March 31, 2025 • 41 mins
A Chicago garage. Seven men against a wall. The rat-tat-tat of Thompson submachine guns. By the time the smoke cleared on Valentine's Day 1929, six were dead, one was dying, and America would never view organized crime the same way again.
The St. Valentine's Day Massacre stands as the bloody crescendo of Prohibition-era violence – a carefully orchestrated hit that revealed the dark underbelly of America's failed experiment with legislating morality. But why did this particular gangland execution capture public imagination and reshape national policy when so many others faded into history?
Chicago's transformation provides our first clues. A booming industrial center rebuilt after devastating fire, the city attracted waves of immigrants seeking opportunity but finding discrimination. In these marginalized neighborhoods, protection rackets evolved into sophisticated criminal organizations, with Al Capone and Bugs Moran emerging as rival kings of the underworld. Their battle for control of Chicago's bootlegging empire would culminate in that blood-soaked garage, though ironically, Moran himself escaped death by simply running late.
The massacre's aftermath proved equally fascinating. While widely believed responsible, Capone maintained the perfect alibi – he was in Florida with his attorneys. No one was ever convicted for the brutal killings, yet the public outrage helped cement Prohibition's failure and caught President Hoover's attention. Federal authorities, unable to pin the murders on Capone, eventually imprisoned him for tax evasion instead – a strange justice for a man responsible for countless deaths.
Beyond the blood and bullets, this episode reveals how failed reform creates unexpected consequences, how violence shapes public opinion, and how sometimes the most violent criminals fall to the most mundane charges. Join us for this exploration of the crime that changed America's relationship with organized crime forever.
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Episode Transcript
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(01:21):
Chicago, Valentine's Day,1929. Snow blankets the streets.
Inside a dirty commercialgarage, seven men line up, thinking
they're about to make aroutine deal. What follows is a brutal
execution. A hail of gunfirethat leaves them all but one of them
dead.
This is the St. Valentine'sDay massacre, one of the most infamous
(01:44):
crimes in American history. Itwasn't just a gangland hit. It became
a turning point in howAmericans viewed organized crime.
And we're here to unravel thestory behind the blood in the snow.
Welcome to history's Greatestcrimes, where we two historians dive
into the most infamous crimesin history, peeling back the layers
(02:04):
to understand their causes,their impact, and what they reveal
about the world we live intoday. I'm Michael.
And I'm Alana. This wasn'tjust a random act of violence. It
was a carefully orchestratedpower move during one of America's
most exciting and yetturbulent times. Prohibition.
Exactly. Al Capone and BugsMoran, two of the most famous and
(02:27):
infamous figures in organizedcrime, were locked in a battle for
control over Chicago'slucrative bootlegging trade. The
massacre was the result ofthat rivalry. But the story doesn't
end there.
So who pulled the trigger?What was the fallout? And how did
this one event help to toppleone of history's most infamous gangsters?
(02:48):
Stick with us as we explorethese questions and more on history's
greatest crimes.
Before we dive into the St.Valentine's Day massacre, we need
to understand Chicago's uniquehistory, how it transformed from
a frontier town into a boomingmetropolis by the early 20th century.
(03:11):
This backdrop is key tounderstanding the forces that created
both the city's growingopportunities and its dark underbelly.
Chicago, a city today of over2 million people, was founded in
1837 and began to grow byleaps and bounds due to the city's
location on Lake Michigan,which made it a crucial hub for trade,
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connecting the Midwest to therest of the country. Railroads expanded
that role even further, makingChicago the gateway to America's
heartland. The city grewrapidly, and by 1870, Chicago was
one of the largest cities inthe country.
But then disaster struck.
What happened?
In 1871, the great ChicagoFire swept through the city, destroying
(03:56):
over three square miles,destroying over 17,000 buildings,
killing more than 300 people,and leaving nearly 100,000 people
homeless.
That must have beendevastating for the people who had
built their whole lives in the city.
And that's absolutely true. Itwas a catastrophe worth over $3.5
billion in today's money. Butinstead of destroying the city, it
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became A turning point. Afterthe fire, Chicago rebuilt itself
Bigger, taller, and moreambitious than before. The city became
a symbol of Americanresilience, known for its skyscrapers,
industrial might, and boomingpopulation. And by the end of the
1800s, the city had risen likea phoenix to become an industrial
powerhouse. The unionstockyards, steel mills and factories
(04:44):
made it the beating heart ofAmerica's economy.
It's such a fascinating storyabout the city of Chicago, but what
I think makes that story evenmore interesting was the concurrent
influx of immigrants to thecity. They were very much a part
of rebuilding the city. Fromthe 1880s through the 1920s, Chicago's
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population exploded as wavesof immigrants arrived, mostly from
southern and eastern Europe,including Italians, Poles, Eastern
European Jews. I'll addthough, that the number of immigrants
heading to Chicago alsoincluded Irish and German immigrants,
as well as black Americans whowere fleeing the segregated South.
They all came in search ofwork and a better life. By 1920,
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roughly 2.7 million peoplelived in Chicago, with just under
40% being foreign born.Between 1890 and 1920, the city's
Polish born population grewnearly sixfold. The Italian born
population rose more thantenfold, and the African American
population increasedEightfold. They settled in ethnic
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neighborhoods, creatingvibrant communities with their own
languages, traditions and businesses.
But these people came withdreams of success. Their neighborhoods
were also marked by povertyand overcrowding. Many immigrants
lived in tenements. With poorsanitation and few resources, they
faced discrimination andracism from both established communities
(06:11):
and the government. The 1920salso saw the reemergence of the Ku
Klux Klan against immigration.That decade also included the Johnson
Reed act, an immigration actwhich severely limited arrivals from
southern and eastern Europe.The targeting of specific immigrant
groups by domestic terroristgroups and through legal policy created
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deep ethnic and racialdivisions in the city.
And in this environment,organized crime found fertile ground.
Gangs often started asneighborhood protection groups, filling
a void where the law failed toserve them. But over time, these
groups evolved into powerfulcriminal organizations.
The power of these criminalorganizations expanded during Prohibition.
(06:55):
When the 18th Amendment passedin 1919, Prohibition banned the production,
sale and transport of alcohol.But Prohibition wasn't just about
banning alcohol. It was partof a larger push to shape a, quote,
better society through reform.This was the Progressive era.
That's right, Michael. TheProgressive era was a time when reformers,
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many of whom were middle classwomen, worked together to end societal
problems that they believedprevented the poor and disadvantaged
from leading successful morallives. One of the main societal problems
that reformers focused on wasalcoholism. They argued that the
common Frequent consumption ofalcohol among Americans led to alcoholism,
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which in turn led to theabandonment and neglect of one's
family, impoverishment,disease and other moral crimes like
prostitution and stealing.Progressives believed in the power
of reform to improve societythrough government intervention.
Like laws and policies, theychampioned ideas like public health,
education, labor rights, andused strong government intervention
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to address the problemscreated by industrialization and
urbanization.
But while the goals of theProgressive era sound positive, inclusive,
even in reality, the noteveryone immediately accepted the
growing presence ofimmigrants. Many native born Americans,
particularly those of AngloSaxon Protestant backgrounds, viewed
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these new immigrants withsuspicion, derision and even prejudice.
They worried that immigrantswere undermining American values
and traditions and preventingprogress within society.
And despite the positivenature of progressive reforms, many
reformers took a ratherpaternalistic approach to immigrants.
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Reformers often viewedimmigrant communities as chaotic
and unruly and in need ofdiscipline and moral uplift. They
saw alcohol as a symbol ofeverything that was wrong with urban
life. Poverty, violence andvice. All of these things they believed
immigrants suffered frombecause of their customs and religious
practices. For progressivereformers, Prohibition wasn't just
(09:13):
about banning alcohol then. Itwas about reshaping society, literally
reshaping immigrants intotheir ideal American.
So at the turn of the century,Prohibition became a cornerstone
of the progressive movement.Organizations like the Anti Saloon
League and the Women'sChristian Temperance Union argued
that alcohol was the rootcause of the current social ills
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and that banning it would leadto a healthier life for families,
safer communities and a moreproductive workforce.
But for many immigrantcommunities, Prohibition felt like
an attack on their identity.Drinking was often woven into cultural
traditions, celebrations,religious ceremonies and social gatherings.
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The saloon then, as much thenas it is today, wasn't just a place
to drink. It was a communityhub where people gathered to share
news, find jobs, and connectwith others.
Prohibition also highlighted adeep divide between rural and urban
America. In rural areas whereprogressive ideals often aligned
with conservative religiousvalues, banning alcohol just made
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sense. But in cities whereimmigrant cultures thrived, it felt
like a moral crusade imposedby outsiders.
This cultural divide fueledresentment. Immigrants and working
class Americans sawProhibition as an effort by elites
to control their behavior anderase their traditions, culture and
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ethnic identities. And theyweren't wrong. Many Prohibition advocates
explicitly linked their causeto the Americanization of immigrant
groups.
When Prohibition went intoeffect in January 1920, it didn't
stop drinking, it just pushedit underground. And organized crime
took advantage of that.Gangsters like Al Capone, who himself
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came from an immigrantbackground, filled the void left
by legal alcohol. Theysupplied the speakeasies with liquor.
They bribed the authorities tolook the other way and built criminal
empires on the backs of a lawthat many Americans simply didn't
respect.
So while prohibition wasrooted in progressive ideals, its
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enforcement created theperfect environment for organized
crime to thrive. And inChicago, it led to a bloody battle
for control between men likeAl Capone and Bugs Moran.
Let's now take a look at howProhibition fueled these rivalries
and set the stage for the St.Valentine's Day Massacre.
(11:50):
Prohibition, enacted by the18th Amendment in 1919, was intended
to make America a more moraland sober society. But instead of
eradicating alcohol, itcreated an enormous black market.
And this is where thebootleggers come in. Just as an aside,
here I find the significanceof bootlegging to American history
(12:10):
really interesting. Michael,would you tell our listeners more
about who they were?
Oh, I would love to. Abootlegger was someone who illegally
manufactured, transported, orsold alcohol. But the term itself
dates back to the 19th centurywhen smugglers would hide flasks
in their boots. But duringprohibition, bootlegging became so
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much more alcohol creation andtransportation on an industrial scale.
That's right, Michael. In thesouthern parts of the nation, bootleggers
making and shipping homemademoonshine began to use souped up
cars to stay ahead of thelocal police and federal agents.
And that would ultimately leadto the development of stock car racing
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and specifically nascar. Butover in Chicago, in the mid east,
bootleggers didn't justsmuggle alcohol, they built empires.
They imported liquor fromCanada, made moonshine and hidden
distilleries galleries, andbribed law enforcement to look the
other way. They supplied thethousands of illegal bars known as
speakeasies, where peoplecould drink, dance, and socialize
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away from the prying eyes ofthe law.
And in Chicago, no bootleggerwas more notorious than Al Capone.
So Al Capone didn't invent thetrade, but he damn near perfected
it. Capone wasn't just sellingalcohol. He was building a criminal
enterprise. He controlled thedistribution networks. He bribed
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the officials and eliminatedrivals with ruthless, violent efficiency.
And he did it with a smile onhis face.
But Capone wasn't alone.Chicago's entire political and law
enforcement system was deeplycorrupt. The city's political machine,
led by figures like mayorWilliam Big Bill Thompson, was notorious
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for its patronage system.Politicians and police officers were
often on the payroll ofgangsters, turning a blind eye to
their activities and violence.
This corruption created asense of lawlessness for many working
class Chicagoans. Gangsterslike Capone were Seen as folk heroes,
people who defied the systemand provided jobs and money and even
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charity to their communities.
But this wasn't just aboutsurvival. Organized crime thrived
on violence. Rivalries betweengangs were common to control aspects
of trade or other areas ofinfluence. And Prohibition turned
these rivalries into deadlyturf wars for control over alcohol.
By the late 1920s, Chicago hadbecome one of the most violent cities
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in America, with dozens ofgang related murders each year.
And that's the backdrop forthe St. Valentine's Day Massacre.
It wasn't just a violentcrime, it certainly was that. But
it was the culmination ofdecades of city growth, large scale
immigration, politicalcorruption and gang violence that
defined Chicago in the early20th century.
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With that history in mind,let's move forward into the decade
of the 1920s. The 1920s areoften called the roaring twenties,
and for good reason. This wasa period of massive social, cultural
and technological changes.After the devastation of World War
I, America was booming. Theeconomy was growing at an unprecedented
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rate, and new mass producedtechnologies like the automobile,
the radio and motion pictureswere revolutionizing daily life.
At the same time, urbanizationwas reshaping the entire country.
For the first time in Americanhistory, more people lived in cities
than in rural areas. Citieslike Chicago became hubs of innovation,
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culture and opportunity. Butas we've also discussed, they became
places of stark inequality andgrowing ethnic tensions.
Culturally, the 1920s weremarked by a clash between tradition
and modernity. The oldergeneration, shaped by Victorian values,
often felt threatened by therise of jazz music, flappers and
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a freer social attitude.Younger generations embraced a more
carefree, consumer drivenlifestyle that sometimes appalled
their parents.
This cultural clash wasn'tjust about fashion or music. It was
about power. Groups like theKu Klux Klan gained influence by
promoting a return to quotetraditional values, while large immigrant
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communities and urban youthpushed for progress and acceptance.
And this is where Prohibitionfits in. The 18th Amendment, which
banned the production, saleand transport of alcohol, was passed
in 1919 and went into effectin 1920. It was supposed to solve
social problems, curb crime,and create a more moral society.
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But by the 1920s and the late1920s, it was clear that Prohibition
wasn't working. The public hadgrown tired of the violence, corruption,
and the hypocrisy that it hadcreated. But for men like Capone
and Moran, Prohibition was thefoundation of their power and they
were willing to kill toprotect it.
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The 1920s were a golden agefor organized crime, and it wasn't
just because of alcohol. As wementioned before, Prohibition provided
a massive Financialopportunity. But these organizations
had already laid thegroundwork through other criminal
enterprises, like gambling,extortion, and prostitution. And
that made it all the easierfor them to turn to supplying illegal
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alcohol to those with the cashto pay for it.
The criminal organizations ofthe time were highly structured,
almost like corporations. Atthe top were the bosses, men like
Capone and Moran, who made thebig decisions and reaped the largest
profits. Beneath them werelieutenants who managed different
aspects of the business, fromsmuggling routes to protection rackets.
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And then there were theenforcers, the muscle who carried
out orders and eliminatedrivals. These were the men responsible
for the violence that becamesynonymous with organized crime during
the 1920s. For them, loyaltywas everything, and betrayal often
meant death.
But it's a tale as old astime. The structure of these organizations
wasn't just about efficiency.It was about control and greed. Keeping
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the organization tightlymanaged, crime bosses could expand
their operations across entirecities, controlling neighborhoods,
industries, and even local governments.
And to make it all the morecomplex, it wasn't just traditional
criminals who enjoyed thetrade of illegal alcohol supplied
by organized crime.Speakeasies, for example, became
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cultural hubs where peoplefrom all walks of life came together
to drink, dance, andsocialize. Many of these establishments
were owned or supplied bycrime syndicates.
At the same time, theseorganizations wielded enormous political
power. They controlledelections. They told people who they
should vote for. They bribedthe officials and even shaped city
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policies. In cities likeChicago, the very lines between legal
and illegal worlds were oftenvery blurred.
And as we've explained before,for many working class families,
organized crime also provideda sense of stability, at least on
the surface. Gangsters offeredjobs, protection, and even charity
in their communities. But thiscame with a cost. Violence, fear,
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and the constant threat ofretribution. And in Chicago, that
violence came to a head due tothe rivalry between gang leaders
Al Capone and Bugs Moran.Let's take a closer look at how these
two men and their gangs cameto dominate the city.
To fully understand the St.Valentine's Day massacre, we really
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do need to know more about thetwo men at the center of it. Al Capone
and Bugs Moran. Their rivalrydefined Chicago's underworld and
their lives leading up to thatbloody day in 1929. Give us a window
into the forces that shape them.
Let's start with AlphonseGabriel Capona, better known as Al
Capone. Born in Brooklyn, NewYork, in 1899, Capone was the son
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of Italian immigrants. Hisparents were working class, his father
a barber and his mother a seamstress.
Capone's early life was markedby a mix of ambition and trouble.
He was a bright student, buthis temper often got him into fights.
He eventually dropped out ofschool and found odd jobs while also
being a part of many differentyouth street gangs.
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By the time he was a teenager,Capone was already drawn into the
world of organized crime. Hestarted as a member of small time
street gangs in Brooklyn,where he learned the ropes of the
criminal underworld. His bigbreak came when he joined the gentleman
gangster Johnny Torrio'sorganization. Torrio, who had immigrated
from southern Italy as a boy,had found success as the leader of
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the infamous Five Points gangin Manhattan. For some time, he was
commonly known as the biggestgangster in America. And as one US
Official put it, Torrio was,quote, the smartest and I dare say
the best of all hoodlums. Bestreferring to talent, not morals.
End quote.
Torrio served as a mentor tothe young Al Capone. And when Torrio
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decided to expand his criminalorganization to Chicago, Capone went
with him. Almost as soon asprohibition began, the windy city
of Chicago had offered anexcellent opportunity to gangsters
for bootle legging. And inChicago, Capone quickly rose through
the ranks to become known forhis charisma and ruthlessness.
By the mid-1920s, Capone hadtaken over Torio's operations. Torio
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had been shot several timesthroughout his gangster career, and
by 1925, it appears that hehad had enough of that lifestyle,
at least in the United States.Torio moved back to Italy with his
wife and mother. Supposedly,he told Capone at the time, quote,
it's all yours, Al me, I'mquitting. It's Europe for me. End
quote. Now, just oneinteresting fact. When Torio left
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the United States in 1925, hewas grossing about $70 million a
year in profits frombootlegging, prostitution, and gambling.
Today, that would equal about$1.2 billion.
That is a mind bogglingnumber, Elena. In the 1920s, with
Capone then in charge, hemaintained and expanded this Chicago
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empire of bootlegging,gambling and prostitution rings.
And Capone wasn't just agangster. He was also a public figure
known for flaunting hisexpensive suits, his flashy lifestyle,
and that Al Capone smile. ButCapone's success came at a cost.
His empire was built onescalating violence. He eliminated
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rivals with brutal efficiency.And his name became synonymous with
the bloody gang wars of theprohibition era.
Now let's turn to Bugs Moran.Born In Minnesota in 1893, Bugs Moran
wasn't his original name. Hewas actually born Adelar Kunin to
a French immigrant father anda mother of Canadian descent.
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That's right, Elena. So BugsMoran was also connected to the wave
of immigration that we've beentalking about. Moran's early life
was marked by rebellion. Hedropped out of school as a teenager
and quickly turned to crime.In his early 20s he fled to Chicago
to avoid his crimes back home.But almost immediately he was back
to his old ways. He was caughttrying to rob a warehouse, taking
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part in a horse stealing ring,even taking part in a robbery involving
the death of a police officer.He robbed a freight car for which
he actually received a varietyof prison and jail sentences for
all of these things. That iswhen young Adelard Coonin first adopted
the name George Moran. It wasthe first name he thought of when
police asked him who he was.George Moran was a violent and unstable
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man who got the name Bugsbecause everyone thought he was nuts
or buggy.
In Chicago, Moran joined theNorthside Gang, a predominantly Irish
organization led by Dean o'Banion. Moran's reputation as a hothead
and a fighter made him a keyfigure in the gang's operations.
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In 1924, O' Banion was gunneddown in his flower shop which had
served as one front for hiscriminal activities. Many believe
that this assassination wasorchestrated by Al Capone and Torrio.
When o' Banion was killed,Moran became a prime leader of the
north side gang. And he wasdetermined to take revenge on Capone
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and his south side gang,escalating the violence in Chicago's
streets. Moran's constanttargeting of Torrio is actually what
encouraged him to leaveChicago for a little for Italy, allowing
Capone to take over.
Unlike Capone, Moran wasn'tknown for his charisma or strategic
thinking. He was more of justa brawler, a man who relied on brute
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force rather than finesse. Therivalry between Capone and Moran
was intense. These two menwere arch enemies when it came to
the business competition andand ideas of revenge. But in reality
they were two sides of thesame coin. Capone the flashy and
calculated Italian Americanmob boss and Moran the hot headed
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Irish American gang leader.
Throughout the 1920s, theirgangs were an all out war for control
of Chicago's lucrativebootlegging market. Each side targeted
the other with assassinationsand sabotage, leaving a trail of
bodies in their wake. But thereal turning point came in 1926 when
Moran attempted to assassinateCapone. Moran's men ambushed Capone
(25:59):
at a restaurant with machineguns. And this drive by shooting
sent over a thousand bulletsinto the building, killing several
people, but actually missingtheir main target.
And don't forget that afterMoran tried and failed to kill Capone
in 1926, Moran had then placeda $50,000 bounty on Capone's head,
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worth roughly $1 milliontoday. The gang war that followed
led to an escalation ofviolence that will culminate in the
1929St. Valentine's Day Massacre.
So we've arrived at themorning of February 14, 1929. Picture
this. Seven members of BugsMoran's Northside gang are at a garage
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on North Clark Street. Theythink they're there for a routine
meeting, possibly abootlegging deal.
Instead, two men dressed aspolice officers walk in, followed
by two others in civilianclothes. The gang members are ordered
to line up against the wall.They think it's a raid, but it's
actually a setup.
What happens next will go downas one of the most brutal crimes
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in American history. Stay with us.
Foreign 10:30am On February14, 1929, seven men are gathered
inside the SMC Cartage Companygarage at 2122 North Clark street
in Chicago. These men are allassociates or members of Bugs Moran's
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north side gang.
Unbeknownst to them, thiswasn't going to be a routine business
meeting. Outside, two mendressed as police officers and two
others in civilian clothesapproached the building. They planned
every detail to make it looklike a police raid.
The fake cops entered first,guns drawn. They ordered Moran's
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men to line up against thewall as if they were going to be
arrested. Thinking that thiswas just a standard raid, the men
complied. They knew how thisworked. They would comply and then
pay some bribes to fix this misunderstanding.
But this was no arrest.Moments later, the other two men
walked in carrying Thompsonmachine submachine guns. Known colloquially
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as tommy guns. These gunscould pump out up to 1200 rounds
per minute. And as a result,in Chicago, Tommy guns actually had
another name, the Chicagotypewriters for the click, click,
click sounds that they made asbullets were fired. What's interesting
is that these guns hadoriginally been manufactured to help
American forces break thestalemate of trench warfare and win
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World War I for the Allies.After World War I ended in 1918,
Tommy Tommy guns wereavailable to the general public for
purchase, and they quicklybecame the signature weapon of organized
crime syndicates, includingthose of Moran and Capone.
Bringing us back to February14th of 1929. The two men holding
the Tommy guns opened fire onMoran's men in the garage. The attackers
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were thorough, making sure noone was left alive. Or so they thought.
The scene was chaotic. Bloodpooling on the floor, walls riddled
with bullets, and the echoesof gunfire still ringing in the morning
air.
When the dust settled, six ofthe men were dead. The seventh, Frank
Gusenberg, was criticallywounded, but still clinging to life.
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He was rushed to the hospital,but even as he lay dying, he refused
to identify his killers.
When asked who shot him,Gusenberg replied, quote, no one.
Nobody shot me. That's thecode of silence these men lived and
died by. It also highlightsthe distrust of the government and
police authorities, as well asthe loyalty, even in death, that
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the mob underworld worked in.
Meanwhile, the fake police andtheir accomplices made a clean getaway.
Witnesses later reportedseeing the men leaving the garage
calmly, even loading theirweapons into a car, as if they were
just wrapping up a routinepolice operation.
When the real police arrived,they were met with one of the grisliest
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crime scenes in history.Photos of the massacre spread quickly,
shocking the nation. Buthere's the thing. The intended target,
Bugs Moran, he wasn't even there.
That's right. Moran had beenrunning late that morning when he
saw the fake police outsidethe garage. He turned around and
avoided the massacrealtogether. But even though Moran
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lived, the loss wasdevastating for his organization.
The seven victims includedhigh ranking members of Moran's gang.
So who was really behind theSt. Valentine's Day Massacre? Well,
the obvious suspect, ofcourse, was Al Capone. And it was
common knowledge that he wasthe undisputed king of Chicago south
side, and one of the mostpowerful mob bosses in the country.
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But proving his role in themassacre was another story altogether.
Capone had both the motive andthe means. The massacre wiped out
key members of Bugs Moran'snorth side gang, Giving Capone greater
control over Chicago'slucrative bootlegging trade. But
there's a catch. Capone wasn'teven in Chicago that day.
(31:09):
Exactly. On February 14, 1929,Capone was reportedly in Florida,
meeting with his attorneys athis Florida home. It's the perfect
alibi. But let's be real,right? Capone didn't really need
to be there personally. He hadplenty of men who would carry out
the job for him.
And one of those men mighthave been Fred Killer Burke, A known
associate of Capone's who wasskilled in using the same weapons
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that were used in themassacre. Burke's fingerprints were
later found on a tommy gun inhis possession, linking him to the
crime. But that wasn't enoughto convict him. Years later, other
criminals would implicate himin the crime. But in the end, no
one was convicted for the St.Valentine's Day massacre.
This is just so crazy to me.With such an obvious murder motive
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and even an eyewitnesses, noone was ever convicted for the St.
Valentine's Day Massacre of 1929.
I agree. And the lack of aconviction means that we'll never
really know all of thedetails. There's another theory that
the massacre was actually asetup to frame Capone. Some believe
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that rival gangs or evencorrupt law enforcement or orchestrated
the attack to turn publicopinion against him. After all, the
massacre brought so much heaton Capone that it marked the beginning
of the end for his empire.Another possibility is that it was
an inside job. Some accountssuggest that someone within Moran's
own gang may have tipped offCapone's men either out of fear or
(32:38):
for personal gang because, youknow, gang loyalty wasn't exactly
ironclad.
And let's not forget BugsMoran himself. While he was clearly
the target, was his survivalentirely coincidental? Or could he
have known about the hint andeven set his men into the trap to
save his own skin?
(32:58):
While there's no hard evidenceto support that the murkiness of
the world of organized crimemeant that anything was a possibility,
what we do know is that themassacre achieved its goal of crippling
Moran's gang, but it came witha cost.
That's right, Elena. The St.Valentine's Day massacre of 1929
weakened Moran's and his gang.But it also had unintended consequences
(33:20):
for Al Capone himself, whomany believe was behind the attack.
The massacre drew so muchattention that it became impossible
for authorities and the publicto ignore the violence continuing
to grip Chicago. And more tothe point, it represented a turning
point in America's war onorganized crime.
(33:40):
Coming up, we'll look at howthis one event helped take down Al
Capone and change the courseof American history.
So News of the St. Valentine'sDay Massacre spread rapidly in the
following days. Newspapersacross the country published graphic
photos of the crime scene, andthe public outcry was deafening.
(34:02):
And in short, the massacrecreated a public relations nightmare
for Capone.
It also caught the attentionof federal authorities, specifically
newly elected PresidentHerbert Hoover, who immediately looked
for a way to bring Capone andgangsters like him down. But they
couldn't pin the massacre onhim. And in reality, they didn't
(34:23):
care what crime actuallybrought an end to his illegal activities.
So Hoover began adding moremoney and agents to the effort to
end organized crime, andspecifically Al Capone's Organized
crime instead of murder oralcohol, bringing down Capone. In
the end, it was not paying histaxes. Capone was arrested on charges
of tax evasion.
(34:43):
That's right, tax evasion.Capone's lifestyle was lavish, and
it didn't exactly match hisreported tax income. By 1931, he
was convicted of tax evasionand sentenced to 11 years in federal
prison. While the massacredidn't directly lead to his conviction,
it certainly turned up theheat on his organization.
(35:05):
And what about Bugs Moran? Weknow the massacre effectively destroyed
his gang, but he managed tosurvive. What happened to him?
Well, similarly, USauthorities targeted his financial
crimes as well. In 1939, hewas convicted of conspiracy to cash
fraudulent checks and robberyand was jailed for five years. When
(35:25):
he emerged in the 1940s, theonce extravagant mob boss was now
nearly penniless and withoutany real power. In 1946, Moran was
arrested for a petty robberyof a tavern and died of lung cancer
two months into his next 10year sentence.
Just, just as an aside, do youremember Johnny Torio, the gentleman
(35:47):
gangster who gave his crimesyndicate over to Al Capone and went
back to Italy in 1925?
Yes. He said he was throughwith organized crime.
That turned out not to becompletely true. When Torrio went
back to Italy, he startedmeddling in organized crime again.
A few Years later, in 1928,Italy's fascist leader, Benito Mussolini,
(36:08):
began putting pressure on theMafia in Italy. That was part of
Mussolini's efforts to expandhis authority over the nation leading
up to World War II. As aresult, Torrio returned to the United
States. As you remember, thefederal authorities often focused
on financial crimes tosuccessfully convict monsters. And
similarly, in 1936, Torrio wasconvicted of income tax evasion.
(36:33):
Why can't mobsters just paytheir taxes now? As we mentioned,
no one was convicted for theirpart in the St. Valentine's Day Massacre.
But despite that, the eventhad a huge impact on policy and encouraged
some major historical shifts.First and foremost, it underscored
the failure of Prohibition asa policy. The 18th amendment was
(36:54):
rooted in progressive idealsthat banning alcohol would solve
societal problems. Butinstead, it created a thriving black
market that enriched criminalslike Al Capone and heightened criminal
activity. It had really theopposite effect.
It all seems to point to apowerful lesson about the limits
of moral legislation. When alaw is wildly unpopular and difficult
(37:17):
to enforce, it often createsmore problems than it solves. Prohibition
didn't eliminate alcohol. Itmade it more dangerous, drove it
underground and empoweredorganized crime and criminals while
eroding trust in lawenforcement and.
As images of the St.Valentine's Day Massacre crime scene
splashed across newspapers in1929, it seemed to symbolize the
(37:39):
failure of Prohibition and thechaos it had unleashed. The public
outcry and the outrage to themassacre and its root causes played
a key role in shiftingattitudes towards Prohibition. By
the early 1930s, there was agrowing consensus that the law was
doing more harm than good.This leading to the 1933 repeal of
(37:59):
the 18th Amendment andprohibition in the new 21st Amendment.
The massacre also highlightsthe corrosive impact of corruption.
In Chicago, organized crimethrived not just because of violence,
but because it had infiltratedthe political and law enforcement
system systems. Judges, policeand politicians were often complicit,
(38:20):
either through bribery or fear.
And this kind of corruptioncreates a sense of lawlessness that
undermines the veryinstitutions meant to protect society.
When the public sees the lawsbeing ignored or manipulated by those
in power, it breeds cynicismand distrust.
And culturally, the St.Valentine's Day massacre remains
one of the most infamouscrimes in American history. It's
(38:43):
been immortalized in books,films and TV shows, often as a symbol
of the brutality and excess ofthe Prohibition era. And the figures
of Al Capone and Bugs Moranare often glamorized and romanticized
as larger than life anti heroes.
And part of that originates inthe broader social, economic, and
cultural forces that drove themassacre in the first place. The
(39:05):
poverty and official andunofficial discrimination that many
immigrants faced created aneed for a special protection and
opportunities from within.Those special protection and opportunities
often evolved into and fromorganized crime.
And that same organized crimethrived within and exploited the
moral boundaries thatprogressive reformers had hoped would
(39:27):
fix the sins of society.Reformers of the progressive age
had hoped that by makingalcohol, gambling and prostitution
illegal, it would help thepoor avoid their vices and improve
their standing in society. Butreality turned out to be quite different.
But while the St. Valentine'sDay massacre mostly stood as a negative
symbol of the RoaringTwenties, it did have a few positive
(39:50):
consequences. The massacrerevealed the need to reform law enforcement
systems to help combatcorruption from within. And in the
process, it also led to a morecoordinated federal approach to combat
organized crime, including thecreation of agencies like the FBI.
In addition, Chicago becamethe first city with an independent
(40:11):
forensic crime laboratory atNorthwestern University. The lab
was initially established inan effort to find the murderers.
So in some ways, the field offorensic science was born out of
this tragedy.
Looking back, the St.Valentine's Day massacre was clearly
an infamous crime in history.But it also offers lessons that are
still relevant today. Whetherit's about creating effective laws,
(40:33):
addressing systemiccorruption, or understanding the
root causes of violence.History has so much to teach us.
And perhaps the most importantlesson is this. When society tries
to impose simple solutions oncomplex problems, the consequences
can be far reaching andunexpected. It's a reminder that
history is always morecomplicated than it seems.
(40:55):
That's all for now. This hasbeen history's greatest crimes. I'm
Michael.
And I'm Alana. Stay curious.
Chicago, Valentine's Day,1929. Snow blankets the streets.
Inside a dirty commercialgarage, seven men line up, thinking
they're about to make aroutine deal. What follows is a brutal
execution. A hail of gunfirethat leaves them all but one of them
dead.
This is the St. Valentine'sDay massacre, one of the most infamous
(01:44):
crimes in American history. Itwasn't just a gangland hit. It became
a turning point in howAmericans viewed organized crime.
And we're here to unravel thestory behind the blood in the snow.
Welcome to history's Greatestcrimes, where we two historians dive
into the most infamous crimesin history, peeling back the layers
(02:04):
to understand their causes,their impact, and what they reveal
about the world we live intoday. I'm Michael.
And I'm Alana. This wasn'tjust a random act of violence. It
was a carefully orchestratedpower move during one of America's
most exciting and yetturbulent times. Prohibition.
Exactly. Al Capone and BugsMoran, two of the most famous and
(02:27):
infamous figures in organizedcrime, were locked in a battle for
control over Chicago'slucrative bootlegging trade. The
massacre was the result ofthat rivalry. But the story doesn't
end there.
So who pulled the trigger?What was the fallout? And how did
this one event help to toppleone of history's most infamous gangsters?
(02:48):
Stick with us as we explorethese questions and more on history's
greatest crimes.
Before we dive into the St.Valentine's Day massacre, we need
to understand Chicago's uniquehistory, how it transformed from
a frontier town into a boomingmetropolis by the early 20th century.
(03:11):
This backdrop is key tounderstanding the forces that created
both the city's growingopportunities and its dark underbelly.
Chicago, a city today of over2 million people, was founded in
1837 and began to grow byleaps and bounds due to the city's
location on Lake Michigan,which made it a crucial hub for trade,
(03:32):
connecting the Midwest to therest of the country. Railroads expanded
that role even further, makingChicago the gateway to America's
heartland. The city grewrapidly, and by 1870, Chicago was
one of the largest cities inthe country.
But then disaster struck.
What happened?
In 1871, the great ChicagoFire swept through the city, destroying
(03:56):
over three square miles,destroying over 17,000 buildings,
killing more than 300 people,and leaving nearly 100,000 people
homeless.
That must have beendevastating for the people who had
built their whole lives in the city.
And that's absolutely true. Itwas a catastrophe worth over $3.5
billion in today's money. Butinstead of destroying the city, it
(04:20):
became A turning point. Afterthe fire, Chicago rebuilt itself
Bigger, taller, and moreambitious than before. The city became
a symbol of Americanresilience, known for its skyscrapers,
industrial might, and boomingpopulation. And by the end of the
1800s, the city had risen likea phoenix to become an industrial
powerhouse. The unionstockyards, steel mills and factories
(04:44):
made it the beating heart ofAmerica's economy.
It's such a fascinating storyabout the city of Chicago, but what
I think makes that story evenmore interesting was the concurrent
influx of immigrants to thecity. They were very much a part
of rebuilding the city. Fromthe 1880s through the 1920s, Chicago's
(05:04):
population exploded as wavesof immigrants arrived, mostly from
southern and eastern Europe,including Italians, Poles, Eastern
European Jews. I'll addthough, that the number of immigrants
heading to Chicago alsoincluded Irish and German immigrants,
as well as black Americans whowere fleeing the segregated South.
They all came in search ofwork and a better life. By 1920,
(05:27):
roughly 2.7 million peoplelived in Chicago, with just under
40% being foreign born.Between 1890 and 1920, the city's
Polish born population grewnearly sixfold. The Italian born
population rose more thantenfold, and the African American
population increasedEightfold. They settled in ethnic
(05:49):
neighborhoods, creatingvibrant communities with their own
languages, traditions and businesses.
But these people came withdreams of success. Their neighborhoods
were also marked by povertyand overcrowding. Many immigrants
lived in tenements. With poorsanitation and few resources, they
faced discrimination andracism from both established communities
(06:11):
and the government. The 1920salso saw the reemergence of the Ku
Klux Klan against immigration.That decade also included the Johnson
Reed act, an immigration actwhich severely limited arrivals from
southern and eastern Europe.The targeting of specific immigrant
groups by domestic terroristgroups and through legal policy created
(06:32):
deep ethnic and racialdivisions in the city.
And in this environment,organized crime found fertile ground.
Gangs often started asneighborhood protection groups, filling
a void where the law failed toserve them. But over time, these
groups evolved into powerfulcriminal organizations.
The power of these criminalorganizations expanded during Prohibition.
(06:55):
When the 18th Amendment passedin 1919, Prohibition banned the production,
sale and transport of alcohol.But Prohibition wasn't just about
banning alcohol. It was partof a larger push to shape a, quote,
better society through reform.This was the Progressive era.
That's right, Michael. TheProgressive era was a time when reformers,
(07:20):
many of whom were middle classwomen, worked together to end societal
problems that they believedprevented the poor and disadvantaged
from leading successful morallives. One of the main societal problems
that reformers focused on wasalcoholism. They argued that the
common Frequent consumption ofalcohol among Americans led to alcoholism,
(07:42):
which in turn led to theabandonment and neglect of one's
family, impoverishment,disease and other moral crimes like
prostitution and stealing.Progressives believed in the power
of reform to improve societythrough government intervention.
Like laws and policies, theychampioned ideas like public health,
education, labor rights, andused strong government intervention
(08:05):
to address the problemscreated by industrialization and
urbanization.
But while the goals of theProgressive era sound positive, inclusive,
even in reality, the noteveryone immediately accepted the
growing presence ofimmigrants. Many native born Americans,
particularly those of AngloSaxon Protestant backgrounds, viewed
(08:27):
these new immigrants withsuspicion, derision and even prejudice.
They worried that immigrantswere undermining American values
and traditions and preventingprogress within society.
And despite the positivenature of progressive reforms, many
reformers took a ratherpaternalistic approach to immigrants.
(08:49):
Reformers often viewedimmigrant communities as chaotic
and unruly and in need ofdiscipline and moral uplift. They
saw alcohol as a symbol ofeverything that was wrong with urban
life. Poverty, violence andvice. All of these things they believed
immigrants suffered frombecause of their customs and religious
practices. For progressivereformers, Prohibition wasn't just
(09:13):
about banning alcohol then. Itwas about reshaping society, literally
reshaping immigrants intotheir ideal American.
So at the turn of the century,Prohibition became a cornerstone
of the progressive movement.Organizations like the Anti Saloon
League and the Women'sChristian Temperance Union argued
that alcohol was the rootcause of the current social ills
(09:36):
and that banning it would leadto a healthier life for families,
safer communities and a moreproductive workforce.
But for many immigrantcommunities, Prohibition felt like
an attack on their identity.Drinking was often woven into cultural
traditions, celebrations,religious ceremonies and social gatherings.
(09:57):
The saloon then, as much thenas it is today, wasn't just a place
to drink. It was a communityhub where people gathered to share
news, find jobs, and connectwith others.
Prohibition also highlighted adeep divide between rural and urban
America. In rural areas whereprogressive ideals often aligned
with conservative religiousvalues, banning alcohol just made
(10:21):
sense. But in cities whereimmigrant cultures thrived, it felt
like a moral crusade imposedby outsiders.
This cultural divide fueledresentment. Immigrants and working
class Americans sawProhibition as an effort by elites
to control their behavior anderase their traditions, culture and
(10:41):
ethnic identities. And theyweren't wrong. Many Prohibition advocates
explicitly linked their causeto the Americanization of immigrant
groups.
When Prohibition went intoeffect in January 1920, it didn't
stop drinking, it just pushedit underground. And organized crime
took advantage of that.Gangsters like Al Capone, who himself
(11:05):
came from an immigrantbackground, filled the void left
by legal alcohol. Theysupplied the speakeasies with liquor.
They bribed the authorities tolook the other way and built criminal
empires on the backs of a lawthat many Americans simply didn't
respect.
So while prohibition wasrooted in progressive ideals, its
(11:26):
enforcement created theperfect environment for organized
crime to thrive. And inChicago, it led to a bloody battle
for control between men likeAl Capone and Bugs Moran.
Let's now take a look at howProhibition fueled these rivalries
and set the stage for the St.Valentine's Day Massacre.
(11:50):
Prohibition, enacted by the18th Amendment in 1919, was intended
to make America a more moraland sober society. But instead of
eradicating alcohol, itcreated an enormous black market.
And this is where thebootleggers come in. Just as an aside,
here I find the significanceof bootlegging to American history
(12:10):
really interesting. Michael,would you tell our listeners more
about who they were?
Oh, I would love to. Abootlegger was someone who illegally
manufactured, transported, orsold alcohol. But the term itself
dates back to the 19th centurywhen smugglers would hide flasks
in their boots. But duringprohibition, bootlegging became so
(12:30):
much more alcohol creation andtransportation on an industrial scale.
That's right, Michael. In thesouthern parts of the nation, bootleggers
making and shipping homemademoonshine began to use souped up
cars to stay ahead of thelocal police and federal agents.
And that would ultimately leadto the development of stock car racing
(12:51):
and specifically nascar. Butover in Chicago, in the mid east,
bootleggers didn't justsmuggle alcohol, they built empires.
They imported liquor fromCanada, made moonshine and hidden
distilleries galleries, andbribed law enforcement to look the
other way. They supplied thethousands of illegal bars known as
speakeasies, where peoplecould drink, dance, and socialize
(13:12):
away from the prying eyes ofthe law.
And in Chicago, no bootleggerwas more notorious than Al Capone.
So Al Capone didn't invent thetrade, but he damn near perfected
it. Capone wasn't just sellingalcohol. He was building a criminal
enterprise. He controlled thedistribution networks. He bribed
(13:34):
the officials and eliminatedrivals with ruthless, violent efficiency.
And he did it with a smile onhis face.
But Capone wasn't alone.Chicago's entire political and law
enforcement system was deeplycorrupt. The city's political machine,
led by figures like mayorWilliam Big Bill Thompson, was notorious
(13:57):
for its patronage system.Politicians and police officers were
often on the payroll ofgangsters, turning a blind eye to
their activities and violence.
This corruption created asense of lawlessness for many working
class Chicagoans. Gangsterslike Capone were Seen as folk heroes,
people who defied the systemand provided jobs and money and even
(14:20):
charity to their communities.
But this wasn't just aboutsurvival. Organized crime thrived
on violence. Rivalries betweengangs were common to control aspects
of trade or other areas ofinfluence. And Prohibition turned
these rivalries into deadlyturf wars for control over alcohol.
By the late 1920s, Chicago hadbecome one of the most violent cities
(14:43):
in America, with dozens ofgang related murders each year.
And that's the backdrop forthe St. Valentine's Day Massacre.
It wasn't just a violentcrime, it certainly was that. But
it was the culmination ofdecades of city growth, large scale
immigration, politicalcorruption and gang violence that
defined Chicago in the early20th century.
(15:07):
With that history in mind,let's move forward into the decade
of the 1920s. The 1920s areoften called the roaring twenties,
and for good reason. This wasa period of massive social, cultural
and technological changes.After the devastation of World War
I, America was booming. Theeconomy was growing at an unprecedented
(15:28):
rate, and new mass producedtechnologies like the automobile,
the radio and motion pictureswere revolutionizing daily life.
At the same time, urbanizationwas reshaping the entire country.
For the first time in Americanhistory, more people lived in cities
than in rural areas. Citieslike Chicago became hubs of innovation,
(15:51):
culture and opportunity. Butas we've also discussed, they became
places of stark inequality andgrowing ethnic tensions.
Culturally, the 1920s weremarked by a clash between tradition
and modernity. The oldergeneration, shaped by Victorian values,
often felt threatened by therise of jazz music, flappers and
(16:12):
a freer social attitude.Younger generations embraced a more
carefree, consumer drivenlifestyle that sometimes appalled
their parents.
This cultural clash wasn'tjust about fashion or music. It was
about power. Groups like theKu Klux Klan gained influence by
promoting a return to quotetraditional values, while large immigrant
(16:35):
communities and urban youthpushed for progress and acceptance.
And this is where Prohibitionfits in. The 18th Amendment, which
banned the production, saleand transport of alcohol, was passed
in 1919 and went into effectin 1920. It was supposed to solve
social problems, curb crime,and create a more moral society.
(16:57):
But by the 1920s and the late1920s, it was clear that Prohibition
wasn't working. The public hadgrown tired of the violence, corruption,
and the hypocrisy that it hadcreated. But for men like Capone
and Moran, Prohibition was thefoundation of their power and they
were willing to kill toprotect it.
(17:18):
The 1920s were a golden agefor organized crime, and it wasn't
just because of alcohol. As wementioned before, Prohibition provided
a massive Financialopportunity. But these organizations
had already laid thegroundwork through other criminal
enterprises, like gambling,extortion, and prostitution. And
that made it all the easierfor them to turn to supplying illegal
(17:41):
alcohol to those with the cashto pay for it.
The criminal organizations ofthe time were highly structured,
almost like corporations. Atthe top were the bosses, men like
Capone and Moran, who made thebig decisions and reaped the largest
profits. Beneath them werelieutenants who managed different
aspects of the business, fromsmuggling routes to protection rackets.
(18:02):
And then there were theenforcers, the muscle who carried
out orders and eliminatedrivals. These were the men responsible
for the violence that becamesynonymous with organized crime during
the 1920s. For them, loyaltywas everything, and betrayal often
meant death.
But it's a tale as old astime. The structure of these organizations
wasn't just about efficiency.It was about control and greed. Keeping
(18:26):
the organization tightlymanaged, crime bosses could expand
their operations across entirecities, controlling neighborhoods,
industries, and even local governments.
And to make it all the morecomplex, it wasn't just traditional
criminals who enjoyed thetrade of illegal alcohol supplied
by organized crime.Speakeasies, for example, became
(18:48):
cultural hubs where peoplefrom all walks of life came together
to drink, dance, andsocialize. Many of these establishments
were owned or supplied bycrime syndicates.
At the same time, theseorganizations wielded enormous political
power. They controlledelections. They told people who they
should vote for. They bribedthe officials and even shaped city
(19:10):
policies. In cities likeChicago, the very lines between legal
and illegal worlds were oftenvery blurred.
And as we've explained before,for many working class families,
organized crime also provideda sense of stability, at least on
the surface. Gangsters offeredjobs, protection, and even charity
in their communities. But thiscame with a cost. Violence, fear,
(19:34):
and the constant threat ofretribution. And in Chicago, that
violence came to a head due tothe rivalry between gang leaders
Al Capone and Bugs Moran.Let's take a closer look at how these
two men and their gangs cameto dominate the city.
To fully understand the St.Valentine's Day massacre, we really
(19:57):
do need to know more about thetwo men at the center of it. Al Capone
and Bugs Moran. Their rivalrydefined Chicago's underworld and
their lives leading up to thatbloody day in 1929. Give us a window
into the forces that shape them.
Let's start with AlphonseGabriel Capona, better known as Al
Capone. Born in Brooklyn, NewYork, in 1899, Capone was the son
(20:22):
of Italian immigrants. Hisparents were working class, his father
a barber and his mother a seamstress.
Capone's early life was markedby a mix of ambition and trouble.
He was a bright student, buthis temper often got him into fights.
He eventually dropped out ofschool and found odd jobs while also
being a part of many differentyouth street gangs.
(20:44):
By the time he was a teenager,Capone was already drawn into the
world of organized crime. Hestarted as a member of small time
street gangs in Brooklyn,where he learned the ropes of the
criminal underworld. His bigbreak came when he joined the gentleman
gangster Johnny Torrio'sorganization. Torrio, who had immigrated
from southern Italy as a boy,had found success as the leader of
(21:08):
the infamous Five Points gangin Manhattan. For some time, he was
commonly known as the biggestgangster in America. And as one US
Official put it, Torrio was,quote, the smartest and I dare say
the best of all hoodlums. Bestreferring to talent, not morals.
End quote.
Torrio served as a mentor tothe young Al Capone. And when Torrio
(21:31):
decided to expand his criminalorganization to Chicago, Capone went
with him. Almost as soon asprohibition began, the windy city
of Chicago had offered anexcellent opportunity to gangsters
for bootle legging. And inChicago, Capone quickly rose through
the ranks to become known forhis charisma and ruthlessness.
By the mid-1920s, Capone hadtaken over Torio's operations. Torio
(21:56):
had been shot several timesthroughout his gangster career, and
by 1925, it appears that hehad had enough of that lifestyle,
at least in the United States.Torio moved back to Italy with his
wife and mother. Supposedly,he told Capone at the time, quote,
it's all yours, Al me, I'mquitting. It's Europe for me. End
quote. Now, just oneinteresting fact. When Torio left
(22:19):
the United States in 1925, hewas grossing about $70 million a
year in profits frombootlegging, prostitution, and gambling.
Today, that would equal about$1.2 billion.
That is a mind bogglingnumber, Elena. In the 1920s, with
Capone then in charge, hemaintained and expanded this Chicago
(22:42):
empire of bootlegging,gambling and prostitution rings.
And Capone wasn't just agangster. He was also a public figure
known for flaunting hisexpensive suits, his flashy lifestyle,
and that Al Capone smile. ButCapone's success came at a cost.
His empire was built onescalating violence. He eliminated
(23:02):
rivals with brutal efficiency.And his name became synonymous with
the bloody gang wars of theprohibition era.
Now let's turn to Bugs Moran.Born In Minnesota in 1893, Bugs Moran
wasn't his original name. Hewas actually born Adelar Kunin to
a French immigrant father anda mother of Canadian descent.
(23:24):
That's right, Elena. So BugsMoran was also connected to the wave
of immigration that we've beentalking about. Moran's early life
was marked by rebellion. Hedropped out of school as a teenager
and quickly turned to crime.In his early 20s he fled to Chicago
to avoid his crimes back home.But almost immediately he was back
to his old ways. He was caughttrying to rob a warehouse, taking
(23:46):
part in a horse stealing ring,even taking part in a robbery involving
the death of a police officer.He robbed a freight car for which
he actually received a varietyof prison and jail sentences for
all of these things. That iswhen young Adelard Coonin first adopted
the name George Moran. It wasthe first name he thought of when
police asked him who he was.George Moran was a violent and unstable
(24:09):
man who got the name Bugsbecause everyone thought he was nuts
or buggy.
In Chicago, Moran joined theNorthside Gang, a predominantly Irish
organization led by Dean o'Banion. Moran's reputation as a hothead
and a fighter made him a keyfigure in the gang's operations.
(24:29):
In 1924, O' Banion was gunneddown in his flower shop which had
served as one front for hiscriminal activities. Many believe
that this assassination wasorchestrated by Al Capone and Torrio.
When o' Banion was killed,Moran became a prime leader of the
north side gang. And he wasdetermined to take revenge on Capone
(24:51):
and his south side gang,escalating the violence in Chicago's
streets. Moran's constanttargeting of Torrio is actually what
encouraged him to leaveChicago for a little for Italy, allowing
Capone to take over.
Unlike Capone, Moran wasn'tknown for his charisma or strategic
thinking. He was more of justa brawler, a man who relied on brute
(25:12):
force rather than finesse. Therivalry between Capone and Moran
was intense. These two menwere arch enemies when it came to
the business competition andand ideas of revenge. But in reality
they were two sides of thesame coin. Capone the flashy and
calculated Italian Americanmob boss and Moran the hot headed
(25:34):
Irish American gang leader.
Throughout the 1920s, theirgangs were an all out war for control
of Chicago's lucrativebootlegging market. Each side targeted
the other with assassinationsand sabotage, leaving a trail of
bodies in their wake. But thereal turning point came in 1926 when
Moran attempted to assassinateCapone. Moran's men ambushed Capone
(25:59):
at a restaurant with machineguns. And this drive by shooting
sent over a thousand bulletsinto the building, killing several
people, but actually missingtheir main target.
And don't forget that afterMoran tried and failed to kill Capone
in 1926, Moran had then placeda $50,000 bounty on Capone's head,
(26:21):
worth roughly $1 milliontoday. The gang war that followed
led to an escalation ofviolence that will culminate in the
1929St. Valentine's Day Massacre.
So we've arrived at themorning of February 14, 1929. Picture
this. Seven members of BugsMoran's Northside gang are at a garage
(26:44):
on North Clark Street. Theythink they're there for a routine
meeting, possibly abootlegging deal.
Instead, two men dressed aspolice officers walk in, followed
by two others in civilianclothes. The gang members are ordered
to line up against the wall.They think it's a raid, but it's
actually a setup.
What happens next will go downas one of the most brutal crimes
(27:06):
in American history. Stay with us.
Foreign 10:30am On February14, 1929, seven men are gathered
inside the SMC Cartage Companygarage at 2122 North Clark street
in Chicago. These men are allassociates or members of Bugs Moran's
(27:30):
north side gang.
Unbeknownst to them, thiswasn't going to be a routine business
meeting. Outside, two mendressed as police officers and two
others in civilian clothesapproached the building. They planned
every detail to make it looklike a police raid.
The fake cops entered first,guns drawn. They ordered Moran's
(27:51):
men to line up against thewall as if they were going to be
arrested. Thinking that thiswas just a standard raid, the men
complied. They knew how thisworked. They would comply and then
pay some bribes to fix this misunderstanding.
But this was no arrest.Moments later, the other two men
walked in carrying Thompsonmachine submachine guns. Known colloquially
(28:12):
as tommy guns. These gunscould pump out up to 1200 rounds
per minute. And as a result,in Chicago, Tommy guns actually had
another name, the Chicagotypewriters for the click, click,
click sounds that they made asbullets were fired. What's interesting
is that these guns hadoriginally been manufactured to help
American forces break thestalemate of trench warfare and win
(28:36):
World War I for the Allies.After World War I ended in 1918,
Tommy Tommy guns wereavailable to the general public for
purchase, and they quicklybecame the signature weapon of organized
crime syndicates, includingthose of Moran and Capone.
Bringing us back to February14th of 1929. The two men holding
the Tommy guns opened fire onMoran's men in the garage. The attackers
(29:00):
were thorough, making sure noone was left alive. Or so they thought.
The scene was chaotic. Bloodpooling on the floor, walls riddled
with bullets, and the echoesof gunfire still ringing in the morning
air.
When the dust settled, six ofthe men were dead. The seventh, Frank
Gusenberg, was criticallywounded, but still clinging to life.
(29:22):
He was rushed to the hospital,but even as he lay dying, he refused
to identify his killers.
When asked who shot him,Gusenberg replied, quote, no one.
Nobody shot me. That's thecode of silence these men lived and
died by. It also highlightsthe distrust of the government and
police authorities, as well asthe loyalty, even in death, that
(29:46):
the mob underworld worked in.
Meanwhile, the fake police andtheir accomplices made a clean getaway.
Witnesses later reportedseeing the men leaving the garage
calmly, even loading theirweapons into a car, as if they were
just wrapping up a routinepolice operation.
When the real police arrived,they were met with one of the grisliest
(30:07):
crime scenes in history.Photos of the massacre spread quickly,
shocking the nation. Buthere's the thing. The intended target,
Bugs Moran, he wasn't even there.
That's right. Moran had beenrunning late that morning when he
saw the fake police outsidethe garage. He turned around and
avoided the massacrealtogether. But even though Moran
(30:28):
lived, the loss wasdevastating for his organization.
The seven victims includedhigh ranking members of Moran's gang.
So who was really behind theSt. Valentine's Day Massacre? Well,
the obvious suspect, ofcourse, was Al Capone. And it was
common knowledge that he wasthe undisputed king of Chicago south
side, and one of the mostpowerful mob bosses in the country.
(30:48):
But proving his role in themassacre was another story altogether.
Capone had both the motive andthe means. The massacre wiped out
key members of Bugs Moran'snorth side gang, Giving Capone greater
control over Chicago'slucrative bootlegging trade. But
there's a catch. Capone wasn'teven in Chicago that day.
(31:09):
Exactly. On February 14, 1929,Capone was reportedly in Florida,
meeting with his attorneys athis Florida home. It's the perfect
alibi. But let's be real,right? Capone didn't really need
to be there personally. He hadplenty of men who would carry out
the job for him.
And one of those men mighthave been Fred Killer Burke, A known
associate of Capone's who wasskilled in using the same weapons
(31:33):
that were used in themassacre. Burke's fingerprints were
later found on a tommy gun inhis possession, linking him to the
crime. But that wasn't enoughto convict him. Years later, other
criminals would implicate himin the crime. But in the end, no
one was convicted for the St.Valentine's Day massacre.
This is just so crazy to me.With such an obvious murder motive
(31:54):
and even an eyewitnesses, noone was ever convicted for the St.
Valentine's Day Massacre of 1929.
I agree. And the lack of aconviction means that we'll never
really know all of thedetails. There's another theory that
the massacre was actually asetup to frame Capone. Some believe
(32:15):
that rival gangs or evencorrupt law enforcement or orchestrated
the attack to turn publicopinion against him. After all, the
massacre brought so much heaton Capone that it marked the beginning
of the end for his empire.Another possibility is that it was
an inside job. Some accountssuggest that someone within Moran's
own gang may have tipped offCapone's men either out of fear or
(32:38):
for personal gang because, youknow, gang loyalty wasn't exactly
ironclad.
And let's not forget BugsMoran himself. While he was clearly
the target, was his survivalentirely coincidental? Or could he
have known about the hint andeven set his men into the trap to
save his own skin?
(32:58):
While there's no hard evidenceto support that the murkiness of
the world of organized crimemeant that anything was a possibility,
what we do know is that themassacre achieved its goal of crippling
Moran's gang, but it came witha cost.
That's right, Elena. The St.Valentine's Day massacre of 1929
weakened Moran's and his gang.But it also had unintended consequences
(33:20):
for Al Capone himself, whomany believe was behind the attack.
The massacre drew so muchattention that it became impossible
for authorities and the publicto ignore the violence continuing
to grip Chicago. And more tothe point, it represented a turning
point in America's war onorganized crime.
(33:40):
Coming up, we'll look at howthis one event helped take down Al
Capone and change the courseof American history.
So News of the St. Valentine'sDay Massacre spread rapidly in the
following days. Newspapersacross the country published graphic
photos of the crime scene, andthe public outcry was deafening.
(34:02):
And in short, the massacrecreated a public relations nightmare
for Capone.
It also caught the attentionof federal authorities, specifically
newly elected PresidentHerbert Hoover, who immediately looked
for a way to bring Capone andgangsters like him down. But they
couldn't pin the massacre onhim. And in reality, they didn't
(34:23):
care what crime actuallybrought an end to his illegal activities.
So Hoover began adding moremoney and agents to the effort to
end organized crime, andspecifically Al Capone's Organized
crime instead of murder oralcohol, bringing down Capone. In
the end, it was not paying histaxes. Capone was arrested on charges
of tax evasion.
(34:43):
That's right, tax evasion.Capone's lifestyle was lavish, and
it didn't exactly match hisreported tax income. By 1931, he
was convicted of tax evasionand sentenced to 11 years in federal
prison. While the massacredidn't directly lead to his conviction,
it certainly turned up theheat on his organization.
(35:05):
And what about Bugs Moran? Weknow the massacre effectively destroyed
his gang, but he managed tosurvive. What happened to him?
Well, similarly, USauthorities targeted his financial
crimes as well. In 1939, hewas convicted of conspiracy to cash
fraudulent checks and robberyand was jailed for five years. When
(35:25):
he emerged in the 1940s, theonce extravagant mob boss was now
nearly penniless and withoutany real power. In 1946, Moran was
arrested for a petty robberyof a tavern and died of lung cancer
two months into his next 10year sentence.
Just, just as an aside, do youremember Johnny Torio, the gentleman
(35:47):
gangster who gave his crimesyndicate over to Al Capone and went
back to Italy in 1925?
Yes. He said he was throughwith organized crime.
That turned out not to becompletely true. When Torrio went
back to Italy, he startedmeddling in organized crime again.
A few Years later, in 1928,Italy's fascist leader, Benito Mussolini,
(36:08):
began putting pressure on theMafia in Italy. That was part of
Mussolini's efforts to expandhis authority over the nation leading
up to World War II. As aresult, Torrio returned to the United
States. As you remember, thefederal authorities often focused
on financial crimes tosuccessfully convict monsters. And
similarly, in 1936, Torrio wasconvicted of income tax evasion.
(36:33):
Why can't mobsters just paytheir taxes now? As we mentioned,
no one was convicted for theirpart in the St. Valentine's Day Massacre.
But despite that, the eventhad a huge impact on policy and encouraged
some major historical shifts.First and foremost, it underscored
the failure of Prohibition asa policy. The 18th amendment was
(36:54):
rooted in progressive idealsthat banning alcohol would solve
societal problems. Butinstead, it created a thriving black
market that enriched criminalslike Al Capone and heightened criminal
activity. It had really theopposite effect.
It all seems to point to apowerful lesson about the limits
of moral legislation. When alaw is wildly unpopular and difficult
(37:17):
to enforce, it often createsmore problems than it solves. Prohibition
didn't eliminate alcohol. Itmade it more dangerous, drove it
underground and empoweredorganized crime and criminals while
eroding trust in lawenforcement and.
As images of the St.Valentine's Day Massacre crime scene
splashed across newspapers in1929, it seemed to symbolize the
(37:39):
failure of Prohibition and thechaos it had unleashed. The public
outcry and the outrage to themassacre and its root causes played
a key role in shiftingattitudes towards Prohibition. By
the early 1930s, there was agrowing consensus that the law was
doing more harm than good.This leading to the 1933 repeal of
(37:59):
the 18th Amendment andprohibition in the new 21st Amendment.
The massacre also highlightsthe corrosive impact of corruption.
In Chicago, organized crimethrived not just because of violence,
but because it had infiltratedthe political and law enforcement
system systems. Judges, policeand politicians were often complicit,
(38:20):
either through bribery or fear.
And this kind of corruptioncreates a sense of lawlessness that
undermines the veryinstitutions meant to protect society.
When the public sees the lawsbeing ignored or manipulated by those
in power, it breeds cynicismand distrust.
And culturally, the St.Valentine's Day massacre remains
one of the most infamouscrimes in American history. It's
(38:43):
been immortalized in books,films and TV shows, often as a symbol
of the brutality and excess ofthe Prohibition era. And the figures
of Al Capone and Bugs Moranare often glamorized and romanticized
as larger than life anti heroes.
And part of that originates inthe broader social, economic, and
cultural forces that drove themassacre in the first place. The
(39:05):
poverty and official andunofficial discrimination that many
immigrants faced created aneed for a special protection and
opportunities from within.Those special protection and opportunities
often evolved into and fromorganized crime.
And that same organized crimethrived within and exploited the
moral boundaries thatprogressive reformers had hoped would
(39:27):
fix the sins of society.Reformers of the progressive age
had hoped that by makingalcohol, gambling and prostitution
illegal, it would help thepoor avoid their vices and improve
their standing in society. Butreality turned out to be quite different.
But while the St. Valentine'sDay massacre mostly stood as a negative
symbol of the RoaringTwenties, it did have a few positive
(39:50):
consequences. The massacrerevealed the need to reform law enforcement
systems to help combatcorruption from within. And in the
process, it also led to a morecoordinated federal approach to combat
organized crime, including thecreation of agencies like the FBI.
In addition, Chicago becamethe first city with an independent
(40:11):
forensic crime laboratory atNorthwestern University. The lab
was initially established inan effort to find the murderers.
So in some ways, the field offorensic science was born out of
this tragedy.
Looking back, the St.Valentine's Day massacre was clearly
an infamous crime in history.But it also offers lessons that are
still relevant today. Whetherit's about creating effective laws,
(40:33):
addressing systemiccorruption, or understanding the
root causes of violence.History has so much to teach us.
And perhaps the most importantlesson is this. When society tries
to impose simple solutions oncomplex problems, the consequences
can be far reaching andunexpected. It's a reminder that
history is always morecomplicated than it seems.
(40:55):
That's all for now. This hasbeen history's greatest crimes. I'm
Michael.
And I'm Alana. Stay curious.
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