ain't there nobody that can shoot this guy so
he don't bounce back that is uh such a wild thing
to say right that is a direct quote from the
infamous 1930s mobster dutch schultz and he's
expressing what had to be just the most profound
frustration of his entire criminal career because
he was talking about a rival who simply refused
to die exactly welcome to today's deep dive i
am your host and with me is our resident historian
to help break this all down glad to be here this
is um A really unbelievable story. It really
is. Our mission today is to unpack a truly defining
chapter of prohibition history and 1920s organized
crime. We are using a comprehensive historical
profile sourced from Wikipedia to explore the
completely bullet -riddled biography of Jack
Legs Diamond. And that quote from Dutch Schultz,
I mean, it captures a sheer disbelief that was
shared not just by rival gangs, but by the police,
the press, and honestly, the general public.
Yeah, we are talking about a figure who survived
so much lead. He seemed entirely immune to the
consequences of his own lifestyle. And I want
you, the listener, to just imagine for a second
living in a time where Manhattan bootleggers
were global celebrities. Oh, absolutely. Splashed
across the front pages of international newspapers.
Right. Yet they couldn't even sit in a hotel
room without dodging actual gunfire. What's fascinating
here is how Jack Diamond's life wasn't just a
string of random violent acts. It functions as
a perfect mirror for the era itself. How so?
Well, when you examine his timeline, You are
looking directly at the lawlessness, the systemic
corruption, and the really ruthless hyper -capitalist
spirit of the underworld between the world wars.
Okay, let's unpack this from the very beginning.
Because a person doesn't just wake up one day
as the most unkillable man in New York. No, you
have to be forged in a very specific environment
for that. Exactly. So Jack Diamond was born in
1897 in Philadelphia to Irish immigrants Sarah
and John Diamond. And the socioeconomic reality
for that family was, well, it was grim. Extremely
grim. His mother suffered from severe arthritis
and eventually passed away from a bacterial infection
and a fever when Jack was just a teenager. And
without any modern social safety nets to rely
on, his father moved the boys to Brooklyn to
find work. And you have to look at what Brooklyn
was at the turn of the century. It was an incredibly
harsh environment for a grieving, impoverished
immigrant family. It's just brutal. Young men
in those neighborhoods faced a really stark choice.
You either take a grueling, highly dangerous
industrial labor job for pennies. Or you find
an illicit way to survive. Right. The streets
essentially became the primary educator for someone
like Jack. And he certainly took that illicit
route. He quickly fell in with a Manhattan street
gang known as the Hudson Dusters. Which is a
great name. It is. As sources note, this wasn't
just some group of pickpockets. The dusters were
notorious on the West Side. They were known for
erratic, violent behavior, often fueled by heavy
cocaine use. Yeah, they were intense. And they
specialized in robbing cargo right off the shipping
docks. So by 1914, Jack is already breaking into
jewelry stores. He eventually gets drafted into
the U .S. Army during World War I. But military
discipline, as you can imagine, clashes completely
with his street upbringing. It's oil and water.
Completely. He deserts. Gets caught. and is sentenced
to Leavenworth Military Prison for two years.
Which is a crucial turning point. I mean, when
you send a young, street -level criminal into
a hardened military prison environment like Leavenworth
in the late 1910s, it doesn't rehabilitate them.
No, not at all. It acts as an advanced networking
opportunity. It hardens whatever empathy they
might have had left. So by the time he's released
in 1921, he's perfectly primed for the explosion
of organized crime that arrives with the 1920s.
That perfectly sets up his entry into the...
big leagues and around this time he earns the
nickname legs ah yes the historical profile gives
us two possible origins for this either he was
an incredibly flamboyant energetic dancer at
the local clubs or or he simply possessed the
ability to run exceptionally fast when his enemies
were chasing him right And given everything we
are about to discuss, the running theory feels
pretty practical. It certainly became a necessary
survival skill. Definitely. So he starts working
as hired muscle and eventually lands a role as
the personal bodyguard for the legendary gambler
Arnold Rothstein. And for those unfamiliar. Rothstein
wasn't your average street thug. He was a titan
of the underworld. He effectively transformed
organized crime from a chaotic street brawl into
a sophisticated corporate structure. But it's
when prohibition makes alcohol illegal across
the United States that Diamond steps out of Rothstein's
shadow and really shows his own terrifying ingenuity.
He finds his niche. He does. He travels to Europe
to secure narcotics and beer. That actually fails,
but he does secure a massive supply of liquor.
What baffles me is how he solved the smuggling
problem when the main ports were heavily policed.
If we connect this to the bigger picture, Prohibition
forced criminals to evolve from mere enforcers
into highly innovative supply chain managers.
Supply chain managers, yeah. Diamond realized
that fighting a heavily armed Coast Guard at
the New York docks was just bad for business.
Instead, he developed a completely decentralized
logistics network. It's so clever. He arranged
for the incoming ships to simply dump partially
full barrels of liquor overboard into the ocean.
Just right into the water. Miles off the coast.
And the tidal currents would naturally carry
these floating barrels right onto the beaches
of Long Island. Which is brilliant. And he didn't
even need a massive crew of mobsters to retrieve
them. He just waited on the shore and paid local
kids a nickel for... every barrel they dragged
out of the surf and brought to his waiting trucks.
A nickel a barrel. Just consider the elegance
of that operation. He bypassed federal jurisdiction,
weaponized the ocean currents, and outsourced
the physical labor to neighborhood children looking
for candy money. It's crazy. It illustrates exactly
why federal agents could never fully shut down
the illicit alcohol trade. The syndicates were
simply out thinking the law. But the corporate
logistics soon gave way to visceral violence.
Following the murder of his boss, Little Augie
Organ, Diamond seizes control of the downtown
Manhattan alcohol distribution. He steps right
into the power vacuum. He establishes his headquarters
at a Broadway speakeasy called the Hotsy Totsy
Club. And in July 1929, the business model takes
a very dark turn. Diamond and an associate get
into a massive brawl with some drunken patrons.
Guns are drawn, three men are shot, and two of
them die right there on the floor. This is where
we see the shift from clever smuggling to the
raw subversion of the justice system. The aftermath
of the Hotsy Totsy shooting really reveals the
sheer scale of intimidation these syndicates
wielded. Because you have a double homicide in
a crowded Broadway club, dozens of people saw
it happen. But when the police arrive to build
their case, the witnesses start vanishing. This
is disappearing. The bartender goes missing.
Three waiters disappear. Even the coat check
girl vanishes without a trace. The authorities
eventually find one of the missing witnesses
shot dead across state lines in New Jersey. Diamonds
is never charged with the murders, although the
city does force the Hotsy Totsy Club to close
its doors. Making an entire staff of civilian
witnesses disappear requires an immense coordinated
network of terror. I mean, they weren't just
hiding from the police. They were actively dismantling
the state's ability to prosecute crime. Yeah,
it's a whole different level. And as Diamond's
territory expanded, he began clashing with other
rising power players, notably Dutch Schultz,
who was aggressively expanding his own operations
out of Harlem. And Diamond's tactics for dealing
with that competition were brutal. He wanted
total monopolies. In 1930, he and his crew kidnap
a truck driver named Grover Parks up in Cairo,
New York. Just a truck driver. Yeah, they just
want to know the origin point of Parks' load
of hard cider. When Parks claims ignorance, Diamond's
men subject him to a brutal beating and torture
before finally letting him go. He actually repeats
this tactic later that year, kidnapping a man
named James Duncan. He's just using brute force
at this point. Diamond manages to beat the state
kidnapping charges, but the federal government
finally pins him down with a four -year sentence.
The walls were rapidly closing in. You have to
picture the multi -front war he was fighting
by the summer of 1930. The local police want
him for murder, the federal agents are pursuing
him for interstate crimes, and rival factions
like Dutch Schultz's crew are actively trying
to assassinate him to absorb his territory. Here's
where it gets really interesting. It's August
1930. The heat in Manhattan is suffocating in
every possible sense. So Legs Diamond decides
he simply needs a vacation. A vacation. He secures
a ticket under the alias John Nolan and boards
the transatlantic ocean liner Belgian Land, setting
sail for Europe. Fleeing to Europe was a standard
play for high profile figures looking to let
the domestic dust settle. But the NYPD quickly
realizes their prime target is missing. They
search the manifests of ships like the Olympic
and the Baltic, but come up empty. Finally, they
send a wireless telegraph out into the Atlantic
to the Belgian land. And they find him. The captain
confirms they have a passenger matching Diamond's
description. And what is the most hunted man
in New York doing? He is spending the entire
voyage lounging in the ship's smoking room, playing
high -stakes poker. Meanwhile, the NYPD initiates
a full -blown diplomatic incident. They begin
frantically telegraphing Scotland Yard, the French
authorities, the Belgian police, issuing a formal
warning that Jack Diamond is inbound, basically
labeling him a highly undesirable character.
That sets off a spectacular international rejection
tour. The Belgian land docks in Plymouth, England.
Detectives from Scotland Yard are waiting at
the gangway. They're not letting him off. No,
they refuse to let him disembark. Diamond tries
to play the innocent tourist for the swarm of
reporters, claiming he is simply traveling to
the French town of Vichy to take the cure for
his health. Taking the cure referred to visiting
natural thermal springs, which was a deeply amusing
alibi for a man who made his fortune selling
bathtub gin and dodging bullets. The European
authorities certainly didn't buy it. They absolutely
did not. So he stays aboard until the ship reaches
Antwerp, Belgium. The moment his foot touches
the dock, Belgian police surround him. Oh, man.
They take him straight to headquarters, process
him and physically place him on a train headed
for Germany. The train. pulls into Aachen, Germany.
The German police are waiting on the platform.
It just keeps going. They arrest him, hold him
in a cell for several days, drive him to the
port of Hamburg, and toss him onto a slow -moving
cargo ship called the Hanover heading right back
to Philadelphia. This sequence reveals so much
about the global perception of America at the
time. The Manhattan bootleg wars were front -page
news worldwide. European governments looked at
the staggering violence of the Prohibition era
and viewed American gangsters as an infectious
disease. Basically a quarantine situation. Exactly.
They treated Diamond's arrival as a literal threat
to national security. So he rides that cargo
ship all the way back across the Atlantic. He
steps off the boat in Philadelphia and the local
police immediately slap cuffs on him. They haul
him before a judge that exact same afternoon.
And what does the judge do? The judge looks at
the exhausted gangster and says, I will release
you, but you have exactly one hour to leave the
city limits of Philadelphia. He traveled thousands
of miles across the ocean, only to be handed
right back to the exact ecosystem he was desperately
trying to escape. And it is a miracle he survived
the return trip because surviving was the defining
characteristic of Legs Diamond. This is how he
earned the moniker the Clay Pigeon of the Underworld.
Right. Let's break down the timeline of the unkillable
man because the sheer volume of lead he absorbed
is staggering. What stands out to you about how
this violence escalated? Well, for context, a
clay pigeon is the fragile ceramic disc launched
into the air during trap shooting. Its sole purpose
for existing is to be shattered. The fact that
the underworld gave him this nickname tells you
how routinely he was targeted. It starts in 1924.
Diamond is hit with shotgun pellets during a
violent dispute over hijacked liquor trucks.
He survives, brushes it off, and goes back to
work. Just back to business. Then we jump to
1927. He's walking down the street on the Lower
East Side, acting as a bodyguard for his boss,
Little Augie Organ. Diamond is actually just
covering a shift for his brother, Eddie. A car
pulls up. Gunmen jump out and open fire. Augie
is killed instantly. Diamond takes two bullets
straight to the chest, just below the heart.
We really have to pause on the medical reality
of 1927. Taking two bullets near the heart before
the invention of modern trauma surgery, before
widespread blood transfusions, and before antibiotics
even existed. That's a death sentence. As usually
a guaranteed death certificate. Yet he is rushed
to Bellevue Hospital and manages a full recovery,
and he perfectly adheres to the underworld code
of silence. When the detectives surround his
hospital bed demanding names, he refuses to offer
a single syllable of cooperation. Incredible.
But the violence just keeps compounding. 5 bullets
at close range. The kinetic energy alone should
have dropped him permanently. But instead of
dying, Diamond drags himself to his feet. Before
he staggers out into the hotel hallway to scream
for help, he manages to pour himself two neat
shots of whiskey and drinks them down. You can't
make this stuff up. He is rushed to Polyclinic
Hospital and, defying all medical logic, he recovers
again. Which brings us to April 1931. He's dining
with friends at the Aratoga Inn, a roadhouse
near Cairo, New York. Gunmen ambush him, shooting
him three more times. He collapses by the front
door, gets driven to an Albany hospital by a
local resident, and delivers one of the most
famous quotes in mob history. He looks up at
the surgeon working on him and says, They have
not yet made the bullet that will kill me. This
raises an important question. When an individual
survives that level of repeated catastrophic
trauma, what does it do to their psyche? It has
to change you. It creates a dual effect. Externally,
his rivals like Dutch Schultz begin to view him
as a mythological figure, questioning if he is
genuinely invincible. But internally, surviving
that many assassination attempts breeds a fatal
level of recklessness. You start to believe your
own myth, which makes you bolder. less cautious,
and ultimately a much larger target. And he pushed
that luck further than anyone in his era. But
the mathematics of probability eventually catch
up with everyone. This brings us to the final
fatal chapter. It's December 1931. Diamond is
up in Albany, New York, standing trial for the
kidnapping of James Duncan. On December 17th,
the jury reads the verdict. Not guilty. Think
about the adrenaline of that moment. He has outmaneuvered
the federal government, survived countless mob
hits, and just walked away from a massive state
trial. He must have felt entirely untouchable.
He is celebrating like a man who has conquered
the world. He goes out to dinner with his family,
and then around 1 .00 a .m., he sends his wife
home and takes his mistress, a showgirl named
Kiki Roberts, to the Rainbow Room at the Kenmore
Hotel. They drink heavily into the early hours
of the morning. Setting the stage for disaster.
Around 4 .30 a .m., heavily intoxicated, he stumbles
back to a rooming house at 67 Dove Street and
passes out on the bed. He is completely isolated.
No bodyguards. His senses dulled by alcohol and
a deep sleep. He has finally let his guard down.
About an hour later, two men slip quietly into
the Dove Street room. One man physically pins
the legendary Legs Diamond to the mattress, while
the second man presses a gun to the back of his
head and fires three times. The clay pigeon finally
shattered. An incredibly abrupt, unceremonious
execution for a man who had lived his entire
adult life at maximum volume. For decades, historians
and the public debated the obvious question.
Who finally killed Legs Diamond? The suspect
list was endless. Dutch Schultz wanted him dead.
The Ollie brothers wanted him dead. The family
of Red Cassidy, another gangster Diamond had
clashed with, wanted revenge. However, the historical
profile highlights a much more complex theory,
famously detailed by author William Kennedy in
his book O Albany. And this theory fundamentally
alters the narrative of 1930s organized crime.
Kennedy's account suggests the hit wasn't ordered
by a rival bootlegger or a syndicate boss from
New York City. The order allegedly came from
Dan O 'Connell, the powerful boss who controlled
the local Democratic political machine in Albany.
Kennedy actually conducted a recorded interview
with O 'Connell in 1974, where the aging political
boss essentially outlined the entire dynamic.
The quotes from that interview are staggering.
O 'Connell stated that Diamond called him up,
announcing he wanted to set up an insurance business
in Albany. Which was just code for selling strong
-arm protection rackets to local merchants. Right,
and O 'Connell sent a message back saying, absolutely
not, you are not operating here, and you'd better
be out of town by tomorrow. O 'Connell explained
the philosophy bluntly, stating, in order for
the mafia to move in, they had to have protection,
and they know they'll never get it in this town.
We settled that years ago. The theory posits
that Albany Police Sergeant William Fitzpatrick
was the man who actually pulled the trigger.
The lore suggests Fitzpatrick sat with Diamond
earlier, warned him to keep moving, and when
Diamond stayed to celebrate his acquittal, the
police sergeant acted as the assassin for the
political machine. Let's pause on the implications
of that. The standard historical narrative frames
the Prohibition era as a battle between righteous
law enforcement and corrupt gangsters. Good guys
versus bad guys. Exactly. But the Albany theory
suggests that in some cities, the local political
apparatus and the police department were the
dominant organized crime syndicate. They held
a state -sponsored monopoly on vice and gambling.
When they assassinated Legs Diamond, they weren't
upholding the law. They were violently eliminating
a corporate competitor. And the aftermath certainly
supports that dark theory. Sergeant Fitzpatrick
was subsequently promoted to chief of the Albany
police. And in a fittingly violent twist, Chief
Fitzpatrick was shot and killed in his own office
in 1945 by one of his own detectives. The cycle
of violence just consumed everyone it touched.
So what does this all mean? We look back at Jack
Legs Diamond, a man whose exploits commanded
international headlines and forced diplomatic
standoffs. Yet... His end was remarkably hollow.
Very hollow. When he was buried at Mount Olivet
Cemetery in Queens a few days after the Albany
shooting, the press noted the glaring absence
of his peers. Out of the 200 spectators, not
a single underworld figure attended the funeral.
Because the loyalty of the syndicates is entirely
transactional. The moment you are no longer a
threat or an asset, you cease to exist tragically
the fallout didn't stop with him a year and a
half later in july 1933 his widow alice kenny
diamond a woman who historically never supported
his criminal enterprises was found shot to death
in her brooklyn apartment the prevailing theory
is that his enemies murdered her simply to ensure
she never shared anything she might have overheard
during their marriage it serves as a grim marker
of the collateral damage these enterprises generated
the violence always bled outside the boundaries
of the gang itself But Diamond's mythology did
embed itself deeply into pop culture. Oh, definitely.
He inspired movies, an episode of the television
series The Untouchables, and in the late 1980s,
a Broadway musical titled Legs Diamond starring
Peter Allen. Though the musical was a spectacular
flop. closing after just 64 performances. Not
everything can be a hit. True. In more recent
decades, Raekwon from the legendary hip -hop
group Wu -Tang Clan adopted the alias Lex Diamond
for his solo projects, proving how enduring that
outlaw persona remains. The outlaw persona is
captivating, but I want to leave you with a final
thought to mull over, building on the reality
of his death in Albany. If the theory holds true,
if the political machines and the police departments
of the 1930s were operating their own violent
monopolies on vice, it makes you wonder about
the history we've been sold. That's a great point.
How much of the glamorous, terrifying myth of
the outlaw gangster was actually just public
relations, where figures like Legs Diamond amplified
in the press to serve as convenient boogeymen,
distracting the public from the fact that the
most successful, untouchable crime syndicates
were the very institutions sworn to protect them.
That is an incredibly provocative way to re -examine
the history of the 1920s. Thank you so much for
joining us on this deep dive. It's been a fascinating
journey through the complex, bullet -riddled
logistics of the Prohibition underworld. Keep
questioning the narratives of the past, keep
exploring the history around you, and we'll catch
you on the next one.