The Underworld Podcast - Santo Trafficante: Havana Nights, Killing Castro and the King of Florida
Episode Date: December 5, 2023The Trafficante crime family ruled Florida for decades, earning the respect and admiration of powerful mobsters like Lucky Luciano, Meyer Lansky and Sam Giancana. Santo Trafficante Sr arrived in Tampa... as a boy from Sicily and took to the underworld with a talent for business, setting up the illegal lottery known as the Bolita before using his Spanish skills to make him indispensable to the powerful five families who wanted to set up shop in Cuba. When his son, Santo Jr, took the reigns, they soon controlled casinos, nightclubs and luxury hotels, as well as narcotics trafficking routes, from Cuba to Miami to Tampa. But the heady days of Fulgencio Batista's Cuba was coming to a close, and the Cuban revolutionaries led by Fidel Castro were going to complicate things. So much so that Trafficante soon found himself in one of America's strangest alliances and even stranger assassination plots. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Go to VANTA.com slash com. New Year's Eve, 1950A in Havana, Cuba. Things aren't looking
so great for Fulgencio Batista, the country's military dictator.
It's been a rough year, and the rebels trying to overthrow him, led by Fidel Castro and
Che Guevara, are getting closer and closer every day.
After a massive military defeat over the summer, he holds a fake election in November
to try to salvage his regime.
This was it, though, for the U.S., who had backed Batista, as the U.S. ambassador of Cuba
tells him that not only were the U.S. not recognized this new government, but that he's
clearly lost control over the country.
and it's time to retire.
Batista gathers a rumored $300 million
and decides to flee
in the early morning hours of the next day,
January 1st, 1959.
Castro and Company are about to take control.
And the U.S. government are not the only ones
caught off guard.
There's another powerful U.S. institution
that are very concerned
to see how things are going to shape out.
And that's the American mafia families.
The Godfather Part 2 wasn't a documentary,
but there's a lot of accuracy there.
See, a mafia,
Syndicate made up of some of the biggest names in American mafia history have heavily invested in Cuba
during Batista's reign. They have a plethora of hotels, casinos, and other businesses, including
the narcotics trade that have been printing money for the mob for years. But now, their cash cow is at
stake, and it's up to the mob's point man in Cuba, Florida mob boss Santo Traficante Jr. to make sure
that everything is all right and the mafia will stay making money. Traficante is mafia royalty. His father, Santo Traficante
Senior, have been a powerful crime boss that ran things in Tampa, Florida for decades,
but also recognized that there was huge potential money-making opportunities in Cuba.
He'd actually sent his son down to a van in the 40s to suss things out and set up a
mafia-run casino.
Junior had taken over the Tampa Bay Mafia leadership in the 50s, also making deals with
heavyweight New York mobsters and on the national front.
They called him the Silent Dawn, and you know how it is like the Gene Lazzania.
He had things running smooth in Cuba for a minute.
and he's been playing both sides,
supporting Batista,
but also supporting the revolutionaries
like any good politician.
But Castro has other ideas.
He's no fan of the casinos,
luxury hotels,
and everything else that goes with it.
Everything is about to go very wrong
for the mafia's Cuban enterprise.
In fact, things go so wrong
that Santo Trophocante Jr. soon finds himself
in a different type of alliance.
It includes other organized crime figures,
but also the CIA,
and as one shared goal,
assassinate Fidel Castro.
This is the Underworld podcast.
Dale.
Welcome back to another episode of the Underworld podcast,
a radio program where two journalists,
myself Danny Gold, and Sean Williams,
take you on a guided tour of scumbags,
dope dealers, and wise guys around the world,
all while teaching valuable lessons about life, love,
and everything in between.
Sean is actually joining us from Port Moresby, right?
Papua New Guinea,
somewhere with a legendary bad guy,
gang problem that most people cannot find on a map. And Sean, I think a question a lot of our
listeners want to know is, what's it like to still believe that long-form print journalism is a
viable career option? But also, what's up in Papua New Guinea? Oh, yeah. Okay, the optimistic
site, I don't know, I'm going to skip the journalism part, but yeah, Moresby, wow, what a
hellscape. It's like basically taken over by gangs. I think it's like pretty similar to what Porta
Prince is at the moment in Haiti as well.
which there's been a bunch of really cool stories about of late.
But I was actually on an island like an hour and a half away from here,
even a place called Bougainville,
which is probably going to be the world's next independent nation.
And there, I guess I can talk about it now because I've been out there.
I was worried about him, like, getting nervous.
But I basically met a guy who is a combination.
Conman, rebel, cult leader, and a self-styled king.
He's like kind of the Colonel Kurtz of Bougainville.
And yeah, when I saw him, he was wearing a red coat and he had a Pugashell headdress that said King in Shell.
So it was pretty, pretty interesting.
But yeah, I don't know what I make of this trip.
It's been a really weird one.
I've read a lot and I've sat around looking at palm trees.
So I guess that's nice, right?
Yeah, it sounds great.
At least you're getting paid for it.
But we are also getting paid here.
So as always, bonus episodes or just support us at patreon.
dot com slash general world podcast there's also youtube tictock instagram whatever else like scribe comment
share all that stuff the uh current contract for my day job is uh is up soon so you know do you guys
want to chip in another 10 or 20k that would really help us out but yeah but yes santo trafficante
junior great name great mobster it's american which we usually stay away from but this story combines
three things that everyone loves, which is Havana in the 1950s, just wild CIA stories,
and Tampa, Florida, which, you know, Ebor City has almost killed us once again.
Sean, aren't you banned from like every single strip club in Tampa?
Oh, it's Pensacola, but I did do a little trip to Tampa one time.
I had a really nice vegan breakfast, actually.
Is that hard-boiled enough for the show?
Or maybe I've got to say I've shot someone at a club.
I don't know.
But, yeah, I've been working on a screenplay that kind of touches on this stuff for like two,
three years now, which is definitely going to get made and make me rich.
But so I'm kind of keen to see what we've got coming up because, yeah, loads of this stuff
is kind of wrapped up in what happened subsequently in the Golden Triangle, weirdly, in Laos and Vietnam.
So, yeah, this is, like, fascinating stuff.
I should add, I can hear, like, birds of paradise, like, or bird of paradises, I don't know,
flying outside the hotel window.
So if you guys hear anything, it's because this hotel was, like, weirdly got an aviary on site,
which is pretty cool.
but not great for podcasting.
So I'll shoot them all after the record.
Yeah, thanks, Bordane.
I guess that's a story for another day.
But actually, I hear good things about Tampa.
I don't think I've ever been.
And this story begins in 1901
when Traficante's father, Santo Traficante Sr.
is 14 years old and he comes from where else.
Sicily, Italy, to America to live.
The Traficontes, they settle in Tampa, of all places.
Tampa is a one-horse city at the time,
just very underdeveloped, swampy.
The young city, you know,
kind of like, I guess, all of Florida back then, right?
I don't think Miami was much in the, in the early 1900s.
But for our international audience, Tampa is on the west coast of Florida.
It's like four hours up from Miami.
I don't think it's quite as rednecky as when you get further north in Florida or like,
you know, further along that coast or in the central area of it.
But like I said, I'm kind of making fun of it.
But I think everyone I know says it's a really good time.
And it is actually famous for the strip clubs, from what I understand.
Santo meets a young lady in the newly burgeoning Italian community of Tampa and he marries her
and she's the daughter of a local Tampa drug dealer and this introduces him into the Tampa
underworlds and Tampa, unlike New York back then, it's not super established in terms of
the crime community, it's an up-and-coming town for organized crime, it's wide open and
ambitious mobsters. They could set up shop anywhere, which is typically called like in open city.
Vegas was like that too. Because of that, there's sort of a power of
vacuum, and it leads to a pretty violent situation, which one magazine, even labeling Tampa as the
hellhole of the Gulf Coast at the time. So our man Santo, he opens up shop. He starts the sort of
small-scale Spanish-style lottery called the Bolita. I went into this in depth, I think, in the
episode we did on the Cuban Mafia up in New York. And actually, Miami, too, was called the
Corporation. I was way back. That might have been like even a year or two ago. It's a good episode,
though. But I think I also talked about how my neighbor still kind of run numbers out of the bodega.
still do the Bolita, but it was like a billion dollar industry, billions of dollars of industry
all in the U.S. back then, without getting too far into it, it's an illegal lottery, basically.
It's a lot of fun if you get bored with falling one leg short on your parleyes every single
weekend, every goddamn time.
Oh, wow, you really lost me.
Is that like going to make a bingo or something?
I'm going to assume, yes.
I don't know what that reference is, but is what?
Is Bolita like that?
It's like a lottery.
Belia, yeah.
It's basically not, you know, it's the same thing as a lottery,
just when we're run out of bodegas and, like, stored fronts and done illegally.
But, yeah.
Traficante's successful operation impresses the most powerful Italian mobster in the city.
This guy, Ignacio Antinori, who is a massive drug trafficker.
And Antenori invites the young Traficante to join his crime family,
and they expand the Bolita to all of the Gulf Coast.
Traficante starts to rake in the cash at this point.
Then in 1914, Luigi Santo Traficante is born.
He's the second of five sons.
They nickname him Santo Jr.
And he's brought around with Santo Senior to various restaurants and events.
Seemingly, he saw something in this son that he didn't see his other sons about entering, you know, this thing of ours.
So when Santo Jr. starts to inquire about seniors' business activities, dad brings him right along into the family business.
And that's just good parenting.
You know, if your child shows an interest in something
and you support him in pursuing that interest,
you're going to want him get him started on it young
unless that interest is, of course,
podcasting, so don't let that happen to your kids.
Yeah, if my son even looks at a magazine,
I'm going to rip it up and enroll in one of the engineering calls
in fucking Papua New Guinea.
I don't know.
But, yeah, I'm just looking forward to the Socranos reference here
because it's coming, isn't it?
Have we already made like a bunch of them, dude?
Oh, God, see, I'm not even up on it.
God, so useless.
Yeah, you're giving that tropical
deliriousness right now. How's, you got food poisoning yet? Oh yeah. Yeah, yeah, yeah. I might have to run
like to the bathroom in about 15 minutes, but we'll see how it goes. Yeah, we'll edit that part out.
In the, in the early 1930s, Traficante Sr. is invited to represent the Tampa Mob at a high level
mob meeting at Atlantic City. And if you haven't seen Borough Empire, I think it goes into this
a bit, but it rules. Great show. I don't think we've recommended it enough. But this is the time when
the mafia is starting to be restructured in New York and nationwide. A lot of you probably know this
history, but this is one like Lucky Luciano, Meyer Lansky, Frank Costello, Bugsie Siegel,
some of the other notable future mob powerhouses they get rid of by killing off the old
school Italian mustache peat bosses who had come over from the old country and did things
sort of the old way. And the thinking was that there was enough of this inter-mafia feuding.
They needed to organize the underworld as a business, less killing, more peaceful coexistence
and working together, which is, you know, very progressive. And they formed the commission and the
Five Families in New York.
Again, you know, this is kind of a well-tread path, but the heads of the five families,
they sit on the commission, and they're almost like a board of directors slash governing
body of the mob.
There's also some other national mob bosses from around the country that are on it as well.
You know, people are here to hear you, you tell the stories, mate, not some trucker hat
wearing comedian from Brent's.
They want you.
I'm like, I'm old for like five with your references today.
I don't even know.
I don't even know who's a truck of wearing
a truck hat wearing comedian from Branson,
but I guess I just want to go to Branson.
I've always wanted to go. Is it good?
You have just like this thing with like weird cities and locations in America.
Like I don't think anyone else I know has spent time in Oklahoma
that's not from Oklahoma.
Yeah, I mean, that's my entire career,
just going to places that no one else wants to go to.
So that's why I'm sitting in a hotel room struggling to not run off to the bathroom.
Did I mention I've got food poison out?
Anyway, the commission wants one point of contact,
not only for the entire state of Florida,
but also for Cuba,
because they're looking to get set up shop there.
They want to invest pretty heavily in narcotics down there.
I think they already were by that point.
But their one problem was that none of them spoke Spanish.
So Santo Sr., since he spent most of his childhood in Florida,
he did speak Spanish,
which is, you know, why everyone should learn a second language.
You never know when it will help you in your career.
Yeah, just learn Spanish, basically.
Don't vote with the other ones.
So he also speaks Italian and English, of course,
which makes him the perfect go-between for New York mobsters since back then.
You know, not only did they not speak Spanish,
some of them barely spoke English.
But this sort of these dealings with the New York mob guys and him getting in good with them,
it really helps grow his power and influence in the national mafia landscape
because they were so powerful.
They just had this outsized influence.
In 1930, Santo Jr. drops out of high school at age 15 with the blessing of his father
who tells him that he isn't going to learn anymore in high school
and that he can learn more from hanging around him,
which is kind of, you know,
Sunny from the Bronx begs to differ,
but Junior starts tagging along with him to meetings in New York,
getting to no high-level figures in the underworld
and really growing up at the highest level of the game,
which is going to serve him really well in the future
and kind of as part of what makes him such a talented,
I don't think that's the right word,
but like successful mobster as he gets older.
He's a really smart guy, really ambitious,
known for not taking no for an answer,
like very persevered, you know?
One of his father's friends
that takes Santo Jr. kind of under his wing
and becomes his mentor is Tommy Lucchese.
Lucchese is a key player
in the Luciano Lansky-Costello
sort of takeover the mafia.
Later, he becomes the underboss
of the Gagliano family,
which is one of the new five New York families
created by the commission.
That boss is extremely low-key,
Tommy Gagliano.
He's extremely under the radar, too,
so under the radar that he basically
gives all his orders through Lucchese,
who was not just the owner-bross, but the de facto street boss.
And he eventually takes over that family in 1951,
and it's renamed Luke Hazy Crime Family,
which it's still called today.
I don't know about much beyond this show, basically.
These guys still pop in New York,
or if they kind of had their wings clip these guys?
Yeah, I mean, look, they're not nowhere near where they were decades ago,
but they're still around.
Like, they still functioned.
They still have bosses.
I think there was just a big bust on the Gambino's family, like a month ago.
But yeah, no, they're still the same name, still around.
still, you know, doing their thing, I guess.
They must be still getting some stuff down, but, you know,
it's like the business is definitely not as good as it was 60, 70 years ago.
Lucchese's closest ally is fellow mob boss and boss of all bosses at the time,
Carlo Gambino, who is head of the Gambino crime family.
They're so close, in fact, that Lucchese's daughter
marries Gambino's son, Tommy.
These two form an alliance to basically dominate the commission and the underworlds.
It's a little bit far in the future, but the point being is
he's a good guy for Santo Jr. to have as a mentor.
Lucchese and Santo Traficante Sr., they also have a narcotics business together that
continues when Junior takes the reins, which is going to happen shortly.
Another reason Traficante Sr. is sending his son up to New York all the time to spend
time with these guys is that there's a mob war going on between Traficante's boss, Ignacio Antinore,
who is now one of the biggest drug traffickers in the country, and a rival mobster named Charlie Wall in Tampa,
who is, I think, not Italian.
But his family, yeah, I think, no, definitely not.
But his family was super powerful legitimately in Tampa.
I think his dad had been the mayor and his mom was the daughter of a different mayor.
So, you know, I feel like it's one of those old school southern things back then where, like, you know, they weren't technically mafiosos, but they basically were powerful politicians who had the run of the place.
The gang war, it's ongoing.
It ends up lasting much of the 30s.
Traficante Sr. He kind of lays low and stays out of the fray, hoping to gain more power by the end of it.
His boss is gunned down in 1940, and Wall is severely weakened, but he wins.
But he loses so many of his men in the war that Traficonte Sr. is able to slide right in,
become the new boss of Tampa, and basically take over all the gambling rackets.
Then in 1946, there was this historic conference of national mafia leaders in Havana.
The backdrop to this conference is that in the 1930s, Lucky Luciano was sentenced to 30 to 50 years in prison.
World War II starts, and by
1942, the U.S. military is concerned about
Italian and German agents
infiltrating the U.S. through the ports
and conducting sabotage against the military
at the waterfront. So U.S. military
intelligence, knowing the mob controls
the waterfront, they approach Lansky
as a conduit to Luciano to make a deal.
And they'll let him out of jail
and deport him in exchange for the mob guys
basically protecting the waterfront from
sabotage. The mob guys agree.
They're all on America's side anyway in the war,
which is interesting. Yeah, I've been
researching a crazy American guy who lived out in the Golden Triaggo. He's going to pop up in
next week's show actually as well. But this Hungarian, his Hungarian family was basically blacklisted
after Bell Harbor. Apparently there was a massive witch hunt for foreign collaborators right
after that. So it led a lot of dual national Americans towards crime. It's like really interesting
stuff. So I guess these guys like, there must have been the other side of the coin. I don't
know, pledging allegiance and getting all kinds of benefits. So I guess it worked both ways.
Yeah, I mean, even though they were Italian or of Italian origin, they did not like Mussolini or
the Nazis and they were, you know, they were patriots in that way in terms of like
trying to help with the, uh, with the war effort. This conference, which is co-hosted by
Luciano Alanski, it's supposed to welcome Luciano back into the fold and settle a bunch of mob
disputes and feuding that have been going on. Junior, he's there actually representing the
Tampa Mafia and his dad. The Traficantes now have a seat at the most powerful mob boss table
out there. And also, side note, Frank Sinatra was the entertainment down there in Havana. Then in
1950, we get the Senate commissions that start looking into organized crime, especially involving
the labor rackets. I think we've talked about those a lot on the show before. Both Santos,
senior, and junior are subpoenaed to appear before the commission, which estimates that they receive
at that point $50 million a year in illegal gambling alone. Charlie Wall, who we mentioned earlier,
the guy who got into the gang war with Traficante's old boss, he testifies about the organized crime
situation in Tampa, and it becomes pretty clear to everyone that the Traficantes are major players,
which obviously is going to increase the heat on them from law enforcement.
So junior and senior decide it's probably best to duck out of the states for a bit and head to Cuba.
Cuba is like popping back then, right?
The casino scene, the nightlife, Havana in 1950s, every bar looks like the Hotel Domano,
which I don't know, man, I've always thought it actually sounded like a really fun place to be at the time,
as long as you were not standing against Batista, but we're in with Italian mob guys.
just, you know, just a good time.
So celebs like, you know, Marilyn Monroe, Frank Sinatra,
they're going down there to perform and to party.
For years, Santos Sr. has been funneling mob money to Batista
to keep the local authorities away from their big narcotics trade.
So they're super well connected and kind of free to do what they want.
Yeah, wasn't that one of the biggest things that pissed off Castro as well,
that Cuba was suddenly overrun by all these flashy Americans and monsters?
I mean, I guess if he'd just like big band tunes instead of whatever he liked,
the whole world could have been a lot different.
I don't know.
I mean, obviously, I don't think he was a fan of them
or luxury hotels at the time.
But I'm not sure.
Was he there?
Was he already in the,
in,
like,
in rural areas fighting when that really became a thing?
I actually,
I don't know.
Yeah,
I'm pretty sure he was.
Did you read that someone?
Yeah.
Yeah.
I mean, it makes sense.
Santo Sr., who was already in poor health,
gets diagnosed with,
uh,
with stomach cancer and basically is on the way out.
He starts handing over the reins to Sonto Jr.,
you know,
who's obviously been training for this,
since he was a kid.
And the Traficontes are then making their move back to Tampa
because the heat has died down.
Santo Jr., he's like a very well-read guy.
He has nerdy glasses.
He's well-groomed.
He isn't like a...
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You know, this is something that a FBI guy said to me once. He's not a D's damn and
those type of gangster. You know, he's kind of a class act. So he's not a thug. He's very low-key.
He's even described as kind by some people. And he's very respected not only by other
mafia figures, but also by legitimate businessman who recognize that he's sharp as hell.
And it kind of makes sense. You know, other mafia guys rise to the ranks by being on the street.
When he was in his youth, he's already attending high-level meetings with his dad or in New York
shadowing other high level guys, like a very solid mafia internship.
And just a real princeling who was groomed for leadership since he was a teenager.
Kind of like, I don't know, it reminds me a little bit of YouTube mafia sensation Michael
Franzisi with the, you know, the gas tax.
I mean, is that our podcast the only one that he's not been on?
I feel like he's been on every single podcast in the world.
And like, I think there was a time when my YouTube algorithm was half, I would say,
like Michael Franzzi videos.
But yeah, go in.
I mean, he really lived
the life so people like his stick and he's
he's a content creator man
like you gotta give him credit. He's like movie
reviews of mafia movies of what's really like he really
knows how to
I love that shit. I think you know, good for
I mean I can't watch it but good for him
he's making money. So now the
Traffa Conte family
they've always been a lot smarter than some of the other
powerful families like they didn't really have that many
members whereas the big five families
in New York they had hundreds of made members
and thousands of associates. The traffic
Conte's, they operated a bit differently. A lot of mobsters wanted to do business in South Florida,
and they would need to either pay the Trafalcante's tribute or need to go into business with them.
So they had this big national backing, so they got a piece of most of the pies that happened in South Florida,
which was kind of a booming industry at the time. They didn't completely control the area,
like the Chicago outfit controlled Chicago. It was just like this different sort of power. But again,
you did not want to cross them.
Juner gets back to Tampa. He's pretty much the boss of the Traficonte family at this point.
There's another mobster though by the name of Jimmy Lumia
who had taken over some of the rackets when they were gone
and one of Junior's first moves is killing him
and seizing total control of the South Florida underworld and Tampa
takes him out. He hunts down the remaining mobsters
in that faction. He kills them one by one. The cops basically
know it's him at this point but the hits are really professionally done
and they just can't hang a charge on anyone. So in 1953
there's this attempt to actually take out Santo Jr.
While he's in his car they pull up alongside him and fire a bunch of shots
but he survives with Justa Grays.
And it actually turns out to be his dad's old rival.
He washed up Charlie Wall who gets murdered a few months later.
But at this point, the Traficante family is just completely in charge of the whole state.
Santos Sr. dies in 1954.
He has a very low-key funeral in typical Traficante fashion.
Junior is now officially the new boss of Florida.
And the transition is pretty smooth because, as we mentioned, he was well respected, well-liked by the commission of national mob leaders.
and even his own crime family really liked him and respected him despite the fact that he was,
for all intents and purposes, a Nepo baby.
So, 1958, he returns to Havana and discovers it's not the same place that he left.
Everyone is on the edge and the rebels have been making huge gains.
And by that point, the mafia owns most, if not all the casinos in Nevada.
And they've been paying off Batista for a while with that too.
They're raking in an estimated $100 million a year.
I actually busted out the inflation calculator for this one,
and it's over a billion dollars in today's terms.
So they're doing quite well,
even though they have partners with other mafia bosses across the U.S.
In those casinos.
They also control prostitution,
other vices that went along with the casinos, drugs, loan sharking, everything.
And several mobsters like Meyer-Lanski own hotels down there too with them.
So there's a lot at stake with this revolution that's happening,
and Junior as the mob's appointment in Cuba is responsible.
Yeah, I feel like this is a pretty easy sell for the commies, though.
Like, I mean, this is pretty easy stuff for Castro just to point and wave his finger at.
I mean, I don't know.
I prefer hanging out in casinos and luxury hotels, but I don't know.
Maybe I'm just a patriotic American, Sean, unlike you.
But yeah, I think, yeah, that was, I think, definitely point part of Castro's, you know,
rise to power, right?
He was pointing at all the, all the rich people that were exploiting Cuba and what was going on there.
Here's what Traficante says of the day Castor took over.
This is from the website of a movie that's actually being pitched about Traficante,
and it doesn't say where they got the quote from.
But here we go.
Well, even before Fidel reached Havana,
because he didn't come down from the mountains until after Batista left,
and he had a walk-a-thon, you could call it,
from the mountains to Havana.
And they kept interviewing him and he kept saying the casinos would close statements to that effect.
The casinos closed without even being notified, notified officially to close.
Everything was in turmoil.
There were people all over the streets
breaking into homes.
There was complete enmity,
and the only thing at that time
was to try and stay alive.
I mean, the woke mob
just walking and cycling everywhere.
God, buy a six wheel in the tuds.
Yeah, you're swinging and missing today, man.
You were getting funnier for a long time,
but I just feel like something about that tropical weather
and that food poisoning.
Is this really...
Yeah, I mean, I've been sitting with no one but myself a company.
Can you imagine how awful that is?
Yeah, I mean, I was encouraging you,
I think, to start with your stand-up career
sometime with the last six months,
but now I'm going to downgrade that to
no encouragement. I actually encourage you to
not make jokes anymore.
We get to 1959.
Batista's out. Castro is in control of Cuba.
Castro, though, being a commie, he does not play
ball with the mobsters and starts closing down in their
casinos in some of their hotels.
Junior, though, he still thinks he has a shot,
but those fantasies come to an end when he's
arrested in a van on unknown charges two weeks
before his daughter's wedding is supposed to take place in
the city. This arrest happens when Castorne's men were executing hundreds of people by firing
Scott. And so the news kind of sends shockwaves throughout the underworld and no one really
knows what Junior's fate is going to be. His wife, Josephine, though, was by a very politically
well-connected family in Florida and they somehow get the Cuban authorities to let him out on a furlough
to attend the wedding. But right when the wedding is over, he's sent back to jail. And unlike
Johnny Sack, he did not cry like a woman. Yeah, okay, I got that one. All right. That's my first one.
Yeah, and the Traficonte crime family, their estimation of Santo as a man does not plummet,
but Santo Jr.'s lawyer eventually gets through to the new Cuban government and he's deported
back to Tampa. They let him live. The legend of Santo Traficonte Jr. usually says that he never
spent a day in jail, but what they mean is that he never spent the day in jail in the U.S.
He did actually spend, I think, a couple months, if not a couple weeks in Cuba. So the mob as a whole
and junior, they take a massive financial hit with the shutting down of their cash cow in Cuba.
you know, Fabe mobster, Meyer Lansy
actually said that Cuba financially ruined him,
though I think he ended up doing pretty okay.
Junior loses casinos and hotels,
but unlike the Lanski's the underworld,
he's continually taking money out of Cuba
when business was good.
You know, the guy was sharp on, like, say,
you know, if you had some money in crypto
that was skyrocketing and you just kind of let it sit there
thinking the number only goes up,
but it doesn't, Sean.
The number also goes down a lot.
So take profit, Sean.
Take profit.
Look, I'm just, I'm going to keep hold of my heck.
Right. But anyway, Traficonte, he's not hurt as badly as the others.
Over the next few years, instead of Russia to Vegas, like some of the other mobsters,
he instead scouts other locations in South America and the Caribbean.
He's got people in the Bahamas, Ecuador, Venezuela, and other locales.
He also spends a lot of time setting stuff up in Miami, just running things there,
getting the Bolita and the nightlife spots happening.
Says that movie website again, Traficanti used his political connections to smooth over immigration issues
and zoning regulations and helped wise guys
cut through the red tape of state regulatory
bureaucracies to obtain liquor and other licenses.
All right. Yeah, he's just helping out small businesses.
Right, exactly.
The corruptible law enforcement and political element
was as present in Miami as it was in Tampa.
The Miami Police Department was riddled with corruption
in the 50s and 60s.
Miami was wide open.
And Traffat Conta had placed himself
in a strategic position
to gain the best advantage from the situation.
He called the shots and pulled all the strings in Bolita.
So yeah, the 60s is all.
when the CIA stuff and the assassinations,
all that stuff starts to happen.
And just a note from before,
Traficonte was part of the conspiracy theory
of assassinating JFK with Carlos Marcello
that we discussed in the Marcello episode
at Lent from a few back.
So if you're interested in the JFK stuff,
go back and listen to that,
but let's talk about the Castro plots now,
which, you know, it's always an interesting thing.
Like sometimes you hear the more outlandish
like silly shit with situations like this,
and I'm kind of like, you know,
were steps actually taken,
or did the office sort of wackadoo shout out some suggestions?
like we should brain possum to carry knives and attack him at night.
And everyone's like, yeah, okay, Carl, great idea, but no one does anything.
But I think in this specific case, there actually were some steps taken.
It's legit.
Yeah, I mean, I want to go out of Carl.
He sounds like a hoot.
Yeah, you know, there's always one guy like that.
So the reporting we're using here for the CIA mafia team.
It actually came up again in a recent political magazine piece.
But in the mid-70s, the CIA mafia plot became known to the general public through some Senate
committee hearings.
but it isn't until 2007 that the CIA admitted that the director at the time offered the mobsters a bounty.
That document was released in 2007 with a bunch of others because the CIA was under pressure
during the Bush presidency for Warren Terror stuff,
and the document declassification dump is called the Family Jewels,
and it's about CIA wrongdoings between 1959 and 1973.
So yeah, there's a lot there, and it's a time-honored American tradition that if you are president,
under some scrutiny, you release old CIA stuff to distract the public.
And this brings us to the 2018 political magazine article.
After more documents come out in a bunch of stuff that Trump releases about the Kennedy assassination and we get the full picture.
So unlike the JFK stuff, this isn't a conspiracy theory.
It's just an actual thing that the CIA and the mafia were trying to get up to.
The plan to get rid of Castro was originally initiated under President Eisenhower,
but was embraced by JFK when he took office as well.
it's unclear how much either president knew about the, like the details, the specifics,
but they both really wanted Castro gone.
The release classified files call for, quote, a sensitive mission requiring gangster type action,
which is, I don't know, just a cool way of describing everything, right?
Yeah.
Because the CIA was reluctant to get any blood on its hands, which, you know, that's why they use these guys.
It doesn't really make any sense, though, if you think about what the CIA in the U.S. did,
like in the 50s and 60s and 70s, but whatever.
They definitely got blood on their hands.
It also doesn't make sense to hire mobsters either
because they do mob hits, right?
They're not sophisticated political assassinations of foreign heads of state abroad,
but nevertheless, the CIA thought this was a good idea.
Oh, yeah, they were like gagging for this stuff.
It was all wrapped up under this project called JM Wave,
and it was actually a blueprint for a bunch of stuff
the agency winds up doing in Laos and Vietnam.
They even had their own James Bond Q character,
this like meatpacking, fortune, air,
just like show up, promoting wacky,
ways to get Castro high or embarrassing
or kill him. And that's when you've
got your possums with knives or you
exploding cigars, poison salt shakers,
LSD vaporizers.
I mean, this is like a pretty
wild time. And Bobby Kennedy,
he's like the most hawkish at a lot of them actually.
And yeah, some of the stuff he was
proposing was insane.
Wait, so did the exploding cigars and poison
salt shakers and LSD stuff? Did that actually
go further than like notes in a
meeting? Like were there any logistics put in place
for that? Yeah, they actually
So the first time they did it, it was a cigar that you'd smoke and you'd just get like a hallucinogen or something.
And then this guy came along, I can't remember his name, the meat packing fortune air.
And he was like, no, no, no, I'm going to make like a mini detonator.
They were just, I don't know, they were kind of kooky, but they did definitely do that stuff.
Wasn't there one where they're going to try to make his beard fall out to like, to, like, you know, ruin his virility as a man?
Which has someone who's had part of my beard fall out.
but it would have had a negative effect on him, I'm sure.
So there's other mobsters involved in this plot.
The first is Sam Giancana, who's the Chicago outfit boss,
who had casino interest in Cuba,
and it's one of the most powerful mob bosses in the country.
And the other is John Roselli, aka Handsome Johnny,
which I mean, it's the ideal nickname for a mobster or for anyone.
He was a member of the Chicago outfit.
He was the mobsman in Hollywood for a while,
and then he shipped at Focus to be the mobsman in Vegas.
After they increased their investment there,
when Castro gave them the boot,
and they want to get casinos up and running.
Roselli and Jean-Connor, they're pals,
and they often go out together and party
and both are friends of Traficante Jr.
We talked about this in the corporation episode as well,
but there's a lot of just wild stuff happening
with Cuban exiles in the 60s,
and I guess later on too, especially in Miami,
anti-Castro plots,
like violent groups forming,
some terrorist, organized crime training,
commando type stuff,
just all sorts of political and violent intrigue
that was just a wild time in America.
The CIA recruits a guy by the name of Robert.
I'm going to mispronounce his last name.
Mahoh?
You know, when they hate you with you, like the EU?
Yeah.
That's pretty much.
Yeah, we'll go with it.
He's an ex-FBI agent and current aid to eventual crazy person
and legendary entrepreneur Howard Hughes.
He becomes the go-between.
Robert approaches Rosselli, who then introduces the Mantha Traficante and Giancana.
And the CIA offers them $150,000 to kill Castro,
which is like a lot of money.
I feel like that that's a good going rate
for killing a head of state.
Which the mobsters declined.
They say they'll actually do it for free
and they cite patriotic reasons
for wanting to help out the government.
But in reality,
they're just kind of doing this
because they want their vastly profitable
Cuban casinos and hotels back.
And they also believe that if they do
this very risky thing for the government,
that it kind of helps them
get out of jail free card
for their own future legal troubles.
And the relationship with the spies,
it comes in handy right off the bat,
later in
1961, when these two CIA
operatives are caught by the FBI
illegally bugging the hotel room
of a Giancana rival
who's involved in some sort of love triangle
with a famous actress, I think,
or singer.
And the CIA does this as a favor
to their new pal Genecana,
but when the FBI wants to press charges,
the CIA brings the matter
to Attorney General RFK,
who's no fan of the mafia,
and he's kind of annoyed by it.
So they agree to drop the charges
to the casino operation can go in,
but they tell the CIA to warn him in advance,
quote, if you ever try to do business with organized crime again.
Yeah, I mean, the thing is,
RFK was like, like I said, the most hawkish guy,
and he actually favored something he called Boom Bang Action against Cuba.
And like, bearing in mind that this time the Soviets are planting missiles on the island.
That's going to be a sure way to trigger a nuclear holocaust.
But, yeah, I don't know.
Like, I reckon he tried to, like, airbrush a lot of stuff that he'd done after that.
But I guess he didn't last a huge amount longer, did he?
Bobby Kennedy, he got offed, like, soon after this, or was it a bit later on?
No, you're thinking of, no, much later on.
His brother gets off.
He gets killed in the late 70s, not in the early 70s.
I mean, sorry, late 60s, not in the early 60s.
But I think that, you know, part of it is probably that he just doesn't, he hates the mafia.
Is that what the mafia?
So while he probably favors, you know, direct action, he probably just doesn't want it done.
by mafia guys. I'm sure he had no problem operating with like, you know, the other sort of Cuban
weird special operatives that they used. But yeah, the first attempt with these mobsters is when
they give a would-be assassin poison pills that the CIA gave them that put in Castro's feud
in Nevada. This would-be assassin is a guy by the name of Juan Orta, who is director general of the
office of the prime minister of Fido Castro, I think a little before that, but he gets cold feet,
doesn't get the job done. But there's, you know, some disputes that Ordo would have ever
even been able to get close to Caster to poison him. And it's Caster who actually says this.
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In his own words, the traitor order
received money from organized crimes, supposedly to help
them reopen casinos. He had nothing to do with the matter. By the time they gave him the poison,
unlike the earlier moments, there was little chance order would see me as by then I was completely
occupied with other matters. So Fidel basically says, like, cold feet or not, this guy wouldn't have
even touched me. And there's a bunch of other plots, including trying to get the CIA to give money
and weapons to a Cuban exile leader named Tony Verona. The mobsters don't actually get a lot done and not
much comes to fruition, though they definitely put in some effort. And Traficonte kind of gets out of the
assassination business pretty quickly, though.
Giancana and Roselli stay involved.
Interestingly enough,
Giancana actually tries another plot
himself and Roselli becomes so personally
invested that he participates in like boat
raids in 62 and
63.
One raid had Genecana so worried
about him that he thought he was actually killed
or captured because he was gone for so long.
And then in 63, JFK
is killed and the castor assassination plots
are basically shelved.
Yeah, I did not know until today that
Rizelli was like a big player in the mafia.
Like he was definitely the agency's point man for a while.
And this sabotage campaign that he like personally went on,
it was one of the CIA's most successful against Castro.
Like a couple agents put thousands of dollars worth of weapons and a U-Haul in Miami.
I think they were all over Miami.
It was insane.
And they gave him the key.
Next minute they got teams bombing train lines,
factories.
They even sunk a Soviet ship, I think, Mordoff and Favanna was saying.
It was pretty daring stuff.
So yeah, I'm going to get into some more of this.
stuff next week, but it racked up cost of like 50 mil, I think, at the time, which is, I don't know how many
bazillions in today's money, like for a year for one op, which is pretty crazy back then.
So this was really like how all future stuff would be done for the CIA for a long time.
Some of the initial reporting and rumors of these castor plots, it comes after the Senate Church
Committee in 1975, which was this committee to investigate abuses by the CIA, NSA, FBI, and the
IRS. So shortly before Giancana is scheduled to testify before these hearings, he's killed in his home.
One theory is, of course, the CIA took him out before he could talk. But another theory is that
Junior actually ordered the hit to prevent him from talking. But they also say a decade earlier,
Jean Conno was sentenced to one year in jail for contempt in 1965, refusing to testify at an unrelated
grand jury. And during that sentence, he was demoted from boss by the real long time power boss
of the Chicago outfit, Tony Ocardo and Paul, Paul Rica, I think is how you say his last name,
who were the real guys basically running Chicago for 40 years.
And the only reason Giancana got the official title as boss in the first place was because
Ricardo thought he was getting too much heat from the IRS in the 50s and had him be boss.
But Gene Conna's boss, he's very flashy, hangs out in nightclubs, he's in these like weird
love triangles, all sorts of nonsense.
So after his jail sentence is up, he flees to Mexico in 66 to supposedly avoid
more grand jury testimony, but probably because the mafia exiled him. And Mexican authorities
arrest and deport him back to the U.S. in the summer of 74, once he's back in the States,
he starts kind of talking and running his mouth about getting back in the action, wanting his
cut of the pie. And an unnamed mafia source in the New York Times said that Sam wanted to
reassert his authority after 10 years, but everything had changed. So while CIA hit of the traffic,
or a Traficante hit would have worked out better for this episode, I actually think it seems pretty clear
at the outfit, were the ones to take him out.
out. Handsome Johnny Roselli does testify the church committee and according to a
1975 New York Times article two tells the committee he was recruited by the CIA to
assassinate Castro. The article said he appeared to the committee under heavy protection
and then he testifies at a 1976 Kennedy assassination committee in April that year and is
scheduled to testify again three months later but he's reported missing as of July 28th,
1976. His body is found in an oil drum floating near Miami a few weeks later. And here we go again
from a New York Times article in 1977. Quote, there was no shortage of suspects ranging from the CIA
to Cuban agents and the mafia itself. Yeah, I think he was one of like 18 people who died mysteriously
either just before or just after they were going to testify at one of these things. So I'm not saying
aliens did it. I'm just saying these are these are facts. Yeah, the article goes on to say that
mafia leaders were upset with Roselli dating back to his testimony.
71 through another mafia
related trial and three guys
went to jail because of that and the mafia
basically started thinking that
Roselli was talking to the feds and
it further says that Roselli's murder was approved
by the commission shortly after he testified in the
Senate committee in 1975
but that it was ultimately the Chicago
Alfit's call and a different source
not in the Times has an informing
quoting Tony A Cardo
we mentioned right before saying
Rosselli was becoming a public source of embarrassment
to Lacosa Nostra. Authorities believe it was a
member of the Traficonti organization who was able to lure Mr. Roselli to his death. So
Traffic Conte actually testified at some of these Senate committees in the 70s about the JFK assassination
and other ones. But other than that, he then leads a pretty low-key life as a mob boss and just kind of
runs things just smooth. Like I said, he kept the violence out and was smart about how he did
things and made a lot of money. In 1983, though, he's indicted on charges that stemmed from a $2 million
$1 FBI sting operation conducted between 1979 and 81.
This is from a 1983 Washington Post article, quote,
the charges are the result of an FBI sting operation in which agents worked undercover for three
years, operating a plush, lucrative club to draw in the underworld figure, said Robert W. Butler,
in charge of the Tampa FBI office.
He, along with 11 other mobsters from the Bonano, Gambino, and Lucchese families are indicted
on conspiracy and racketeering charges.
Quote, the indictment alleged that for a percentage of the profits,
Acante would allow top nationwide crime families to engage in unlawful activities such as bookmaking,
gambling, and control of sanitation business on the west coast of the state. You know, as I mentioned
earlier, he didn't have that big of a family, but he would cut deals with other families to allow
them to operate in his territory for a taste of profits. And this indictment is actually about
the Kingscourt Bottle Club, which is portrayed in the movie Donnie Brasco, which is based,
of course, on the undercover exploits of FBI agent Joe Pistone, who actually interviewed this year
for a different project that I'm working on
that will be out next year.
All right, what's he like?
You know, straight shooter.
Okay.
I guess, you know, had a lot to say.
Yeah.
I think he has a podcast of his own,
but, you know, anyway,
I think in the movie it makes it seem
more like they got in trouble
because they failed to pay off the local cops,
but clearly this was a much more sophisticated FBI operation.
Santo is 69 at the time, which, nice.
He gets out on $50,000 bail,
and his lawyer continued delays the trial
citing his old age and health issues.
He actually goes on to win the case
because his lawyer argues that it is built
mostly on hearsay evidence from Dominic,
sunny black, Napolitano,
who is unable to testify,
even if he was willing to do so
because he's killed in 1981
for introducing Donnie Brascoe
to the Bonanno family.
The judge agrees with Santos' lawyer,
says the evidence is too weak,
gets out on a mistrial in 86,
pisses off the government
because they spent a lot of money on it,
and he gets removed from another trial
the following year for his poor health,
which actually ends up making sense
because he dies in March of 1987
because of health complications that year.
So I guess, yeah, all in all,
a pretty good mafia career
for the Santo Senior and Santo Junior Traficante family
because they never did a day in American jail.
They both die of natural causes
when they're pretty old.
Santo Jr. has two daughters
who never really get involved with organized crime,
but still have a ton of money,
and the family gets out,
you know, a whole lot of money
and not so much in the dire consequences department.
So maybe crime does pay.
Yeah, crime definitely pays.
And speaking of which, I'm off to buy a kilo of boganville and gold on the black market.
Only joking, I'm actually going to run to the bathroom because I'm still sick.
So, yeah, cheers for that.
Love how you kept bringing that up for the audience.
I'm sure they were.
I just want to give a vivid image.
Just think about that.
But anyway, yeah, next week, patreon.com, underworld podcast.
Yeah.
Take care.
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