Retired Kansas City Police Intelligence Unit detective Gary Jenkins welcomes back organized crime historian and author John Binder for an in-depth discussion about his new book, The Chicago Outfit During the 1960s.
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Together, they explore one of the most important yet often overlooked decades in the history of the Chicago mob.
The conversation examines how the Chicago Outfit evolved during the 1960s under powerful figures like Sam Giancana and Anthony Accardo. John Binder explains how the Outfit expanded beyond traditional rackets into massive gambling operations, Las Vegas casinos, labor racketeering, prostitution, truck hijacking, and narcotics trafficking. Gary and John discuss the transition from the old Prohibition-era gangsters to a new generation of mobsters emerging from the infamous 42 Gang. The episode details how Giancana cultivated loyal associates, enforced discipline through violence, and helped reshape the Outfit’s power structure during a turbulent period marked by gangland murders and internal rivalries.
The discussion also explores the Outfit’s extensive network of political corruption in Chicago. Binder explains how mob-controlled wards, corrupt politicians, and labor influence allowed organized crime to manipulate elections and maintain enormous influence over city government and law enforcement.
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The Chicago Outfit During the 1960s by John Binder
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transcript
[00:00:00] hey, all you wiretappers. Good to be back here in studio of Gangland Wire. This is Gary Jenkins. I’m a retired Kansas City Intelligence Unit detective, now podcaster and documentary filmmaker and author. Check my website. I got links to everything I’ve done. The renaissance man.
Yeah, really. So I welcome John Binder. John Binder from Chicago. Hey, guys. I’m really am happy to have you on again. We just did another show with John. Pleasure is mine. This is absolutely my pleasure, and I think it’s partly my fault that you and I haven’t done this before. I think I dropped the ball several years ago, ’cause I got crazy busy with stuff.
Oh, interesting. I can’t remember. I’ve said before I tried to g- I think I tried to get a hold of him, but I can’t really remember how I first started. Yeah. And I don’t remember. All of a sudden it’s, it’s four or five years later, I’ve been doing this podcast I think maybe six years.
I’ve been the first mafia podcast- Okay … in the United States. That was before anybody else. Sonny Franzese and Sammy the Bull and all you guys, I was out here first, so I paved the way for them. Of [00:01:00] course, they make a lot more money than I do at it. They actually make money at it. Me, I do it for the pleasure, the sheer pleasure of doing this.
And whatever you guys wanna give me out there, I’ll always take a donation. And of course I’ve got some ads on here now. But anyhow John’s got a new book out The Chicago Outfit During the 1960s. Now, John’s a, been a real expert, and his tour covers the Prohibition Era. A- and your last one was the Beer Wars?
The book that came out in 2017 is called Al Capone’s Beer Wars. That’s the short title. And that’s a I like to describe it as a complete history of organized crime in Chicagoland during Prohibition.
Not just who shot whom, but who were the major bootlegging gangs, what were they doing how much money was coming in from bootlegging, as well as other things like gambling, narcotics to some extent prostitution, labor and business racketeering what was going on with gangland killings. And then also the other side of the fence, what was the fight by the authorities, broadly defined, police, politicians, et cetera, [00:02:00] against organized crime during Prohibition in Chicago.
All right, great. So now we’re gonna talk about Chicago in the ’60s, moving a little forward. Which a lot of you guys are maybe a little more familiar with, because there’s a lot that’s been done on this. Because I think probably primarily because of Anthony Accardo. That guy he’s almost like Al Capone as far as people having interest in him.
And this is when this is during his heyday, really, is he came up- … and then backed off a little bit. But there’s a lot of interesting stuff going on in the 1960s. So where do you start your book at? What, there’s a pivotal event or something you start your book with? No, the book is meant to be a a full story about what the Chicago Outfit was like during the 1960s.
The upper leadership the more run-of-the-mill members, the lower level members, what they did to make money, which was anything they thought they could get away with. Yeah. With, again a look at gangland killings during that era. To give a whole view of j- like what that entity was and [00:03:00] what it did.
And it ranges across a broad spectrum. There’s the glamorous stuff. Oh, they secretly own Vegas casinos and, Yeah … they had their hooks into some politicians. And then there’s the not very glamorous stuff of hijacking trucks and, running peep shows and selling pornography and God knows, whatever else.
And then there’s the violence and the threat of violence. Really, yeah. They were definitely Some of those guys were what you would describe as a terrorist today in their extortion activities, ’cause they were the- … masters of extortion. Let’s talk about Sam Giancana maybe first, ’cause he would be…
To me, I think of the ’60s, I think of Sam Giancana as much as I do Accardo. Yeah, Sam Giancana was the operating boss of the Chicago Outfit from 1957 to 1966. In Chicago structure, starting in, in, in my estimation, in 1947, they had an operating boss ran things on a day-to-day basis. But unlike all the other Cosa Nostra crime families, there was [00:04:00] a guy in Chicago above the operating boss, what is often called the chairman of the board.
The operating boss still answered to that guy. For years, it was Accardo’s operating boss and Paul Rica above him. When Accardo stepped out of the operating boss’s job in ’57, he didn’t step down, he stepped up. He became chairman of the board, and then Giancana replaced him as operating boss. But Giancana, in his some 10-year reign as operating boss, still answered to two guys: Accardo and also Paul Rica, who was retired or semi-retired chairman of the board.
Interesting. I’ve read that. That was Chicago structure. Yeah I’ve heard that before, but he- Rica was such a reclusive character that there’s not really a lot out there about Paul Rica. I did a show just on him. No biographies. Yeah, there… Yeah, there’s not, and it’s really hard to find information about Paul Rica.
He was a, he was the ultimate mobster. If you can keep your name and face out of- … the newspapers [00:05:00] and out of the public that well, that’s like our Nick Civella in Kansas City. That guy, he didn’t go out to joints. He didn’t… You know- … you just never saw him out except once in a great while.
So Rica had to be the same way. He was good Yeah I know you haven’t asked me about this, but, if I’m asked to, who are the the five most successful leaders in the history of American organized crime, the Cosa Nostra, I would name the following five people: Capone, Ricardo, Rica, Lucky Luciano, and probably Carlo Gambino.
Now, the New Yorkers ain’t gonna that ’cause I put three Chicagoans in there, but there’s a reason for that. Chicago Outfit was much more successful in its heyday than any of the Cos- other Cosa Nostra crime families. There’s federal government estimates that in 1961, and this is what I’m basing this on, the Chicago Outfit’s revenues during the year 1961 from all sources anywhere on the planet Earth, [00:06:00] $6 million When the federal government estimate is that all of American organized crime is taking in revenues of 20 to 22 million. So they’ve got about 30% of that, and this is one Cosa Nostra crime family. We don’t have exact numbers for the big five families in New York, but if you look at some reasonable estimates, any way you slice it, Chicago’s revenues are bigger than any of the five families in New York.
I think they deserve those three spots- … as the most successful of the various Cosa Nostra crime families. Yeah. New York is gonna scream, but hey, sorry guys. Yeah. They’ll scream. Just look at the comments down in the YouTube. You’ll s- you’ll see all the screaming about it, but, sure. This was during the time when the old 42 gang members were… had arisen from, in the Capone shadow and Nitty’s shadow and the shadow of those Capone-era people up into running the [00:07:00] whole thing. So talk… Can you talk about that, that the 42 gang people that moved into Upa and, Sure.
The 42 gang was a street gang in the Taylor Street area, roughly speaking, probably a bit broader than that, on the near West Side of Chicago. They were in their heyday as a street gang in the 1920s. In 1929, they sh- some of them started to work as hired muscle for a smaller near West Side bootlegger.
But, what we’re really getting into is then a bunch of them graduated up, the saner ones, ’cause some of them were quite crazy- … into the Outfit and became full Outfit members. That includes guys like Sam Giancana, the Buccieri brothers, Fio and Frank Willie Dedono guys you might not- I’ve heard so much about Anthony “Pineapples” El Dorado.
There’s a whole bunch of them. You might even say some of them probably rose up, Chuck English, on Giancana’s coattails. A lot of them were very close to Sam Giancana and reached their their pinnacle in organized [00:08:00] crime probably during the years Sam Giancana was boss. And Giancana, he had from what I’ve seen, he had quite a network of people that were really loyal to him.
More loyal to him maybe than to the greater organization. Seemed to me like he, It seemed to me like he engendered that kind of loyalty, ’cause of what happened after he got killed. They killed off… They were then able to kill off a couple other guys after Giancana got killed. There, there certainly was no great internal revolt when Giancana got deposed in 1966 or when he was killed in 1975.
It just wasn’t there. Nobody’s gonna buck in ’66, no one’s gonna buck O’Caro and Ricca. Ricca is gone by ’75, but- Yeah … in ’75, no one’s gonna buck- Okay … tony Accardo. Probably the most prominent casualty in the wake of Giancana Chuck English, who as I mentioned, was… knew him going all the way back to the Taylor Street days and the 42 Gang.
And apparently Chuckie English was very [00:09:00] dissatisfied with the state of affairs regarding Giancana, et cetera, and that might have been what got Chuck English killed then, although he got killed about 10 years after Giancana. So if he was running around shooting his mouth off they cut him a lot of slack for quite a few years then.
But there’s claims that he was upset with what happened, and Giancana was shooting his mouth off. Interesting. So as they’re developing their rackets and a lot of the, a lot of it was extortion, but the gambling d- developed a huge, I think they had all the off-track betting before you could really do off-track betting and- for the… ‘Cause you had, what, two or three racetracks in Chicago, and- Easily … what were the, what were their profit centers? Was it gambling was their main profit center in the ’60s? Yeah. During the 1960s the bulk of their revenues would’ve been from gambling, as it was for years in the post-Prohibition era.
There would’ve been juice lending. They got con- The outfit got control of that sometime in the 1950s. Previously, [00:10:00] that had been just independent individuals would be doing illegal high-interest loans and trying to collect in one way or another. Labor racketeering some narcotics. But it takes a while for narco- narcotics to be a really big revenue source for American organized crime.
You got, early on, no offense, but, Who were the heavy narcotic users. These people seen as junkies, disreputable- Yeah … and jazz musicians. Yeah. And it’s only during the ’60s you start to get the real recreational, broad recreational drug use, that then has reformed itself, festered itself, broadened itself into, the cocaine craze a few decades later.
Now you’ve got heroin derivatives, fentanyl use, Yeah … broad spread for one reason or another, all that stuff. But so I mentioned narcotics there. Some prostitution, although the era of free love really cuts into that racket, doesn’t it? Yeah. Yeah. Hijacking, hijacking valuable shipments off of- Yeah
Interstate [00:11:00] trucks and stuff. And then- So those would be among the big money makers … how did you… Could you get into much about how organized they were with their hijacking of trucks and boosters out there, but mainly hijacking of trucks and products and then having fencing outlets? Who was big players in that opera- part of the operation?
The out- the Outfit was very active as I think were the major Cosa Nostra crime families in most cases around the country- Yeah … in terms of hijacking, valuable shipments. During the ’60s a trailer truck full of color TVs. Yeah. That was valuable. Then, of course, you gotta turn it around and you gotta fence it.
There was other instances where Outfit guys that knew about a shipbuild- shipment of silver bullion by truck, and mainline Outfit guys then were arrested and convicted for grabbing that. As we’ve talked about, Gary, if there’s a way to make an illegal buck and they think they can get away with it, these guys will do it.
Yeah. They’re incredibly canny and clever and diabolical about finding these illegal angles. If we go do this [00:12:00] and this, forget it’s illegal, we can get away with that and make some serious money here, so let’s do it.” Yeah that’s for sure. But I remember some kind of well-known story about Sam Giancana moving into the numbers racket that was primarily operated in the Black community and by Black gamblers and the Black gangsters.
Teddy Roe, and I can’t remember the other guy’s name. Yeah. That was- Sure. The Jones brothers … that was quite a story there. Did you look into that? Yeah I’m quite familiar with that. Num- the numbers or what in Chicago was called policy, and we don’t need to get into just how they played the game, how they drew numbers and, as a gambler, what you had to win.
But it was different than the numbers in New York. But policy, that goes way back to before the Civil War- In Chicago. It’s a myth that was invented in the 1890s. Goes way, way back and evolves, but by like the 1930s, heavily centered in the Black community- … in Chicago, as opposed to [00:13:00] previously it had been like, more or less all, all across various parts of the city.
Capone left those guys alone. His successor, Frank Nitty, left the policy guys alone for one reason or another. But by about maybe 1943 or so, it looks like Sam Giancana suggested to Tony Accardo these guys, instead of whatever, having a live and let live, why just muscle them? Why don’t you just take them over?
And by about 1945, for one reason or another, Accardo decides this is a very good idea. So Giancana becomes essentially the point man on that. He’s got a stable or crew of gunmen, and they start pushing in on all the policy guys, intimidating them, threatening them, kidnapping them, partly to squeeze money out of them, partly to get a signal to them of this isn’t a random kidnapping, by the way.
Yeah. Trying to get them out of policy. And by about 19 maybe 55 or so at the latest, [00:14:00] all the major policy operations in Chicago that have been independent have been taken over by The Outfit, including- Wow … the… Teddy Roe, as you said, Teddy Roe had balls. He had the b- I don’t know what you say.
He had the balls of an elephant- Yeah … on, on a six-foot guy’s frame. He’s, he wouldn’t take it. He… they pushed the Jones brothers out. Teddy Roe, one of the lieutenants, then filled the void, took over their rackets from them and he fought back. Yeah. I remember it seemed like he killed somebody.
Was it a Buccieri brother or a brother to somebody? It was- the the gentleman known as Fat Lenny Caifano- Caifano … was shot and killed- Marshall Caifano’s brother, yeah … as he tried to probably strong arm grab Teddy Roe. There’s debate about that. Did Teddy Roe himself step out of the car ’cause Caifano was in a car behind him, came racing up to their car, got out and ran up to him, or Teddy Roe had some tough Chicago coppers moonlighting as his bodyguards.
Did one of those guys step out of the car? [00:15:00] Yeah. Bang. Headshot. That’s the end of of Fat Lenny Caifano. So you, you can… Jury might be a little bit out on that one- Yeah … but one way or another, they blew up Fat Lenny Caifano when he went after Teddy Roe. That’s Marshall Caifano’s brother.
They’re both 42s. Yeah. 42. That’s what I was thinking. I remember who Marshall Caifano was. Yeah. I’d forgotten that his brother was, yeah. And so Teddy Roe probably took credit for it no matter what on the streets. He wanted… That’d give him a certain street rep. It didn’t hurt his reputation. No. They came after me and I put them in the cemetery.
Yeah. A- and of course- Yep … they ended up taking it over. You just, you cannot resist these guys. You can fight them. You can fight them for a while, but you’re, at that point in time, if you’re gonna fight them on their turf, you’re gonna lose, ’cause they were rough. Yeah. The out- you’re right, the Outfit was that powerful.
They finally caught up with Teddy Roe in 1952, and then that was that. They shot and killed him, I think, right outside the building he lived in on the South Side of Chicago. Yeah. And moving on up in the ’60s in that gambling what [00:16:00] do you got? I’m always been curious about this Ken Eto, Tokyo Joe. How did did you get into that?
How’d that happen? Ken Eto is of Japanese extraction. I think he was if I looked into his background, I believe he’s from California. He was, as a young man, he was interned, as were many Japanese Americans- … during World War II, put in an internment camp. Gets himself out to Chicago after having, I think, some legal trouble maybe for gambling out west.
And he becomes for years sort of the point man for the Outfit on gambling both in the the Chinese community and also the bo- for the Bolita-type games, which are just a lottery-type game. It was popular in Chicago’s Latino community way back when. He’s a non-Italian face that they found convenient to use, and then also I think they used some non-Italian faces once they took over policy. The customers, who were largely Black, might not have seen, might not have been happy [00:17:00] seeing these Italian American faces now- Yeah … visibly running things. So they put some Black front men and some other guys in as front men, you know- Yeah
in the operations themselves. But it was their game. They were o- they were there a step behind in the scene, scenes. Interesting. And the ’60s, that was during the time when it seems to me like as the crews were developing and they started extorting a lot of money. Sure. But they also started getting into politics a little bit.
And by the end of the ’60s, I would say they had this Fred Roti and what was that other guy that used to- DiAco. DiAco. Do you remember Joe- John DiAco in the First Ward … John DiAco and Fred Ward yeah, or Fred Roti and- Roti, yeah … I think there’s one other guy at the one that would always sat at the counselor’s road table that they put the hidden microphone on.
But I interviewed that that lawyer God, I’ll say- Bob Cooley … Cooley. Bob Cooley. I interviewed Bob Cooley, and he was all in, in and around that. And that was more up into the- Sure … the [00:18:00] ’80s when that happened. But it really started in the ’60s. So you deal much with that, with their move into politics?
‘Cause it was slowly but surely. They really moved into the court system, it looked to me like. Not the city government particularly, although they did get a lot of nice city contracts, and they got some nice city jobs- Yeah … for guys. Yeah, I talk about some of that. One of the things I talk about in this book is also the fight against organized crime, not just the Outfit- and what they did. And, I single out a variety of fearless, incorruptible people in law enforcement, whether it’s state, local, or federal. But I also talk about a couple of corrupt politicians. I think both of them are are from that First Ward group there you mentioned- Yeah … in terms of Councilor Rothengam.
The Capone gang already had its hooks into certain wards’ political structure in Chicago back in the ’20s, and the outgrowth of that is in 1960 there’s some five wards where the Democratic Party apparatus is directly controlled by the Chicago [00:19:00] Outfit in Chicago. Five, five out of 50 wards in Chicago.
And everybody knew it. Everybody knew it. If the alderman or the committeeman, that’s, those are the Outfit’s guys. They do exactly what the Outfit tells them to do. Premier one was the First Ward, which for years controlled or covered as a political entity. That ward was the downtown area south of there, and for years just west of there around Taylor Street.
Wow. That’s, Yeah, they had some of those certain judges in some of those court system where they had it wired. It was unbelievable. Yeah, some of the stuff that went on was unfathomable. This side of New Orleans, nobody would believe that. This side of Chicago, New Orleans, nobody would believe it.
They… This happens in, inside, the officialdom, politicians, elected polit- and judges? This actually happens? Yeah. Oh, yeah. I mean- Yeah, around Chicago and New Orleans, yes. Yeah, New Orleans, yeah. It’s the Big Easy, it’s just, that’s part of the life. [00:20:00] Yeah. But Chicago, the whole deal about getting a bench trial for a murderer and then rigging- the judge, and then he can al- you can always find a little bit of reasonable doubt. All you need is a smidgen of reasonable doubt, and he only got the one trier of fact, and he makes a decision. And, Harry Aleman’s the most famous case where he had to get tried again. Yeah. But it was, That, that, that judge got $10,000 and he, at that point he didn’t care about reasonable doubt.
He sold out. And people used to ask me about that. How could- They get a judge for only, quote, $10,000. And I said competition keeps prices down for everybody.” He wasn’t the only corrupt judge in Cook County. If he wouldn’t do it, somebody else would do it for 10,000. So in his mind, better take the 10,000 or they’ll go, they’ll go get-
somebody else, and then they’ll have the case assigned to that judge and not to the guy who then actually- Yeah … was the, was… I think it was Maloney was the judge who, Maloney. Yeah … who got paid off to do it. Yeah. Maloney was his name. [00:21:00] Yeah. So competition- Committed suicide … keeps prices down for everybody, Gary.
Yeah. Yeah. Yeah, that’s true. Committed suicide later, but… So what, let’s talk about labor racketeering. That’s also a time- Sure … when they really got sophisticated with their labor racketeering and got into that Teamsters pension fund, and getting those loans out of that- … which became a national, had a national impact really.
Talk, tell, tell- … tell about what you uncovered and what you’ve got in there about labor racketeering. There’s, again, a long tradition of that. Again I’m, I may be going longer into this than you want, but it’s in the… By the 1890s or early 1900s that labor racketeering in Chicago, where as soon as the unions get established among the working men, there’s people who start taking over unions for the benefit of they and their friends, not for the guys who are working in the union.
And then a lot of the bootleg gangs, Capone gang being the premier example, start to push heavily into that in the late 1920s. Yeah. It’s estimated in the early 1930s that organized [00:22:00] crime had its hooks to one extent or another in about two-thirds of the union locals in the Chicago area. Now, that means some were squeaky clean, but a lot of the unions or union locals were either totally controlled or were somewhat influenced at that point by organized crime.
And in the case of the Outfit then, still into the 1960s. You say Teamsters at that point in time and everybody knows- Yeah … the Outfit heavily had their hooks into the Teamsters, as did many other crime families around the country into their Teamsters locals. Yeah. But there are a lot of other unions as well.
Great source of revenue, ’cause if you can control a couple unions, you can do all kinds of stuff- Yeah … that you couldn’t otherwise get away with. Yeah I think they also learned that there’s a lot of political power. When you control a union you just need one guy to tell his guys, “Okay, you vote for this alderman,” or, “You vote for this guy”- and they’ll all vote for him. You only have to influence- … one guy. Yep. And so there’s a lot of political power [00:23:00] in the union. Plenty of money. Yeah, if the Teamsters nationally s- you know, Hoffa or somebody says, “You vote for this guy for president, I don’t want you to vote…” As he did. He hated the Kennedys, so he endorsed Nixon, I believe, at one point in time- Yeah.
If I remember this correctly. Although, it- They always en- for years en- endorsed Democrats left and right, but Hoffa hated the c- Jack and and Bobby Kennedy so much- Yeah … that he went for Nixon. I think it was in ’60. He got all these previous Democrat people to vote, never voted for anybody but a Democrat in their entire life, and even nobody in their family there voted for anybody but a Democrat, to vote for a Republican- Yeah
who Republicans hate unions. Yeah, they’re like, they’re like- They hate unions. Come on. … Jimmy Hoffa’s son, what’s the Republican Party? I don’t know what that is. I mean- Yeah. O- okay, all right, guys. Forget it. Just find Nixon on the ballot- Yeah. … and then just vote. Forget about the whole party thing.
It’s too complicated for you, but- Yeah. … vote for this guy Nixon. N-I-X-O-N, okay? Really? Because I said so. I’m [00:24:00] Jimmy Hoffa. Yeah. And speaking of the Kennedys, of course, this is during the time when Johnny Roselli and, the, all the Kennedy assassination, the theories out there. Did you deal in, did you get into that at all?
Not into the Kennedy assassination, but I have done quite a bit of research on these claims that the Chi- that Sam Giancana and the Chicago Outfit got JFK elected in 1960. There’s absolutely no evidence to support that. Yeah. It’s one of the great urban legends or myths of our time. So I do mention that in the book very briefly- Okay
but with, in the references, a reference to a academic journal article I wrote on the subject that looks at the voting numbers, et cetera, to keep this brief. Yeah. Interesting. Yeah. It’s we’ll get a lot of comments on that too. It’s I did a story on Chuck Nicoletti and his possibility that he was down in Dallas at that time, and I’d tell you that thing blew- yeah
that thing blew up, man. It blew up. A lot of people has a lot of interest in that and… But we like our conspiracy [00:25:00] theories. It makes life more interesting, I think, for us, and it’s, … i’m trying to think what else. Some of the gambling activities during that time when as sports gambling got more and more prevalent.
It’s, so prevalent today that with the- … gambling apps and everything, but they really pioneered, I think, that sports gambling and made it much, much more popular. And I think it was like- Yeah … Joe, I read something where Joe Ferriola, who was a… He was out of Cicero- … I think.
He was a capo. He started telling his guys to line up all these sports gamblers just like Capone had all the bootleggers lined up and start paying us tribute. Was there any truth to that story? Absolutely. I think his motto was, “Everybody pays.” Got it. Yeah. Once the big interest in sports gambling started…
‘Cause way back when, our… Your, my grandfather wasn’t here in the United States. I’m an immigrant myself, but your grandfather’s generation, gambling meant horse racing to most of them. Yeah. Then the interest in college professional sports gets really big, and gambling on it immediately follows.[00:26:00]
Then by the early ’80s, Joe Ferriola says, “All right, we’re gonna line up in the Chicago area all the the sports bookies.” There ain’t no two ways about it at that point. And they do- … in some cases, the hard way. Guys guys resisted and got killed. Yeah. So yeah, that happens under Joe Ferriola- Interesting
when he’s the boss. Yeah. So what else was going on Chicago outfit-wise during the 1960s that maybe most people don’t know about? Let’s see. We’ve covered a broad range of stuff. The book gets into the sort of, as I… We made mentions already, the full gamut of what these guys did. Man, if there was a way to make a buck, they’d do it.
This guy is running peep shows in the South Loop for them and some pornography. This other guy runs some low-level prostitution. This guy over here is, involved in hijacking. This guy over there, again, if they could find a way to make a crooked buck, and in, in a simple parlance, if they, they don’t wanna get caught, so if they think they can get away with it, quote, “by and [00:27:00] large,” they’ll do it. So the, through the stories of these individual guys, this outfit member, that outfit member, you get a real look at, what the whole organization was doing left front, and center in terms of some, in some cases, not a lot of money’s coming from boot. There’s some money coming from it, as well as the real big stuff. As we said, during the ’60s, the gambling, the labor racketeering some business racketeering some prostitution still some narco- Yeah. Interesting. Again, one more question maybe.
What about Jackie Cerone? Did you look at him at all? He’s always been a mystery guy to me. Looks like our… Oh. Yeah, go ahead. Go ahead. Did you hear my question? Oh. Did you hear my question about Jackie Cerone? Yeah, I did. Yeah, I- Okay … I think we lost our connection, so I’ll go on.
I’ll go back- I had the… I had the audio that whole time. Okay. Until… you were just frozen, but now you’re back now, so it’s all right. Okay. I’ll just throw a picture over that- Okay … [00:28:00] when you’re frozen, okay. Yeah. So tell me about Jackie Cerone. Jackie Cerone, he comes out of the Grand Avenue neighborhood on the very near northwest side of Chicago there, as did a number of prominent Outfit guys over the years.
I think at one time he was probably the driver bodyguard for Cardo. Yeah. And that’s not a flunky’s job that, when they appoint you to that position with one of the top guys, that’s a little bit like if you’re a young guy and you’re promoted to be the personal assistant of the president, the CEO, sorry, of IBM.
You go around with that guy, you see everything that guy sees you’re privy to everything that’s going on. You’re a guy they’re grooming probably for much bigger stuff already. So that Cerone, from there Cerone was no stranger to gangland violence. He’s p- I think pretty clearly by his own admission they caught him on a, I think on a wiretap once involved with, he shotgunned one of the Black Policy guys in the early ’50s. The guy didn’t die, much to Jackie’s [00:29:00] disappointment, but- … he shotgunned Big Jim Martin anyway and and doing other stuff. Jackie Cerone could be quite violent when the opportunity called for it, and he rises up to be in the very upper echelon.
At minimum he’s the under boss at one point in time. Yeah. Some debate about whether he was ever really the boss or not of The Outfit. Yeah, wasn’t he Didn’t they pick him up on a wire down in Florida bragging about the torture of that William Action Jackson, the big fat bookie they thought was snitching to Roemer?
Yeah. They… these guys are sitting around going in g- great graphic detail about what they did to Action Jackson, and the stuff is that they’re giggling about it. The facts are they put him on a meat hook and then they tortured him with a cattle prod and God knows what else.
And they’re giggling about it. It was crazy. Yeah, it was. Or laughing about it. Yeah, it’s a pretty wild crew there of I think one of the Buccieri brothers Jackie Cerone, and probably three or four other guys. And it lasted several days. [00:30:00] Yeah, I read that Amazing stuff … yeah, it was amazing. It truly was am- that’s why I’m like, “Where’d this guy come from?
What was his childhood like?” That you could do shit like that. I don’t know. Yeah, they they didn’t especially Al- a lot of these guys, Italian Americans are raised as Catholics. The Ten Commandments never quite sunk in with any of them guys. Yeah, really. None of those Ten Commandments.
None of them. They probably broke every single one of them. Yeah. Maybe honor thy mother and father. Yeah. Yeah, probably did that. But nine of them they broke, Gary. Yeah. Yes. It’s a crazy wild bunch up there, that’s, that is for sure. They did have Chicago- the stories … wired The stories abound- They-
that the history is fascinating. And yeah, I fi- I find it somewhat ironic, they by and large don’t seem to or can’t or don’t make any money off of their history, but guys like you and I can. So thank you Outfit. Yeah. Really. Much appreciated. Yeah. Again, seem like they spend [00:31:00] all their money on lawyers and then they go to jail for long periods of time- And doing illegal stuff
yeah. They don’t they gamble. I tell you, they spend a lot of money on gambling. A lot of people lose a lot of money on gamblers. These dope dealers that they’ll make millions and millions of dollars and go blow every bit of it in Las Vegas, come back and then start trying to do another run again to…
I know several- Yep … of them actually. They- Yeah, they, Out of- Capone himself was a… You could describe him as a degenerate gambler. By Capone’s own estimate he… I think he told a reporter in 1929 that he’d lost $8 million gambling since he came to Chicago. He comes to Chicago at the very end of, according to his own granddaughter, like very end of 1919.
He gambled left and right. He acted like there’s always gonna be more money there next week, and for many weeks there was- Yeah … until he goes to prison and there’s not. Yeah. Yeah. It’s crazy. Yeah, they- Yep … so many of them just blow it all, even though they’ve had it at one time. Yeah, the man was not a saver, Cap- Capone’s case.[00:32:00]
Yeah, the Chicago Outfit during the 1960s, it was a really exciting time for the Outfit, wasn’t it? It was just crazy. Wild and crazies. They were- it, it- … moving into all the rackets … yeah. It… to put it into perspective, we all know, they do illegal things, they hurt people that threaten to hurt them, but in their chosen profession, being gangsters with them, the Outfit, they’re incredibly good at it.
And I say that without, any respect for them per se, just as I would say in his chosen profession as a general, Napoleon was great at it. Yeah. The fact that he got millions of people killed trying to conquer Europe, I don’t have any respect for him either, but, Yeah … but the Outfit, they’re really good at, Their chosen field Yeah, that’s for sure.
And as you said before I think, yeah, I don’t… That, if that… But if they have to play by the rules of everybody else in a legitimate business, they don’t do so well. As long as they can play by their own rules- Nope … they’re immensely successful. [00:33:00] Yep. Abso- absolutely. If, and, people ask me is organized crime gonna go away?” No, not… As long as there is something that society makes illegal which- Yeah … people in society still want, they will try and consume it, and then on the other side of that equation, someone will be willing, even though it’s illegal, to provide it and make money off it.
Yeah. It’s like I do this- it’s only in… I joke, it’s only in Holland where everything is legal. In the Netherlands where everything is legal that we don’t… And that’s not true, everything’s legal, but it’s only in the Netherlands where everything is legal that we don’t have organized crime.
Yeah. And they’ve got their own organized criminals, but they’re more transnational criminals, not just in Holland. Yeah, the narcotics trade, to be honest, precise, is not perfectly legal in Holland, and there’s a lot of narcotics being brought in, and that’s illegal. But a lot of other stuff, the use is, I believe, legal.
Yeah. Prostitution is legal. Gambling I’m not so aware of whether it’s perfectly legal [00:34:00] at casinos in in the Netherlands. Yeah. But a lot of things are legal there. And it’s not Chicago, is it? Chicago’s a whole big beautiful, brawling gritty city. It’s the Second City, man. It’s something. I… and in some ways in organized crime you allege that they’re the first city.
So New Yorkers, take that, huh? We’ll keep that fight going. I think if you l- if you look at the numbers for what the Outfit was at its height, and that might strike people as weird, but one of 25 or 28 Coast- crime families was that big. Yeah, but they had their tentacles in a whole- Yeah
bunch of other stuff. Even though there was a Coast-associated crime family in Milwaukee, the Outfit controlled that. Madison, Wisconsin’s crime family was probably controlled by Milwaukee, was controlled by the Outfit. Springfield and Rockford, Illinois, controlled by the Outfit. The entire state of Illinois, controlled by the Outfit.
For years the northwest corner of Indiana, controlled by the Outfit. Yeah. The Kansas City crime family for years, controlled by the Outfit. Yeah. Dallas- Yeah, people- … the [00:35:00] Outfit had their hooks in Dallas. Yeah, Des Moines. Parts of California, south and north. Yeah. Now you get- they just sent, like you said, that Charlie Gioe and then later that Louis Fratto down from Chicago to, run all the gambling in Des Moines and Council Bluffs and all across- Yeah
Iowa. And believe me, those farmers like to gamble. That goes back to Prohibition. The Capone gang had a guy before Louis Fratto- Oh, did they? … around Dubuque, et cetera, running at least eastern Iowa, and then Louis got that. Wow. Or Is it L- Louis, Yeah, I believe it’s Louis F- yeah, who used the name Louis, Lou Farrell.
Lou Farrell, yeah. That was Louis Frato. You’re exactly correct. Yeah. Among the various nefari- nefarious Frato brothers. Yeah, they’re… That, that is… That’s a whole story in itself, isn’t it? And, today there’s a Rudy Frato that’s a high-ranking- Exactly … guy. Yeah. Rudy I believe Rudy Frato is at the…
among the guys at the very top of The Outfit right now. Yeah. That’s, From humble roots sprang the Frato family into all, comedians and [00:36:00] nationally known comedians and mobsters and everything else. It’s an interesting family. Yep. All right. John Binder. His book is The Chicago Outfit During the 1960s.
You got one last story- Thank you, Gary … one last story you find particularly interesting in this book that’d entice people and they wanna go get that book for some other stories like that? Let’s see. We touched on one of the interesting things from the ’60s, which is, of course, the torture-murder of Action Jackson, which was- Yeah
Very well known and shows just what The Outfit’s capable of. Gosh, on this one you caught me a little bit blindsided. One other, particularly, we also talked about that it’s a myth that Gene Kahn and The Outfit elected Jack Kennedy. Yeah. They knew exactly what Jack and Bobby Kennedy were about, that they hated organized crime, and that they had targeted The Outfit at the time.
They were not gonna move a muscle to try and get JFK elected, and it shows if you go look at the the voting [00:37:00] nationally in some ways and around parts of Chicago. There’s no evidence that The Outfit did anything for Jack Kennedy- Yeah … in terms of delivering the votes. Yeah. And in fact, that they probably worked the major labor unions to vote against Jack Kennedy.
Yeah, they wanted to- So there’s your evidence … they wanted to vote for Nixon. But… And just Chicago, talking about Jack Kennedy here in Chicago, Chicago was a Democratic town, and it still is. It’s always been a Democratic city. Yeah. And the bulk of the people are gonna vote for a Democrat. You don’t need to go out and entice them to vote for a Democrat.
They’re gonna do it anyhow. Yes, especially in 1960. A young, charismatic Irish American Catholic in a very heavily not just Irish, but Catholic town, Chicago, that gets you votes. Yeah. So of course Jack Kennedy did better than Nixon, but that’s not… had nothing to do with The Outfit per se- Yeah … doing anything on his behalf.
They couldn’t stand him. Yeah, and then you could probably go back to your earlier [00:38:00] book about prohibition era and dissuade or d- discount that rumor that Joe Kennedy was a big… made… their father made a ton of money in bootlegging. Bootlegging. ‘Cause the way I understand, he- Actually, he ha- he made money out of it after the prohibition was over because he owned all the- Yes
stock in these companies in Seagrams Seven and some of the other high-end alcohol. And then when s- bootlegging or prohibition was over, then he was positioned to then make a shitload of money. That’s the way I read it. Yeah, me too. Yeah, once prohibition is over, then it’s very clear he’s one of the first guys to start bringing Canadian whiskey, et cetera, back into the country, things like that.
But there’s no evidence at all that he was involved with the Canadian distilleries during prohibition. There was a Joe Kennedy who bought a bunch of booze from one of them, but it’s been determined that was another Joseph Kennedy who lived somewhere in Canada, not the Joe Kennedy- Yeah … father of the RFK, JFK, and Teddy [00:39:00] Kennedy.
All right. We’re probably gonna be in a lot of trouble for saying all this stuff, but that’s okay. We like trouble. One last story. Sure, yeah. The Villa Venice. The Villa Venice. The Venice, yeah. The 19- Connors Venice. He tried to… he tried to bring Las Vegas to Chicago, it looked to be like.
Tell the guys about that Villa Venice story. That’s an interesting story. Didn’t last very long, but it’s, Villa… Yeah. The Villa Venice under one name or another that, that place had been there. That was an old roadhouse with obviously gambling and God knows what else. Yeah. Bootlegging during prohibition.
Goes way back. It became the Villa Venice, and Gene Kahn and some of his guys I think were the actual owners. Outfit guys with an interest in the place. And in the early 1960s they got Sinatra and the Rat Pack to play the Villa Venice for I think a week or so. I believe the backstory is at that point Gene Kahn and some of his guys were very upset with Sinatra and the Rat Pack, so they put pressure on them, [00:40:00] as they did on some other stuff, to come and play it and paid them next to nothing to do it- Yeah
as opposed to their usual their usual rate. There, there are stories of Sinatra flying into, if somebody’s daughter, like Accardo’s daughter, is having a birthday party they’d have Sinatra fly into Chicago, sing Happy Birthday at the birthday party, and then he’d get on a plane and get back out again.
In some sense they’re… They didn’t l- they didn’t like him very much for various reasons, and they were mi- mistreating him that way. He probably didn’t get paid for that even, but- Yeah … “You’re gonna come in, and then you’re gonna leave right away. Then you go back, ’cause I said so.” Yeah Mr.
Big, Mr. Big Time. Yeah. For whatever reason, Sinatra allowed himself to be controlled by a variety of different mob people across the whole, New York and Chicago particularly. For whatever reason. I don’t know if we’ll ever know the real reason, but he maybe just liked brushing with, brushing with the gangsters.
A lot of people… There’s people out there just like brushing up against these gangsters, and then being able to- [00:41:00] Yes … go tell stories about how they know- Yeah … this gangster, know that gangster. A lot of people in the entertainment industry the classic example might be, like, Dean Martin.
They put up with those guys ’cause back in the day, that’s who owns major clubs in a lot of cities. They own major casinos. It’s not good for your career as an entertainer if you’re running around publicly badmouthing organized crime. That may cost you some very big gigs. So probably a lot of Italian American entertainers or other entertainers very much, looked the other way, put up with these guys.
But Sinatra really liked to pal around with them would be, just a first level statement. He and Giancana were like this, buddy. Yeah. Yeah. Interesting. All right. John Binder of the Chicago mob- Thank you so much, Gary … during the 1960s. Thanks a lot for coming on.
Been a pleasure. I look forward to taking your… I look forward to taking your tour here in a few weeks. Thank you. And good to good to through this medium meet all you wiretappers and talk to you [00:42:00] guys as well. All right, great. Thank you for listening. All right, John. Thank you. Thank you, Gary.
Thank you so much.