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Underworld Enigima: Sam Giancana

Gangland Wire host, retired Detective Gary Jenkins, reports on the life and legacy of Sam Mooney Giancana, a prominent figure in the Chicago outfit and the mafia world. Giancana’s enigmatic nature and shadowy dealings are explored, tracing his journey from a member of the 42 gang to the pinnacle of the Chicago outfit. Known for his ruthlessness and criminal prowess, Giancana’s rise in the criminal underworld during the Prohibition era is detailed, showcasing his involvement in illegal activities like gambling, liquor distribution, and political rackets.

The host sheds light on Giancana’s connections with influential figures like Al Capone, his alleged role in John F. Kennedy’s presidential victory, and his entanglement with the CIA in plots to assassinate Fidel Castro. The interview further brings to light Giancana’s partnership with Richard Cain, a corrupt law enforcement officer turned mob associate, expanding their operations to include gun smuggling, espionage, and international intrigues.

The narrative takes a dark turn as Giancana’s mysterious death in 1975 is analyzed, with several theories suggesting mob involvement, internal power struggles, and CIA conspiracies behind his assassination. The interview speculates on potential conspirators, including Tony Accardo, Santo Trafficante Jr., and even the CIA, reflecting the convoluted web of betrayal, power dynamics, and covert operations that characterized Giancana’s tumultuous life.

Ultimately, Sam Giancana’s legacy endures as a symbol of the murky intersections between crime and espionage, leaving behind a trail of unsolved mysteries, political entanglements, and violent retribution. The host encourages engagement from listeners, offering insights into mob history, sharing anecdotes, and inviting discussion on the complex and intriguing world of organized crime.
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[0:00] Hey, all you wiretappers out there, back here in the studio of Gangland Wire.
You know, I’m doing these little kind of short, down-and-dirty bios of major mob guys, because I got to realizing that everybody doesn’t know all the details that maybe I know or that I’ve read about.
I know a lot of you guys know a lot of stuff. A lot of you know a lot more than I know.
But everybody doesn’t know everything about all these different guys.
And I may mention the name, you know, Tommy Lucchese, Three Finger Lucchese.
You might mention Vito Genovese or just, you know, Genovese, the Genovese family.
So putting out these shorties to say this is who these guys are is bonus episode.
So today I’m going to deal with the life and legacy of Sam Mooney Giancana, unveiling the enigma.
And he was an enigmatic figure, which I think means I’m using that $25 word there, aren’t I? Which I think means he was kind of a shadowy character, kind of hard to understand, had a lot of secrets. And he did.
You know, he like went to Mexico for quite a while. He had business interest all around the world and gaming in casinos and gambling.
And he wouldn’t share some of that, which some of that came back to bite him, I think, in the end.

[1:14] But he was born in 1908, May 24th in Chicago.
He was he was a Chicago outfit guy.
And he starts out. his journey into the crime world as a teenager in the 42 gang.
Now, they say it wasn’t because they lived on 42nd Street. It was because it was Alibaba and the 40 Thieves.
And with Alibaba, that made 41.
And then so they wanted to say they had 42 members in their gang.
So they called themselves the 42 gang. That’s a good story, isn’t it?
Giancana’s Rise in Chicago Outfit

[1:45] But he’s going to go to the pinnacle of the Chicago outfit, but it’s a long tail woven throughout with intrigue, power, and a lot of clandestine activities, including stuff with the CIA.
So as a young man, Giancana’s proudness as a getaway driver and a lethal force, I mean, he was a guy that would kill without hesitation.

[2:09] Earned him a reputation in a 42 gang that caught the attention of the Capone group, of course.
And Capone was the man during that time.
These were the young Turks and Capone was a guy running everything in Chicago.
So they started taking a Cardo. He came out of the circus gang, Giancana and a couple others. I can’t remember their names came out of the 42 gang.

[2:31] But by the end of Prohibition in the 1930s, he was seamlessly integrated into the criminal web of the Chicago outfit.
And they controlled all the illegal gambling and liquor distribution during Prohibition. They had gotten their clutches into any liquor distribution.
Prohibition’s over. They’re not going to let that go. And political rackets.
And they also had stuff going down all the way down the Midwest, Kansas City, and then down into Louisiana. Indiana.
Giancana, he had a knack for finding profit centers for the outfit.
He knew he could smell money.
So during the 50s, they didn’t pay much attention to the South Side, to the Black community.
There were Black gangsters earning huge sums from the lottery.

[3:17] Gen Cana befriended one of these guys and learned the business and then pretty soon forced him to retire.
And then this This guy just said, OK, and he left the city. Well, there was another black policy baron named Theodore Rowe who then moved in on this black group that Jen Cannon was trying to take over. And they started a war.
And Teddy Rowe would not back down.
He would not back down. They had a shootout. I believe he shot and killed Johnny Roselli’s brother or another guy.
Anyhow, he shot and killed one of the major mob guys brothers in a shootout.
And but by the end, policy baron Theodore Rowe, Teddy Rowe, is killed.

[4:01] Sam Giancana will rise to the top of the outfit. And in 1957, he becomes the out front boss as Accardo, who has really been the boss since after the war.
He and Paul The/Waiter Ricca had been the boss and Accardo had been kind of out front.
Like now Sam Giancana is going to be out front. Cardo is going to take a step back.
He still maintained a lot of power and a lot of say-so.
Intrigue and Plots Unravel

[4:29] Now we’ll get up into the 60s. Here’s where we get into this intrigue and these different plots that are going on.
There are whispers that Giancana had something to do with John F.
Kennedy’s 1960 presidential victory and by getting out the vote for him in Chicago.
Well, I never did buy that story particularly particularly because they could get out the Democrats were going to win in Chicago anyhow.
So I don’t really understand that, but a lot of people say that Giancana believes that his influence put Kennedy over the top and handed him the presidential victory. There might be more to that story.
Many claim that the mafia then would guide the political fate of any major candidate during those years.

[5:16] And also during the 1960s, Giancana became entangled with the CIA or the Central Intelligence Agency because they were frantically trying to kill Fidel Castro and their own little plots and plans with their own people was not coming to fruition, was not working.
You know, they got hold of Santo Trafficante Jr., who was the mob boss down in Tampa, and Carlos Marcelo, who was down in New Orleans because they had a lot of connections to Cuba.
And then JFK gets assassinated about this time.
And as we all know, there’s tons of information out there that link Traficante and Carlos Marcelo to the murder of JFK.
And this is all back to Cuba, the failed Bay of Pigs operation that Kennedy, like Kennedy, let him down. You know, it really is complicated.
Well, also during this time, to keep it going.

[6:11] Giancana takes in a guy named Richard Cain, who is a Chicago, actually a Cook County deputy sheriff, had been a Chicago policeman.
He was just corrupt as heck.
And he was really the bag man for the outfit at one time to carry bribes back to sheriff’s detectives, to the sheriff’s office, was vice squad and different people on the Chicago Police Department.
He also had a connection to the CIA. This is already, you know, web of different connections.
And here we’ve got Richard Cain moving in. He’s side by side with Sam Giancana.
His connections expanded way beyond the outfit and the outfits, gambling and smuggling operations.
He really expanded out. He was involved with some the training of the Cuban people for the Bay of Pigs.
He was involved in smuggling operations down through Central America, down to Panama, gambling in Iran, gambling casinos.
He was Giancana’s man on a lot of that. Giancana got action out of this.
When they engaged in activities that transcended conventional organized crime, Sam Giancana and Richard Cain, they got approached to do different things and probably had something to do with some of this.
Some of it’s rumor, there was armed smuggling to the Middle East for the Israeli Mossad.
And that went through Ponant Panama.
That was their connections down to Panama.
Intersection of Mafia and CIA

[7:36] The mafia and intelligence community really intersected when this plot came out to kill Castro.
Richard Cain was all entangled in the middle of that. And Giancana supposedly made a claim that, yeah, he could get that done.

[7:52] Never did seem to get it done, but this was an elusive kind of a legacy that Giancana has left, one of the many elusive legacies that he’s left when being tied up with Richard Cain.
Their partnership really exemplifies the blurred lines between crime and espionage, and you have to wonder what their influence was.
What was the outfit’s influence on historical events? You know, the murder of JFK, the attempted assassination of Fidel Castro, smuggling guns for the Mossad through Panama and that kind of a thing.
And these are really murky waters because you can’t nobody can find out about this intelligence stuff because it’s probably it’s going to be classified forever.
And a lot of it they don’t ever write down. They just, you know, do it and go on.
They also had, you know, he had promised he would eliminate Castro.
And, you know, he was having an affair with a woman named Judith Exner, and she was having an affair with JFK at the same time.
So now we got him back to JFK this course before he’s killed.
So it’s all, I tell you, he is an enigma. He truly is.
His aunt was an enigma. They had a grand jury going.
In 1965, there was a grand jury going, trying to find out about this whole mob and Castro, killing Castro.

[9:12] And there was a church committee trying to see the intelligence abuses of the 60s and 70s. And of course, he wouldn’t talk.
Giancana’s Return and Subsequent Events

[9:21] He left town. He went to Mexico. Mexico Richard Cain became this guy that would carry messages back and forth between Mexico and the United in Chicago Aiuppa Joey Dove’s Aiuppa will rise to be the out front boss while and Giancana is in Mexico and he gets called just before 1975 sometime in 1975 he comes back to the United States and he’s kind of trying to he’s making some moves to Two.
To maybe move back into the outfit he’s been gone for a long time he’s also been subpoenaed to appear before what was known as the church committee and one night June the 19th 1975.

[10:05] There’s a lingering mystery from that that there’s been theories all swirling everywhere all around when that night somebody with a 22 caliber silenced pistol put several rounds in the back of Sam Giancana’s head as he was bending over a stove, cooking sausages and peppers.
And there’s all kinds of mysteries and all kinds of whispers about this.
Many, a lot of speculation. Most people agree that that night, one of the first mysteries, most people agree that night that police were usually outside Giancana’s house, kept him under constant surveillance.

[10:45] Surprisingly, the night that he was killed, the police were missing.
One theory is Tony Accardo, who is now the outfit boss above, actually above Joey Aiuppa.
So Aiuppa would have had a part in this.
You don’t kill somebody like Sam Giancana without everybody agreeing, even maybe calling back to or going back to New York to the commission and getting their approval, laying out your case and getting their approval.
Accardo really had been the one that sidelined him and made him go to Mexico.
Or maybe he went on his own. See, we don’t really know for sure.
A lot of speculation here.
Mob politics often involves high stakes movements and things you don’t understand because they’re doing one thing over here to keep your attention from over there.
And you got all these eyes on them and informants in them and newspaper men frantically trying to find out what’s going on and keeping making book on them, as we say, keeping everything they write down and they do in the book and then putting it together from a historical perspective, maybe in a year.
So he was making these strategic maneuvers to get him back in.
There’s also grudges in the underworld.
You know, he probably stepped on some toes. That might have been an unsettled score.

[11:59] Now, one of the most talked about stories maybe is that Tony Spilotro did this because he lived close by.
They claimed that he could walk over to Gen Conner’s house, kill him, walk back, and they found the gun along what might be that path.
Giancana had had a little party earlier that evening.
There’s a guy named one of his old compadres, Dominic Butch Blossie, was there at that party.
Most serious students of the Chicago outfit, I think, will agree that his old friend and longtime associate, Dominic Butch Blossie, shot Giancana that night.
The Ocardo story really came from a corrupt police chief that another mob guy went to right after this happened and said, you know, I think the old man really liked Tony Spilotro, kind of laying it out between the lines like they do. He said, you know, the old man really likes Spilotro.
And so then this corrupt chief of police knows what his part of this is to then go around and spread the rumor that Tony Spilotro did it.

[12:59] Butch Blasi had been at this party earlier in that evening, and the story goes, and it’s been reported by decent sources, that he left and then came back.
Giancana was in this downstairs kitchen that night and cooking up some sausage and peppers for whatever reason late at night, shot him in the back of the head, got back in his car and left.
And, you know, one thing we can’t agree on, there wasn’t any surveillance out there that night. Now, there’s an outfit member named Nicholas Calabrese who was in the family secrets trial for his brother, Frank Calabrese, senior.
And that whole crew that he ran had been killing a lot of people in Chicago.

[13:36] He claims that Anthony Asscardo was part of this killing.
He doesn’t really get in any more details, but he did claim that Capo Angelo La Pietra is one that got rid of the gun and the silencer after the murder, which doesn’t make sense. I mean, what do you do? Just go out and throw it along the side of the road?
I mean, Blasey threw it out along the side of the road. That’s a deal with a mob murder.
You do the killing, and as soon as you get away from the scene, you get rid of that gun.
You know, make sure it’s clean of prints, and you get rid of a gun.
You know, today, they don’t do that. Probably they make sure they melt it down and throw it in a river or something because of DNA.
But back then, DNA was not a thing. All you needed was to get your fingerprints off of it. But Nick Calabrese claimed that his brother, Frank Calabrese, and a guy named Johnny, Ronnie Jarrett, which was part of their crew, made the suppressor.
And they probably were making, you know, we served a search warrant on our guy, Tuffy DeLuna’s house here in Kansas City.
And we found plans on how do you make a sound suppressor for a .22 caliber pistol. So I don’t know.
I’m going with Butch Blasi. Your close friend is the one that’s going to do it, is pretty much…

[14:43] Tried-and-true theory. There is another kind of far-out theory that mob boss Santo Traficante Jr.
From Tampa ordered his murder because he was afraid that Giancana was going to testify about the mob’s involvement in CIA plots to kill Castro, and Traficante was probably even more involved in this plot, but I don’t buy that either.
If he had done it, it had got permission from Accardo and Aiuppa.
But Giancana’s murder did coincide with the discovery of the decomposing remains of Johnny Rosselli, who was another outfit guy that was involved in this plot to kill Castro.
He’d been shot and chopped up and put in an oil drum and dumped just off the coast of Florida, close to Miami.

[15:29] And most suspect that Traficante took care of that murder for him.
Although it was a Chicago guy and they could easily send, you know, somebody like Frank Sweese down there to take care of that one or that any one of the, a number of other guys could go down to Florida and catch Roselli and catch him unawares and do him in.
So I’m not sure if that would even be true or not.
The Enigma of Sam Giancana

[15:51] The really far-fetched story is that the CIA directly had one of their agents kill Giancana because they didn’t want him talking about, you know, his links to the agency. But, you know, I don’t think they really ever had the guts to do anything like that.
And of course, they do not have any knowledge of it. They’ve been under such a microscope off and on over the years that nothing officially has ever come out or even close.

[16:16] He was connected to him he was involved in the kill castro plots he was involved in a lot of stuff with him down there in that area but i i just don’t believe they did it the enigma of sam Giancana endures way beyond his death and and to this day you know leaves us to ponder these intricate threads of betrayal and international intrigue and gun running and killing political political enemies of the United States and power struggles within the Chicago outfit and different alliances within the outfit that he maybe made as he was trying to come back.
And Richard Cain, his buddy, got killed, was a victim of, he was in a restaurant in Chicago and three guys came in.
I think one of them they claimed was Harry Aleman. They were outfit killers.
And you would have had to have been an outfit killer to do Richard Cain.
But anyhow, they came in and And lined everybody in the restaurant up against the wall like they were going to do a hold up.
And then one of them shot him right in the face with a shotgun and left everybody else standing there. Didn’t try to rob the place.
Had a getaway car waiting right outside.
You know, this is the life of Sam Giancana. So next time you hear me talk about Mooney or Sam Giancana or Giancana in another story, you’ll know a lot more about our friend Sam Mooney Giancana.
So thanks a lot, guys. Guys, don’t forget to watch out for motorcycles when you’re out there.
And if you have a problem with PTSD and you’ve been in the service, be sure and go to that VA website.

[17:45] And if you have a problem with drugs or alcohol, our friend Anthony Ruggiano, former Gambino man, is a drug and alcohol counselor down in Florida.
And he has on his website, he has a hotline number or his YouTube page.
Just Google or noodle around and find Anthony Ruggiano and you’ll find it.
But be sure to like and subscribe and maybe give me a review if you’re on the app, on the audio app.
Give me some comments. You got any ideas for stories?
You want any particular mob boss you want me to cover pretty quick?
And one of these shorties, why make a comment on the YouTube special?
I really see those. And we’ve got our Facebook page, a gangland wire podcast group.

[18:24] I’ve got a page too, but that’s not quite the same. The group is a little more intimate. There’s a lot of activity on the group.
So there’s a lot of interesting comments. So if you get on the group, be sure and scroll down and look at some of the different comments.
You’ll see people arguing about things, and you’ll see people that are really connected to real-life mobsters back in the day, and you’ll see people telling stories.
We’ll put up a picture of a restaurant or a bar that a lot of mob guys went to, and you’ll see people telling stories about, you know, what they remember about that place.
So it’s really been an interesting, fun way to, you know, keep up with this mob history and help people experience, you know, relive the good old days, as we say, you know, as coppers get together and we tell stories about the good old days.
Of course, we’re always much braver and better and faster and cooler than it really was back then.
But, you know, that’s how it is. So thanks a lot, guys.

2 thoughts on “Underworld Enigima: Sam Giancana”

    1. Brina, thaks for asking. Terence and I have talked about it but we have never pulled a trigger to actually put it on. I will be sure to post it on here and on the Gangland Wire Facebook group if we ever do.

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