September 11, 2025 • 12 mins
Mobstercast Chronicles presents: Eugene “Checkers” Smaldone: Denver’s Gentleman Gangster — Discover the story of Eugene “Checkers” Smaldone, the smooth-talking mobster who ruled Denver’s underworld with charm, generosity, and old-school Mafia values. From bootlegging to gambling, and from community benefactor to feared racketeer, Checkers embodied the paradox of the American gangster who was as beloved as he was dangerous.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to the deep dive. We take the sources you
provide and while we dig into these fascinating stories, hopefully
making you the most informed person in the room.
Speaker 2 (00:09):
That's the goal.
Speaker 1 (00:10):
Today. We're actually heading somewhere maybe a little unexpected in
American mafia history based on the materials you've shared. When
you think organized crime in the US, I mean most
people picture New York, right, or maybe Chicago.
Speaker 2 (00:23):
Absolutely those are the big ones. Yeah, maybe Miami later on.
Speaker 1 (00:26):
But Denver, Denver, Colorado, that's not usually top of mine.
Speaker 2 (00:29):
It's really not. And that's what makes this story so intriguing,
isn't it. Your sources really bring to life this hidden chapter.
Denver had a surprisingly deep underworld, and right.
Speaker 1 (00:40):
At the center of it all, according to these documents,
is this figure Eugene Checkers small Dollar Checkers, Hey, and
his story isn't your typical straightforward mob boss narrative. He
complicates things. I mean, he was definitely feared, no doubt
about that, oh for sure, but also somehow beloved in
parts of the community. It raises this core question I
want to explore, how does one guy become both a
(01:02):
notorious gangster and a cherished local figure it's.
Speaker 2 (01:06):
A fascinating contradiction. And these sources, they show a man
whose life really tied Denver to the wider reach of
the American mafia. We're going to unpack this mix the
old school values, the undeniable ruthlessness, but also this surprising generosity.
Speaker 1 (01:26):
Denver's gentleman gangster.
Speaker 2 (01:28):
Exactly prepared to have maybe some perceptions challenged here.
Speaker 1 (01:31):
Okay, So to get how this gentleman gangster could even
happen in Denver, we probably need to start at the beginning, right,
the immigrant.
Speaker 2 (01:37):
Story, definitely, that's key context.
Speaker 1 (01:39):
Your sources show the small Done family arriving in Denver
early twentieth century, and like so many Italian families back then,
they've faced huge hurdles, discrimination, finding.
Speaker 2 (01:50):
Work, yeah, just navigating a whole new world. It wasn't easy.
Speaker 1 (01:53):
And Eugene smalldone, he's born right into this November third,
nineteen ten. It sounds like they weren't just aiming to
scrape by.
Speaker 2 (01:59):
Though not at all. And that's where prohibition comes in. Right,
starting in nineteen twenty, your sources really highlight this. It
created this massive, uh let's call it an opportunity, the
lucrative one hugely lucrative for many immigrants, especially Italians, who
were often shut out of you know, respectable jobs because
of that discrimination you mentioned. Bootlegging was away.
Speaker 1 (02:20):
In a fast trek to making money exactly. Yeah.
Speaker 2 (02:23):
But what's interesting here, and the sources point this out,
is the small dones weren't just like small time hustlers.
They thought bigger. They saw an organized.
Speaker 1 (02:32):
Structure and actual operation.
Speaker 2 (02:33):
Right. They saw the chaos of prohibition not just as
a hustle, but as an entrepreneurial opening.
Speaker 1 (02:40):
So real ambition there, not just a couple of speakeasies.
They wanted to be the players in Denver's underworld.
Speaker 2 (02:46):
That seems to be the picture.
Speaker 1 (02:47):
Yeah.
Speaker 2 (02:48):
Yeah, they weren't content just participating. They aimed for control,
and that ambition, combined with the times, really set the stage.
Speaker 1 (02:55):
Okay, let's talk about the nickname Checkers mom nicknames they
always mean something, right, they stick.
Speaker 2 (03:00):
They absolutely do. It's like shorthand for their whole persona.
Speaker 1 (03:03):
And Checkers really seems to fit him. Based on these materials,
two main theories pop up. One simple enough, he was
great at the game Checkers, always thinking ahead m HM,
strategic or maybe more broadly, it just reflected his mind,
quick calculating, always two moves ahead, you know, in life,
not just on a board.
Speaker 2 (03:23):
And it's a really stark contrast when you look at
his brothers, Clyde and Clarence Chauncey Chauncey right, your sources
suggest they were the ones making headlines more often, more
overt violence, more arrests, kind of the classic gangster image.
A muscle perhaps, Checkers, though, he deliberately built a different front. Smooth, personable,
(03:45):
diplomatic even That's how he got respect both inside and
outside the criminal world.
Speaker 1 (03:49):
He could talk his way through things.
Speaker 2 (03:51):
He was often the mediator, the smoother over. He could
walk into a tense situation and calm it down. That
was crucial for the family success.
Speaker 1 (03:58):
So that nickname Checker. It wasn't just about a game.
It was about his whole strategic approach, less route force,
more finesse exactly.
Speaker 2 (04:06):
It was about outthinking the competition, the law everyone a
very different style than many of his peers, especially back then.
While the brothers might handle the rough stuff, Checkers was
the strategist, the negotiator.
Speaker 1 (04:19):
And that strategic mind, that Checker's brain, it clearly fueled
the whole operation. How did he actually build the empire?
Your sources say it started like many, with bootlegging during Prohibition.
Speaker 2 (04:30):
Right, and they got good fast. By the late nineteen thirties,
the Small Dones were apparently the top bootleggers in Denver.
Speaker 1 (04:38):
And this wasn't just backtub jin was it. The material
suggests something more organized.
Speaker 2 (04:43):
Oh much more. Your sources emphasized their organizational skill. Think
about it. Controlling supply routes sometimes way beyond Colorado, hanging
off the right people, absolutely, police politicians. Building that network
of protection was vital, and managing distributors, making sure the
product got out. It was a complex, efficient machine.
Speaker 1 (05:03):
Then Prohibition ends, a lot of bootleggers just went busted.
Speaker 2 (05:06):
Right now, many did. Their whole business model disappeared overnight, But.
Speaker 1 (05:09):
Not the Small Dones. Your sources show they just shifted gears.
Speaker 2 (05:13):
How they pivoted really smart. They took the networks, the capital,
the influence they'd built from bootlegging and applied it elsewhere exactly.
Dambling was huge, loan sharking, other rackets. Your sources described
their gambling operations as top notch illegal casinos, big book making, setups,
numbers games apparently run as professionally as anything legal in Vegas,
(05:37):
hidden behind legitimate fronts. Yeah, and this really shows their adaptability,
their business sense. They became the de facto mafia family
in Denver. It wasn't like New York with warring fashions.
Speaker 1 (05:48):
They dominated pretty much, and.
Speaker 2 (05:51):
Their reach went beyond Denver into Wyoming, Nebraska. Sources even
mentioned links to early Vegas. Checkers was the strategist in all.
Speaker 1 (05:59):
This, pulling this strings. So it wasn't just running the
games but also managing relationships, keeping things smooth. How often
did his diplomacy actually work?
Speaker 2 (06:07):
That was maybe his key skill, according to these accounts,
keeping the peace. Rivals always pop upright, but Checkers often
managed to sort out disputes with words.
Speaker 1 (06:15):
Negotiation, the gentleman gangster.
Speaker 2 (06:17):
That's the reputation calm in the storm. Now, the sources
are clear, force was always an option, it had to
be sure, but his first move was usually diplomacy that
made him stand out.
Speaker 1 (06:25):
Okay, but this part, this is where it gets really complex,
isn't it. The robinhood side of Checkers.
Speaker 2 (06:30):
It's the core of the paradox.
Speaker 1 (06:31):
Absolutely, we've got the roof of strategists, the crime boss.
But then your sources are full of these stories, handing
out cash to neighbors down on their luck, HM, paying
bills for struggling families, just quietly slipping twenties to kids
on the street. It feels jarring. How did the sources
explain this?
Speaker 2 (06:52):
So the why it resonated is crucial for many in
Denver's Italian American community facing those hardships. We talked about
feeling ignored by the system.
Speaker 1 (07:02):
He was someone who helps You've seen.
Speaker 2 (07:03):
Almost as a protector. Yeah, a kind of unofficial faithty net.
His generosity wasn't just random kindness. It built incredible loyalty.
It was like social.
Speaker 1 (07:11):
Capital, which also served us protection.
Speaker 2 (07:13):
Definitely protection from rivals from the law to some extent.
And his public image was carefully maintained. Attended church, dress, sharp,
always polite.
Speaker 1 (07:22):
A charmer even to the enemies.
Speaker 2 (07:24):
Apparently so your sources mentioned even cops admitting, maybe reluctantly,
that he had charm, that he could have been a
credit to the community if he'd gone straight. He embodied
those coosonostra ideas family, honor, respect, but outside the law.
Speaker 1 (07:41):
Wow. So the generosity was functional too. It cemented his place,
his power within that community. Providing something the official world
maybe wasn't precisely.
Speaker 2 (07:50):
It's that idea of parallel governance. When the state doesn't
meet needs, sometimes figures like him step in for better
or worse.
Speaker 1 (07:57):
But despite the charm, the community support, the law was always.
Speaker 2 (08:01):
There, always breathing down their necks.
Speaker 1 (08:03):
Your sources detail constant pressure, especially in the forties and fifties,
police raids, gambling guns, busted slot machines.
Speaker 2 (08:10):
Hauled away bookies, getting arrested constantly.
Speaker 1 (08:12):
Yet the small dons and Checkers in particular seemed almost teflon.
How do they keep bouncing back?
Speaker 2 (08:18):
There's a combination of things, according to these materials. Yeah, influence, definitely,
good lawyers they could afford the best.
Speaker 1 (08:23):
And maybe witnesses getting forgetful.
Speaker 2 (08:25):
That's strongly hinted at in the sources. Yes, witnesses disappearing
or suddenly changing their stories before trial. It made convictions
very difficult, especially against the top guys like Checkers. He
was good at delegating, keeping his hands clean.
Speaker 1 (08:39):
So he avoided the long prison sentences that took down
other mocksters. Lots of fines, probation maybe, while others took
the fall often.
Speaker 2 (08:47):
Yes, he had this remarkable knack for staying just out
of reach even when things got hot. But then the
FED started paying more attention.
Speaker 1 (08:55):
Things changed in the sixties.
Speaker 2 (08:57):
Yeah, the FBI really intensified its focus on organized crime nationally.
Denver wasn't flying under the radar anymore. But the real
hammer blow, the thing that changed the whole game.
Speaker 1 (09:06):
Was CRICO AH, the right co act racketeer influenced and
corrupt organizations. That was seventies eighties exactly.
Speaker 2 (09:14):
And it gave prosecutors massive new power because now they
didn't just have to prove individual crimes, TI.
Speaker 1 (09:20):
Gu target the whole enterprise right.
Speaker 2 (09:22):
Show a pattern of racketeering activity. This was huge. Leaders
like Checkers, who maybe weren't directly involved in every single act,
could still be held accountable for the organization's overall criminal conduct.
Speaker 1 (09:34):
So their old tricks keeping distance witnesses vanishing that became.
Speaker 2 (09:38):
Harder, much harder. Cho made it easier to connect the dots.
Wire taps became more useful. Surveillance got tighter, and ICO
offered incentives for informants people inside the organization willing to testify.
Speaker 1 (09:50):
That must have really eroded their power structure.
Speaker 2 (09:53):
It chipped away relentlessly. Your sources paint a picture of
the golden age of Denver's underworld fading, like elsewhere, under
this intense legal pressure. The old ways just weren't working
as well.
Speaker 1 (10:04):
So as that era declined, what happened to Checkers in
his later years. Did he fade away, go down in flames?
Speaker 2 (10:10):
Neither? Really. He remained a respected figure in Denver, even
as the mafia's influence weakened. He kept that reputation generous,
gentlemanly right to the end, according to the sources.
Speaker 1 (10:20):
And his end was different, very different.
Speaker 2 (10:22):
From many East Coast bosses who met violent ends. Checkers
lived a long life, relatively peacefully, still in Denver. He
died in nineteen ninety two. He was eighty two. Wow,
and his funeral apparently was quite something. Drew a huge
diverse crowd, law abiding folks alongside underworld figures. It really
showed how woven into the fabric of the city he was.
Speaker 1 (10:43):
So looking back, what's the takeaway from Checker Smoldoon's life
based on these materials, It's incredibly complex.
Speaker 2 (10:51):
Deeply complex. You have a man who absolutely committed serious crimes,
ran a legal operations, operated outside the law, no question
but then he's also remembered, genuinely remember by many for
his generosities, dignity, his role as a community protector.
Speaker 1 (11:05):
In a way, it really underscores that the mafia story
in America isn't monolithic, is it not at all?
Speaker 2 (11:10):
The Smolder name is part of Denver's history. Now it
proves organized crime wasn't just New York or Chicago. These
local bosses, like Checkers, they left their own distinct marks
on their cities. Makes you wonder how many other Checkers
there were in other unexpected places.
Speaker 1 (11:24):
He really was more than just a mobster, a walking paradox.
Your sources show him ordering illegal bets one.
Speaker 2 (11:30):
Minute and paying someone's rent the next.
Speaker 1 (11:32):
A criminal, yes, but also somehow a gentleman. It's endlessly fascinating, and.
Speaker 2 (11:38):
His story it adds this really valuable, nuanced layer to
understanding American organized crime. It wasn't just about the crime itself.
It was about culture, community, loyalty, power, and these incredibly
complicated legacies left by people who operated on both sides
of the law.
Speaker 1 (11:57):
He wasn't capone or gaudy, maybe not globally famous.
Speaker 2 (12:00):
But in Denver, larger than life, a true local legend.
Shaped by the community he both served and exploited.
Speaker 1 (12:06):
So thinking about everything these sources present, what does Checker's
life make you consider about how we define good and
bad or maybe where those lines get incredibly blurry between
community leader and criminal boss, especially in certain times and places.
Speaker 2 (12:20):
It definitely challenges simple labels.
Speaker 1 (12:21):
It really does something to think about as you delve
deeper into these materials yourself
Welcome to the deep dive. We take the sources you
provide and while we dig into these fascinating stories, hopefully
making you the most informed person in the room.
Speaker 2 (00:09):
That's the goal.
Speaker 1 (00:10):
Today. We're actually heading somewhere maybe a little unexpected in
American mafia history based on the materials you've shared. When
you think organized crime in the US, I mean most
people picture New York, right, or maybe Chicago.
Speaker 2 (00:23):
Absolutely those are the big ones. Yeah, maybe Miami later on.
Speaker 1 (00:26):
But Denver, Denver, Colorado, that's not usually top of mine.
Speaker 2 (00:29):
It's really not. And that's what makes this story so intriguing,
isn't it. Your sources really bring to life this hidden chapter.
Denver had a surprisingly deep underworld, and right.
Speaker 1 (00:40):
At the center of it all, according to these documents,
is this figure Eugene Checkers small Dollar Checkers, Hey, and
his story isn't your typical straightforward mob boss narrative. He
complicates things. I mean, he was definitely feared, no doubt
about that, oh for sure, but also somehow beloved in
parts of the community. It raises this core question I
want to explore, how does one guy become both a
(01:02):
notorious gangster and a cherished local figure it's.
Speaker 2 (01:06):
A fascinating contradiction. And these sources, they show a man
whose life really tied Denver to the wider reach of
the American mafia. We're going to unpack this mix the
old school values, the undeniable ruthlessness, but also this surprising generosity.
Speaker 1 (01:26):
Denver's gentleman gangster.
Speaker 2 (01:28):
Exactly prepared to have maybe some perceptions challenged here.
Speaker 1 (01:31):
Okay, So to get how this gentleman gangster could even
happen in Denver, we probably need to start at the beginning, right,
the immigrant.
Speaker 2 (01:37):
Story, definitely, that's key context.
Speaker 1 (01:39):
Your sources show the small Done family arriving in Denver
early twentieth century, and like so many Italian families back then,
they've faced huge hurdles, discrimination, finding.
Speaker 2 (01:50):
Work, yeah, just navigating a whole new world. It wasn't easy.
Speaker 1 (01:53):
And Eugene smalldone, he's born right into this November third,
nineteen ten. It sounds like they weren't just aiming to
scrape by.
Speaker 2 (01:59):
Though not at all. And that's where prohibition comes in. Right,
starting in nineteen twenty, your sources really highlight this. It
created this massive, uh let's call it an opportunity, the
lucrative one hugely lucrative for many immigrants, especially Italians, who
were often shut out of you know, respectable jobs because
of that discrimination you mentioned. Bootlegging was away.
Speaker 1 (02:20):
In a fast trek to making money exactly. Yeah.
Speaker 2 (02:23):
But what's interesting here, and the sources point this out,
is the small dones weren't just like small time hustlers.
They thought bigger. They saw an organized.
Speaker 1 (02:32):
Structure and actual operation.
Speaker 2 (02:33):
Right. They saw the chaos of prohibition not just as
a hustle, but as an entrepreneurial opening.
Speaker 1 (02:40):
So real ambition there, not just a couple of speakeasies.
They wanted to be the players in Denver's underworld.
Speaker 2 (02:46):
That seems to be the picture.
Speaker 1 (02:47):
Yeah.
Speaker 2 (02:48):
Yeah, they weren't content just participating. They aimed for control,
and that ambition, combined with the times, really set the stage.
Speaker 1 (02:55):
Okay, let's talk about the nickname Checkers mom nicknames they
always mean something, right, they stick.
Speaker 2 (03:00):
They absolutely do. It's like shorthand for their whole persona.
Speaker 1 (03:03):
And Checkers really seems to fit him. Based on these materials,
two main theories pop up. One simple enough, he was
great at the game Checkers, always thinking ahead m HM,
strategic or maybe more broadly, it just reflected his mind,
quick calculating, always two moves ahead, you know, in life,
not just on a board.
Speaker 2 (03:23):
And it's a really stark contrast when you look at
his brothers, Clyde and Clarence Chauncey Chauncey right, your sources
suggest they were the ones making headlines more often, more
overt violence, more arrests, kind of the classic gangster image.
A muscle perhaps, Checkers, though, he deliberately built a different front. Smooth, personable,
(03:45):
diplomatic even That's how he got respect both inside and
outside the criminal world.
Speaker 1 (03:49):
He could talk his way through things.
Speaker 2 (03:51):
He was often the mediator, the smoother over. He could
walk into a tense situation and calm it down. That
was crucial for the family success.
Speaker 1 (03:58):
So that nickname Checker. It wasn't just about a game.
It was about his whole strategic approach, less route force,
more finesse exactly.
Speaker 2 (04:06):
It was about outthinking the competition, the law everyone a
very different style than many of his peers, especially back then.
While the brothers might handle the rough stuff, Checkers was
the strategist, the negotiator.
Speaker 1 (04:19):
And that strategic mind, that Checker's brain, it clearly fueled
the whole operation. How did he actually build the empire?
Your sources say it started like many, with bootlegging during Prohibition.
Speaker 2 (04:30):
Right, and they got good fast. By the late nineteen thirties,
the Small Dones were apparently the top bootleggers in Denver.
Speaker 1 (04:38):
And this wasn't just backtub jin was it. The material
suggests something more organized.
Speaker 2 (04:43):
Oh much more. Your sources emphasized their organizational skill. Think
about it. Controlling supply routes sometimes way beyond Colorado, hanging
off the right people, absolutely, police politicians. Building that network
of protection was vital, and managing distributors, making sure the
product got out. It was a complex, efficient machine.
Speaker 1 (05:03):
Then Prohibition ends, a lot of bootleggers just went busted.
Speaker 2 (05:06):
Right now, many did. Their whole business model disappeared overnight, But.
Speaker 1 (05:09):
Not the Small Dones. Your sources show they just shifted gears.
Speaker 2 (05:13):
How they pivoted really smart. They took the networks, the capital,
the influence they'd built from bootlegging and applied it elsewhere exactly.
Dambling was huge, loan sharking, other rackets. Your sources described
their gambling operations as top notch illegal casinos, big book making, setups,
numbers games apparently run as professionally as anything legal in Vegas,
(05:37):
hidden behind legitimate fronts. Yeah, and this really shows their adaptability,
their business sense. They became the de facto mafia family
in Denver. It wasn't like New York with warring fashions.
Speaker 1 (05:48):
They dominated pretty much, and.
Speaker 2 (05:51):
Their reach went beyond Denver into Wyoming, Nebraska. Sources even
mentioned links to early Vegas. Checkers was the strategist in all.
Speaker 1 (05:59):
This, pulling this strings. So it wasn't just running the
games but also managing relationships, keeping things smooth. How often
did his diplomacy actually work?
Speaker 2 (06:07):
That was maybe his key skill, according to these accounts,
keeping the peace. Rivals always pop upright, but Checkers often
managed to sort out disputes with words.
Speaker 1 (06:15):
Negotiation, the gentleman gangster.
Speaker 2 (06:17):
That's the reputation calm in the storm. Now, the sources
are clear, force was always an option, it had to
be sure, but his first move was usually diplomacy that
made him stand out.
Speaker 1 (06:25):
Okay, but this part, this is where it gets really complex,
isn't it. The robinhood side of Checkers.
Speaker 2 (06:30):
It's the core of the paradox.
Speaker 1 (06:31):
Absolutely, we've got the roof of strategists, the crime boss.
But then your sources are full of these stories, handing
out cash to neighbors down on their luck, HM, paying
bills for struggling families, just quietly slipping twenties to kids
on the street. It feels jarring. How did the sources
explain this?
Speaker 2 (06:52):
So the why it resonated is crucial for many in
Denver's Italian American community facing those hardships. We talked about
feeling ignored by the system.
Speaker 1 (07:02):
He was someone who helps You've seen.
Speaker 2 (07:03):
Almost as a protector. Yeah, a kind of unofficial faithty net.
His generosity wasn't just random kindness. It built incredible loyalty.
It was like social.
Speaker 1 (07:11):
Capital, which also served us protection.
Speaker 2 (07:13):
Definitely protection from rivals from the law to some extent.
And his public image was carefully maintained. Attended church, dress, sharp,
always polite.
Speaker 1 (07:22):
A charmer even to the enemies.
Speaker 2 (07:24):
Apparently so your sources mentioned even cops admitting, maybe reluctantly,
that he had charm, that he could have been a
credit to the community if he'd gone straight. He embodied
those coosonostra ideas family, honor, respect, but outside the law.
Speaker 1 (07:41):
Wow. So the generosity was functional too. It cemented his place,
his power within that community. Providing something the official world
maybe wasn't precisely.
Speaker 2 (07:50):
It's that idea of parallel governance. When the state doesn't
meet needs, sometimes figures like him step in for better
or worse.
Speaker 1 (07:57):
But despite the charm, the community support, the law was always.
Speaker 2 (08:01):
There, always breathing down their necks.
Speaker 1 (08:03):
Your sources detail constant pressure, especially in the forties and fifties,
police raids, gambling guns, busted slot machines.
Speaker 2 (08:10):
Hauled away bookies, getting arrested constantly.
Speaker 1 (08:12):
Yet the small dons and Checkers in particular seemed almost teflon.
How do they keep bouncing back?
Speaker 2 (08:18):
There's a combination of things, according to these materials. Yeah, influence, definitely,
good lawyers they could afford the best.
Speaker 1 (08:23):
And maybe witnesses getting forgetful.
Speaker 2 (08:25):
That's strongly hinted at in the sources. Yes, witnesses disappearing
or suddenly changing their stories before trial. It made convictions
very difficult, especially against the top guys like Checkers. He
was good at delegating, keeping his hands clean.
Speaker 1 (08:39):
So he avoided the long prison sentences that took down
other mocksters. Lots of fines, probation maybe, while others took
the fall often.
Speaker 2 (08:47):
Yes, he had this remarkable knack for staying just out
of reach even when things got hot. But then the
FED started paying more attention.
Speaker 1 (08:55):
Things changed in the sixties.
Speaker 2 (08:57):
Yeah, the FBI really intensified its focus on organized crime nationally.
Denver wasn't flying under the radar anymore. But the real
hammer blow, the thing that changed the whole game.
Speaker 1 (09:06):
Was CRICO AH, the right co act racketeer influenced and
corrupt organizations. That was seventies eighties exactly.
Speaker 2 (09:14):
And it gave prosecutors massive new power because now they
didn't just have to prove individual crimes, TI.
Speaker 1 (09:20):
Gu target the whole enterprise right.
Speaker 2 (09:22):
Show a pattern of racketeering activity. This was huge. Leaders
like Checkers, who maybe weren't directly involved in every single act,
could still be held accountable for the organization's overall criminal conduct.
Speaker 1 (09:34):
So their old tricks keeping distance witnesses vanishing that became.
Speaker 2 (09:38):
Harder, much harder. Cho made it easier to connect the dots.
Wire taps became more useful. Surveillance got tighter, and ICO
offered incentives for informants people inside the organization willing to testify.
Speaker 1 (09:50):
That must have really eroded their power structure.
Speaker 2 (09:53):
It chipped away relentlessly. Your sources paint a picture of
the golden age of Denver's underworld fading, like elsewhere, under
this intense legal pressure. The old ways just weren't working
as well.
Speaker 1 (10:04):
So as that era declined, what happened to Checkers in
his later years. Did he fade away, go down in flames?
Speaker 2 (10:10):
Neither? Really. He remained a respected figure in Denver, even
as the mafia's influence weakened. He kept that reputation generous,
gentlemanly right to the end, according to the sources.
Speaker 1 (10:20):
And his end was different, very different.
Speaker 2 (10:22):
From many East Coast bosses who met violent ends. Checkers
lived a long life, relatively peacefully, still in Denver. He
died in nineteen ninety two. He was eighty two. Wow,
and his funeral apparently was quite something. Drew a huge
diverse crowd, law abiding folks alongside underworld figures. It really
showed how woven into the fabric of the city he was.
Speaker 1 (10:43):
So looking back, what's the takeaway from Checker Smoldoon's life
based on these materials, It's incredibly complex.
Speaker 2 (10:51):
Deeply complex. You have a man who absolutely committed serious crimes,
ran a legal operations, operated outside the law, no question
but then he's also remembered, genuinely remember by many for
his generosities, dignity, his role as a community protector.
Speaker 1 (11:05):
In a way, it really underscores that the mafia story
in America isn't monolithic, is it not at all?
Speaker 2 (11:10):
The Smolder name is part of Denver's history. Now it
proves organized crime wasn't just New York or Chicago. These
local bosses, like Checkers, they left their own distinct marks
on their cities. Makes you wonder how many other Checkers
there were in other unexpected places.
Speaker 1 (11:24):
He really was more than just a mobster, a walking paradox.
Your sources show him ordering illegal bets one.
Speaker 2 (11:30):
Minute and paying someone's rent the next.
Speaker 1 (11:32):
A criminal, yes, but also somehow a gentleman. It's endlessly fascinating, and.
Speaker 2 (11:38):
His story it adds this really valuable, nuanced layer to
understanding American organized crime. It wasn't just about the crime itself.
It was about culture, community, loyalty, power, and these incredibly
complicated legacies left by people who operated on both sides
of the law.
Speaker 1 (11:57):
He wasn't capone or gaudy, maybe not globally famous.
Speaker 2 (12:00):
But in Denver, larger than life, a true local legend.
Shaped by the community he both served and exploited.
Speaker 1 (12:06):
So thinking about everything these sources present, what does Checker's
life make you consider about how we define good and
bad or maybe where those lines get incredibly blurry between
community leader and criminal boss, especially in certain times and places.
Speaker 2 (12:20):
It definitely challenges simple labels.
Speaker 1 (12:21):
It really does something to think about as you delve
deeper into these materials yourself
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