of Chicago may have been easier to kind of distance
yourself from it a little bit. Um And from the
police's point of view, they weren't really making things too
hard on the gangsters anyway. Local mobs often paid off
cops to look the other way while bootleg alcohol shipments
(04:04):
were on the move. Some cops even participated. They would
get paid off and they would write on trucks to
make sure that the alcohol actually reached its destination the
way it was supposed to. And some politicians were in
the pockets of gangsters too, So those of you who
watched gangster flicks, you're probably familiar with this whole dirty cop,
dirty politician thing. But for for those of you like
(04:25):
romantic comedies, it is just a little background that the
scene of what was going on during these so called
bootleg wars, but we should give you a little more
background two on this. It's not all about bootlegging. They're
also ethnic hostilities involved. That was a really big part
of the rivalries between the gangs and UM. There were
two main gangs in Chicago. Obviously there are many, but
(04:47):
two of the major ones. One was on the South
Side and it was an Italian gang. The other was
on the North Side. It was an Irish gang. And
in the early nineteen twenties a guy named John Torrio
became the leader of the South Side Italian gang and
he originally came from New York and was part of
the Five Points gang there, which had tammany hall connections.
(05:11):
He probably heard of the Five Points gang before, but
it didn't take him long to start to really get
into the Chicago mob scene and make a pretty big
impact there. He worked for the Chicago gangster Big Jim
Colossemo as his business manager, and UM really started to
build his name from there. Yeah, big gym Colosemo. We
(05:32):
should probably say he was kind of an old school
gangster of the gambling and prostitution variety of that we
mentioned before, So that was sort of his deal and
and uh, Torio worked for him. After Prohibition. He was
one of the first to really try to organize this
whole underworld of gangsters, and so many thought of him
as quote to the thinking man's criminal. He really wanted
(05:54):
to make the most of prohibition from a business standpoint,
so that was his whole thing. He wanted to actually
a void strife and bloodshed. His motto was there's plenty
for everyone, and he wanted to work with gangs. He
really worked with them to divide up the territory so
that everyone got a share of Chicago's bootlegging profits. So
so sort of modernized thing. Yeah, and kind of the
(06:15):
opposite of what you think a gangster would be doing. Yeah, exactly.
And he's pretty important though, not just for this ushering
in this new era of gangsterdom, but because he brings
in another young gangster from New York City named al Capone,
and I've heard of him. He may have heard of him,
and um, yeah, he takes al Capone under his wing,
(06:35):
and al later says, quote, I looked on Johnny like
my advisor and father. So you have the the established
gangster and the gangster in training, and they make quite
a pair. Indeed, at the same time, though, there was
sort of a similar kind of thing going on on
the other side of town. Torrio's counterpart on the north
side was a guy named Dion O'Banion, and he was
(06:56):
a roughneck who'd grown up in Chicago's Little Hell neighborhood, which,
for those of you who know Chicago, is now the
area where Cabrini Green, the Public Housing Project housing complex stands.
And Obanion, like Torrio, had a couple of protegees of
his own. Uh. They were Jimie Weiss and George bugs
Moran and perhaps kind of strange for a gangster, for
(07:18):
a tough guy, this was something interesting of note about Obanion.
He had a passion for flowers. He was part owner
of a flower shop called show Fields, and he really
loved to serve customers and apparently could be found on
any given day making flower arrangements. He also provided flowers
for these lavish gangster funerals um which sometimes these funerals
(07:42):
were described as being so huge they were like funerals
fit for kings, and sometimes they had up to like
a hundred thousand dollars and in flowers definite you I
mentioned you were starting to watch The Wire definitely reminded
me of the Wire. These elaborate funerals and elaborate floral displays.
But um, I guess it helps tie things in a
little bit to Valentine's Day. It does passion for flower.
(08:05):
I'm glad you brought that up, Sarah, or totally coming
out of left field, but again we have to go
sort of in a negative, non lovey, devy direction to
say that there was some trouble that did start around
this time when Obanion he went to war with the Italians.
Basically he offered to sell Torrio half interest in something
(08:25):
called the Stephen Brewery, which was one of his interests
that that Obanion owned, and he was responsible for getting
Torio basically caught in a police raid as the steel
was going down. On top of that, he ended up
keeping the five thousand dollars that he made off of
the steel. So not a very friendly gesture towards his
gangster leader counterpart there. Yeah, I think you were saying
(08:47):
earlier his motives were a little unclear and all of
the yeah, he was apparently tipped off about this raid beforehand,
which was what was sort of sketchy about the whole
thing and why Torio ended up getting so at about it. Um.
It obviously wasn't a coincidence, but we can't really figure
out I guess today whether O'Banion just thought it was
(09:08):
funny or if you just wanted to see what would happen.
I mean, it's kind of unclear what he really wanted
to do. Um, he probably just wanted to mess with
Torio and UM, you know, kind of put his rival
gang member in a in a bad place because apparently
O'Banion didn't really have any previous charges at this point,
so he wasn't going to get in trouble. But for
Toria it was a different story. So well, and it
(09:30):
certainly won him no friends. And on November tenth, three
guys walk into Schofield's flower shop on North State Street,
UM saying that they want to pick up a wreath
for the funeral of Mike Merlo, who was a prominent
member of the Italian community. And when one of the
guys reached out to shake O'Banion's hand, it seems like
(09:52):
a pretty nice thing to do. Doesn't seem violent or
we're scary. Um, it turns out that he was just
trying to keep Obanion from reaching for his own gun.
Apparently he kept multiple guns on him at all times, um.
And then the other two guys pull out their guns
and shoot Obanion in the flower shop six times. So certainly,
(10:13):
whatever Obanion's attentions were towards Torrio, Torrio did not much
care for him. No, he obviously did not like that.
But on the bright side, if you want to look
at it as a bright side, Obagion's funeral was apparently
the most lavish that had been thrown for a gangster yet,
and Capone sent a basket of Rosa's kind of a
cheeky bove as we discussed earlier Sarah, but he sent
(10:33):
a basket of roses signed from Al So really nice guy.
But this was sort of, I guess, the whole um
event that set off the chain of events that will
lead to the main story, the Valentine's Day massacre that
we're discussing, Because right after this happened, retaliation soon followed
Himie Weiss, who um he ended up taking over for Obanion,
(10:54):
that's his protege that we mentioned before, and he did
in fact attack and severely Wood and John Torrio, who
was then forced to retire, Torrio left Chicago and turned
over his empire to Capone. So now we have big
Alve versus Himie Weiss, and after that Capone advice. Their
mobs were at war essentially for a couple of years,
(11:15):
and some sources say that Capone tried to make peace
with Vice, you know, get it, so they could get
back to business and stop fighting each other. But Weiss
was sort of a crazy guy who was homicidal and
apparently just kept on rebelling. They couldn't work out any
sort of mob treaty. Yeah, So eventually, because he had to,
(11:37):
I'm sure, Capone ordered Weiss's murder and had him gunned
down with machine guns on North State Street, pretty much
right where Obanion got murdered. Um. It was right in
front of show Fields, because that's where Weiss had kept
his offices, right above the flower shop, and that was
on October eleven. And just stop ordering my flowers from
(11:58):
there at them. Yeah, I think I would switch office locations,
but he did not, um, and so he met his
death there. He met his demise. But this left George
bugs Moran in charge of the North Side Gang. So
now we've kind of hopefully you guys aren't too confused.
But now we've kind of set up all the characters
I think in this in this little play we have
going on here, Um and Marian. He was kind of
(12:21):
a thug too. Yeah, he was definitely better known for
his brawn than for his brains. He wasn't. He wasn't
the leader that his predecessor had been, Obanion. And he
got his nickname Bugs from his temper tantrums to which
is not exactly equality you want to see in the
leader of a gang like this for a leader of
(12:42):
anything for that, Yeah, exactly. So, even though there was
a peace treaty organized in nine between the leading gangsters,
it really didn't look like peace was going to happen
because it was it seemed pretty likely that Bugs Moran
would eventually go off the handle himself. Yeah, and in
these two sides just kind of kept going at each other.
(13:02):
And yeah, Moran and Campone, the North Side Gang and
the South Side Gang, and so it just seemed like
they were going to keep trying to take each other
out and antagonizing each other as much as they could.
And sure enough, even during these years of relative peacetime,
Moran continued to kind of try to stir up trouble
with Capone and his gang. For example, he gave a
(13:24):
kind of silent support to a north Sider named Joe
Alo who tried to assassinate Capone a few times. So
he wasn't the one who was doing the assassination attempts,
but he was sort of tacit encouraging them. Yes. Um.
Another thing, a couple of his own men, Pete and
Frank Gusenberg, who will come up later. They wounded one
(13:46):
of Capone's best guys, one of his right hand men. Um,
a boxer turn gangster named machine gun Jack mcgern. Yeah.
So Marian was certainly not on Al Capone's Valentine's list,
if we're going to make a little joke about our
title here, Um, but he was on another list. He was,
(14:07):
And this is where we start to kind of get
to the heart of our story. In early nine, Moran
was offered and he purchased a shipment of Canadian old
log cabin whiskey, which had supposedly been hijacked from Capone.
And this transaction went off so well, it went off
pretty much without a hitch, so that when the same
people offered Moran another shipment for a great price. He
(14:28):
agreed to it, of course, and that delivery was supposed
to happen at ten thirty in the morning on St.
Valentine's Day, and Moran himself was supposed to be there
to oversee it. And it was to take place at SMC.
Cartage Company, a garage and North Clark Street, which was
basically a depot for Moran's bootleg operation and he kept
some of his trucks there and things like that. Yes,
(14:48):
so we're gonna set the scene for this Valentine's Day morning.
It was cold and dreary and gray, and there were
seven guys at the garage by about ten am. Six
of them we're part of Moran's gang. There were the
Goosenberg brothers who we mentioned earlier, Pete and Frank. There
was a bootlegger named Adam Hayer, a speakeasy boss named
(15:10):
al Wine Shank, and a safecracker named John May who
did a little sidework for Moran as an auto mechanic,
and finally a bank robber James Clark. But then there
was another guy there too who was not part of
the gang. He was Dr Reinhardt Swimmer, who was an optometris. Um,
he was not there performing medical exams. He was he
(15:34):
was just like a friend, kind of a gangster groupie.
He would hang out with these tough guys and brag
to to his own friends about it. Um, sort of
a strange addition to the party. I'd say, Yeah, strange idea.
I think, just a someone who wants to hang around
this kind of underworld scene, but go check out people's
eyes later in the day. Weird, yeah, Um, Or maybe
(15:57):
you were checking out the eyes first and then going
to the gangster stuf. Of maybe this was just a
random morning activity anyway. Also in attendance was May's German
shepherd high Ball, and he was there tied to an
axle of a truck. So again just sort of setting up, Um,
what this morning looked like. Now, all of these guys
except for May, who was dressed in overalls working on
(16:19):
trucks of course, Um, they were all dressed up in
suits and ties. Around ten thirty, a black Cadillac drives
up outside the garage. Four or five men get out
of the car at this point. Um. Eye witness accounts
differ as to how many people they are actually worry
you'll see it described both ways, I think, depending on
which you read UM. A couple of the men were
dressed up in police uniforms and the others are in
(16:40):
clothes that may resemble what detectives might wear. They were
wearing sort of top coats or trench coats. UM. One
description has one of the guys at least wearing a fedora,
so more normal clothing, not uniforms. And when they walked
into the building, the seven men inside, this is what
people generally believe is that they must have a woomed.
It was just a routine police raid because they appeared
(17:03):
to immediately just comply with whatever they wanted. They were
asked to line up against the wall, and they did so.
At that point, the police, or at least the men
who they thought were police, opened fire on them with
two Tommy guns and they emptied seventy bullets into them
that way and then finish off with a few more
shotgun blasts, so really violent, violent scene. Neighbors say that
(17:25):
they heard popping noises and pneumatic drills and sounds like
a car backfiring and a dog howling. So poor high
Ball is in there watching all going through all of
this and so when the men walked out, these four
or five unknown men, it looked like just cops leading
(17:46):
out plain clothes guys, the men who looked kind of
like detectives when they were walking in, leading them out,
possibly at gunpoint, like they were in custody. And then
they all got into the car and they sped away.
And at the end of it, six of the guy
eyes were dead, but miraculously one of them had survived,
Frank Goosenberg, he was still alive, just barely. And this
(18:07):
is where the story starts to get a little weird. Yeah,
this is the point where accounts of what was said
and the details really start to get murky. Cops questioned
Goosenberg like he's lying there with full of bullets and
and they're trying to ask him what happened. Some accounts
say that he said, nobody shot me. And the assumption
here is that he was sticking to the gangster's code,
(18:30):
which was basically, you don't snitch on other gangsters, even
if it's someone right, don't say a thing, even if
it's someone from a rival gang. Other accounts, including an
account that's come to light recently, say that Goosenberg actually
said cops did it, So we'll talk about that a
little more in a minute. Frank dies, however, a few
hours later in the hospital, and they never learn anything
(18:50):
else from him about it. Moran, in case you forgot
about him in the story, he never shows up that day,
even though he's supposed to. It said that he was
seen in the area, but for it all went down,
that maybe he drove by, saw the cops getting out
of the caddy and just assumed it was a normal
police rate and got out of there. Um. But needless
to say, he did not die on that day. So
(19:13):
that leaves us with the question who who did it?
Who is responsible over the Saint Valentine State massacre? And
some people believed for a while that it could have
actually been the police, That these people weren't just in
police costumes, they were some sort of rogue police outfit um,
because after all, they did look like cops. They were
(19:33):
driving what looked like a cop car. Um. And we
know that not all of the cops in Chicago at
this time, we're we're straight knowing most of the backstory
that we know now. Also too, though most assumed at
the time that it was Capone, he himself, though had
a rock hard alibi. He was just sunning himself in Miami,
(19:53):
catching some rays and he owned an estate down there,
so he was not even in the state nowhere in
the area, so that was how he got himself sort
of out of it. But still it could have been
a guy. It could have been his guys, and I
think the general consensus now is that machine gun Jack
mcgern actually organized the whole event for capone um and
perhaps may have even been a shooter. Here's just some
(20:16):
examples of reasons that people might think this. He had
been spotted in nearby Lincoln Park and even outside SMC
Cartridge that morning, so right outside the building where it happened.
Pretty suspicious, right. Mcgern claimed, however, that he had appropriately
for Valentine's Day, been in bed all morning with his girlfriend,
who was a very attractive blonde golfer named Louise Rolf
(20:39):
and the papers ended up christening her the blonde Alibi
after this, and so that's where that famous moniker comes from.
I'm sure some of you have probably heard it. But
because of this blonde alibi that he had, he was
never really brought to trial, even though um he was
charged with the crime and a lot of people thought
it was him. Yeah, So while most people still assume
(21:00):
Capone those guys did it eighty two years after the fact,
there's a new theory about who organized the Valentine's Day massacre,
and it came out of a recent book called Get Capone,
which was released last year by the Chicago author Jonathan
i And it claims that this entirely different mobster, one
(21:21):
not connected to the North Side or the South Side gangs.
A guy named William White, also known as three Fingered Jack,
was the one who was responsible. Yeah. Apparently one of
Moran's guys killed White's cousin, a guy named William Davern Jr.
In a bar fight, and the Valentine's Day massacre was
supposedly White's revenge for the whole thing. The really convincing
(21:43):
part about this here's what it is. William Davern Jr's
dad was a Chicago police sergeant, so White could have
easily arranged to get some of the props, police uniforms,
the car, all of the police paraphernali in general from him. Also,
I points to the sheer kind of violence of the event.
It seems like a really passionate killing rather than a
(22:06):
business like one. I guess, yeah, you have kind of
unimportant players killed in it, caught up in it, right,
And another point he brings up is that the police
talk to eyewitnesses who claimed that a person who was
driving the black Cadillac was missing a finger like three
fingered jack, just like three fingered jack. Um. And he
also just points out if Capone wanted to kill Moran,
(22:28):
why was Moran allowed to live after that? And I
think that's a great point too. I mean, he knew
where Moran was. And if Moran is really the one
that Capone had the beef with, then you think he'd
be able to take him out. I mean he was
al Capone. Yeah, and Miran is the guy who's supposed
to be there. It's it's kind of a fluke that
he's not right. So what evidence does I have of this? Um?
The main thing is this letter from a guy named
(22:49):
Frank T. Ferrell, who had apparently been doing some undercover
investigation of an unspecified nature at the time of the massacre.
We're not really sure what that means, but that's his
explanation for how he's involved in all this. And the
letter was from Ferrell to John Edgar Hoover, who was
the head of the FBI at that time. So that's
basically what he's basing this off of. And then he's
gone in fact checked some of these things and that's
(23:11):
how he's put this theory together. However, some historians have
already found holes in this theory. Yeah, and the big
one is that Jack White, three Fingered Jack was supposed
to be in jail during this time. Yeah, that would
seem to take him out of the equation a little bit.
But I explained this away by saying he actually told
Chicago's ABC affiliate this um that White bribed his way out.
(23:32):
He bribed his way out of jail to commit the crime,
and then got back in and was released later that year.
So that kind of explains that. But even if you
can explain it away, there's another issue there. The gun.
The gun, Yeah, the gun involved in White's cousin shooting.
The whole thing that would have set this off in
the first place, actually belonged to the McGurn gang, not
(23:52):
to Miran, So that kind of destroys the revenge motive.
I don't know if I think that really takes away
If the cousin was and he thought that Moran had
killed him or Moran's gang, then you know three finger
Jack would think the same thing. Exactly how was he
to know um unless he also had access to this
ballistics report that Chicago's ABC had access to. UM. Regardless,
(24:16):
the theory that I composes as to why this other
possibility wasn't pursued, which was because investigators just wanted to
get Capone, probably has some kernel of truth to it.
Citizens in general at this time were really shocked by
the massacre. There were really graphic photos of it published
in the paper, and although these gang slangs were really
nothing new, the massacre really made it seem like things
(24:39):
were getting out of control, So it hardened public opinion
against Capone at that point. Yeah, and Hoover also took
office the same year of the crime, less than a
month earlier actually, and he wanted to try to make
an example of Capone, and eventually they ended up getting
Capone on tax evasion pretty pretty famously. There's a actually
(25:00):
been a previous podcast on that that Kenneth and Josh did. UM.
So they stuck him with an eleven year sentence. He
was eventually released in nineteen thirty nine after spending a
little time in Alcatraz, and he died in nineteen forty
seven at age forty eight from complications from syphilis. So um,
pretty pretty out of it by the end, right, and
(25:23):
Moran's career went downhill after the massacre too. He was
reduced to smaller bank robberies and ended up spending time
in prison actually for a couple of them, and eventually
died in prison in nineteen fifty seven of lung cancer.
Not to be outdone, machine gun mcgarn kind of went
downhill after that as well after Capone's arrest. Especially his
clubs closed during the depression, and he ended up a
(25:45):
small time drug dealer, so he fell pretty far and
in the end he was gunned down in a bowling
alley in nineteen thirty six and left. His dead body
was left actually with a comic valentine in his hand,
and it read, you've lost your job, You've lost stru dough,
your jewels and handsome houses. But things could be worse.
You know, you haven't lost your trousers like that. You
(26:07):
probably have to imagine it said in this kind of
tough guy gangster accent to make the rhyme scheme work.
But but that's not very valentine E. No, not again,
not a nice thing to do. As for the bootleg Wars, though,
they pretty much ended with the re legalization of liquor
in ninety three, but mobs they stuck around definitely. UM
(26:28):
labor and business racketeering sort of came in to replace
the trading of alcohol. Legal alcohol and mob leaders they
had seen how this greater cooperation among them that Torrio
had kind of pushed them towards. They saw how this
actually helped them get bigger profits. So this led to
an organized crime syndicate and the mobs that you still
(26:50):
stick around to some extent today. Yeah, you probably saw
him on the news a few weeks ago, I think
so the recent bust. So I'm still out there. So
like us, that's it for pleasant Valentine's story today. Happy
Valentine's Day. Valentine's Day everyone. We'll come up with a
love story soon to make up for it. This one
was just kind of hard to resist. Um and I
(27:11):
guess that brings us to listener mail. So we have
a letter from Janet and she says, Hi, Sarah and Dablina.
I can't tell you how excited I was when I
saw the Madame da Pumpadu episode come up in the
iTunes feed. I had to text my bff right away
to let her know she is a fan as well.
We were both hoping you would mention her tryst with
(27:33):
Doctor Who. Did you know the Doctor snogged Madame da Pompader.
If you've never seen the show, then you should at
least check out the episode called The Girl in the Fireplace.
You would love it. We've gotten a lot of mentions
for this episode of a lot of Doctor Who slash
stuff you missed in history class fans. So so I'm glad.
I mean, I had no idea that I was also, um,
(27:55):
you know, we're helping helping unite people's love of television
in history with one episode. Well, if you would like
to learn a little bit more about some of the
topics that we talked about in today's episode about the St.
Valentine's Day massacre, you can look up a little bit
more about how prohibition works by visiting our homepage and
(28:16):
typing in prohibition at www dot how stuff works dot com.
For more on this and thousands of other topics, visit
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Welcome to Stuff You Missed in History Class from how
Stuff Works dot Com. Hello, and welcome to the podcast.
I'm Sarah Dowdy and I'm Deblina Charko Boardy, and we
have a Valentine's story that may kind of change the
way you think about Valentine's Day. Valentine's Day, of course,
(00:23):
usually conjures up images of hearts, flowers and pretty lace
trimmed cards, but if you're from Chicago or you're a
true crime buff then it may have very different connotations.
And that's because it was February fourteenth nine that the
Valentine's Day massacre, which was one of the most famous
unsolved crimes in US history, went down in the Windy City.
(00:44):
It was obviously a terribly brutal crime, and it incorporated
a lot of the unsavory elements in Chicago, all the
stuff that was going down at the same time, gangsters, bootlegging,
dirty cops, and we don't want to leave out the
top guns stuff. Lena and I were talking about it earlier.
I liked you said, the Tommy guns are pretty much
another character, and there an extra person almost in this.
(01:08):
But but we didn't get a chance to go too
much into that that they do. That you play a
part here, but it all actually starts with something that
was intended to make life a little more virtuous, and
that was prohibition. And that's kind of like the irony
of the whole thing is that prohibition is what sort
of instigated this whole kind of wave of events that
(01:29):
is going to happen here. But we have a whole
podcast about prohibition. But the general just was that in
January n the eighteenth Amendment to the Constitution went into effect,
and this prohibited the manufacturer, the sale, the export, the import,
the transportation, all that having to do with alcoholic beverages.
It didn't ban personal possession and consumption though, so that
(01:50):
was kind of sort of an extra side note to it.
You could you could drink it if you had it,
so if you had your own personal stash, you could
consume it. You just couldn't buy it. They were just
to see ming that if you procured any you'd be
breaking laws anyways. Um, So prohibition almost immediately started a
new wave of organized crime, which was centered around bootlegging.
(02:11):
I mean, it really did start immediately. Some sources described
whiskey trucks in freight cars in Chicago being hijacked just
an hour after prohibition went into effect, and um Katie
and I did an episode on the molasses explosion. That's
another sort of immediate effect of prohibition, or leading up
to it, at least people people reacted quickly. Yeah. I've
(02:35):
even seen prohibition described as the engine that drove the
gangster era. So again sort of seeing the irony here
of wanting to do something good but having it all
sort of terribly ironic, terribly wrong immediately. So we should
give a little background to this though. There were gangs
before this, but they were mostly weren't too things like
(02:56):
muggings and robberies, and as far as business interests went,
they controlled gambling and prostitution type establishments to make money.
So with bootlegging, though, gangster saw the opportunity to really
turn crime into more of a business, into up their
profits considerably. Along with that, though, came the inevitable jostling
for territory between rival gangs, you know, I mean turf wars.
(03:19):
That's basically how we think of gangs today too, definitely,
and in Chicago is most notorious for that, right, It
was notorious, I guess for the outright gang on gang warfare.
The gangs there, they didn't even really try to hide
it or conceal it at all. The gangs attacks on
each other were often really horrible and gory, but it
was mostly just gang on gang violence. They generally avoided
(03:40):
attacking just your normal, average citizen on the street. Um
also avoided attacking cops, so I guess as a citizen
of Chicago may have been easier to kind of distance
yourself from it a little bit. Um And from the
police's point of view, they weren't really making things too
hard on the gangsters anyway. Local mobs often paid off
cops to look the other way while bootleg alcohol shipments
(04:04):
were on the move. Some cops even participated. They would
get paid off and they would write on trucks to
make sure that the alcohol actually reached its destination the
way it was supposed to. And some politicians were in
the pockets of gangsters too, So those of you who
watched gangster flicks, you're probably familiar with this whole dirty cop,
dirty politician thing. But for for those of you like
(04:25):
romantic comedies, it is just a little background that the
scene of what was going on during these so called
bootleg wars, but we should give you a little more
background two on this. It's not all about bootlegging. They're
also ethnic hostilities involved. That was a really big part
of the rivalries between the gangs and UM. There were
two main gangs in Chicago. Obviously there are many, but
(04:47):
two of the major ones. One was on the South
Side and it was an Italian gang. The other was
on the North Side. It was an Irish gang. And
in the early nineteen twenties a guy named John Torrio
became the leader of the South Side Italian gang and
he originally came from New York and was part of
the Five Points gang there, which had tammany hall connections.
(05:11):
He probably heard of the Five Points gang before, but
it didn't take him long to start to really get
into the Chicago mob scene and make a pretty big
impact there. He worked for the Chicago gangster Big Jim
Colossemo as his business manager, and UM really started to
build his name from there. Yeah, big gym Colosemo. We
(05:32):
should probably say he was kind of an old school
gangster of the gambling and prostitution variety of that we
mentioned before, So that was sort of his deal and
and uh, Torio worked for him. After Prohibition. He was
one of the first to really try to organize this
whole underworld of gangsters, and so many thought of him
as quote to the thinking man's criminal. He really wanted
(05:54):
to make the most of prohibition from a business standpoint,
so that was his whole thing. He wanted to actually
a void strife and bloodshed. His motto was there's plenty
for everyone, and he wanted to work with gangs. He
really worked with them to divide up the territory so
that everyone got a share of Chicago's bootlegging profits. So
so sort of modernized thing. Yeah, and kind of the
(06:15):
opposite of what you think a gangster would be doing. Yeah, exactly.
And he's pretty important though, not just for this ushering
in this new era of gangsterdom, but because he brings
in another young gangster from New York City named al Capone,
and I've heard of him. He may have heard of him,
and um, yeah, he takes al Capone under his wing,
(06:35):
and al later says, quote, I looked on Johnny like
my advisor and father. So you have the the established
gangster and the gangster in training, and they make quite
a pair. Indeed, at the same time, though, there was
sort of a similar kind of thing going on on
the other side of town. Torrio's counterpart on the north
side was a guy named Dion O'Banion, and he was
(06:56):
a roughneck who'd grown up in Chicago's Little Hell neighborhood, which,
for those of you who know Chicago, is now the
area where Cabrini Green, the Public Housing Project housing complex stands.
And Obanion, like Torrio, had a couple of protegees of
his own. Uh. They were Jimie Weiss and George bugs
Moran and perhaps kind of strange for a gangster, for
(07:18):
a tough guy, this was something interesting of note about Obanion.
He had a passion for flowers. He was part owner
of a flower shop called show Fields, and he really
loved to serve customers and apparently could be found on
any given day making flower arrangements. He also provided flowers
for these lavish gangster funerals um which sometimes these funerals
(07:42):
were described as being so huge they were like funerals
fit for kings, and sometimes they had up to like
a hundred thousand dollars and in flowers definite you I
mentioned you were starting to watch The Wire definitely reminded
me of the Wire. These elaborate funerals and elaborate floral displays.
But um, I guess it helps tie things in a
little bit to Valentine's Day. It does passion for flower.
(08:05):
I'm glad you brought that up, Sarah, or totally coming
out of left field, but again we have to go
sort of in a negative, non lovey, devy direction to
say that there was some trouble that did start around
this time when Obanion he went to war with the Italians.
Basically he offered to sell Torrio half interest in something
(08:25):
called the Stephen Brewery, which was one of his interests
that that Obanion owned, and he was responsible for getting
Torio basically caught in a police raid as the steel
was going down. On top of that, he ended up
keeping the five thousand dollars that he made off of
the steel. So not a very friendly gesture towards his
gangster leader counterpart there. Yeah, I think you were saying
(08:47):
earlier his motives were a little unclear and all of
the yeah, he was apparently tipped off about this raid beforehand,
which was what was sort of sketchy about the whole
thing and why Torio ended up getting so at about it. Um.
It obviously wasn't a coincidence, but we can't really figure
out I guess today whether O'Banion just thought it was
(09:08):
funny or if you just wanted to see what would happen.
I mean, it's kind of unclear what he really wanted
to do. Um, he probably just wanted to mess with
Torio and UM, you know, kind of put his rival
gang member in a in a bad place because apparently
O'Banion didn't really have any previous charges at this point,
so he wasn't going to get in trouble. But for
Toria it was a different story. So well, and it
(09:30):
certainly won him no friends. And on November tenth, three
guys walk into Schofield's flower shop on North State Street,
UM saying that they want to pick up a wreath
for the funeral of Mike Merlo, who was a prominent
member of the Italian community. And when one of the
guys reached out to shake O'Banion's hand, it seems like
(09:52):
a pretty nice thing to do. Doesn't seem violent or
we're scary. Um, it turns out that he was just
trying to keep Obanion from reaching for his own gun.
Apparently he kept multiple guns on him at all times, um.
And then the other two guys pull out their guns
and shoot Obanion in the flower shop six times. So certainly,
(10:13):
whatever Obanion's attentions were towards Torrio, Torrio did not much
care for him. No, he obviously did not like that.
But on the bright side, if you want to look
at it as a bright side, Obagion's funeral was apparently
the most lavish that had been thrown for a gangster yet,
and Capone sent a basket of Rosa's kind of a
cheeky bove as we discussed earlier Sarah, but he sent
(10:33):
a basket of roses signed from Al So really nice guy.
But this was sort of, I guess, the whole um
event that set off the chain of events that will
lead to the main story, the Valentine's Day massacre that
we're discussing, Because right after this happened, retaliation soon followed
Himie Weiss, who um he ended up taking over for Obanion,
(10:54):
that's his protege that we mentioned before, and he did
in fact attack and severely Wood and John Torrio, who
was then forced to retire, Torrio left Chicago and turned
over his empire to Capone. So now we have big
Alve versus Himie Weiss, and after that Capone advice. Their
mobs were at war essentially for a couple of years,
(11:15):
and some sources say that Capone tried to make peace
with Vice, you know, get it, so they could get
back to business and stop fighting each other. But Weiss
was sort of a crazy guy who was homicidal and
apparently just kept on rebelling. They couldn't work out any
sort of mob treaty. Yeah, So eventually, because he had to,
(11:37):
I'm sure, Capone ordered Weiss's murder and had him gunned
down with machine guns on North State Street, pretty much
right where Obanion got murdered. Um. It was right in
front of show Fields, because that's where Weiss had kept
his offices, right above the flower shop, and that was
on October eleven. And just stop ordering my flowers from
(11:58):
there at them. Yeah, I think I would switch office locations,
but he did not, um, and so he met his
death there. He met his demise. But this left George
bugs Moran in charge of the North Side Gang. So
now we've kind of hopefully you guys aren't too confused.
But now we've kind of set up all the characters
I think in this in this little play we have
going on here, Um and Marian. He was kind of
(12:21):
a thug too. Yeah, he was definitely better known for
his brawn than for his brains. He wasn't. He wasn't
the leader that his predecessor had been, Obanion. And he
got his nickname Bugs from his temper tantrums to which
is not exactly equality you want to see in the
leader of a gang like this for a leader of
(12:42):
anything for that, Yeah, exactly. So, even though there was
a peace treaty organized in nine between the leading gangsters,
it really didn't look like peace was going to happen
because it was it seemed pretty likely that Bugs Moran
would eventually go off the handle himself. Yeah, and in
these two sides just kind of kept going at each other.
(13:02):
And yeah, Moran and Campone, the North Side Gang and
the South Side Gang, and so it just seemed like
they were going to keep trying to take each other
out and antagonizing each other as much as they could.
And sure enough, even during these years of relative peacetime,
Moran continued to kind of try to stir up trouble
with Capone and his gang. For example, he gave a
(13:24):
kind of silent support to a north Sider named Joe
Alo who tried to assassinate Capone a few times. So
he wasn't the one who was doing the assassination attempts,
but he was sort of tacit encouraging them. Yes. Um.
Another thing, a couple of his own men, Pete and
Frank Gusenberg, who will come up later. They wounded one
(13:46):
of Capone's best guys, one of his right hand men. Um,
a boxer turn gangster named machine gun Jack mcgern. Yeah.
So Marian was certainly not on Al Capone's Valentine's list,
if we're going to make a little joke about our
title here, Um, but he was on another list. He was,
(14:07):
And this is where we start to kind of get
to the heart of our story. In early nine, Moran
was offered and he purchased a shipment of Canadian old
log cabin whiskey, which had supposedly been hijacked from Capone.
And this transaction went off so well, it went off
pretty much without a hitch, so that when the same
people offered Moran another shipment for a great price. He
(14:28):
agreed to it, of course, and that delivery was supposed
to happen at ten thirty in the morning on St.
Valentine's Day, and Moran himself was supposed to be there
to oversee it. And it was to take place at SMC.
Cartage Company, a garage and North Clark Street, which was
basically a depot for Moran's bootleg operation and he kept
some of his trucks there and things like that. Yes,
(14:48):
so we're gonna set the scene for this Valentine's Day morning.
It was cold and dreary and gray, and there were
seven guys at the garage by about ten am. Six
of them we're part of Moran's gang. There were the
Goosenberg brothers who we mentioned earlier, Pete and Frank. There
was a bootlegger named Adam Hayer, a speakeasy boss named
(15:10):
al Wine Shank, and a safecracker named John May who
did a little sidework for Moran as an auto mechanic,
and finally a bank robber James Clark. But then there
was another guy there too who was not part of
the gang. He was Dr Reinhardt Swimmer, who was an optometris. Um,
he was not there performing medical exams. He was he
(15:34):
was just like a friend, kind of a gangster groupie.
He would hang out with these tough guys and brag
to to his own friends about it. Um, sort of
a strange addition to the party. I'd say, Yeah, strange idea.
I think, just a someone who wants to hang around
this kind of underworld scene, but go check out people's
eyes later in the day. Weird, yeah, Um, Or maybe
(15:57):
you were checking out the eyes first and then going
to the gangster stuf. Of maybe this was just a
random morning activity anyway. Also in attendance was May's German
shepherd high Ball, and he was there tied to an
axle of a truck. So again just sort of setting up, Um,
what this morning looked like. Now, all of these guys
except for May, who was dressed in overalls working on
(16:19):
trucks of course, Um, they were all dressed up in
suits and ties. Around ten thirty, a black Cadillac drives
up outside the garage. Four or five men get out
of the car at this point. Um. Eye witness accounts
differ as to how many people they are actually worry
you'll see it described both ways, I think, depending on
which you read UM. A couple of the men were
dressed up in police uniforms and the others are in
(16:40):
clothes that may resemble what detectives might wear. They were
wearing sort of top coats or trench coats. UM. One
description has one of the guys at least wearing a fedora,
so more normal clothing, not uniforms. And when they walked
into the building, the seven men inside, this is what
people generally believe is that they must have a woomed.
It was just a routine police raid because they appeared
(17:03):
to immediately just comply with whatever they wanted. They were
asked to line up against the wall, and they did so.
At that point, the police, or at least the men
who they thought were police, opened fire on them with
two Tommy guns and they emptied seventy bullets into them
that way and then finish off with a few more
shotgun blasts, so really violent, violent scene. Neighbors say that
(17:25):
they heard popping noises and pneumatic drills and sounds like
a car backfiring and a dog howling. So poor high
Ball is in there watching all going through all of
this and so when the men walked out, these four
or five unknown men, it looked like just cops leading
(17:46):
out plain clothes guys, the men who looked kind of
like detectives when they were walking in, leading them out,
possibly at gunpoint, like they were in custody. And then
they all got into the car and they sped away.
And at the end of it, six of the guy
eyes were dead, but miraculously one of them had survived,
Frank Goosenberg, he was still alive, just barely. And this
(18:07):
is where the story starts to get a little weird. Yeah,
this is the point where accounts of what was said
and the details really start to get murky. Cops questioned
Goosenberg like he's lying there with full of bullets and
and they're trying to ask him what happened. Some accounts
say that he said, nobody shot me. And the assumption
here is that he was sticking to the gangster's code,
(18:30):
which was basically, you don't snitch on other gangsters, even
if it's someone right, don't say a thing, even if
it's someone from a rival gang. Other accounts, including an
account that's come to light recently, say that Goosenberg actually
said cops did it, So we'll talk about that a
little more in a minute. Frank dies, however, a few
hours later in the hospital, and they never learn anything
(18:50):
else from him about it. Moran, in case you forgot
about him in the story, he never shows up that day,
even though he's supposed to. It said that he was
seen in the area, but for it all went down,
that maybe he drove by, saw the cops getting out
of the caddy and just assumed it was a normal
police rate and got out of there. Um. But needless
to say, he did not die on that day. So
(19:13):
that leaves us with the question who who did it?
Who is responsible over the Saint Valentine State massacre? And
some people believed for a while that it could have
actually been the police, That these people weren't just in
police costumes, they were some sort of rogue police outfit um,
because after all, they did look like cops. They were
(19:33):
driving what looked like a cop car. Um. And we
know that not all of the cops in Chicago at
this time, we're we're straight knowing most of the backstory
that we know now. Also too, though most assumed at
the time that it was Capone, he himself, though had
a rock hard alibi. He was just sunning himself in Miami,
(19:53):
catching some rays and he owned an estate down there,
so he was not even in the state nowhere in
the area, so that was how he got himself sort
of out of it. But still it could have been
a guy. It could have been his guys, and I
think the general consensus now is that machine gun Jack
mcgern actually organized the whole event for capone um and
perhaps may have even been a shooter. Here's just some
(20:16):
examples of reasons that people might think this. He had
been spotted in nearby Lincoln Park and even outside SMC
Cartridge that morning, so right outside the building where it happened.
Pretty suspicious, right. Mcgern claimed, however, that he had appropriately
for Valentine's Day, been in bed all morning with his girlfriend,
who was a very attractive blonde golfer named Louise Rolf
(20:39):
and the papers ended up christening her the blonde Alibi
after this, and so that's where that famous moniker comes from.
I'm sure some of you have probably heard it. But
because of this blonde alibi that he had, he was
never really brought to trial, even though um he was
charged with the crime and a lot of people thought
it was him. Yeah, So while most people still assume
(21:00):
Capone those guys did it eighty two years after the fact,
there's a new theory about who organized the Valentine's Day massacre,
and it came out of a recent book called Get Capone,
which was released last year by the Chicago author Jonathan
i And it claims that this entirely different mobster, one
(21:21):
not connected to the North Side or the South Side gangs.
A guy named William White, also known as three Fingered Jack,
was the one who was responsible. Yeah. Apparently one of
Moran's guys killed White's cousin, a guy named William Davern Jr.
In a bar fight, and the Valentine's Day massacre was
supposedly White's revenge for the whole thing. The really convincing
(21:43):
part about this here's what it is. William Davern Jr's
dad was a Chicago police sergeant, so White could have
easily arranged to get some of the props, police uniforms,
the car, all of the police paraphernali in general from him. Also,
I points to the sheer kind of violence of the event.
It seems like a really passionate killing rather than a
(22:06):
business like one. I guess, yeah, you have kind of
unimportant players killed in it, caught up in it, right,
And another point he brings up is that the police
talk to eyewitnesses who claimed that a person who was
driving the black Cadillac was missing a finger like three
fingered jack, just like three fingered jack. Um. And he
also just points out if Capone wanted to kill Moran,
(22:28):
why was Moran allowed to live after that? And I
think that's a great point too. I mean, he knew
where Moran was. And if Moran is really the one
that Capone had the beef with, then you think he'd
be able to take him out. I mean he was
al Capone. Yeah, and Miran is the guy who's supposed
to be there. It's it's kind of a fluke that
he's not right. So what evidence does I have of this? Um?
The main thing is this letter from a guy named
(22:49):
Frank T. Ferrell, who had apparently been doing some undercover
investigation of an unspecified nature at the time of the massacre.
We're not really sure what that means, but that's his
explanation for how he's involved in all this. And the
letter was from Ferrell to John Edgar Hoover, who was
the head of the FBI at that time. So that's
basically what he's basing this off of. And then he's
gone in fact checked some of these things and that's
(23:11):
how he's put this theory together. However, some historians have
already found holes in this theory. Yeah, and the big
one is that Jack White, three Fingered Jack was supposed
to be in jail during this time. Yeah, that would
seem to take him out of the equation a little bit.
But I explained this away by saying he actually told
Chicago's ABC affiliate this um that White bribed his way out.
(23:32):
He bribed his way out of jail to commit the crime,
and then got back in and was released later that year.
So that kind of explains that. But even if you
can explain it away, there's another issue there. The gun.
The gun, Yeah, the gun involved in White's cousin shooting.
The whole thing that would have set this off in
the first place, actually belonged to the McGurn gang, not
(23:52):
to Miran, So that kind of destroys the revenge motive.
I don't know if I think that really takes away
If the cousin was and he thought that Moran had
killed him or Moran's gang, then you know three finger
Jack would think the same thing. Exactly how was he
to know um unless he also had access to this
ballistics report that Chicago's ABC had access to. UM. Regardless,
(24:16):
the theory that I composes as to why this other
possibility wasn't pursued, which was because investigators just wanted to
get Capone, probably has some kernel of truth to it.
Citizens in general at this time were really shocked by
the massacre. There were really graphic photos of it published
in the paper, and although these gang slangs were really
nothing new, the massacre really made it seem like things
(24:39):
were getting out of control, So it hardened public opinion
against Capone at that point. Yeah, and Hoover also took
office the same year of the crime, less than a
month earlier actually, and he wanted to try to make
an example of Capone, and eventually they ended up getting
Capone on tax evasion pretty pretty famously. There's a actually
(25:00):
been a previous podcast on that that Kenneth and Josh did. UM.
So they stuck him with an eleven year sentence. He
was eventually released in nineteen thirty nine after spending a
little time in Alcatraz, and he died in nineteen forty
seven at age forty eight from complications from syphilis. So um,
pretty pretty out of it by the end, right, and
(25:23):
Moran's career went downhill after the massacre too. He was
reduced to smaller bank robberies and ended up spending time
in prison actually for a couple of them, and eventually
died in prison in nineteen fifty seven of lung cancer.
Not to be outdone, machine gun mcgarn kind of went
downhill after that as well after Capone's arrest. Especially his
clubs closed during the depression, and he ended up a
(25:45):
small time drug dealer, so he fell pretty far and
in the end he was gunned down in a bowling
alley in nineteen thirty six and left. His dead body
was left actually with a comic valentine in his hand,
and it read, you've lost your job, You've lost stru dough,
your jewels and handsome houses. But things could be worse.
You know, you haven't lost your trousers like that. You
(26:07):
probably have to imagine it said in this kind of
tough guy gangster accent to make the rhyme scheme work.
But but that's not very valentine E. No, not again,
not a nice thing to do. As for the bootleg Wars, though,
they pretty much ended with the re legalization of liquor
in ninety three, but mobs they stuck around definitely. UM
(26:28):
labor and business racketeering sort of came in to replace
the trading of alcohol. Legal alcohol and mob leaders they
had seen how this greater cooperation among them that Torrio
had kind of pushed them towards. They saw how this
actually helped them get bigger profits. So this led to
an organized crime syndicate and the mobs that you still
(26:50):
stick around to some extent today. Yeah, you probably saw
him on the news a few weeks ago, I think
so the recent bust. So I'm still out there. So
like us, that's it for pleasant Valentine's story today. Happy
Valentine's Day. Valentine's Day everyone. We'll come up with a
love story soon to make up for it. This one
was just kind of hard to resist. Um and I
(27:11):
guess that brings us to listener mail. So we have
a letter from Janet and she says, Hi, Sarah and Dablina.
I can't tell you how excited I was when I
saw the Madame da Pumpadu episode come up in the
iTunes feed. I had to text my bff right away
to let her know she is a fan as well.
We were both hoping you would mention her tryst with
(27:33):
Doctor Who. Did you know the Doctor snogged Madame da Pompader.
If you've never seen the show, then you should at
least check out the episode called The Girl in the Fireplace.
You would love it. We've gotten a lot of mentions
for this episode of a lot of Doctor Who slash
stuff you missed in history class fans. So so I'm glad.
I mean, I had no idea that I was also, um,
(27:55):
you know, we're helping helping unite people's love of television
in history with one episode. Well, if you would like
to learn a little bit more about some of the
topics that we talked about in today's episode about the St.
Valentine's Day massacre, you can look up a little bit
more about how prohibition works by visiting our homepage and
(28:16):
typing in prohibition at www dot how stuff works dot com.
For more on this and thousands of other topics, visit
how stuff works dot com. To learn more about the podcast,
click on the podcast icon in the upper right corner
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Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.