March 31, 2025 • 40 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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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Michael (00:11):
Picture this 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 brutalexecution, a hail of gunfire
that leaves them all but one ofthem dead.
Alana (00:31):
This is the St Valentine's Day Massacre, one of
the most infamous crimes inAmerican history.
It wasn't just a gangland hit.
It became a turning point inhow Americans viewed organized
crime, and we're here to unravelthe story behind the blood in
the snow.
Michael (00:48):
Welcome to History's Greatest Crimes, where we two
historians dive into the mostinfamous crimes in history,
peeling back the layers tounderstand their causes, their
impact and what they revealabout the world we live in today
.
I'm Michael.
Alana (01:02):
And I'm Elena.
This wasn't just a random actof violence.
It was a carefully orchestratedpower move during one of
America's most exciting and yetturbulent times.
Michael (01:13):
prohibition- Exactly, al Capone and Bugs Moran, two of
the most famous and infamousfigures in organized crime, were
locked in a battle for controlover Chicago's lucrative
bootlegging trade.
The massacre was the result ofthat rivalry, but the story
doesn't end there.
Alana (01:30):
So who pulled the trigger , what was the fallout and how
did this one event help totopple one of history's most
infamous gangsters?
Stick with us as we explorethese questions and more on
history's greatest crimes.
Michael (01:56):
Before we dive into the St Valentine's Day Massacre, we
need to understand Chicago'sunique history, how it
transformed from a frontier towninto a booming metropolis by
the early 20th century.
This backdrop is key tounderstanding the forces that
created both the city's growingopportunities and its dark
underbelly.
Alana (02:10):
Chicago, a city today of over 2 million people, was
founded in 1837 and began togrow by leaps and bounds due to
the city's location on LakeMichigan, which made it a
crucial hub for trade connectingthe Midwest to the rest of the
country.
Railroads expanded that roleeven further, making Chicago the
gateway to America's heartland.
(02:32):
The city grew rapidly and by1870, chicago was one of the
largest cities in the country.
Michael (02:39):
But then disaster struck.
Alana (02:41):
What happened In?
Michael (02:42):
1871, the Great Chicago Fire swept through the city
destroying over three squaremiles, destroying over 17,000
buildings, killing more than 300people and leaving nearly
100,000 people homeless.
Alana (02:58):
That must have been devastating for the people who
had built their whole lives inthe city.
Michael (03:03):
And that's absolutely true.
It was a catastrophe worth over$3.5 billion in today's money.
But instead of destroying thecity, it became a turning point.
After the fire, chicago rebuiltitself bigger, taller and more
ambitious than before.
The city became a symbol ofAmerican resilience, known for
its skyscrapers, industrialmight and booming population,
(03:26):
and by the end of the 1800s thecity had risen like a phoenix to
become an industrial powerhouse.
The union stockyards, steelmills and factories made it the
beating heart of America'seconomy.
Alana (03:38):
It's such a fascinating story about the city of Chicago,
but what I think makes thatstory even more interesting was
the concurrent influx ofimmigrants to the city.
They were very much a part ofrebuilding the city.
From the 1880s through the1920s, chicago's population
exploded as waves of immigrantsarrived, mostly from Southern
(04:00):
and Eastern Europe, includingItalians, poles, eastern
European Jews.
I'll add, though, that thenumber of immigrants heading to
Chicago also included Irish andGerman immigrants, as well as
Black Americans, who werefleeing the segregated South.
They all came in search of workand a better life.
By 1920, roughly 2.7 millionpeople lived in Chicago, with
(04:23):
just under 40% beingforeign-born.
Between 1890 and 1920, thecity's Polish-born population
grew nearly six-fold, theItalian-born population rose
more than ten-fold, and theAfrican-American population
increased eight-fold.
They settled in ethnicneighborhoods, creating vibrant
communities with their ownlanguages, traditions and
(04:45):
businesses.
Michael (04:46):
But these people came with dreams of success.
Their neighborhoods were alsomarked by poverty and
overcrowding.
Many immigrants lived intenements with poor sanitation
and few resources.
They faced discrimination andracism from both established
communities and the government.
The 1920s also saw there-emergence of the Ku Klux Klan
(05:07):
against immigration.
That decade also included theJohnson-Reed Act, an immigration
act which severely limitedarrivals from Southern and
Eastern Europe.
The targeting of specificimmigrant groups by domestic
terrorist groups and throughlegal policy created deep ethnic
and racial divisions in thecity.
Alana (05:27):
And in this environment organized crime found fertile
ground.
Gangs often started asneighborhood protection groups
filling a void where the lawfailed to serve them, but over
time these groups evolved intopowerful criminal organizations.
Michael (05:43):
The power of these criminal organizations expanded
during Prohibition when the 18thAmendment passed in 1919.
Prohibition banned theproduction, sale and transport
of alcohol.
But Prohibition wasn't justabout banning alcohol.
It was part of a larger push toshape a quote better society
(06:03):
through reform.
This was the progressive era.
Alana (06:07):
That's right, michael.
The progressive era was a timewhen reformers, many of whom
were middle class women, workedtogether to end societal
problems that they believedprevented the poor and
disadvantaged from leadingsuccessful, moral lives.
One of the main societalproblems that reformers focused
on was alcoholism.
(06:27):
They argued that the common,frequent consumption of alcohol
among Americans led toalcoholism, which in turn led to
the abandonment and neglect ofone's family, impoverishment,
disease and other moral crimeslike prostitution and stealing.
Progressives believed in thepower of reform to improve
society through governmentintervention like laws and
(06:49):
policies.
They championed ideas likepublic health, education, labor
rights and used stronggovernment intervention to
address the problems created byindustrialization and
urbanization.
Michael (07:02):
But while the goals of the progressive era sound
positive, inclusive even, inreality not everyone immediately
accepted the growing presenceof immigrants.
Many native-born Americans,particularly those of
Anglo-Saxon Protestantbackgrounds, viewed these new
immigrants with suspicion,derision and even prejudice.
(07:23):
They worried that immigrantswere undermining American values
and traditions and preventingprogress within society.
Alana (07:32):
And despite the positive nature of progressive reforms,
many reformers took a ratherpaternalistic approach to
immigrants.
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
(07:52):
urban life poverty, violence andvice All of these things they
believed immigrants sufferedfrom because of their customs
and religious practices.
For progressive reformers,prohibition wasn't just about
banning alcohol then it wasabout reshaping society,
literally reshaping immigrantsinto their ideal American.
Michael (08:13):
So at the turn of the century, prohibition became a
cornerstone of the progressivemovement.
Organizations like theAnti-Saloon League and the
Women's Christian TemperanceUnion argued that alcohol was
the root cause of the currentsocial ills and that banning it
would lead to a healthier lifefor families, safer communities
(08:33):
and a more productive workforce.
Alana (08:36):
But for many immigrant communities, prohibition felt
like an attack on their identity.
Drinking was often woven intocultural traditions.
Tack on their identity.
Drinking was often woven intocultural traditions,
celebrations, religiousceremonies and social gatherings
.
The saloon, as much then as itis today, wasn't just a place to
drink.
It was a community hub wherepeople gathered to share news
(09:03):
find jobs and connect withothers.
Michael (09:03):
Prohibition also highlighted a deep divide
between rural and urban America.
In rural areas, whereprogressive ideals often aligned
with conservative religiousvalues, banning alcohol just
made sense, but in cities, whereimmigrant cultures thrived, it
felt like a moral crusadeimposed by outsiders.
Alana (09:21):
This cultural divide fueled resentment.
Immigrants and working classAmericans saw prohibition as an
effort by elites to controltheir behavior and erase their
traditions, culture and ethnicidentities.
And they weren't wrong.
Many prohibition advocatesexplicitly linked their cause to
the Americanization ofimmigrant groups, to the
(09:42):
Americanization of immigrantgroups.
Michael (09:44):
When Prohibition went into effect in January 1920, it
didn't stop drinking, it justpushed it underground, and
organized crime took advantageof that.
Gangsters like Al Capone, whohimself came from an immigrant
background, filled the void leftby legal alcohol.
They supplied the speakeasieswith liquor, they bribed the
(10:10):
authorities to look the otherway and built criminal empires
on the backs of a law that manyAmericans simply didn't respect.
Alana (10:13):
So, while prohibition was rooted in progressive ideals,
its enforcement created theperfect environment for
organized crime to thrive, andin Chicago it led to a bloody
battle for control between menlike Al Capone and Bugs Moran.
Michael (10:29):
Let's now take a look at how prohibition fueled these
rivalries and set the stage forthe St Valentine's Day Massacre.
Alana (10:41):
Prohibition enacted by the 18th Amendment in 1919 was
intended to make America a moremoral and sober society.
But instead of eradicatingalcohol, it created an enormous
black market.
And this is where thebootleggers come in.
Just as an aside here, I findthe significance of bootlegging
to American history reallyinteresting.
(11:02):
Michael, would you tell ourlisteners more about who they
were?
Michael (11:06):
Oh, I would love to.
A bootlegger was someone whoillegally manufactured,
transported or sold alcohol, butthe term itself dates back to
the 19th century, when smugglerswould hide flasks in their
boots.
But during prohibition,bootlegging became so much more
Alcohol creation andtransportation on an industrial
(11:26):
scale.
Alana (11:27):
That's right, michael.
In the southern parts of thenation, bootleggers making and
shipping homemade moonshinebegan to use souped up cars to
stay ahead of the local policeand federal agents, and that
would ultimately lead to thedevelopment of stock car racing
and specifically NASCAR.
But over in Chicago, in theMideast, bootleggers didn't just
(11:47):
smuggle alcohol, they builtempires.
They imported liquor fromCanada, made moonshine in hidden
distilleries and bribed lawenforcement to look the other
way.
They supplied the thousands ofillegal bars known as
speakeasies, where people coulddrink, dance and socialize away
from the prying eyes of the law.
Michael (12:06):
And in Chicago no bootlegger was 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 the distributionnetworks, he bribed the
officials and eliminated rivalswith ruthless, violent
(12:30):
efficiency.
And he did it with a smile onhis face.
Alana (12:34):
But Capone wasn't alone.
Chicago's entire political andlaw enforcement system was
deeply corrupt.
The city's political machine,led by figures like Mayor
William Big Bill Thompson, wasnotorious for its patronage
system.
Politicians and police officerswere often on the payroll of
gangsters, turning a blind eyeto their activities and violence
(12:57):
.
Michael (12:58):
This corruption created a sense of lawlessness For many
working class Chicagoans.
Gangsters like Capone were seenas folk heroes, people who
defied the system and providedjobs and money, and even charity
, to their communities.
Alana (13:14):
But this wasn't just about survival.
Organized crime thrived onviolence.
Rivalries between gangs werecommon to control aspects of
trade or other areas ofinfluence, and prohibition
turned these rivalries intodeadly turf wars for control
over alcohol.
By the late 1920s, chicago hadbecome one of the most violent
(13:34):
cities in America, with dozensof gang-related murders each
year.
Michael (13:39):
And that's the backdrop for the St Valentine's Day
massacre.
It wasn't just a violent crimeit certainly was that but it was
the culmination of decades ofcity growth, large-scale
immigration, politicalcorruption and gang violence
that defined Chicago in theearly 20th century.
Alana (13:58):
With that history in mind , let's move forward into the
decade of the 1920s.
The 1920s are often called theRoaring 20s, and for good reason
.
This was a period of massivesocial, cultural and
technological change.
After the devastation of WorldWar I, america was booming.
The economy was growing at anunprecedented rate and new
(14:21):
mass-produced technologies likethe automobile, the radio and
motion pictures wererevolutionizing daily life.
Michael (14:28):
At the same time, urbanization was reshaping the
entire country.
For the first time in Americanhistory, more people lived in
cities than in rural areas.
Cities like Chicago became hubsof innovation, culture and
opportunity, but, as we've alsodiscussed, they became places of
stark inequality and growingethnic tensions.
Alana (14:50):
Culturally, the 1920s were marked by a clash between
tradition and modernity.
The older generation, shaped byVictorian values, often felt
threatened by the rise of jazzmusic, flappers and a freer
social attitude.
Younger generations embraced amore carefree, consumer-driven
lifestyle that sometimesappalled their parents.
Michael (15:13):
This cultural clash wasn't just about fashion or
music.
It was about power.
Groups like the Ku Klux Klangained influence by promoting a
return, to quote, traditionalvalues, while large immigrant
communities and urban youthpushed for progress and
acceptance.
Alana (15:31):
And this is where prohibition fits in.
The 18th Amendment which bannedthe production, sale and
transport of alcohol, was passedin 1919 and went into effect in
1920.
It was supposed to solve socialproblems, curb crime and create
a more moral society.
Michael (15:48):
But by the 1920s and the late 1920s, it was clear
that prohibition wasn't working.
The public had grown tired ofthe violence, corruption and the
hypocrisy that it had created.
But for men like Capone andMoran, prohibition was the
foundation of their power andthey were willing to kill to
protect it.
Alana (16:09):
The 1920s were a golden age for organized crime, and it
wasn't just because of alcohol.
As we mentioned before,prohibition provided a massive
financial opportunity, but thethese organizations had already
laid the groundwork throughother criminal enterprises like
gambling, extortion andprostitution, and that made it
all the easier for them to turnto supplying illegal alcohol to
(16:33):
those with the cash to pay forit.
Michael (16:35):
The criminal organizations of the time were
highly structured, almost likecorporations.
At the top were the bosses, menlike Capone and Moran who made
the big decisions and reaped thelargest profits.
Men like Capone and Moran whomade the big decisions and
reaped the largest profits.
Beneath them were lieutenantswho managed different aspects of
the business, from smugglingroutes to protection rackets.
Alana (16:53):
And then there were the enforcers, the muscle who
carried out orders andeliminated rivals.
These were the men responsiblefor the violence that became
synonymous with organized crimeduring the 1920s.
For them, loyalty waseverything, and betrayal often
meant death.
Michael (17:09):
But it's a tale as old as time.
The structure of theseorganizations wasn't just about
efficiency.
It was about control and greed.
Keeping the organizationtightly managed, crime bosses
could expand their operationsacross entire cities,
controlling neighborhoods,industries and even local
governments.
Alana (17:29):
And to make it all the more complex, it wasn't just
traditional criminals whoenjoyed the trade of illegal
alcohol supplied by organizedcrime.
Speakeasies, for example,became cultural hubs where
people from all walks of lifecame together to drink, dance
and socialize.
Many of these establishmentswere owned or supplied by crime
syndicates.
Michael (17:50):
At the same time, these organizations wielded enormous
political power.
They controlled elections, theytold people who they should
vote for, they bribed theofficials and even shaped city
policies.
In cities like Chicago, thevery lines between legal and
illegal worlds were often veryblurred.
Alana (18:09):
And, as we've explained before, for many working class
families, organized crime alsoprovided a sense of stability,
at least on the surface.
Gangsters offer jobs,protection and even charity in
their communities, but this camewith a cost Violence, fear and
the constant threat ofretribution.
And in Chicago that violencecame to a head due to the
(18:31):
rivalry between gang leaders AlCapone and Bugs Moran.
Let's take a closer look at howthese two men and their gangs
came to dominate the city.
Michael (18:45):
To fully understand the St Valentine's Day massacre, we
really do need to know moreabout the two men at the center
of it, al Capone and Bugs Moran.
Their rivalry defined Chicago'sunderworld, and their lives
leading up to that bloody day in1929 give us a window into the
forces that shaped them.
Alana (19:04):
Let's start with Alphonse Gabriel Capone, better known as
Al Capone, born in Brooklyn,new York, in 1899,.
Capone was the son of Italianimmigrants.
His parents were working class,his father a barber and his
mother a seamstress.
Michael (19:20):
Capone's early life was marked by a mix of ambition and
trouble.
He was a bright student, buthis temper often got him into
fights.
He eventually dropped.
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 manydifferent youth street gangs.
Alana (19:36):
By the time he was a teenager, capone was already
drawn into the world oforganized crime.
He started as a member ofsmall-time street gangs in
Brooklyn, where he learned theropes of the criminal underworld
.
His big break came when hejoined the gentleman gangster
Johnny Torrio's organization.
Torrio, who had immigrated fromsouthern Italy as a boy, had
(19:58):
found success as the leader ofthe infamous Five Points Gang in
Manhattan.
For some time.
He was commonly known as thebiggest gangster in America and,
as one US official put it,torrio was quote the smartest
and, I dare say, the best of allhoodlums.
Best referring to talent notmorals.
End quote.
Michael (20:19):
Torrio served as a mentor to the young Al Capone,
and when Torrio decided toexpand his criminal organization
to Chicago, capone went withhim Almost as soon as
Prohibition began.
The windy city of Chicago hadoffered an excellent opportunity
to gangsters for bootlegging,and in Chicago Capone quickly
rose to the ranks to becomeknown for his charisma and
(20:41):
ruthlessness.
Alana (20:42):
By the mid-1920s, capone had taken over Torrio's
operations.
Torrio had been shot severaltimes throughout his gangster
career and by 1925, it appearsthat he had had enough of that
lifestyle, at least in theUnited States.
Torrio moved back to Italy withhis wife and mother.
Supposedly he told Capone atthe time quote it's all yours,
(21:04):
al Me, I'm quitting, it's Europefor me.
End quote.
Now just one interesting fact.
When Torrio left the UnitedStates in 1925, he was grossing
about $70 million a year inprofits from bootlegging,
prostitution and gambling.
Today that would equal about$1.2 billion.
Michael (21:24):
That is a mind-boggling number, elena.
In the 1920s, with Capone thenin charge, he maintained and
expanded this Chicago empire ofbootlegging, 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 Caponesmile.
(21:46):
But Capone's success came at acost.
His empire was built onescalating violence.
He eliminated rivals withbrutal efficiency and his name
became synonymous with thebloody gang wars of the
Prohibition era.
Alana (22:01):
Now let's turn to Bugs Moran, born in Minnesota in 1893
, bugs Moran wasn't his originalname, he was actually born
Adelar Kunin, to a Frenchimmigrant father and a mother of
Canadian descent.
Michael (22:15):
That's right, Elena.
So Bugs Moran was alsoconnected to the wave of
immigration that we've beentalking about.
Moran's early life was markedby rebellion.
He dropped out of school as ateenager and quickly turned to
crime.
In his early 20s he fled toChicago to avoid his crimes back
home, but almost immediately hewas back to his old ways.
He was caught trying to rob awarehouse, taking part in a
(22:37):
horse-stealing ring, even takingpart in a robbery involving the
death of a police officer.
He robbed a freight car, forwhich he actually received a
variety of prison and jailsentences.
For all of these things, thatis when young Adelard Coonan
first adopted the name GeorgeMoran.
It was the first name hethought of when police asked him
who he was.
(22:58):
George Moran was a violent andunstable man who got the name
Bugs because everyone thought hewas nuts or buggy.
Alana (23:07):
In Chicago, moran joined the North Side Gang, a
predominantly Irish organizationled by Dean O'Banion.
Moran's reputation as a hotheadand a fighter made him a key
figure in the gang's operations.
In 1924, o'banion was gunneddown in his flower shop, which
had served as one front for hiscriminal activities.
(23:28):
Many believed that thisassassination was orchestrated
by Al Capone and Torrio.
When O'Banion was killed, moranbecame a prime leader of the
(23:49):
North Side Gang and he wasdetermined to take revenge on
Capone and his South Side Gang.
Escalating the violence inChicago's streets.
Moran's constant targeting ofTorrio is actually what
encouraged him to leave Chicagofor Italy, allowing Capone to
take over.
Michael (23:55):
Unlike Capone, Moran wasn't known for his charisma or
strategic thinking.
He was more of just a brawler,a man who relied on brute force
rather than finesse.
The rivalry between Capone andMoran was intense.
These two men were arch enemieswhen it came to the business,
competition and ideas of revenge.
(24:16):
But in reality they were twosides of the same coin Capone,
the flashy and calculatedItalian-American mob boss, and
Moran, the hot-headedIrish-American gang leader.
Alana (24:28):
Throughout the 1920s, their gangs were an all-out war
for control of Chicago'slucrative bootlegging market.
Each side targeted the otherwith assassinations and sabotage
, leaving a trail of bodies intheir wake.
But the real turning point camein 1926, when Moran attempted
to assassinate Capone.
(24:48):
Moran's men ambushed Capone ata restaurant with machine guns,
and this drive-by shooting sentover a thousand bullets into the
building, killing severalpeople but actually missing
their main target.
Michael (25:02):
And don't forget that after Moran tried and failed to
kill Capone in 1926, Moran hadthen placed a $50,000 bounty on
Capone's head, worth roughly $1million today.
The gang war that followed ledto an escalation of violence
that will culminate in the 1929St Valentine's Day Massacre.
Alana (25:24):
So we've arrived at the morning of February 14th 1929,
st Valentine's Day Massacre.
So we've arrived at the morningof February 14th 1929.
Picture this Seven members ofBugs Moran's Northside gang are
at a garage on North ClarkStreet.
They think they're there for aroutine meeting, possibly a
bootlegging deal.
Michael (25:41):
Instead, two men dressed as police officers walk
in, followed by two others incivilian clothes.
The gang members are ordered toline up against the wall.
They think it's a raid, butit's actually a setup.
Alana (25:54):
What happens next will go down as one of the most brutal
crimes in American history.
Stay with us.
Michael (26:05):
It's around 10.30 am on February 14th 1929.
Seven men are gathered insidethe SMC Carthage Company garage
at 2122 North Clark Street inChicago.
These men are all associates ormembers of Bugs Moran's
Northside gang.
Alana (26:23):
Unbeknownst to them, this wasn't going to be a routine
business meeting.
Outside, two men dressed aspolice officers and two others
in civilian clothes approachedthe building.
They planned every detail tomake it look like a police raid.
Michael (26:38):
The fake cops entered first.
Guns drawn, they orderedMoran's men to line up against
the wall as if they were goingto be arrested, Thinking that
this was just a standard raid.
The men complied.
They knew how this worked.
They would comply and then paysome bribes to fix this
misunderstanding.
Alana (26:55):
But this was no arrest.
Moments later, the other twomen walked in carrying Thompson
submachine guns, knowncolloquially as Tommy guns.
These guns could pump out up to1,200 rounds per minute and as
a result, in Chicago Tommy gunsactually had another name, the
Chicago typewriters, for theclick, click, click sounds that
(27:17):
they made as bullets were fired.
What's interesting is thatthese guns had originally been
manufactured to help Americanforces break the stalemate of
trench warfare and win World WarI for the Allies.
After World War I ended in 1918, Tommy guns were available to
the general public for purchase,and they quickly became the
signature weapon of organizedcrime syndicates, including
(27:40):
those of Moran and Capone.
Michael (27:43):
Bringing us back to February 14th of 1929, the two
men holding the Tommy gunsopened fire on Moran's men in
the garage.
The attackers were thorough,making sure no one was left
alive, or so they thought.
The scene was chaotic, bloodpooling on the floor, walls
riddled with bullets and theechoes of gunfire still ringing
(28:04):
in the morning air.
Alana (28:05):
When the dust settled, six of the men were dead.
The seventh, frank Gusenberg,was critically wounded but still
clinging to life.
He was rushed to the hospitalbut even as he lay dying, he
refused to identify his killers.
Michael (28:20):
When asked who shot him , gusenberg replied quote no one
, nobody shot me.
That's the code of silencethese men lived and died by.
Asked who shot him, gussenbergreplied quote no one, nobody
shot me.
That's the code of silencethese men lived and died by.
It also highlights the distrustof the government and police
authorities, as well as theloyalty, even in death, that the
mob underworld worked in.
Alana (28:40):
Meanwhile, the fake police and their accomplices
made a clean getaway.
Police and their accomplicesmade a clean getaway.
Witnesses later reported seeingthe men leaving the garage
calmly, even loading theirweapons into a car, as if they
were just wrapping up a routinepolice operation.
Michael (28:54):
When the real police arrived, they were met with one
of the grisliest crime scenes inhistory.
Photos of the massacre spreadquickly, shocking the nation.
But here's the thing theintended target Bugs Moran.
He wasn't even there.
Alana (29:09):
That's right.
Moran had been running latethat morning.
When he saw the fake policeoutside the garage, he turned
around and avoided the massacrealtogether.
But even though Moran lived,the loss was devastating for his
organization.
The seven victims includedhigh-ranking members of Moran's
gang.
Michael (29:27):
So who was really behind the St Valentine's Day
massacre?
Well, the obvious suspect, ofcourse, was Al Capone, and it
was common knowledge that he wasthe undisputed king of
Chicago's South Side and one ofthe most powerful mob bosses in
the country.
But proving his role in themassacre was another story
altogether.
Alana (29:44):
Capone had both the motive and the means.
The massacre wiped out keymembers of Bugs Moran's North
Side gang, giving Capone greatercontrol over Chicago's
lucrative bootlegging trade.
But there's a catch Caponewasn't even in Chicago that day.
Michael (30:01):
Exactly On February 14th 1929, capone was reportedly
in Florida meeting with hisattorneys at his Florida home.
It's the perfect alibi.
But let's be real right.
Capone didn't really need to bethere personally.
He had plenty of men who wouldcarry out the job for him.
Alana (30:17):
And one of those men might have been Fred Killer
Burke, a known associate ofCapone's, who was skilled in
using the same weapons that wereused in the massacre.
Burke's fingerprints were laterfound on a Tommy gun in his
possession, linking him to thecrime, but that wasn't enough to
convict him.
Years later, other criminalswould implicate him in the crime
(30:37):
, but in the end no one wasconvicted for the St Valentine's
Day massacre.
Michael (30:42):
This is just so crazy to me.
With such an obvious murdermotive, and even in eyewitnesses
, no one was ever convicted forthe St Valentine's Day massacre
of 1929.
Alana (30:55):
I agree, and the lack of a conviction means that we'll
never really know all of thedetails.
There's another theory, thatthe massacre was actually a
setup to frame Capone.
Some believe that rival gangsor even corrupt law enforcement
orchestrated the attack to turnpublic opinion against him.
After all, the massacre broughtso much heat on Capone that it
(31:16):
marked the beginning of theempire.
Another possibility is that itwas an inside job.
Some accounts suggest thatsomeone within Moran's own gang
may have tipped off Capone's men, either out of fear or for
personal gang, because, you know, gang loyalty wasn't exactly
ironclad.
Michael (31:34):
And let's not forget Bugs Moran himself.
While he was clearly the target, was his survival entirely
coincidental?
Or could he have known aboutthe hint and even set his men
into the trap to save his ownskin?
Alana (31:49):
While there's no hard evidence to support that the
murkiness of the world oforganized crime meant that
anything was a possibility, whatwe do know is that the massacre
achieved its goal of cripplingMoran's gang, but it came with a
cost.
Michael (32:03):
That's right.
The St Valentine's Day Massacreof 1929 weakened Moran and his
gang, but it also had unintendedconsequences for Al Capone
himself, who many believe wasbehind the attack.
The massacre drew so muchattention that it became
impossible for authorities andthe public to ignore the
violence continuing to gripChicago and, more to the point,
(32:26):
it represented a turning pointin America's war on organized
crime.
Alana (32:31):
Coming up.
We'll look at how this oneevent helped take down Al Capone
and change the course ofAmerican history.
Michael (32:43):
So news of the St Valentine's Day massacre spread
rapidly.
In the following days,newspapers across the country
published graphic photos of thecrime scene and the public
outcry was deafening.
And, in short, the massacrecreated a public relations
nightmare for Capone.
Alana (32:59):
It also caught the attention of federal authorities
, specifically newly electedPresident Herbert Hoover, who
immediately looked for a way tobring Capone and gangsters like
him down.
But they couldn't pin themassacre on him and in reality
they didn't care what crimeactually brought an end to his
illegal activities.
So Hoover began adding moremoney and agents to the effort
(33:21):
to end organized crime, andspecifically Al Capone's
organized crime, instead ofmurder or alcohol bringing down
Capone.
In the end it was not payinghis taxes.
Capone was arrested on chargesof tax evasion.
Michael (33:34):
That's right Tax evasion.
Capone's lifestyle was lavishand it didn't exactly match his
reported tax income.
By 1931, he was convicted oftax evasion and sentenced to 11
years in federal prison.
While the massacre didn'tdirectly lead to his conviction,
it certainly turned up the heaton his organization.
Alana (33:56):
And what about Bugs Moran ?
We know the massacreeffectively destroyed his gang,
but he managed to survive.
What happened to him?
Michael (34:04):
Well.
Similarly, us authoritiestargeted his financial crimes as
well.
In 1939, he was convicted ofconspiracy to cash fraudulent
checks and robbery and wasjailed for five years.
When he emerged in the 1940s,the once extravagant mob boss
was now nearly penniless andwithout any real power.
In 1946, moran was arrested fora petty robbery of a tavern and
(34:29):
died of lung cancer two monthsinto his next 10-year sentence.
Alana (34:34):
Just as an aside, do you remember Johnny Torrio, the
gentleman gangster who gave hiscrime syndicate over to Al
Capone and went back to Italy in1925?
Michael (34:43):
Yes, he said he was through with organized crime.
Alana (34:46):
That turned out not to be completely true.
When Torrio went back to Italy,he started meddling in
organized crime again.
A few years later, in 1928,italy's fascist leader, benito
Mussolini, began puttingpressure on the mafia in Italy.
That was part of Mussolini'sefforts to expand his authority
over the nation leading up toWorld War II.
(35:07):
As a result, torrio returned tothe United States.
As you remember, the federalauthorities often focused on
financial crimes to successfullyconvict mobsters, and similarly
, in 1936, torrio was convictedof income tax evasion.
Michael (35:24):
Why can't mobsters just pay their taxes?
Now, as we mentioned, no onewas convicted for their part in
the St Valentine's Day massacre,but despite that, the event had
a huge impact on policy andencouraged some major historical
shifts.
First and foremost, itunderscored the failure of
prohibition as a policy.
The 18th Amendment was rootedin progressive ideals that
(35:47):
banning alcohol would solvesocietal problems, but instead
it created a thriving blackmarket that enriched criminals
like Al Capone and heightenedcriminal activity.
It had really the oppositeeffect.
Alana (36:00):
It all seems to point to a powerful lesson about the
limits of moral legislation.
When a law is wildly unpopularand difficult to enforce, it
often creates more problems thanit solves.
Prohibition didn't eliminatealcohol.
It made it more dangerous,drove it underground and
empowered organized crime andcriminals, while eroding trust
(36:22):
in law enforcement.
Michael (36:23):
And as images of the St Valentine's Day massacre crime
scene splashed across newspapersin 1929, it seemed to symbolize
the failure of Prohibition andthe chaos it had unleashed.
The public outcry and theoutrage to the massacre and its
root causes played a key role inshifting attitudes towards
Prohibition.
By the early 1930s, there was agrowing consensus that the law
(36:45):
was doing more harm than good,this leading to the 1933 repeal
of the 18th Amendment andprohibition in the new 21st
Amendment.
Alana (36:55):
The massacre also highlights the corrosive impact
of corruption In Chicago.
Organized crime thrived notjust because of violence, but
because it had infiltrated thepolitical and law enforcement
systems.
Judges, police and politicianswere often complicit, either
through bribery or fear.
Michael (37:13):
And this kind of corruption creates a sense of
lawlessness that undermines thevery institutions meant to
protect society.
When the public sees the lawsbeing ignored or manipulated by
those in power, it breedscynicism and distrust.
Alana (37:27):
And culturally.
The St Valentine's Day massacreremains one of the most
infamous crimes in Americanhistory.
It's been immortalized in books, films and TV shows, often as a
symbol of the brutality andexcess of the Prohibition era,
and the figures of Al Capone andBugs Moran are often glamorized
and romanticized aslarger-than-life antiheroes.
Michael (37:49):
And part of that originates in the broader social
, economic and cultural forcesthat drove the massacre in the
first place.
The poverty and official andunofficial discrimination that
many immigrants faced created aneed for a special protection
and opportunities from within.
Those special protection andopportunities often evolved into
(38:09):
and from organized crime.
Alana (38:11):
And that same organized crime thrived within and
exploited the moral boundariesthat progressive reformers had
hoped would fix the sins ofsociety.
Reformers of the progressiveage had hoped that by making
alcohol, gambling andprostitution illegal, it would
help the poor avoid their vicesand improve their standing in
society, but reality turned outto be quite different.
Michael (38:35):
But while the St Valentine's Day massacre mostly
stood as a negative symbol ofthe Roaring Twenties, it did
have a few positive consequences.
The massacre revealed the needto reform law enforcement
systems to help combatcorruption from within, and in
the process it also led to amore coordinated federal
approach to combat organizedcrime, including the creation of
(38:56):
agencies like the FBI.
Alana (38:58):
In addition, Chicago became the first city with an
independent forensic crimelaboratory at Northwestern
University.
The lab was initiallyestablished in an effort to find
the murderers, so in some waysthe field of forensic science
was born out of this tragedy.
Michael (39:14):
Looking back, the St Valentine's Day Massacre was
clearly an infamous crime inhistory, but it also offers
lessons that are still relevanttoday.
Whether it's about creatingeffective laws, addressing
systemic corruption orunderstanding the root causes of
violence, history has so muchto teach us.
Alana (39:30):
And perhaps the most important lesson is this when
society tries to impose simplesolutions on complex problems,
the consequences can befar-reaching and unexpected.
It's a reminder that history isalways more complicated than it
seems.
Michael (39:46):
That's all for now.
This has been History'sGreatest Crimes.
I'm Michael.
Alana (39:51):
And I'm Elena, stay curious Bye.
Picture this 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 brutalexecution, a hail of gunfire
that leaves them all but one ofthem dead.
Alana (00:31):
This is the St Valentine's Day Massacre, one of
the most infamous crimes inAmerican history.
It wasn't just a gangland hit.
It became a turning point inhow Americans viewed organized
crime, and we're here to unravelthe story behind the blood in
the snow.
Michael (00:48):
Welcome to History's Greatest Crimes, where we two
historians dive into the mostinfamous crimes in history,
peeling back the layers tounderstand their causes, their
impact and what they revealabout the world we live in today
.
I'm Michael.
Alana (01:02):
And I'm Elena.
This wasn't just a random actof violence.
It was a carefully orchestratedpower move during one of
America's most exciting and yetturbulent times.
Michael (01:13):
prohibition- Exactly, al Capone and Bugs Moran, two of
the most famous and infamousfigures in organized crime, were
locked in a battle for controlover Chicago's lucrative
bootlegging trade.
The massacre was the result ofthat rivalry, but the story
doesn't end there.
Alana (01:30):
So who pulled the trigger , what was the fallout and how
did this one event help totopple one of history's most
infamous gangsters?
Stick with us as we explorethese questions and more on
history's greatest crimes.
Michael (01:56):
Before we dive into the St Valentine's Day Massacre, we
need to understand Chicago'sunique history, how it
transformed from a frontier towninto a booming metropolis by
the early 20th century.
This backdrop is key tounderstanding the forces that
created both the city's growingopportunities and its dark
underbelly.
Alana (02:10):
Chicago, a city today of over 2 million people, was
founded in 1837 and began togrow by leaps and bounds due to
the city's location on LakeMichigan, which made it a
crucial hub for trade connectingthe Midwest to the rest of the
country.
Railroads expanded that roleeven further, making Chicago the
gateway to America's heartland.
(02:32):
The city grew rapidly and by1870, chicago was one of the
largest cities in the country.
Michael (02:39):
But then disaster struck.
Alana (02:41):
What happened In?
Michael (02:42):
1871, the Great Chicago Fire swept through the city
destroying over three squaremiles, destroying over 17,000
buildings, killing more than 300people and leaving nearly
100,000 people homeless.
Alana (02:58):
That must have been devastating for the people who
had built their whole lives inthe city.
Michael (03:03):
And that's absolutely true.
It was a catastrophe worth over$3.5 billion in today's money.
But instead of destroying thecity, it became a turning point.
After the fire, chicago rebuiltitself bigger, taller and more
ambitious than before.
The city became a symbol ofAmerican resilience, known for
its skyscrapers, industrialmight and booming population,
(03:26):
and by the end of the 1800s thecity had risen like a phoenix to
become an industrial powerhouse.
The union stockyards, steelmills and factories made it the
beating heart of America'seconomy.
Alana (03:38):
It's such a fascinating story about the city of Chicago,
but what I think makes thatstory even more interesting was
the concurrent influx ofimmigrants to the city.
They were very much a part ofrebuilding the city.
From the 1880s through the1920s, chicago's population
exploded as waves of immigrantsarrived, mostly from Southern
(04:00):
and Eastern Europe, includingItalians, poles, eastern
European Jews.
I'll add, though, that thenumber of immigrants heading to
Chicago also included Irish andGerman immigrants, as well as
Black Americans, who werefleeing the segregated South.
They all came in search of workand a better life.
By 1920, roughly 2.7 millionpeople lived in Chicago, with
(04:23):
just under 40% beingforeign-born.
Between 1890 and 1920, thecity's Polish-born population
grew nearly six-fold, theItalian-born population rose
more than ten-fold, and theAfrican-American population
increased eight-fold.
They settled in ethnicneighborhoods, creating vibrant
communities with their ownlanguages, traditions and
(04:45):
businesses.
Michael (04:46):
But these people came with dreams of success.
Their neighborhoods were alsomarked by poverty and
overcrowding.
Many immigrants lived intenements with poor sanitation
and few resources.
They faced discrimination andracism from both established
communities and the government.
The 1920s also saw there-emergence of the Ku Klux Klan
(05:07):
against immigration.
That decade also included theJohnson-Reed Act, an immigration
act which severely limitedarrivals from Southern and
Eastern Europe.
The targeting of specificimmigrant groups by domestic
terrorist groups and throughlegal policy created deep ethnic
and racial divisions in thecity.
Alana (05:27):
And in this environment organized crime found fertile
ground.
Gangs often started asneighborhood protection groups
filling a void where the lawfailed to serve them, but over
time these groups evolved intopowerful criminal organizations.
Michael (05:43):
The power of these criminal organizations expanded
during Prohibition when the 18thAmendment passed in 1919.
Prohibition banned theproduction, sale and transport
of alcohol.
But Prohibition wasn't justabout banning alcohol.
It was part of a larger push toshape a quote better society
(06:03):
through reform.
This was the progressive era.
Alana (06:07):
That's right, michael.
The progressive era was a timewhen reformers, many of whom
were middle class women, workedtogether to end societal
problems that they believedprevented the poor and
disadvantaged from leadingsuccessful, moral lives.
One of the main societalproblems that reformers focused
on was alcoholism.
(06:27):
They argued that the common,frequent consumption of alcohol
among Americans led toalcoholism, which in turn led to
the abandonment and neglect ofone's family, impoverishment,
disease and other moral crimeslike prostitution and stealing.
Progressives believed in thepower of reform to improve
society through governmentintervention like laws and
(06:49):
policies.
They championed ideas likepublic health, education, labor
rights and used stronggovernment intervention to
address the problems created byindustrialization and
urbanization.
Michael (07:02):
But while the goals of the progressive era sound
positive, inclusive even, inreality not everyone immediately
accepted the growing presenceof immigrants.
Many native-born Americans,particularly those of
Anglo-Saxon Protestantbackgrounds, viewed these new
immigrants with suspicion,derision and even prejudice.
(07:23):
They worried that immigrantswere undermining American values
and traditions and preventingprogress within society.
Alana (07:32):
And despite the positive nature of progressive reforms,
many reformers took a ratherpaternalistic approach to
immigrants.
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
(07:52):
urban life poverty, violence andvice All of these things they
believed immigrants sufferedfrom because of their customs
and religious practices.
For progressive reformers,prohibition wasn't just about
banning alcohol then it wasabout reshaping society,
literally reshaping immigrantsinto their ideal American.
Michael (08:13):
So at the turn of the century, prohibition became a
cornerstone of the progressivemovement.
Organizations like theAnti-Saloon League and the
Women's Christian TemperanceUnion argued that alcohol was
the root cause of the currentsocial ills and that banning it
would lead to a healthier lifefor families, safer communities
(08:33):
and a more productive workforce.
Alana (08:36):
But for many immigrant communities, prohibition felt
like an attack on their identity.
Drinking was often woven intocultural traditions.
Tack on their identity.
Drinking was often woven intocultural traditions,
celebrations, religiousceremonies and social gatherings
.
The saloon, as much then as itis today, wasn't just a place to
drink.
It was a community hub wherepeople gathered to share news
(09:03):
find jobs and connect withothers.
Michael (09:03):
Prohibition also highlighted a deep divide
between rural and urban America.
In rural areas, whereprogressive ideals often aligned
with conservative religiousvalues, banning alcohol just
made sense, but in cities, whereimmigrant cultures thrived, it
felt like a moral crusadeimposed by outsiders.
Alana (09:21):
This cultural divide fueled resentment.
Immigrants and working classAmericans saw prohibition as an
effort by elites to controltheir behavior and erase their
traditions, culture and ethnicidentities.
And they weren't wrong.
Many prohibition advocatesexplicitly linked their cause to
the Americanization ofimmigrant groups, to the
(09:42):
Americanization of immigrantgroups.
Michael (09:44):
When Prohibition went into effect in January 1920, it
didn't stop drinking, it justpushed it underground, and
organized crime took advantageof that.
Gangsters like Al Capone, whohimself came from an immigrant
background, filled the void leftby legal alcohol.
They supplied the speakeasieswith liquor, they bribed the
(10:10):
authorities to look the otherway and built criminal empires
on the backs of a law that manyAmericans simply didn't respect.
Alana (10:13):
So, while prohibition was rooted in progressive ideals,
its enforcement created theperfect environment for
organized crime to thrive, andin Chicago it led to a bloody
battle for control between menlike Al Capone and Bugs Moran.
Michael (10:29):
Let's now take a look at how prohibition fueled these
rivalries and set the stage forthe St Valentine's Day Massacre.
Alana (10:41):
Prohibition enacted by the 18th Amendment in 1919 was
intended to make America a moremoral and sober society.
But instead of eradicatingalcohol, it created an enormous
black market.
And this is where thebootleggers come in.
Just as an aside here, I findthe significance of bootlegging
to American history reallyinteresting.
(11:02):
Michael, would you tell ourlisteners more about who they
were?
Michael (11:06):
Oh, I would love to.
A bootlegger was someone whoillegally manufactured,
transported or sold alcohol, butthe term itself dates back to
the 19th century, when smugglerswould hide flasks in their
boots.
But during prohibition,bootlegging became so much more
Alcohol creation andtransportation on an industrial
(11:26):
scale.
Alana (11:27):
That's right, michael.
In the southern parts of thenation, bootleggers making and
shipping homemade moonshinebegan to use souped up cars to
stay ahead of the local policeand federal agents, and that
would ultimately lead to thedevelopment of stock car racing
and specifically NASCAR.
But over in Chicago, in theMideast, bootleggers didn't just
(11:47):
smuggle alcohol, they builtempires.
They imported liquor fromCanada, made moonshine in hidden
distilleries and bribed lawenforcement to look the other
way.
They supplied the thousands ofillegal bars known as
speakeasies, where people coulddrink, dance and socialize away
from the prying eyes of the law.
Michael (12:06):
And in Chicago no bootlegger was 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 the distributionnetworks, he bribed the
officials and eliminated rivalswith ruthless, violent
(12:30):
efficiency.
And he did it with a smile onhis face.
Alana (12:34):
But Capone wasn't alone.
Chicago's entire political andlaw enforcement system was
deeply corrupt.
The city's political machine,led by figures like Mayor
William Big Bill Thompson, wasnotorious for its patronage
system.
Politicians and police officerswere often on the payroll of
gangsters, turning a blind eyeto their activities and violence
(12:57):
.
Michael (12:58):
This corruption created a sense of lawlessness For many
working class Chicagoans.
Gangsters like Capone were seenas folk heroes, people who
defied the system and providedjobs and money, and even charity
, to their communities.
Alana (13:14):
But this wasn't just about survival.
Organized crime thrived onviolence.
Rivalries between gangs werecommon to control aspects of
trade or other areas ofinfluence, and prohibition
turned these rivalries intodeadly turf wars for control
over alcohol.
By the late 1920s, chicago hadbecome one of the most violent
(13:34):
cities in America, with dozensof gang-related murders each
year.
Michael (13:39):
And that's the backdrop for the St Valentine's Day
massacre.
It wasn't just a violent crimeit certainly was that but it was
the culmination of decades ofcity growth, large-scale
immigration, politicalcorruption and gang violence
that defined Chicago in theearly 20th century.
Alana (13:58):
With that history in mind , let's move forward into the
decade of the 1920s.
The 1920s are often called theRoaring 20s, and for good reason
.
This was a period of massivesocial, cultural and
technological change.
After the devastation of WorldWar I, america was booming.
The economy was growing at anunprecedented rate and new
(14:21):
mass-produced technologies likethe automobile, the radio and
motion pictures wererevolutionizing daily life.
Michael (14:28):
At the same time, urbanization was reshaping the
entire country.
For the first time in Americanhistory, more people lived in
cities than in rural areas.
Cities like Chicago became hubsof innovation, culture and
opportunity, but, as we've alsodiscussed, they became places of
stark inequality and growingethnic tensions.
Alana (14:50):
Culturally, the 1920s were marked by a clash between
tradition and modernity.
The older generation, shaped byVictorian values, often felt
threatened by the rise of jazzmusic, flappers and a freer
social attitude.
Younger generations embraced amore carefree, consumer-driven
lifestyle that sometimesappalled their parents.
Michael (15:13):
This cultural clash wasn't just about fashion or
music.
It was about power.
Groups like the Ku Klux Klangained influence by promoting a
return, to quote, traditionalvalues, while large immigrant
communities and urban youthpushed for progress and
acceptance.
Alana (15:31):
And this is where prohibition fits in.
The 18th Amendment which bannedthe production, sale and
transport of alcohol, was passedin 1919 and went into effect in
1920.
It was supposed to solve socialproblems, curb crime and create
a more moral society.
Michael (15:48):
But by the 1920s and the late 1920s, it was clear
that prohibition wasn't working.
The public had grown tired ofthe violence, corruption and the
hypocrisy that it had created.
But for men like Capone andMoran, prohibition was the
foundation of their power andthey were willing to kill to
protect it.
Alana (16:09):
The 1920s were a golden age for organized crime, and it
wasn't just because of alcohol.
As we mentioned before,prohibition provided a massive
financial opportunity, but thethese organizations had already
laid the groundwork throughother criminal enterprises like
gambling, extortion andprostitution, and that made it
all the easier for them to turnto supplying illegal alcohol to
(16:33):
those with the cash to pay forit.
Michael (16:35):
The criminal organizations of the time were
highly structured, almost likecorporations.
At the top were the bosses, menlike Capone and Moran who made
the big decisions and reaped thelargest profits.
Men like Capone and Moran whomade the big decisions and
reaped the largest profits.
Beneath them were lieutenantswho managed different aspects of
the business, from smugglingroutes to protection rackets.
Alana (16:53):
And then there were the enforcers, the muscle who
carried out orders andeliminated rivals.
These were the men responsiblefor the violence that became
synonymous with organized crimeduring the 1920s.
For them, loyalty waseverything, and betrayal often
meant death.
Michael (17:09):
But it's a tale as old as time.
The structure of theseorganizations wasn't just about
efficiency.
It was about control and greed.
Keeping the organizationtightly managed, crime bosses
could expand their operationsacross entire cities,
controlling neighborhoods,industries and even local
governments.
Alana (17:29):
And to make it all the more complex, it wasn't just
traditional criminals whoenjoyed the trade of illegal
alcohol supplied by organizedcrime.
Speakeasies, for example,became cultural hubs where
people from all walks of lifecame together to drink, dance
and socialize.
Many of these establishmentswere owned or supplied by crime
syndicates.
Michael (17:50):
At the same time, these organizations wielded enormous
political power.
They controlled elections, theytold people who they should
vote for, they bribed theofficials and even shaped city
policies.
In cities like Chicago, thevery lines between legal and
illegal worlds were often veryblurred.
Alana (18:09):
And, as we've explained before, for many working class
families, organized crime alsoprovided a sense of stability,
at least on the surface.
Gangsters offer jobs,protection and even charity in
their communities, but this camewith a cost Violence, fear and
the constant threat ofretribution.
And in Chicago that violencecame to a head due to the
(18:31):
rivalry between gang leaders AlCapone and Bugs Moran.
Let's take a closer look at howthese two men and their gangs
came to dominate the city.
Michael (18:45):
To fully understand the St Valentine's Day massacre, we
really do need to know moreabout the two men at the center
of it, al Capone and Bugs Moran.
Their rivalry defined Chicago'sunderworld, and their lives
leading up to that bloody day in1929 give us a window into the
forces that shaped them.
Alana (19:04):
Let's start with Alphonse Gabriel Capone, better known as
Al Capone, born in Brooklyn,new York, in 1899,.
Capone was the son of Italianimmigrants.
His parents were working class,his father a barber and his
mother a seamstress.
Michael (19:20):
Capone's early life was marked by a mix of ambition and
trouble.
He was a bright student, buthis temper often got him into
fights.
He eventually dropped.
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 manydifferent youth street gangs.
Alana (19:36):
By the time he was a teenager, capone was already
drawn into the world oforganized crime.
He started as a member ofsmall-time street gangs in
Brooklyn, where he learned theropes of the criminal underworld
.
His big break came when hejoined the gentleman gangster
Johnny Torrio's organization.
Torrio, who had immigrated fromsouthern Italy as a boy, had
(19:58):
found success as the leader ofthe infamous Five Points Gang in
Manhattan.
For some time.
He was commonly known as thebiggest gangster in America and,
as one US official put it,torrio was quote the smartest
and, I dare say, the best of allhoodlums.
Best referring to talent notmorals.
End quote.
Michael (20:19):
Torrio served as a mentor to the young Al Capone,
and when Torrio decided toexpand his criminal organization
to Chicago, capone went withhim Almost as soon as
Prohibition began.
The windy city of Chicago hadoffered an excellent opportunity
to gangsters for bootlegging,and in Chicago Capone quickly
rose to the ranks to becomeknown for his charisma and
(20:41):
ruthlessness.
Alana (20:42):
By the mid-1920s, capone had taken over Torrio's
operations.
Torrio had been shot severaltimes throughout his gangster
career and by 1925, it appearsthat he had had enough of that
lifestyle, at least in theUnited States.
Torrio moved back to Italy withhis wife and mother.
Supposedly he told Capone atthe time quote it's all yours,
(21:04):
al Me, I'm quitting, it's Europefor me.
End quote.
Now just one interesting fact.
When Torrio left the UnitedStates in 1925, he was grossing
about $70 million a year inprofits from bootlegging,
prostitution and gambling.
Today that would equal about$1.2 billion.
Michael (21:24):
That is a mind-boggling number, elena.
In the 1920s, with Capone thenin charge, he maintained and
expanded this Chicago empire ofbootlegging, 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 Caponesmile.
(21:46):
But Capone's success came at acost.
His empire was built onescalating violence.
He eliminated rivals withbrutal efficiency and his name
became synonymous with thebloody gang wars of the
Prohibition era.
Alana (22:01):
Now let's turn to Bugs Moran, born in Minnesota in 1893
, bugs Moran wasn't his originalname, he was actually born
Adelar Kunin, to a Frenchimmigrant father and a mother of
Canadian descent.
Michael (22:15):
That's right, Elena.
So Bugs Moran was alsoconnected to the wave of
immigration that we've beentalking about.
Moran's early life was markedby rebellion.
He dropped out of school as ateenager and quickly turned to
crime.
In his early 20s he fled toChicago to avoid his crimes back
home, but almost immediately hewas back to his old ways.
He was caught trying to rob awarehouse, taking part in a
(22:37):
horse-stealing ring, even takingpart in a robbery involving the
death of a police officer.
He robbed a freight car, forwhich he actually received a
variety of prison and jailsentences.
For all of these things, thatis when young Adelard Coonan
first adopted the name GeorgeMoran.
It was the first name hethought of when police asked him
who he was.
(22:58):
George Moran was a violent andunstable man who got the name
Bugs because everyone thought hewas nuts or buggy.
Alana (23:07):
In Chicago, moran joined the North Side Gang, a
predominantly Irish organizationled by Dean O'Banion.
Moran's reputation as a hotheadand a fighter made him a key
figure in the gang's operations.
In 1924, o'banion was gunneddown in his flower shop, which
had served as one front for hiscriminal activities.
(23:28):
Many believed that thisassassination was orchestrated
by Al Capone and Torrio.
When O'Banion was killed, moranbecame a prime leader of the
(23:49):
North Side Gang and he wasdetermined to take revenge on
Capone and his South Side Gang.
Escalating the violence inChicago's streets.
Moran's constant targeting ofTorrio is actually what
encouraged him to leave Chicagofor Italy, allowing Capone to
take over.
Michael (23:55):
Unlike Capone, Moran wasn't known for his charisma or
strategic thinking.
He was more of just a brawler,a man who relied on brute force
rather than finesse.
The rivalry between Capone andMoran was intense.
These two men were arch enemieswhen it came to the business,
competition and ideas of revenge.
(24:16):
But in reality they were twosides of the same coin Capone,
the flashy and calculatedItalian-American mob boss, and
Moran, the hot-headedIrish-American gang leader.
Alana (24:28):
Throughout the 1920s, their gangs were an all-out war
for control of Chicago'slucrative bootlegging market.
Each side targeted the otherwith assassinations and sabotage
, leaving a trail of bodies intheir wake.
But the real turning point camein 1926, when Moran attempted
to assassinate Capone.
(24:48):
Moran's men ambushed Capone ata restaurant with machine guns,
and this drive-by shooting sentover a thousand bullets into the
building, killing severalpeople but actually missing
their main target.
Michael (25:02):
And don't forget that after Moran tried and failed to
kill Capone in 1926, Moran hadthen placed a $50,000 bounty on
Capone's head, worth roughly $1million today.
The gang war that followed ledto an escalation of violence
that will culminate in the 1929St Valentine's Day Massacre.
Alana (25:24):
So we've arrived at the morning of February 14th 1929,
st Valentine's Day Massacre.
So we've arrived at the morningof February 14th 1929.
Picture this Seven members ofBugs Moran's Northside gang are
at a garage on North ClarkStreet.
They think they're there for aroutine meeting, possibly a
bootlegging deal.
Michael (25:41):
Instead, two men dressed as police officers walk
in, followed by two others incivilian clothes.
The gang members are ordered toline up against the wall.
They think it's a raid, butit's actually a setup.
Alana (25:54):
What happens next will go down as one of the most brutal
crimes in American history.
Stay with us.
Michael (26:05):
It's around 10.30 am on February 14th 1929.
Seven men are gathered insidethe SMC Carthage Company garage
at 2122 North Clark Street inChicago.
These men are all associates ormembers of Bugs Moran's
Northside gang.
Alana (26:23):
Unbeknownst to them, this wasn't going to be a routine
business meeting.
Outside, two men dressed aspolice officers and two others
in civilian clothes approachedthe building.
They planned every detail tomake it look like a police raid.
Michael (26:38):
The fake cops entered first.
Guns drawn, they orderedMoran's men to line up against
the wall as if they were goingto be arrested, Thinking that
this was just a standard raid.
The men complied.
They knew how this worked.
They would comply and then paysome bribes to fix this
misunderstanding.
Alana (26:55):
But this was no arrest.
Moments later, the other twomen walked in carrying Thompson
submachine guns, knowncolloquially as Tommy guns.
These guns could pump out up to1,200 rounds per minute and as
a result, in Chicago Tommy gunsactually had another name, the
Chicago typewriters, for theclick, click, click sounds that
(27:17):
they made as bullets were fired.
What's interesting is thatthese guns had originally been
manufactured to help Americanforces break the stalemate of
trench warfare and win World WarI for the Allies.
After World War I ended in 1918, Tommy guns were available to
the general public for purchase,and they quickly became the
signature weapon of organizedcrime syndicates, including
(27:40):
those of Moran and Capone.
Michael (27:43):
Bringing us back to February 14th of 1929, the two
men holding the Tommy gunsopened fire on Moran's men in
the garage.
The attackers were thorough,making sure no one was left
alive, or so they thought.
The scene was chaotic, bloodpooling on the floor, walls
riddled with bullets and theechoes of gunfire still ringing
(28:04):
in the morning air.
Alana (28:05):
When the dust settled, six of the men were dead.
The seventh, frank Gusenberg,was critically wounded but still
clinging to life.
He was rushed to the hospitalbut even as he lay dying, he
refused to identify his killers.
Michael (28:20):
When asked who shot him , gusenberg replied quote no one
, nobody shot me.
That's the code of silencethese men lived and died by.
Asked who shot him, gussenbergreplied quote no one, nobody
shot me.
That's the code of silencethese men lived and died by.
It also highlights the distrustof the government and police
authorities, as well as theloyalty, even in death, that the
mob underworld worked in.
Alana (28:40):
Meanwhile, the fake police and their accomplices
made a clean getaway.
Police and their accomplicesmade a clean getaway.
Witnesses later reported seeingthe men leaving the garage
calmly, even loading theirweapons into a car, as if they
were just wrapping up a routinepolice operation.
Michael (28:54):
When the real police arrived, they were met with one
of the grisliest crime scenes inhistory.
Photos of the massacre spreadquickly, shocking the nation.
But here's the thing theintended target Bugs Moran.
He wasn't even there.
Alana (29:09):
That's right.
Moran had been running latethat morning.
When he saw the fake policeoutside the garage, he turned
around and avoided the massacrealtogether.
But even though Moran lived,the loss was devastating for his
organization.
The seven victims includedhigh-ranking members of Moran's
gang.
Michael (29:27):
So who was really behind the St Valentine's Day
massacre?
Well, the obvious suspect, ofcourse, was Al Capone, and it
was common knowledge that he wasthe undisputed king of
Chicago's South Side and one ofthe most powerful mob bosses in
the country.
But proving his role in themassacre was another story
altogether.
Alana (29:44):
Capone had both the motive and the means.
The massacre wiped out keymembers of Bugs Moran's North
Side gang, giving Capone greatercontrol over Chicago's
lucrative bootlegging trade.
But there's a catch Caponewasn't even in Chicago that day.
Michael (30:01):
Exactly On February 14th 1929, capone was reportedly
in Florida meeting with hisattorneys at his Florida home.
It's the perfect alibi.
But let's be real right.
Capone didn't really need to bethere personally.
He had plenty of men who wouldcarry out the job for him.
Alana (30:17):
And one of those men might have been Fred Killer
Burke, a known associate ofCapone's, who was skilled in
using the same weapons that wereused in the massacre.
Burke's fingerprints were laterfound on a Tommy gun in his
possession, linking him to thecrime, but that wasn't enough to
convict him.
Years later, other criminalswould implicate him in the crime
(30:37):
, but in the end no one wasconvicted for the St Valentine's
Day massacre.
Michael (30:42):
This is just so crazy to me.
With such an obvious murdermotive, and even in eyewitnesses
, no one was ever convicted forthe St Valentine's Day massacre
of 1929.
Alana (30:55):
I agree, and the lack of a conviction means that we'll
never really know all of thedetails.
There's another theory, thatthe massacre was actually a
setup to frame Capone.
Some believe that rival gangsor even corrupt law enforcement
orchestrated the attack to turnpublic opinion against him.
After all, the massacre broughtso much heat on Capone that it
(31:16):
marked the beginning of theempire.
Another possibility is that itwas an inside job.
Some accounts suggest thatsomeone within Moran's own gang
may have tipped off Capone's men, either out of fear or for
personal gang, because, you know, gang loyalty wasn't exactly
ironclad.
Michael (31:34):
And let's not forget Bugs Moran himself.
While he was clearly the target, was his survival entirely
coincidental?
Or could he have known aboutthe hint and even set his men
into the trap to save his ownskin?
Alana (31:49):
While there's no hard evidence to support that the
murkiness of the world oforganized crime meant that
anything was a possibility, whatwe do know is that the massacre
achieved its goal of cripplingMoran's gang, but it came with a
cost.
Michael (32:03):
That's right.
The St Valentine's Day Massacreof 1929 weakened Moran and his
gang, but it also had unintendedconsequences for Al Capone
himself, who many believe wasbehind the attack.
The massacre drew so muchattention that it became
impossible for authorities andthe public to ignore the
violence continuing to gripChicago and, more to the point,
(32:26):
it represented a turning pointin America's war on organized
crime.
Alana (32:31):
Coming up.
We'll look at how this oneevent helped take down Al Capone
and change the course ofAmerican history.
Michael (32:43):
So news of the St Valentine's Day massacre spread
rapidly.
In the following days,newspapers across the country
published graphic photos of thecrime scene and the public
outcry was deafening.
And, in short, the massacrecreated a public relations
nightmare for Capone.
Alana (32:59):
It also caught the attention of federal authorities
, specifically newly electedPresident Herbert Hoover, who
immediately looked for a way tobring Capone and gangsters like
him down.
But they couldn't pin themassacre on him and in reality
they didn't care what crimeactually brought an end to his
illegal activities.
So Hoover began adding moremoney and agents to the effort
(33:21):
to end organized crime, andspecifically Al Capone's
organized crime, instead ofmurder or alcohol bringing down
Capone.
In the end it was not payinghis taxes.
Capone was arrested on chargesof tax evasion.
Michael (33:34):
That's right Tax evasion.
Capone's lifestyle was lavishand it didn't exactly match his
reported tax income.
By 1931, he was convicted oftax evasion and sentenced to 11
years in federal prison.
While the massacre didn'tdirectly lead to his conviction,
it certainly turned up the heaton his organization.
Alana (33:56):
And what about Bugs Moran ?
We know the massacreeffectively destroyed his gang,
but he managed to survive.
What happened to him?
Michael (34:04):
Well.
Similarly, us authoritiestargeted his financial crimes as
well.
In 1939, he was convicted ofconspiracy to cash fraudulent
checks and robbery and wasjailed for five years.
When he emerged in the 1940s,the once extravagant mob boss
was now nearly penniless andwithout any real power.
In 1946, moran was arrested fora petty robbery of a tavern and
(34:29):
died of lung cancer two monthsinto his next 10-year sentence.
Alana (34:34):
Just as an aside, do you remember Johnny Torrio, the
gentleman gangster who gave hiscrime syndicate over to Al
Capone and went back to Italy in1925?
Michael (34:43):
Yes, he said he was through with organized crime.
Alana (34:46):
That turned out not to be completely true.
When Torrio went back to Italy,he started meddling in
organized crime again.
A few years later, in 1928,italy's fascist leader, benito
Mussolini, began puttingpressure on the mafia in Italy.
That was part of Mussolini'sefforts to expand his authority
over the nation leading up toWorld War II.
(35:07):
As a result, torrio returned tothe United States.
As you remember, the federalauthorities often focused on
financial crimes to successfullyconvict mobsters, and similarly
, in 1936, torrio was convictedof income tax evasion.
Michael (35:24):
Why can't mobsters just pay their taxes?
Now, as we mentioned, no onewas convicted for their part in
the St Valentine's Day massacre,but despite that, the event had
a huge impact on policy andencouraged some major historical
shifts.
First and foremost, itunderscored the failure of
prohibition as a policy.
The 18th Amendment was rootedin progressive ideals that
(35:47):
banning alcohol would solvesocietal problems, but instead
it created a thriving blackmarket that enriched criminals
like Al Capone and heightenedcriminal activity.
It had really the oppositeeffect.
Alana (36:00):
It all seems to point to a powerful lesson about the
limits of moral legislation.
When a law is wildly unpopularand difficult to enforce, it
often creates more problems thanit solves.
Prohibition didn't eliminatealcohol.
It made it more dangerous,drove it underground and
empowered organized crime andcriminals, while eroding trust
(36:22):
in law enforcement.
Michael (36:23):
And as images of the St Valentine's Day massacre crime
scene splashed across newspapersin 1929, it seemed to symbolize
the failure of Prohibition andthe chaos it had unleashed.
The public outcry and theoutrage to the massacre and its
root causes played a key role inshifting attitudes towards
Prohibition.
By the early 1930s, there was agrowing consensus that the law
(36:45):
was doing more harm than good,this leading to the 1933 repeal
of the 18th Amendment andprohibition in the new 21st
Amendment.
Alana (36:55):
The massacre also highlights the corrosive impact
of corruption In Chicago.
Organized crime thrived notjust because of violence, but
because it had infiltrated thepolitical and law enforcement
systems.
Judges, police and politicianswere often complicit, either
through bribery or fear.
Michael (37:13):
And this kind of corruption creates a sense of
lawlessness that undermines thevery institutions meant to
protect society.
When the public sees the lawsbeing ignored or manipulated by
those in power, it breedscynicism and distrust.
Alana (37:27):
And culturally.
The St Valentine's Day massacreremains one of the most
infamous crimes in Americanhistory.
It's been immortalized in books, films and TV shows, often as a
symbol of the brutality andexcess of the Prohibition era,
and the figures of Al Capone andBugs Moran are often glamorized
and romanticized aslarger-than-life antiheroes.
Michael (37:49):
And part of that originates in the broader social
, economic and cultural forcesthat drove the massacre in the
first place.
The poverty and official andunofficial discrimination that
many immigrants faced created aneed for a special protection
and opportunities from within.
Those special protection andopportunities often evolved into
(38:09):
and from organized crime.
Alana (38:11):
And that same organized crime thrived within and
exploited the moral boundariesthat progressive reformers had
hoped would fix the sins ofsociety.
Reformers of the progressiveage had hoped that by making
alcohol, gambling andprostitution illegal, it would
help the poor avoid their vicesand improve their standing in
society, but reality turned outto be quite different.
Michael (38:35):
But while the St Valentine's Day massacre mostly
stood as a negative symbol ofthe Roaring Twenties, it did
have a few positive consequences.
The massacre revealed the needto reform law enforcement
systems to help combatcorruption from within, and in
the process it also led to amore coordinated federal
approach to combat organizedcrime, including the creation of
(38:56):
agencies like the FBI.
Alana (38:58):
In addition, Chicago became the first city with an
independent forensic crimelaboratory at Northwestern
University.
The lab was initiallyestablished in an effort to find
the murderers, so in some waysthe field of forensic science
was born out of this tragedy.
Michael (39:14):
Looking back, the St Valentine's Day Massacre was
clearly an infamous crime inhistory, but it also offers
lessons that are still relevanttoday.
Whether it's about creatingeffective laws, addressing
systemic corruption orunderstanding the root causes of
violence, history has so muchto teach us.
Alana (39:30):
And perhaps the most important lesson is this when
society tries to impose simplesolutions on complex problems,
the consequences can befar-reaching and unexpected.
It's a reminder that history isalways more complicated than it
seems.
Michael (39:46):
That's all for now.
This has been History'sGreatest Crimes.
I'm Michael.
Alana (39:51):
And I'm Elena, stay curious Bye.
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