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The Many Murders of Marshall Caifano

Retired Intelligence Detective Gary Jenkins brings you the best in mob history with his unique perception of the mafia. Marshall Caifano was a dangerous yet unassuming figure from Chicago’s mob scene.
Background of Marshall Caifano:
Caifano, a physically small but influential figure in the Chicago outfit, was brought up by Paul Ricca, a key behind-the-scenes figure in the outfit. Unlike the loud and flashy mobsters, Caifano operated quietly, focusing on strategic connections and criminal activities.
Caifano’s Activities:
Caifano was known for his involvement in various criminal activities, including the murder of mobster Bugsy Siegel in Los Angeles, which paved the way for the Chicago outfit to take over Las Vegas. He was also implicated in several other murders and extortion attempts.
Caifano’s Style:
Despite his criminal activities, Caifano maintained a low profile, appearing well-dressed and unassuming. He was known for his intelligence and ability to stay out of the spotlight, unlike other more flamboyant mobsters. Conclusion: Caifano’s story illustrates the complex and dangerous world of organized crime, where individuals like him operated in the shadows, wielding significant influence. His life and activities shed light on the inner workings of the Chicago outfit and its impact on various criminal enterprises.

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Marshall Caifano
Gary Jenkins: well, hey, all you wiretappers out there back here in studio gangland wire. This is Gary Jenkins, retired Kansas City police intelligence detective. I worked a mob for 14 years altogether here in Kansas City from here to really to Las Vegas.
We helped uncover the scheme and, you know, reached out to Chicago and Milwaukee and Cleveland. Anyhow. I’ve been telling these mob stories for a few years now in the podcast. Here’s another one. Kind of a short little story about a very unassuming but very dangerous little guy named Marshalll Caifano.
from Chicago. Now, Marshall Caifano, I know that Red knew him and knows a lot about him. So you might want to check out Red Wemette channel or the Las Vegas blog, my blog with Adam Flowers. They may have a whole story on Marshall Caifano. This is kind of a short little story about him. He was a little guy.[00:01:00]
And when he got old, I remember I ran into a couple of these mob guys, really old guys, guys out of the 30s that were still alive in the 70s. I got on the elevator with two of them once. Turned out they were going to their lawyer’s office. It was Joe Filardo and Tano Lococo. These were dangerous, dangerous men in the 30s.
They were like these tiny little shriveled up. thin silver haired kind of, you know, like five foot tall, 105 pound, 110 pound guys. That’s the way Marshalll Caifano ended up and he was always was, they always were little guys, but He was a little guy physically, but he was a huge guy in the outfit and and he was a quiet guy, you know Paul Rico kind of brought him up.
Paul was came out of the thirties is you know, kind of the behind the scenes boss when Accardo was more out front. Ricca was in penitentiary [00:02:00] down here at Leavenworth for a while and Cardo was really running things. He was going back Ricca forth and getting instructions. And when Ricca came back, he never really assumed like any kind of out front.
Kind of a role while Accardo was more out front Ricca was a really bright guy and, and he knew that he needed to stay in the background and, and pull the strings. He learned that from Al Capone, you know, Al Capone, he was all out there and everything, and the government went after him big time. They, the Chicago outfit guys had figured out, you know, stay in the background if you can.
Now he led the other as a, this one newspaper reporter. Called them loudmouth buffoons, and they get snazzy nicknames, you know, Joey the Clown, and Joey Doves Aiuppa, and of course these weren’t loudmouth buffoons, well, Joey Lombardo was, Aiuppa wasn’t, but, but there was plenty of them out there, and they got publicity, so they got the heat.
Rico ca is really [00:03:00] supremely intelligent, they say, he knew what he needed to make this thing work besides, you know, guys that were willing to steal and do the gambling and, and take over the numbers rackets and, and, you know, infiltrate the teamsters. He needed top law enforcement people, politicians and judges.
to be on the take and get them under control. And, and these like swaggering apes playing the tough guy up there on Rush Street on Friday nights, you know, they’re not, you know, they’re not going to do it. He needs the little, what he called the little guys and to do the heavy work and to make the connections and quiet little guys that were more, a little more sophisticated.
Now, Caifano, you know, he, he proved him. earned his bones as a kid as you have to do as a man. He was a boxer when he was a kid. He had a cauliflower ear even, and, but it wasn’t really his boxing skills. You know, Joey Doves Aiuppa was [00:04:00] bought under Joey O’Brien. A lot of these guys did. But it wasn’t his boxing skills that really frightened people.
A lot of people were frightened of Marshall Caifano. He threw in his fall buddy, his fall partner, was Vincent the Saint Inseraro, who was a little guy too. But boy, they, somebody said, you know, if they stood on top of each other’s shoulders, they couldn’t change the light bulb, couldn’t get up to the light bulb, but these guys were feared killers.
They were close to Anthony Accardo, of course, they came up under Paul Ricca, and these are the guys that did the heavy work, more than any of the other guys did personally. For example, in the 40s, Caifano was sent out to Los Angeles, about the time Bugsy Siegel was building Las Vegas into a gambling empire, a mecca, and he didn’t quite survive to get to that.
According to Gus Russo’s book, The Outfit, Bugsy Siegel was sitting in his Beverly [00:05:00] Hills home with a Caifano associate. named Alan Smiley when somebody else arrived and that’s the end of Bugsy Siegel. Now see, there’s Caifano right in and around the murder of Bugsy Siegel.
20 minutes, 30 minutes later, Chicago outfit. Well, really, they’re one of their chief bookies and their main guy in Las Vegas at the time, Gus Greenbaum, appears at the Flamingo Hotel, which Bugsy had been building, said, you know, he just tells them, we’re taking over, you know, that was, that was it. And, and from then on, and the outfit really ran that.
I mean, they had to kick back and Mayor Lansky and, and Luciano and the, the Eastern mobs had money in it, but they all. Ran it together. It’ll eventually, you know, Chicago will make a deal with them where they’re solely in Las Vegas and the Eastern mobs have Atlantic city. But early on, they all had to join in and keep the peace out there.
You know, in an [00:06:00] interesting kind of on the Hollywood era, which, you know, Paul Ricca went to jail for a long time for extorting money from Hollywood theaters or Hollywood movie. Companies and infiltrated the unions out there. They according to the godfather of the New York family, Corleone’s killed Bugsy Siegel or a Bugsy Siegel character.
But they never made a movie about Paul Rica. There’s never been a movie made about Paul Rica or Anthony Accardo or any of these big time Chicago guys. I don’t understand that. Maybe somebody out there, out there can tell me. Another thing, Marshalll Caifano, and I did a whole story just on this particularly, about a woman, there’s a guy named Nick Circella, who was a good friend of Caifano’s, and he had an extortion trial going on, and his lover, a woman named Estelle Carey, and a former Dice girl, at his joint, was going to cooperate for the federal prosecutors, and all of a sudden this guy’s in jail, I believe [00:07:00] at the time, and, and her body is found ice picked to death and burnt at her, her apartment, and Caifano was the prime suspect.
Of course, that case was never solved because it was Chicago. There’s another unsolved murder. In 1950, a Chicago police lieutenant named William Drury, Was killed the there was a strangulation of a mobster in Chicago named Russian Willie Strauss, and there was a 73 shotgun killing of Richard Cain in Rose’s Sandwich Shop. Caifano was suspected of being part of that.
In 1950s, the outfit moved in on the black policy rackets, and that was Sam Giancana that kind of got that going, and really that was how he, you know, really became important with the outfit, because he was a guy that Moved in on this black policy, and there was a lot of money in it, and there were some people [00:08:00] that tried to kidnap policy king, black dude named Theodore, Theodore Rose over again, and in the 1950s, the outfit moved in on the black policy rackets.
This was Sam Giancana primarily instigating this, and really when he took those over, that was a big, a large amount of money that the outfit got to start, you know, sharing in. There was a policy king, a black guy named Teddy Rowe, or Theodore Rowe, and he refused to, to give in to the outfit, refused to give in to Giancana, and, and somebody sent some people to kill Teddy Rowe, and in that shootout, Teddy Rowe was armed, he killed Caifano’s brother, and stopped this kidnapping attempt.
He pled self-defense and about a year later Teddy Rowe was blown apart by two men with shotguns. Caifano of course was questioned about that and you know, you know Caifano was part of that. He took a hit in [00:09:00] 1964. He was convicted of trying to extort 60, 000 from an oil tycoon named Ray Ryan who was from Indiana and Ray Ryan had testified against him.
Got released from prison on that one on the extortion attempt in the 1970s and Ray Ryan was so afraid of Caifano that he offered to pay him a million dollars so he wouldn’t remain mad at him, he didn’t, he could all keep his money, you know, I mean he could stay on the streets. Over again, so this, this oil man, when, when Caifano got out of, when, when Caifano got out of the penitentiary out of this attempted extortion of the oil man, Ray Ryan, he made an offer to pay Caifano a million dollars so he could, you know, walk the streets freely and not be worried about being murdered.
According to a witness in another case, Caifano told Joy the Clown Lombardo, said, let’s just take that million dollars and [00:10:00] then kill him anyway. That’s the kind of guy Caifano was. But again, a little perfectly manicured, perfectly dressed, unassuming kind of guy. You know, he was not out there in any manner.
1977, Ryan’s car was blown up with Ryan in it and nobody was ever charged, so apparently Caifano did hold a grudge, huh?
There’s another guy in Chicago, a mob. Associate, it was a banker named Joe Testa. Caifano had been after Testa for a long time, claiming that Testa owed him two million dollars. Testa said, you know, I don’t figure I owe you. Well, 1961, he turned the ignition key on in his car and he goes up. Another murder directly linked to Marshall Caifano.
Now, Caifano was in prison when this happened, but you know, what a better, what better cover than being in prison? You know, hey, I don’t know anything about it. Yeah, we did have an argument, [00:11:00] we did have a conflict, but I was in prison, I couldn’t do anything. 1960, Marshalll Caifano gets 20 years for fencing stolen stock certificates.
That was a big deal back then. These stocks, you could steal these stock certificates and they were like fungible or they were, they were just like certificates. They were like money. And then they counterfeited them a lot, but they could steal them and then go someplace else and sell them. There’s really no way to track them.
So, He had almost a century, almost, so Marshalll Caifano had about a hundred years of blood and fear. I mean, you live to be in his 90s. He had, he had at least 80 years of being a feared killer. And he’s just a guy, you know, another story that Red Moment tells is after there was a million dollar robbery, a Purlator armored car service had Inside job and the guys got over a million dollars [00:12:00] and red says that he walked into some place and they were cutting up that money.
He was going to see Marshalll Caifano and Caifano was there and. And they just like looked at him and he looked at them and he said he just turned around and walked back out. So I find out he was, he had his fingers in a lot of stuff over a long time, you know, if you could, if you could get into his mind, if you could get into his mind, you could like, you could solve a lot of crime in Chicago and, and explain a lot of things that have happened over the years.
So That’s a little short story about Marshalll Caifano. So if you have a problem, if you have a problem with drugs or alcohol. Don’t forget, I like to ride motorcycles, if you have a, don’t forget, I like to ride motorcycles, so watch out for motorcycles when you’re out there on the streets. If you have a problem with PTSD and you’ve been in the service, be sure and go to the VA website and get that hotline number.
Hand in hand is [00:13:00] drug and alcohol addiction, whether you’ve been in the service or not. You got drug and alcohol addiction, you need to get a hold of Gambino soldier, Anthony Ruggiano, he has a hotline on his website, and a hotline on, probably on his YouTube channel, he’s a drug and alcohol counselor down in Florida, so get a hold of him, and, and he can get you squared away.
Don’t forget to like and subscribe and tell your friends about it. Join our Facebook group. We got about 60,000 people on it. A lot of great discussions. A lot of crazies on that too trying to post porn but I don’t let the porn get on there guys and I don’t let the scammers and the The people that are trying to put up fake websites to get your credit card number.
We really monitor that closely, although I got two helpers on it and it’s kind of hard. I mean, it becomes a little more work than what I want, but it’s kind of fun too. And I see people making connections and telling a lot of good stories. I’d like to get some more Chicago people on it. Got a lot of New York and Philly [00:14:00] people on it.
Las Vegas, a little bit of California, and we had one guy in Kansas City was posting stuff who was kind of, you know, along the edges of it all of his life, and then another guy who belongs to it, who is Kansas City guy, he he’s He started making complaints, just making comments and complaining that this guy was putting up these Kansas City pictures and complained, well, you know, these people still have family out there and it scared, scared the other guy off.
So always another drama on Facebook. So thanks a lot, guys.

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