October 13, 2025 • 13 mins
In this episode of Mobstercast Chronicles, we uncover the life of Anthony “Tony” Milano — the quiet, calculating underboss who kept the Cleveland Mafia running smoothly for over fifty years. From the bootlegging wars of Prohibition to the mob explosions of the 1970s, Milano’s steady hand and old-world loyalty made him one of organized crime’s most enduring figures. Discover how a man who rarely sought the spotlight became the backbone of one of America’s most powerful crime families.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome back to the deep dive. So when you think
about American organized crime, you know the big names usually
come with big personalities, right Capone, gottie, guys known for flash,
for violence, for headlines.
Speaker 2 (00:13):
Absolutely they dominate the narrative. But today we're taking a
deep dive into someone who played a very different game exactly.
Speaker 1 (00:19):
We're focusing on Anthony Milano, the longtime underboss of the
Cleveland crime family. He wasn't flashy, he wasn't loud, right.
Speaker 2 (00:28):
Our listener pointed us towards sources on him, and the
real story here is how he built this incredible, like
five decade run of influence through well through silence, loyalty,
and just sheer discipline.
Speaker 1 (00:40):
He was the quiet strategist, the kinsiglier figure, the guy
keeping the peace behind the curtains.
Speaker 2 (00:45):
Yeah, the mission today is really to unpack that. How
did this guy, Anthony Milano become so influential by not
being the typical mob boss. He was the steady hand,
the architect of stability.
Speaker 1 (00:56):
You could say architect di stability. I like that. It
sounds almost contrad victory for a crime family. Stability isn't
usually the first word that comes to mind.
Speaker 2 (01:04):
No, it isn't and that's what makes him fascinating.
Speaker 1 (01:06):
So where do we start tracing these roots? How did
he develop this this different approach.
Speaker 2 (01:12):
Well, you got to look at his origins. He was
born back in eighteen eighty eight near Naples in Italy,
Santa Zeppi, Visiviano, and he came over to Cleveland pretty
early on early nineteen hundreds. And the Cleveland he arrived
in was well as an industrial powerhouse, steel mills, factory, the.
Speaker 1 (01:30):
Real boomtown, which means lots of jobs, but also lots
of immigrants packed together right forming their own little neighborhoods,
ethnic enclaves exactly, and.
Speaker 2 (01:39):
That kind of environment. It's footle ground for well, for
gangs and factions fighting over turf, over opportunities legal or otherwise.
Speaker 1 (01:46):
Okay, so the scene is set. How does Milano fit
into this?
Speaker 2 (01:49):
Well, the sources really emphasized the dynamic between him and
his brother Frank Mulano. They were sort of a package deal,
but polar opposites. How So, Frank was the outgoing one, charismatic, ambitious,
the natural leader, the face of the operation. Anthony. Anthony
was quiet, reserved, detail oriented. He was the stabilizer, the
loyal number two.
Speaker 1 (02:08):
So even from the beginning, Anthony wasn't angling for the spotlight.
He understood his role was different, it seems so.
Speaker 2 (02:15):
Frank built the alliances, took the public risks. Anthony focused
on making sure the structure held up, that the operation
ran smoothly. He wanted the system to work, not necessarily
to be the guy running it out front.
Speaker 1 (02:27):
That contrast is key. Frank waned the title. Anthony wanted
the foundation to be solid, and.
Speaker 2 (02:33):
That foundation became incredibly important when prohibition hit.
Speaker 1 (02:37):
Ah. Yes, the big opportunity.
Speaker 2 (02:39):
Huge and for Cleveland, its location was perfect right there
on Lake Erie.
Speaker 1 (02:44):
Direct line to Canada, meaning easy access to illegal liquor,
a bootlater's dream.
Speaker 2 (02:49):
Absolutely, Cleveland became a major hub, and Anthony's role in
this wasn't cracking heads. It was organization, pure operations.
Speaker 1 (02:56):
So logistics, money management.
Speaker 2 (02:59):
Exactly, managing the supply lines, tracking the cash, making sure
the guys doing the work were managed efficiently, all done quietly,
crucially without attracting too much heat from the cops. He
knew noise was bad for business.
Speaker 1 (03:10):
Makes sense, but running a smooth operation doesn't mean you
avoid conflict, especially over something as valuable as booze and
the ingredients to make it.
Speaker 2 (03:18):
No, definitely not. And that led directly to the corn
sugar war in the late nineteen twenties, big conflict.
Speaker 1 (03:24):
Corn sugar the key ingredient for making moonshine back then, right,
So this was a fight over controlling the supply chain.
Speaker 2 (03:31):
Precisely, it was mainly between the faction. The Milanos were
allied with the Lenardos and the Pirollo brothers, and it
got nasty.
Speaker 1 (03:39):
How nasty?
Speaker 2 (03:40):
Well, a major turning point was when their main ally
Joe Leonardo, was murdered in nineteen twenty seven. Things really
escalated then a lot of bloodshed.
Speaker 1 (03:49):
And in that kind of situation, most guys would react
with more violence, right I for and I established dominance
through force, That's.
Speaker 2 (03:55):
The typical playbook. But Anthony his strength wasn't brute force.
It was strategy calculation.
Speaker 1 (04:01):
So instead of just grabbing a gun, he saw the
mild says, what a problem to be self strategically.
Speaker 2 (04:07):
Sort of, yeah, he treated it like a chess match almost.
While the bullets were flying, he was quietly working behind
the scenes form alliances, shoring up support, basically positioning Frank
to win through better organization and political maneuvering, not just
by outgunning the other side.
Speaker 1 (04:23):
Thinking long term, even in the middle of a war.
Speaker 2 (04:26):
Always he was looking several moves ahead.
Speaker 1 (04:28):
So when the smoke cleared from the Corn Sugar War.
Speaker 2 (04:31):
Frank Mulano came out on top as the recognized boss
of Cleveland. But everyone knew Anthony's quiet strategy was a
huge part of why.
Speaker 1 (04:40):
And this success wasn't just local, was it. This elevated
Cleveland on a national level.
Speaker 2 (04:45):
It really did, because shortly after, in nineteen thirty one,
you had the end of the Castelomeries War in New York,
big shake up in the mafia nationwide.
Speaker 1 (04:53):
Right the war that led to Lucky Luciano establishing the
National Crime Syndicate and the Commission.
Speaker 2 (04:58):
Exactly and for listeners maybe not super familiar. The Commission
was essentially the mafia's board of directors. Settled disputes, approved bosses,
coordinated things nationally. A very big deal and Frank Milano,
Frank Milano got invited to join. He was given a
seat on the Commission representing Cleveland. That was rare, especially
for a family outside the Five Families of New York
(05:20):
or Chicago. It gave Cleveland serious clout.
Speaker 1 (05:23):
Wow, and Anthony's role in that was ensuring Cleveland acted
like a national player deserving of that seat.
Speaker 2 (05:29):
You could say that maintaining that stability and projecting competence
was crucial. But then comes a major test for Anthony's
whole philosophy. What happened nineteen thirty five. Frank Milano gets
indicted on tax evasion charges. Big trouble. He has to
flee the country, basically goes into exile in Mexico.
Speaker 1 (05:46):
Okay, so the boss is gone. That usually spells chaos, right,
power vacuum infighting almost always.
Speaker 2 (05:51):
Yeah, that's typically when families just implode or fall into
bloody succession wars. But this is where Anthony's real genius,
his commitment to structure shines through. He stepped up, he
stepped in as underboss and acting boss. But here's the key.
He didn't make a grab for the top spot himself.
He easily could have tried.
Speaker 1 (06:10):
He had the power of the respect for.
Speaker 2 (06:11):
Sure, but instead he focused purely on stability, on ensuring
a smooth transition. He acted as the bridge.
Speaker 1 (06:19):
How do you manage a smooth transition in the underworld?
What does that actually involve keeping the peace between factions.
Speaker 2 (06:26):
It involves managing the politics and the money. He kept
control of the family's operations, the finances, and crucially, he
managed the ambitions of other potential successors. He made sure
key lieutenants were either satisfied or neutralized politically speaking, without
resorting to wide scale violence. Okay, he essentially maneuvered things
(06:46):
so that John Scalish, someone he trusted and could work with,
took over as the official boss. He handed Scalish a
unified family, not a fractured mess.
Speaker 1 (06:55):
That prevented another war.
Speaker 2 (06:57):
Absolutely, it solidified his reputation as someone who put the
organization's health above his own personal ambition.
Speaker 1 (07:04):
That's incredibly rare and incredibly valuable. It made him indispensable totally.
Speaker 2 (07:08):
And that move basically ushered in what's often called the
Cleveland Families Golden age under Scalish, with Anthony firmly established
as the trusted underboss for decades.
Speaker 1 (07:17):
The master of quiet power as you called it.
Speaker 2 (07:19):
Yeah, he perfected that persona.
Speaker 1 (07:21):
The sources mentioned him being seen as an elder statesman
that implies respect, not just fear. But if he kept
such a low profile, how did he command that kind
of respect even nationally. Wouldn't being invisible kind of work
against him.
Speaker 2 (07:35):
It's a paradox, isn't it. But in that world where
betrayal is almost expected, his consistency was his power. Everyone
knew Anthony Mulana wasn't going to stab his boss Scalish
in the back. He wasn't driven by ego or greed
for the top job.
Speaker 1 (07:51):
He embodied that code of silence Samarta.
Speaker 2 (07:54):
Absolutely, discipline, discretion, loyalty. He lived it. No flashy cars,
no public fights, no drawing attention. He was predictable in
his restraint.
Speaker 1 (08:02):
The ultimate neutral, reliable figure.
Speaker 2 (08:04):
Exactly, and that made him trustworthy. So if there was
a dispute, say between Detroit and Cleveland over some gambling territory.
Speaker 1 (08:10):
Anthony might be the guy called into.
Speaker 2 (08:12):
Mediate often, yeah, because everyone knew he'd be fair, measured
and focused on what was best for the overall system,
not just his own angle. He wasn't trying to skim
off the top or play favorites.
Speaker 1 (08:22):
There's that great quote from an FBI agent, something like
uh Milano didn't need to shout when he spoke, people listened.
Speaker 2 (08:29):
That sums it up. Perfectly earned authority, not demanded.
Speaker 1 (08:32):
And This quiet authority allowed the Scalish era to be
so stable and prosperous for the family for decades.
Speaker 2 (08:39):
They expanded efficiently into things like labor racketeering, Las Vegas casinos,
legitimate businesses as fronts, all while keeping that low profile
Anthony insisted on, kept the internal peace, kept the money
flowing smoothly.
Speaker 1 (08:53):
It sounds almost peaceful for a crime family.
Speaker 2 (08:57):
Relatively speaking. For a long time it was, but nothing
lasts forever would change time. By the nineteen seventies, a
new generation was coming up, less discipline, maybe greedier, definitely louder,
less respect for the.
Speaker 1 (09:10):
Old ways, and that clashed with Mulano's entire philosophy massively.
Speaker 2 (09:14):
This generational shift set the stage for disaster. Cleveland got
dragged into one of the most notorious violent mob wars ever,
the war with Danny Green.
Speaker 1 (09:22):
Oh right, the Irish gangster car bombings, public assassinations that
was all over the news, complete chaos.
Speaker 2 (09:28):
Total chaos. It was everything Anthony had worked for decades
to avoid headlines, federal attention, public bloodshed, the exact opposite
of his quiet approach.
Speaker 1 (09:39):
And even then, in his eighties he was still the underboss.
Did he try to stop it.
Speaker 2 (09:43):
He did. He was still there, still respected as the
elder statesman, and he warned them. He urged caution, restraint.
He told the new leadership, guys like James la Connolly,
that this open warfare, this public violence, was suicide. It
would bring the full weight of the FBI down on.
Speaker 1 (09:58):
Them, because it's the one the government can't ignore.
Speaker 2 (10:01):
Exactly, public bombings that demands a response. But his warnings
they went unheeded, and.
Speaker 1 (10:08):
He was proven right, wasn't he. The war decimated the
Cleveland leadership, arrests.
Speaker 2 (10:13):
Killings, devastatingly right. The Feds came in hard, dismantled much
of the family's power structure. It was the end of
an era.
Speaker 1 (10:20):
But Milano himself he survived.
Speaker 2 (10:22):
His personal discipline, his low profile kept him largely insulated
from the direct fallout. He'd warned them. They didn't listen,
and he watched his philosophy of quiet control basically crumble.
But he lived at his last few years quietly.
Speaker 1 (10:35):
When did he pass away?
Speaker 2 (10:36):
Died in nineteen seventy eight. He was eighty nine years old,
one of the very last guys standing from that original
Prohibition generation. A living monument to restraint.
Speaker 1 (10:45):
Really incredible longevity. It really is a testament to his approach.
Never got greedy, never got sloppy, never let ego drive
him into a stupid fight or onto the front page.
Speaker 2 (10:54):
And the story doesn't quite end there. There's a fascinating epilogue. Really,
his son, Peter J. Mulano. He didn't stay in Cleveland.
He went out west to Los Angeles, Okay, and Peter
Milana rose through the ranks there, eventually becoming a major
figure some say the boss of the La crime family.
Speaker 1 (11:10):
Wow. So the Milano name held significant power in two
completely separate mafia families, Cleveland and La. That's highly unusual.
Speaker 2 (11:18):
Extremely unusual. It suggests that Anthony's approach, that foundation of discipline, structure,
and quite maneuvering wasn't just tied to Cleveland politics. It
was a transmissible skill set based on intelligence and adaptability.
Speaker 1 (11:31):
It speaks volumes about the strength of that underlying philosophy,
It really does.
Speaker 2 (11:36):
He was almost like a philosopher of the underworld, understanding
that true lasting power came from structure, respect, and reputation,
not just fear and violence. Discipline outlasts disruption.
Speaker 1 (11:49):
So Anthony Milana, the quiet Architect. His story is such
a counter narrative. It reminds you, doesn't it, that sometimes
the most influential people in any field, crime or business
or politics are the ones you never hear about.
Speaker 2 (12:01):
The ones working behind the scenes, building influence through patients,
earning respect decade after decade.
Speaker 1 (12:07):
Yeah, not through ego or making the most noise.
Speaker 2 (12:09):
And his life really does offer this broader inside. I
think you look at any organization with a hierarchy, criminal, corporate, whatever,
they all face change, they all face internal conflict, generational shifts.
Anthony's absolute focus on internal order, on financial control, on
keeping things quiet omerta. It suggests that may be the
key to long term survival for any structured group is
(12:31):
minimizing that internal friction and crucially avoiding unwanted external attention.
Speaker 1 (12:36):
So, thinking about that incredible longevity, the cross regional success
of the Milano name, what does Anthony's dedication to silence
and order tell us about what it takes for any
complex organization to weather storms. Maybe the biggest danger isn't
always the external threat, but the unchecked ego within. That's
definitely something to chew on.
Speaker 2 (12:57):
It really makes you think, it seems the loudest voice,
don't often build the things.
Speaker 1 (13:01):
That last the longest, well said, Thanks for digging into
this one with us. We'll see you next time on
the Deep Dive
Welcome back to the deep dive. So when you think
about American organized crime, you know the big names usually
come with big personalities, right Capone, gottie, guys known for flash,
for violence, for headlines.
Speaker 2 (00:13):
Absolutely they dominate the narrative. But today we're taking a
deep dive into someone who played a very different game exactly.
Speaker 1 (00:19):
We're focusing on Anthony Milano, the longtime underboss of the
Cleveland crime family. He wasn't flashy, he wasn't loud, right.
Speaker 2 (00:28):
Our listener pointed us towards sources on him, and the
real story here is how he built this incredible, like
five decade run of influence through well through silence, loyalty,
and just sheer discipline.
Speaker 1 (00:40):
He was the quiet strategist, the kinsiglier figure, the guy
keeping the peace behind the curtains.
Speaker 2 (00:45):
Yeah, the mission today is really to unpack that. How
did this guy, Anthony Milano become so influential by not
being the typical mob boss. He was the steady hand,
the architect of stability.
Speaker 1 (00:56):
You could say architect di stability. I like that. It
sounds almost contrad victory for a crime family. Stability isn't
usually the first word that comes to mind.
Speaker 2 (01:04):
No, it isn't and that's what makes him fascinating.
Speaker 1 (01:06):
So where do we start tracing these roots? How did
he develop this this different approach.
Speaker 2 (01:12):
Well, you got to look at his origins. He was
born back in eighteen eighty eight near Naples in Italy,
Santa Zeppi, Visiviano, and he came over to Cleveland pretty
early on early nineteen hundreds. And the Cleveland he arrived
in was well as an industrial powerhouse, steel mills, factory, the.
Speaker 1 (01:30):
Real boomtown, which means lots of jobs, but also lots
of immigrants packed together right forming their own little neighborhoods,
ethnic enclaves exactly, and.
Speaker 2 (01:39):
That kind of environment. It's footle ground for well, for
gangs and factions fighting over turf, over opportunities legal or otherwise.
Speaker 1 (01:46):
Okay, so the scene is set. How does Milano fit
into this?
Speaker 2 (01:49):
Well, the sources really emphasized the dynamic between him and
his brother Frank Mulano. They were sort of a package deal,
but polar opposites. How So, Frank was the outgoing one, charismatic, ambitious,
the natural leader, the face of the operation. Anthony. Anthony
was quiet, reserved, detail oriented. He was the stabilizer, the
loyal number two.
Speaker 1 (02:08):
So even from the beginning, Anthony wasn't angling for the spotlight.
He understood his role was different, it seems so.
Speaker 2 (02:15):
Frank built the alliances, took the public risks. Anthony focused
on making sure the structure held up, that the operation
ran smoothly. He wanted the system to work, not necessarily
to be the guy running it out front.
Speaker 1 (02:27):
That contrast is key. Frank waned the title. Anthony wanted
the foundation to be solid, and.
Speaker 2 (02:33):
That foundation became incredibly important when prohibition hit.
Speaker 1 (02:37):
Ah. Yes, the big opportunity.
Speaker 2 (02:39):
Huge and for Cleveland, its location was perfect right there
on Lake Erie.
Speaker 1 (02:44):
Direct line to Canada, meaning easy access to illegal liquor,
a bootlater's dream.
Speaker 2 (02:49):
Absolutely, Cleveland became a major hub, and Anthony's role in
this wasn't cracking heads. It was organization, pure operations.
Speaker 1 (02:56):
So logistics, money management.
Speaker 2 (02:59):
Exactly, managing the supply lines, tracking the cash, making sure
the guys doing the work were managed efficiently, all done quietly,
crucially without attracting too much heat from the cops. He
knew noise was bad for business.
Speaker 1 (03:10):
Makes sense, but running a smooth operation doesn't mean you
avoid conflict, especially over something as valuable as booze and
the ingredients to make it.
Speaker 2 (03:18):
No, definitely not. And that led directly to the corn
sugar war in the late nineteen twenties, big conflict.
Speaker 1 (03:24):
Corn sugar the key ingredient for making moonshine back then, right,
So this was a fight over controlling the supply chain.
Speaker 2 (03:31):
Precisely, it was mainly between the faction. The Milanos were
allied with the Lenardos and the Pirollo brothers, and it
got nasty.
Speaker 1 (03:39):
How nasty?
Speaker 2 (03:40):
Well, a major turning point was when their main ally
Joe Leonardo, was murdered in nineteen twenty seven. Things really
escalated then a lot of bloodshed.
Speaker 1 (03:49):
And in that kind of situation, most guys would react
with more violence, right I for and I established dominance
through force, That's.
Speaker 2 (03:55):
The typical playbook. But Anthony his strength wasn't brute force.
It was strategy calculation.
Speaker 1 (04:01):
So instead of just grabbing a gun, he saw the
mild says, what a problem to be self strategically.
Speaker 2 (04:07):
Sort of, yeah, he treated it like a chess match almost.
While the bullets were flying, he was quietly working behind
the scenes form alliances, shoring up support, basically positioning Frank
to win through better organization and political maneuvering, not just
by outgunning the other side.
Speaker 1 (04:23):
Thinking long term, even in the middle of a war.
Speaker 2 (04:26):
Always he was looking several moves ahead.
Speaker 1 (04:28):
So when the smoke cleared from the Corn Sugar War.
Speaker 2 (04:31):
Frank Mulano came out on top as the recognized boss
of Cleveland. But everyone knew Anthony's quiet strategy was a
huge part of why.
Speaker 1 (04:40):
And this success wasn't just local, was it. This elevated
Cleveland on a national level.
Speaker 2 (04:45):
It really did, because shortly after, in nineteen thirty one,
you had the end of the Castelomeries War in New York,
big shake up in the mafia nationwide.
Speaker 1 (04:53):
Right the war that led to Lucky Luciano establishing the
National Crime Syndicate and the Commission.
Speaker 2 (04:58):
Exactly and for listeners maybe not super familiar. The Commission
was essentially the mafia's board of directors. Settled disputes, approved bosses,
coordinated things nationally. A very big deal and Frank Milano,
Frank Milano got invited to join. He was given a
seat on the Commission representing Cleveland. That was rare, especially
for a family outside the Five Families of New York
(05:20):
or Chicago. It gave Cleveland serious clout.
Speaker 1 (05:23):
Wow, and Anthony's role in that was ensuring Cleveland acted
like a national player deserving of that seat.
Speaker 2 (05:29):
You could say that maintaining that stability and projecting competence
was crucial. But then comes a major test for Anthony's
whole philosophy. What happened nineteen thirty five. Frank Milano gets
indicted on tax evasion charges. Big trouble. He has to
flee the country, basically goes into exile in Mexico.
Speaker 1 (05:46):
Okay, so the boss is gone. That usually spells chaos, right,
power vacuum infighting almost always.
Speaker 2 (05:51):
Yeah, that's typically when families just implode or fall into
bloody succession wars. But this is where Anthony's real genius,
his commitment to structure shines through. He stepped up, he
stepped in as underboss and acting boss. But here's the key.
He didn't make a grab for the top spot himself.
He easily could have tried.
Speaker 1 (06:10):
He had the power of the respect for.
Speaker 2 (06:11):
Sure, but instead he focused purely on stability, on ensuring
a smooth transition. He acted as the bridge.
Speaker 1 (06:19):
How do you manage a smooth transition in the underworld?
What does that actually involve keeping the peace between factions.
Speaker 2 (06:26):
It involves managing the politics and the money. He kept
control of the family's operations, the finances, and crucially, he
managed the ambitions of other potential successors. He made sure
key lieutenants were either satisfied or neutralized politically speaking, without
resorting to wide scale violence. Okay, he essentially maneuvered things
(06:46):
so that John Scalish, someone he trusted and could work with,
took over as the official boss. He handed Scalish a
unified family, not a fractured mess.
Speaker 1 (06:55):
That prevented another war.
Speaker 2 (06:57):
Absolutely, it solidified his reputation as someone who put the
organization's health above his own personal ambition.
Speaker 1 (07:04):
That's incredibly rare and incredibly valuable. It made him indispensable totally.
Speaker 2 (07:08):
And that move basically ushered in what's often called the
Cleveland Families Golden age under Scalish, with Anthony firmly established
as the trusted underboss for decades.
Speaker 1 (07:17):
The master of quiet power as you called it.
Speaker 2 (07:19):
Yeah, he perfected that persona.
Speaker 1 (07:21):
The sources mentioned him being seen as an elder statesman
that implies respect, not just fear. But if he kept
such a low profile, how did he command that kind
of respect even nationally. Wouldn't being invisible kind of work
against him.
Speaker 2 (07:35):
It's a paradox, isn't it. But in that world where
betrayal is almost expected, his consistency was his power. Everyone
knew Anthony Mulana wasn't going to stab his boss Scalish
in the back. He wasn't driven by ego or greed
for the top job.
Speaker 1 (07:51):
He embodied that code of silence Samarta.
Speaker 2 (07:54):
Absolutely, discipline, discretion, loyalty. He lived it. No flashy cars,
no public fights, no drawing attention. He was predictable in
his restraint.
Speaker 1 (08:02):
The ultimate neutral, reliable figure.
Speaker 2 (08:04):
Exactly, and that made him trustworthy. So if there was
a dispute, say between Detroit and Cleveland over some gambling territory.
Speaker 1 (08:10):
Anthony might be the guy called into.
Speaker 2 (08:12):
Mediate often, yeah, because everyone knew he'd be fair, measured
and focused on what was best for the overall system,
not just his own angle. He wasn't trying to skim
off the top or play favorites.
Speaker 1 (08:22):
There's that great quote from an FBI agent, something like
uh Milano didn't need to shout when he spoke, people listened.
Speaker 2 (08:29):
That sums it up. Perfectly earned authority, not demanded.
Speaker 1 (08:32):
And This quiet authority allowed the Scalish era to be
so stable and prosperous for the family for decades.
Speaker 2 (08:39):
They expanded efficiently into things like labor racketeering, Las Vegas casinos,
legitimate businesses as fronts, all while keeping that low profile
Anthony insisted on, kept the internal peace, kept the money
flowing smoothly.
Speaker 1 (08:53):
It sounds almost peaceful for a crime family.
Speaker 2 (08:57):
Relatively speaking. For a long time it was, but nothing
lasts forever would change time. By the nineteen seventies, a
new generation was coming up, less discipline, maybe greedier, definitely louder,
less respect for the.
Speaker 1 (09:10):
Old ways, and that clashed with Mulano's entire philosophy massively.
Speaker 2 (09:14):
This generational shift set the stage for disaster. Cleveland got
dragged into one of the most notorious violent mob wars ever,
the war with Danny Green.
Speaker 1 (09:22):
Oh right, the Irish gangster car bombings, public assassinations that
was all over the news, complete chaos.
Speaker 2 (09:28):
Total chaos. It was everything Anthony had worked for decades
to avoid headlines, federal attention, public bloodshed, the exact opposite
of his quiet approach.
Speaker 1 (09:39):
And even then, in his eighties he was still the underboss.
Did he try to stop it.
Speaker 2 (09:43):
He did. He was still there, still respected as the
elder statesman, and he warned them. He urged caution, restraint.
He told the new leadership, guys like James la Connolly,
that this open warfare, this public violence, was suicide. It
would bring the full weight of the FBI down on.
Speaker 1 (09:58):
Them, because it's the one the government can't ignore.
Speaker 2 (10:01):
Exactly, public bombings that demands a response. But his warnings
they went unheeded, and.
Speaker 1 (10:08):
He was proven right, wasn't he. The war decimated the
Cleveland leadership, arrests.
Speaker 2 (10:13):
Killings, devastatingly right. The Feds came in hard, dismantled much
of the family's power structure. It was the end of
an era.
Speaker 1 (10:20):
But Milano himself he survived.
Speaker 2 (10:22):
His personal discipline, his low profile kept him largely insulated
from the direct fallout. He'd warned them. They didn't listen,
and he watched his philosophy of quiet control basically crumble.
But he lived at his last few years quietly.
Speaker 1 (10:35):
When did he pass away?
Speaker 2 (10:36):
Died in nineteen seventy eight. He was eighty nine years old,
one of the very last guys standing from that original
Prohibition generation. A living monument to restraint.
Speaker 1 (10:45):
Really incredible longevity. It really is a testament to his approach.
Never got greedy, never got sloppy, never let ego drive
him into a stupid fight or onto the front page.
Speaker 2 (10:54):
And the story doesn't quite end there. There's a fascinating epilogue. Really,
his son, Peter J. Mulano. He didn't stay in Cleveland.
He went out west to Los Angeles, Okay, and Peter
Milana rose through the ranks there, eventually becoming a major
figure some say the boss of the La crime family.
Speaker 1 (11:10):
Wow. So the Milano name held significant power in two
completely separate mafia families, Cleveland and La. That's highly unusual.
Speaker 2 (11:18):
Extremely unusual. It suggests that Anthony's approach, that foundation of discipline, structure,
and quite maneuvering wasn't just tied to Cleveland politics. It
was a transmissible skill set based on intelligence and adaptability.
Speaker 1 (11:31):
It speaks volumes about the strength of that underlying philosophy,
It really does.
Speaker 2 (11:36):
He was almost like a philosopher of the underworld, understanding
that true lasting power came from structure, respect, and reputation,
not just fear and violence. Discipline outlasts disruption.
Speaker 1 (11:49):
So Anthony Milana, the quiet Architect. His story is such
a counter narrative. It reminds you, doesn't it, that sometimes
the most influential people in any field, crime or business
or politics are the ones you never hear about.
Speaker 2 (12:01):
The ones working behind the scenes, building influence through patients,
earning respect decade after decade.
Speaker 1 (12:07):
Yeah, not through ego or making the most noise.
Speaker 2 (12:09):
And his life really does offer this broader inside. I
think you look at any organization with a hierarchy, criminal, corporate, whatever,
they all face change, they all face internal conflict, generational shifts.
Anthony's absolute focus on internal order, on financial control, on
keeping things quiet omerta. It suggests that may be the
key to long term survival for any structured group is
(12:31):
minimizing that internal friction and crucially avoiding unwanted external attention.
Speaker 1 (12:36):
So, thinking about that incredible longevity, the cross regional success
of the Milano name, what does Anthony's dedication to silence
and order tell us about what it takes for any
complex organization to weather storms. Maybe the biggest danger isn't
always the external threat, but the unchecked ego within. That's
definitely something to chew on.
Speaker 2 (12:57):
It really makes you think, it seems the loudest voice,
don't often build the things.
Speaker 1 (13:01):
That last the longest, well said, Thanks for digging into
this one with us. We'll see you next time on
the Deep Dive
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