Santo Trafficante: Havana Nights, Killing Castro and the King of Florida
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New Year's Eve 1958 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 to Cuba tells him that not only were the U.S. not recognize 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 II 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 alright and the mafia will stay making money.

Traficante is mafia royalty. His father, Santo Traficante Sr., had 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. It actually sent his son down to Havana in the 40s to suss things out and set up a mafia-run casino. Jr. 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 Don, and you know how it is, like the Jean Lasagna. 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 Traficante Jr. soon finds himself in a different type of alliance. It includes other organized crime figures, but also the CIA, and has one shared goal, assassinate Fidel Castro. This is the Underworld Podcast. Dale. Dale. 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 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?

Ah, yeah. Okay, the optimistic side. 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 Port-au-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. Yeah.

uh, and there, I guess I can talk about it now cause I've been out there. I was wondering, I'm worried about him like getting nervous, but, uh, I basically met a guy who is a combination con man, rebel, uh, cult leader and a self styled King. He's like kind of the Colonel Kurtz of Bougainville, but, uh,

Yeah, when I saw him, he was wearing a red coat and he had a Pooka Shell headdress that said King in Shell. So it was pretty, pretty interesting. But yeah.

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.com slash general world podcast. There's also YouTube, TikTok, Instagram, whatever else, like, scribe, comment, share all that stuff.

The current contract for my day job is up soon. So, you know, if you guys want to chip in another 10 or 20K, that would really help us out. But yeah. But yes, Santo Traficante Jr., great name, great mobster. He'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, Ybor City has almost killed us once again. Sean, aren't you banned from like every single strip club in Tampa? Oh, there'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 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. So I'm kind of keen to see what we've got coming up because 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 bird of paradises, I don't know, flying outside the hotel window. So if you guys hear anything, it's because this hotel has 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, Brodane.

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 Chafacantes, they settle in Tampa of all places. Tampa is a one horse city at the time, just very underdeveloped, swampy, young city, kind of like I guess all of Florida back then, right? I don't think Miami was much 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 redneck-y 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 an open city. Vegas was like that too.

Because of that, there's sort of a power 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 in Miami too, it was called the corporation. I was way back. That might've been like even a year or two ago. It's a good episode though.

But I think I also talked about how my neighbors still kind of run numbers out of the bodega. They still do the bolita, but it was like a billion dollar industry, billions of dollars of industry all in the US 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 parlays every single weekend, every goddamn time. Oh, wow. You really lost me. Is that like going to Mecca 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. It's basically not... It's the same thing as a lottery, just run out of bodegas and storefronts 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 Antinori 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 Sr. to various restaurants and events. Seemingly, he saw something in this son that he didn't see in his other sons about entering this thing of ours. So when Santo Jr. starts to inquire about Sr.'s business activities...

Dad brings him right along into the family business. And that's just good parenting. If your child shows an interest in something and you support him in pursuing that interest, you're going to want to 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 him on an engineering course in fucking Papua New Guinea. I don't know. But yeah, I'm just looking forward to the Sopranos reference here because it's coming, isn't it? 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 getting 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 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 Borac 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 when Lucky Luciano, Meyer Lansky, Frank Costello, Bugsy 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 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 tell the stories, mate, not some trucker hat wearing comedian from Brents. They want you. I see.

I'm like, I'm over like five with your references today. I don't even know. I don't even know who's a trucker 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? Well, you have just like this, 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 poisoning? No, no.

Anyway, the commissioner wants one point of contact, not only for the entire state of Florida, but also for Cuba, because they're looking to get a 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 Santos 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 bother 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 know 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 know if that's the right word, but successful mobster as he gets older. He's a really smart guy, really ambitious, known for not taking no for an answer, very persevered. One of his father's friends that takes Santo Jr. under his wing and becomes his mentor is Tommy Lucchese.

Luke Casey 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 is extremely under the radar too. So under the radar that he basically gives all his orders through Luke Casey, who is not just the underboss, 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 like much beyond this show, basically. Are these guys still popping it in New York or have they kind of had their wings clipped these days? Yeah, I mean, look, they're not nowhere near where they were decades ago, but they're still around. Like they still function. 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 doing their thing, I guess. They must be still getting some stuff done, but it's like the business is definitely not as good as it was 60, 70 years ago.

Luke Casey'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 Luke Casey'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 Antinori, 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. Yeah.

The gang war, it's ongoing. It ends up lasting much of the 30s. Tropicante 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 Tropicante 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's this historic conference of national mafia leaders in Havana, which

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 Triangle. He's going to pop up in next week's show actually as well. But this Hungarian, his Hungarian family was basically blacklisted after Pearl 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, they 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 war effort.

This conference, which is co-hosted by Luciano Olansky, 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 Bay 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 Sr. and Jr. 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 Tropicante's old boss, he testifies about the organized crime situation in Tampa, and it becomes pretty clear to everyone that the Tropicantes are major players, which...

It 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, 1950s, every bar looks like the hotel Delmano, which, uh,

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 were in with Italian mob guys. Just a good time. So celebs like 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 just liked 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 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 somewhere? Yeah. I mean, it makes sense.

Santo Sr., who was already in poor health, gets diagnosed with stomach cancer and basically is on the way out. He starts handing over the reins to Santo Jr., who's obviously been training for this day since he was a kid. And the Tropicantes are then making their move back to Tampa because the heat has died down. Santo Jr., he's a very well-read guy. He has nerdy glasses. He's well-groomed. He isn't like a...

This is something that an FBI guy said to me once. He's not a deez, dem, and does type of gangster. 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 businessmen who recognize that he's sharp as hell. And it kind of makes sense. 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 has 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 gas tax. Yeah.

I mean, is 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 Francesi videos. But yeah, go him. Well done. I mean, he really lived a life. So people like his shtick and he's a, he's a content creator, man. Like you got to give him credit. He has like movie reviews of mafia movies of what's real. Like he really knows how to. Yeah, 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 Trapacante family...

They've always been a lot smarter than some of the other powerful families. 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 Tropicantes, they operated a bit differently. A lot of mobsters wanted to do business in South Florida, and they would need to either pay the Tropicantes 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.

Junior gets back to Tampa. He's pretty much the boss of the Traficante 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 just a graze. And it actually turns out to be his dad's old rival, the washed up Charlie Wall, who gets murdered a few months later. But at this point, the Tropicante 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. Jr. is now officially the new boss of Florida, and the transition is pretty smooth because, as we mentioned, he had...

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 Havana. 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 US in those casinos. They also control prostitution.

you know, other vices that went along with the casinos, drugs, loan sharking, everything.

And several mobsters like Meyer Lansky 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 point man 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 part of Castro's rise to power. He was pointing at all the rich people that were exploiting Cuba and what was going on there. Here's what Traficante says of the day Castro 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. Quote, well, even before Fidel reached Havana, because he didn't come down from the mountains until after Batista had 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 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. Come on, buy a six-wheeler, Littards. 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 just really... Yeah, I mean, I've been sitting with no one but myself for 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 over the last six months, but now I feel like 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 their casinos and 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 Havana on unknown charges two weeks before his daughter's wedding is supposed to take place in the city. This arrest happens when Castor and his 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 happened.

Junior's fate is going to be. His wife, Josephine, though, is from 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 Traficante 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 Traficante Jr. usually says that he never spent a day in jail, but what they mean is that he never spent a day in jail in the US. He did actually spend, I think, a couple months, if not a couple weeks in Cuba. So the mob as a whole and Jr., they take a massive financial hit with the shutting down of their cash cow in Cuba.

You know, Fabe mobster Meyer Lansky actually said that Cuba financially ruined him, though I think he ended up doing pretty okay. Junior loses casinos and hotels, but unlike the Lanskys in 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 going to keep holding my hex, all right? Yeah. But anyway, Chafikante, he's not hurt as badly as the others. Over the next few years, instead of rushing 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, Traficante 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. Oh, yeah, he's just helping out small businesses. Right, exactly. The corruptible law enforcement 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 Trafficante 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 Boldito. So yeah, the 60s is also when the CIA stuff and the assassinations, all that stuff starts to happen. And just a note from before, Trafficante was part of the conspiracy theory of assassinating JFK with Carlos Marcello that we discussed in the Marcello episode at length from a few back years.

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 suggestion like we should train possums 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 with 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 war on terror stuff. And the document declassification dump is called the family jewels. And it's about, about CIA wrongdoings between 1959 and 1973. So yeah, there's a, 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 that,

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. Like 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 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, uh, 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. Doesn't really make any sense, though, if you think about what the CIA in the US 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 just like show up proposing wacky ways to get Castro high or embarrassing or kill him.

And that's when you've got your possums with knives or your 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 just get like a hallucinogen or something. And then this guy came along, I can't remember his name, the meatpacking fortune 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 ruin his virility as a man? Which as someone who's had part of my beard fall out, 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 interests in Cuba and is 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 mob's man in Hollywood for a while, and then he shifted focus to be the mob's man in Vegas after they increased their investment there when Castro gave them the boot and they wanted to get casinos up and running. Rosselli and Giancana, they're pals, and they often go out together and party, and both are friends of Traficante Jr.,

And 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 terrorists, organized crime training, uh, commando type stuff, just all sorts of political, uh, and violent intrigue. That was just a wild time in America. Yeah.

The CIA recruits a guy by the name of Robert, I'm going to mispronounce his last name, Maho. You know, when they hit you with the EU. Maho? Yeah, that's pretty much. Yeah, we'll go with it. He's an ex-FBI agent and current aide to eventual crazy person and legendary entrepreneur Howard Hughes. He becomes the go-between and Robert approaches Roselli who then introduces the man to Traficante and Giancana and the CIA offers them $150,000 to kill Castro which is

Like a lot of money. I feel like that's a good going rate for killing a head of state. Which the mobsters decline. They say they'll actually do it for free and they cite patriotic reasons for wanting to help out the government. But in reality, you know, 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 a 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 this 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, famous actress, I think.

or Singer. And the CIA does this as a favor to their new pal, Gene Khanna. 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 so the casino operation can go in. But they tell the CIA to warn them in advance, quote, if you ever try to do business with organized crime again. Pfft.

Yeah, I mean, the thing is, RFK was like, like I said, the most hawkish guy. And he actually favoured 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. I reckon he tried to airbrush a lot of stuff that he'd done after that. But yeah.

I guess he didn't last a huge amount longer, did he? Bobby Kennedy, he got offed 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 part of it is probably that he just doesn't... He hates the mafia. He's at war with the mafia. So while he probably...

direct action, he probably just doesn't want it done by mafia guys. I'm sure he had no problem operating with the other sort of Cuban weird special operatives that they used. But 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 Havana. 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 Fidel Castro. I think a little before that, but he gets cold feet, doesn't get the job done. But there's some disputes that Orta would have even been able to get close to Castro to poison him. And it's Castro who actually says this. This is from a Reuters article in 2007.

In his own words, the traitor Orta received money from organized crime 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 Orta 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 Trafficante 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 boat raids in 62 and 63. One raid had Giancana 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 Castro assassination plots are basically shelved.

Yeah, I did not know until today that Roselli was a big player in the mafia. He was definitely the agency's point man for a while. And this sabotage campaign that he personally went on, it was one of the CIA's most successful against Castro.

by a couple agents put thousands of dollars worth of weapons in a U-Haul in Miami 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 moored off of Havana or something it was pretty daring stuff

So yeah, I'm going to get into some more of this stuff next week, but it racked up costs 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.

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 castle 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

But another theory is that Junior actually ordered the hit to prevent him from talking. But they also say a decade earlier, Gene Cano was sentenced to one year in jail for contempt in 1965 for refusing to testify at an unrelated grand jury. And during that sentence, he was demoted from boss by the real longtime power boss of the Chicago outfit, Tony Accardo and Paul Ricca, 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 Giancana's boss is very flashy, hangs out at nightclubs, he's in these 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 US 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 and 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 a CIA hit or a traffic contact hit would have worked out better for this episode, I actually think it seems pretty clear that the outfit were the ones that take him out.

Handsome Johnny Roselli does testify at the church committee and according to a 1975 New York Times article too, 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 of 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, you know, 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 in 71 through another mafia-related trial. 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 outfit's call. And a different source not in the Times has an informant quoting Tony Accardo, who we mentioned right before, saying, So, Trafficante 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 stem from a $2 million 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 figures, said Robert W. Butler, in charge of the Tampa FBI office. He, along with 11 other mobsters from the Bonanno, Gambino, and Lucchese families, are indicted on conspiracy and racketeering charges.

Quote, the indictment alleged that for a percentage of the profits, Traficante 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 the profits. And this indictment is actually about the Kings Court 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 I actually interviewed this year for a different project that I'm working on that will be out next year. Alright, 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 Sonny Black Napolitano, who was unable to testify, even if he was willing to do so because he's killed in 1981 for introducing Donnie Brasco 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 Sr. and Santo Jr. 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 Bougainvillean 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 thrilled to... I just wanted to give a vivid image. To think about that. But anyway, yeah, next week, patreon.com, Underworld Podcast. Yeah, take care. ...

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