July 8, 2025 • 10 mins
the Chicago Outfit’s most enduring and enigmatic figures. From his rise through the mob ranks to his courtroom antics and ultimate downfall in the Family Secrets trial, discover how Lombardo balanced charm, cunning, and cold-blooded crime in a life that spanned the golden era of organized crime.
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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're the podcast that goes
deep into complex stories to give you the insights you
really need. That's the goal, and today we're digging into
the life of a pretty fascinating and maybe unsettling figure
known as Joey the Clown.
Speaker 2 (00:15):
Yeah, that nickname, it suggests something light, almost funny, doesn't
it exactly?
Speaker 1 (00:18):
Yeah, but just Patrick Lombardo, the man we're talking about, well,
his life was anything but a joke. His name might
not be as huge as say al Capone, but his
story tells you, maybe even more about how the Chicago
outfit really changed over time.
Speaker 2 (00:33):
I'd agree with that. Lombardo, he really he embodied the
contradictions baked into organized crime. He could be incredibly charming,
you know, that easy smile, but underneath just completely ruthless,
soft spoken people said, but also deeply feared. And his
career it went on for more than fifty years. It
basically connects the mobs violent heyday to its more buttoned
(00:54):
down modern version.
Speaker 1 (00:55):
So our mission today is to really unpack Lombardo's life crimes, sure,
but also his his lasting image. Maybe we want to
pull out the key bits of knowledge so you can
understand the guy behind the smile, and you know what
his whole story reveals about the mob itself. It's adaptability,
its methods, and maybe it's end.
Speaker 2 (01:15):
Okay, let's dive in Joseph Patrick Lombardo. He was born
January first, nineteen twenty nine, right there on Chicago's West Side. Okay, oh,
working class neighborhood, mostly Itellian American back then, and it
was the kind of place where look, book smarts weren't
the main thing, right, it was more about street smarts exactly.
Power came from who you knew. Loyalty was everything, and
(01:36):
your reputation that was your currency, not some diploma.
Speaker 1 (01:40):
And that environment clearly shaped him. He didn't have much
formal schooling. It sounds like he got pulled into petty
stuff pretty young.
Speaker 2 (01:47):
Yeah, police knew about him by his twenties, low level things.
Speaker 1 (01:50):
But even then he wasn't just some thug, right The
sources mentioned this mix. He had intelligence, real charisma, but
also discretion. He knew when keep quiet. How did that
set him apart so early on?
Speaker 2 (02:03):
That combination was gold, especially when he was coming up
because this was post World War two and the Chicago
outfit itself was changing how so well, it was moving away, consciously,
moving away from the really public, bloody violence of the
Capone era. They wanted something more disciplined, more well, almost
business like, aw and Lombardo, with his savvy, his trustworthiness,
(02:26):
his ability to operate quietly, he was exactly what the
bosses were looking for. He caught their eye.
Speaker 1 (02:31):
So he was the right man at the right time
for this new evolving outfit, and by the sixties he's
a trusted lieutenant.
Speaker 2 (02:38):
What were his specialties the new profit centers really labor
union racketeering. That was huge, loan sharking, illegal gambling. But
the big one, the really invaluable connection, was with the
Teamsters union officials.
Speaker 1 (02:49):
Why was that specific connection so powerful.
Speaker 2 (02:52):
Oh, it was everything. It gave the outfit access to
huge amounts of money, legitimate cover through pension uns. It
was the golden goose. Lombardo became a master at working
behind the scenes, you know, steering deals, making sure the
outfit got it sliced from casinos, from construction, whatever, often
without leaving fingerprints. It was about influence money, not just
(03:15):
breaking legs.
Speaker 1 (03:16):
And this knack for being subtle, for feming almost.
Speaker 2 (03:20):
Yeah, harmless, that's where the nickname comes in, isn't it
Joey the clown?
Speaker 1 (03:23):
That's it. He'd cracked jokes, he had that easy smile,
he put on this lighthearted act, especially in cord Or
if the police were questioning him.
Speaker 2 (03:29):
So the nickname stuck because of that public persona right, but.
Speaker 1 (03:33):
It was absolutely a deliberate mask, a facade. Underneath that
clown was a cold, calculating guy who did not tolerate
mistakes or disloyalty. With brilliant camouflage really let him operate
right under everyone's noses.
Speaker 2 (03:46):
That ability to blend in to disarm people. It must
have been perfect for the outfit's next big play in
the seventies and eighties, The Las Vegas Skim.
Speaker 1 (03:55):
Absolutely central, but in his typical style, quietly pulling the strings.
Speaker 2 (03:58):
How did you do?
Speaker 1 (03:59):
It?
Speaker 2 (04:00):
Used those teamsters connections the pension funds to funnel massive
loans to casino developers in Vegas, seemingly legit loans, Oh
good loans, But of course there was an understanding, very
clear one. The outfit gets a piece of the action,
skimming cash right off the top, millions of dollars before
it was even counted.
Speaker 1 (04:19):
And this whole scheme this became the target of that
big FBI investigation Operation straw Man.
Speaker 2 (04:24):
That's the one they were trying to unravel, the whole
Vegas skimming operation and the Union connection.
Speaker 1 (04:30):
Now, Lombardo wasn't directly nabbed for the skimming itself in
that initial wave, but his connections were key. He ended
up getting convicted in eighty two, right for trying to
bribe a US senator.
Speaker 2 (04:41):
Yeah, conspiracy to brab Senator Howard Cannon got fifteen years
for that, And honestly, at that point most people figured, Okay,
that's it for Joey the clown. He's done.
Speaker 1 (04:49):
Fifteen years is a long time, Especially then, you'd think
his career was over.
Speaker 2 (04:53):
You would, and for many mobsters it would have been.
But Lombardo, well, he wasn't typical. Even in prison, he
kept his head down, kept his network alive, coded messages,
loyal guys on the outside, always work in the angles, always,
And then he gets out in nineteen ninety two, tries
to lay low, at least on the surface, but then
(05:13):
he pulls this stunt, classic Lombardo.
Speaker 1 (05:17):
The newspaper ad. I remember reading about this. He took
out a classified ad in the Chicago Tribune.
Speaker 2 (05:22):
Can you believe it? It literally said, quote, I am not
a member of the outfit, I am not a criminal,
I am a retired businessman.
Speaker 1 (05:30):
That's just audacious. What was the point just thumbing his
nose at everyone?
Speaker 2 (05:34):
Pretty much? It was pure theater, totally unbelievable, obviously to
anyone who knew anything. But it was his way of saying,
I'm back, I'm still Joey, and I play by my
own rules. A laugh aimed right at the Feds. But
you knew that wouldn't be the end of it. The
Feds weren't laughing.
Speaker 1 (05:49):
No, I imagine not. Yeah, And sure enough they came back,
didn't they with Operation Family Secrets in the early two
thousand Oh Yeah.
Speaker 2 (05:55):
And this wasn't just another investigation. This was huge, probably
one of the biggest hits on the outfit ever, and
it was built on testimony from guys inside mob turncoats
like Frank Calabres Junior testifying against his own father.
Speaker 1 (06:09):
That must have sent shockwaves through the organization.
Speaker 2 (06:11):
Absolutely terrifying for them, because Family Secrets started uncovering stuff
that went back decades old murders, loan shocking the whole racket,
and in two thousand and five, the indictments came down.
Joseph Lombardo was charged with conspiracy, extortion, and his alleged
part in a very specific murder from nineteen seventy four.
Speaker 1 (06:31):
Daniel Seifert, the businessman who was about to testify against
him back then.
Speaker 2 (06:35):
That's the one. The accusation was that Lombardo was directly
involved in silencing him permanently. For a guy who built
his career on staying in the shadows, that kind of
direct murder charge was huge.
Speaker 1 (06:46):
And what did Lombardo do when the indictment hit He.
Speaker 2 (06:48):
Did what he did best. When cornered, he vanished, just disappear.
Speaker 1 (06:52):
On the run at his age yep, became.
Speaker 2 (06:54):
A fugitive, sparked this massive nationwide manhunt. Took them nearly
nine months to find him.
Speaker 1 (06:59):
Wow, where did they finally catch him?
Speaker 2 (07:01):
Hiding out in Elmwood Park, Illinois, living under a fake name.
He was seventy seven years old, still trying to stay
one step ahead.
Speaker 1 (07:07):
So that leads us to the big trial. In two
thousand and seven, Samlely's Secrets trial, Lombardo, alongside other top outfit.
Speaker 2 (07:13):
Guys, right and the prosecution, laid out this picture of
him as this key player for decades, involved in violence,
involved in the money. But the real bombshell was the
focus on the Daniel Seifert murder.
Speaker 1 (07:25):
What were the details there?
Speaker 2 (07:27):
Seifert was ambushed, shot down right in front of his
wife and young son, just days before he was scheduled
to testify against Lombardo and others. Prosecutors argued Lombardo didn't
just okay it, He personally orchestrated it, made sure the
witness problem went.
Speaker 1 (07:41):
Away, chilling, and that must have really undermined the whole
Joey the clown image.
Speaker 2 (07:45):
It cut right through it. And despite his age his
health issues, the jurid got it. Convicted on all counts,
sentenced to life in prison.
Speaker 1 (07:53):
Life, so the system finally got him. But even then,
even behind bars, he apparently kept up that persona, didn't
he the gangster?
Speaker 2 (08:00):
Reports from prison? Yeah, inmates, guards, even reporters noted he
was still polite, respectful, had that sharp humor, always the gentleman,
even in a maximum security facility.
Speaker 1 (08:10):
It's such a strange contrast, isn't it. Compared to the
stereotype of a modern gangster, he seemed like something from
a different time. Suits a code, cunning over just pure brutality.
Speaker 2 (08:21):
He absolutely embodied that bygone era and sticking to that
image even facing life without parole. It says a lot
about him about his commitment to that identity.
Speaker 1 (08:31):
So Joseph Lombardo died in prison October nineteen, twenty nineteen.
He was ninety years old.
Speaker 2 (08:35):
Yeah, serving that life sentence at a federal medical center,
and his death it really felt like the closing of
a chapter. One of the very last big names from
the Outfit's peak years was gone. You get the sense
that even within what's left of the Outfit, there was
this quiet acknowledgment that his era was truly over.
Speaker 1 (08:52):
His legacy is just full of those contradictions we talked about.
Was he the charming old guy with a quick wit, yeah,
or the ruthless killer using qu is a weapon.
Speaker 2 (09:00):
Probably both right. And his life story it mirrors the
Outfit's own story perfectly. From copone's open warfare through that
period of corporate style corruption Lombardo specialized in right down
to the slow decline under relentless federal pressure.
Speaker 1 (09:14):
And he survived so long, longer than most. Hey, why
you said it wasn't because he was the toughest.
Speaker 2 (09:20):
No, it was because he was adaptable. He understood how
the game was changing. He was maybe the quintessential twentieth
century mob boss in that sense, lived by the code,
rose through the ranks quietly, and never really broke even
at the end, kept that mask on, the clown smile
hiding something much darker.
Speaker 1 (09:38):
So Joey the clown. Maybe he didn't change the game,
but he definitely represented a specific powerful phase of it.
Suits union control, that feeling of being untouchable for so.
Speaker 2 (09:50):
Long, for a very long time. Yeah, he outlasted so many,
dodged serious time for decades, a symbol of the outfit
staying power in a way. But like you said, the
bill eventually came due.
Speaker 1 (09:59):
Which brings us to the final thought. Think about his end,
dying in prison, age ninety, far from Chicago streets. It's
maybe a stark reminder, isn't it. Crime might seem to
pay for a while, maybe even a long while in.
Speaker 2 (10:10):
His case, but that final invoice, a life sentence, It
does arrive eventually. So what does this whole story really
tell you about the actual cost of that life, about
how real that power and control actually is, even for
someone as cunning as Lombardo, and you know, can someone
like that ever truly just retire
Welcome to the Deep Dive. We're the podcast that goes
deep into complex stories to give you the insights you
really need. That's the goal, and today we're digging into
the life of a pretty fascinating and maybe unsettling figure
known as Joey the Clown.
Speaker 2 (00:15):
Yeah, that nickname, it suggests something light, almost funny, doesn't
it exactly?
Speaker 1 (00:18):
Yeah, but just Patrick Lombardo, the man we're talking about, well,
his life was anything but a joke. His name might
not be as huge as say al Capone, but his
story tells you, maybe even more about how the Chicago
outfit really changed over time.
Speaker 2 (00:33):
I'd agree with that. Lombardo, he really he embodied the
contradictions baked into organized crime. He could be incredibly charming,
you know, that easy smile, but underneath just completely ruthless,
soft spoken people said, but also deeply feared. And his
career it went on for more than fifty years. It
basically connects the mobs violent heyday to its more buttoned
(00:54):
down modern version.
Speaker 1 (00:55):
So our mission today is to really unpack Lombardo's life crimes, sure,
but also his his lasting image. Maybe we want to
pull out the key bits of knowledge so you can
understand the guy behind the smile, and you know what
his whole story reveals about the mob itself. It's adaptability,
its methods, and maybe it's end.
Speaker 2 (01:15):
Okay, let's dive in Joseph Patrick Lombardo. He was born
January first, nineteen twenty nine, right there on Chicago's West Side. Okay, oh,
working class neighborhood, mostly Itellian American back then, and it
was the kind of place where look, book smarts weren't
the main thing, right, it was more about street smarts exactly.
Power came from who you knew. Loyalty was everything, and
(01:36):
your reputation that was your currency, not some diploma.
Speaker 1 (01:40):
And that environment clearly shaped him. He didn't have much
formal schooling. It sounds like he got pulled into petty
stuff pretty young.
Speaker 2 (01:47):
Yeah, police knew about him by his twenties, low level things.
Speaker 1 (01:50):
But even then he wasn't just some thug, right The
sources mentioned this mix. He had intelligence, real charisma, but
also discretion. He knew when keep quiet. How did that
set him apart so early on?
Speaker 2 (02:03):
That combination was gold, especially when he was coming up
because this was post World War two and the Chicago
outfit itself was changing how so well, it was moving away, consciously,
moving away from the really public, bloody violence of the
Capone era. They wanted something more disciplined, more well, almost
business like, aw and Lombardo, with his savvy, his trustworthiness,
(02:26):
his ability to operate quietly, he was exactly what the
bosses were looking for. He caught their eye.
Speaker 1 (02:31):
So he was the right man at the right time
for this new evolving outfit, and by the sixties he's
a trusted lieutenant.
Speaker 2 (02:38):
What were his specialties the new profit centers really labor
union racketeering. That was huge, loan sharking, illegal gambling. But
the big one, the really invaluable connection, was with the
Teamsters union officials.
Speaker 1 (02:49):
Why was that specific connection so powerful.
Speaker 2 (02:52):
Oh, it was everything. It gave the outfit access to
huge amounts of money, legitimate cover through pension uns. It
was the golden goose. Lombardo became a master at working
behind the scenes, you know, steering deals, making sure the
outfit got it sliced from casinos, from construction, whatever, often
without leaving fingerprints. It was about influence money, not just
(03:15):
breaking legs.
Speaker 1 (03:16):
And this knack for being subtle, for feming almost.
Speaker 2 (03:20):
Yeah, harmless, that's where the nickname comes in, isn't it
Joey the clown?
Speaker 1 (03:23):
That's it. He'd cracked jokes, he had that easy smile,
he put on this lighthearted act, especially in cord Or
if the police were questioning him.
Speaker 2 (03:29):
So the nickname stuck because of that public persona right, but.
Speaker 1 (03:33):
It was absolutely a deliberate mask, a facade. Underneath that
clown was a cold, calculating guy who did not tolerate
mistakes or disloyalty. With brilliant camouflage really let him operate
right under everyone's noses.
Speaker 2 (03:46):
That ability to blend in to disarm people. It must
have been perfect for the outfit's next big play in
the seventies and eighties, The Las Vegas Skim.
Speaker 1 (03:55):
Absolutely central, but in his typical style, quietly pulling the strings.
Speaker 2 (03:58):
How did you do?
Speaker 1 (03:59):
It?
Speaker 2 (04:00):
Used those teamsters connections the pension funds to funnel massive
loans to casino developers in Vegas, seemingly legit loans, Oh
good loans, But of course there was an understanding, very
clear one. The outfit gets a piece of the action,
skimming cash right off the top, millions of dollars before
it was even counted.
Speaker 1 (04:19):
And this whole scheme this became the target of that
big FBI investigation Operation straw Man.
Speaker 2 (04:24):
That's the one they were trying to unravel, the whole
Vegas skimming operation and the Union connection.
Speaker 1 (04:30):
Now, Lombardo wasn't directly nabbed for the skimming itself in
that initial wave, but his connections were key. He ended
up getting convicted in eighty two, right for trying to
bribe a US senator.
Speaker 2 (04:41):
Yeah, conspiracy to brab Senator Howard Cannon got fifteen years
for that, And honestly, at that point most people figured, Okay,
that's it for Joey the clown. He's done.
Speaker 1 (04:49):
Fifteen years is a long time, Especially then, you'd think
his career was over.
Speaker 2 (04:53):
You would, and for many mobsters it would have been.
But Lombardo, well, he wasn't typical. Even in prison, he
kept his head down, kept his network alive, coded messages,
loyal guys on the outside, always work in the angles, always,
And then he gets out in nineteen ninety two, tries
to lay low, at least on the surface, but then
(05:13):
he pulls this stunt, classic Lombardo.
Speaker 1 (05:17):
The newspaper ad. I remember reading about this. He took
out a classified ad in the Chicago Tribune.
Speaker 2 (05:22):
Can you believe it? It literally said, quote, I am not
a member of the outfit, I am not a criminal,
I am a retired businessman.
Speaker 1 (05:30):
That's just audacious. What was the point just thumbing his
nose at everyone?
Speaker 2 (05:34):
Pretty much? It was pure theater, totally unbelievable, obviously to
anyone who knew anything. But it was his way of saying,
I'm back, I'm still Joey, and I play by my
own rules. A laugh aimed right at the Feds. But
you knew that wouldn't be the end of it. The
Feds weren't laughing.
Speaker 1 (05:49):
No, I imagine not. Yeah, And sure enough they came back,
didn't they with Operation Family Secrets in the early two
thousand Oh Yeah.
Speaker 2 (05:55):
And this wasn't just another investigation. This was huge, probably
one of the biggest hits on the outfit ever, and
it was built on testimony from guys inside mob turncoats
like Frank Calabres Junior testifying against his own father.
Speaker 1 (06:09):
That must have sent shockwaves through the organization.
Speaker 2 (06:11):
Absolutely terrifying for them, because Family Secrets started uncovering stuff
that went back decades old murders, loan shocking the whole racket,
and in two thousand and five, the indictments came down.
Joseph Lombardo was charged with conspiracy, extortion, and his alleged
part in a very specific murder from nineteen seventy four.
Speaker 1 (06:31):
Daniel Seifert, the businessman who was about to testify against
him back then.
Speaker 2 (06:35):
That's the one. The accusation was that Lombardo was directly
involved in silencing him permanently. For a guy who built
his career on staying in the shadows, that kind of
direct murder charge was huge.
Speaker 1 (06:46):
And what did Lombardo do when the indictment hit He.
Speaker 2 (06:48):
Did what he did best. When cornered, he vanished, just disappear.
Speaker 1 (06:52):
On the run at his age yep, became.
Speaker 2 (06:54):
A fugitive, sparked this massive nationwide manhunt. Took them nearly
nine months to find him.
Speaker 1 (06:59):
Wow, where did they finally catch him?
Speaker 2 (07:01):
Hiding out in Elmwood Park, Illinois, living under a fake name.
He was seventy seven years old, still trying to stay
one step ahead.
Speaker 1 (07:07):
So that leads us to the big trial. In two
thousand and seven, Samlely's Secrets trial, Lombardo, alongside other top outfit.
Speaker 2 (07:13):
Guys, right and the prosecution, laid out this picture of
him as this key player for decades, involved in violence,
involved in the money. But the real bombshell was the
focus on the Daniel Seifert murder.
Speaker 1 (07:25):
What were the details there?
Speaker 2 (07:27):
Seifert was ambushed, shot down right in front of his
wife and young son, just days before he was scheduled
to testify against Lombardo and others. Prosecutors argued Lombardo didn't
just okay it, He personally orchestrated it, made sure the
witness problem went.
Speaker 1 (07:41):
Away, chilling, and that must have really undermined the whole
Joey the clown image.
Speaker 2 (07:45):
It cut right through it. And despite his age his
health issues, the jurid got it. Convicted on all counts,
sentenced to life in prison.
Speaker 1 (07:53):
Life, so the system finally got him. But even then,
even behind bars, he apparently kept up that persona, didn't
he the gangster?
Speaker 2 (08:00):
Reports from prison? Yeah, inmates, guards, even reporters noted he
was still polite, respectful, had that sharp humor, always the gentleman,
even in a maximum security facility.
Speaker 1 (08:10):
It's such a strange contrast, isn't it. Compared to the
stereotype of a modern gangster, he seemed like something from
a different time. Suits a code, cunning over just pure brutality.
Speaker 2 (08:21):
He absolutely embodied that bygone era and sticking to that
image even facing life without parole. It says a lot
about him about his commitment to that identity.
Speaker 1 (08:31):
So Joseph Lombardo died in prison October nineteen, twenty nineteen.
He was ninety years old.
Speaker 2 (08:35):
Yeah, serving that life sentence at a federal medical center,
and his death it really felt like the closing of
a chapter. One of the very last big names from
the Outfit's peak years was gone. You get the sense
that even within what's left of the Outfit, there was
this quiet acknowledgment that his era was truly over.
Speaker 1 (08:52):
His legacy is just full of those contradictions we talked about.
Was he the charming old guy with a quick wit, yeah,
or the ruthless killer using qu is a weapon.
Speaker 2 (09:00):
Probably both right. And his life story it mirrors the
Outfit's own story perfectly. From copone's open warfare through that
period of corporate style corruption Lombardo specialized in right down
to the slow decline under relentless federal pressure.
Speaker 1 (09:14):
And he survived so long, longer than most. Hey, why
you said it wasn't because he was the toughest.
Speaker 2 (09:20):
No, it was because he was adaptable. He understood how
the game was changing. He was maybe the quintessential twentieth
century mob boss in that sense, lived by the code,
rose through the ranks quietly, and never really broke even
at the end, kept that mask on, the clown smile
hiding something much darker.
Speaker 1 (09:38):
So Joey the clown. Maybe he didn't change the game,
but he definitely represented a specific powerful phase of it.
Suits union control, that feeling of being untouchable for so.
Speaker 2 (09:50):
Long, for a very long time. Yeah, he outlasted so many,
dodged serious time for decades, a symbol of the outfit
staying power in a way. But like you said, the
bill eventually came due.
Speaker 1 (09:59):
Which brings us to the final thought. Think about his end,
dying in prison, age ninety, far from Chicago streets. It's
maybe a stark reminder, isn't it. Crime might seem to
pay for a while, maybe even a long while in.
Speaker 2 (10:10):
His case, but that final invoice, a life sentence, It
does arrive eventually. So what does this whole story really
tell you about the actual cost of that life, about
how real that power and control actually is, even for
someone as cunning as Lombardo, and you know, can someone
like that ever truly just retire
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