The Most Successful American Mobster EVER: Tony Accardo
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It's 1939. Europe is in a crisis and in Nova Scotia, Canada on a fishing expedition. A Chicago man has just caught a very big fish. It's a 400 pound tuna and the local press are besides themselves. So much so that he's photographed with it, put in the front page of the papers and all that.

Shortly after that photo's in the papers, the Chicago newspapers gain wind of it. And they have a new nickname to bestow on one of the leaders of one of, if not the most powerful organized crime organization in the country, the Chicago outfit. Tony Accardo will now be known as the Big Tuna in the Chicago papers. Yeah, the Big Tuna. A decade earlier though, Accardo earns a very different nickname. This one bestowed by legendary mobster Al Capone.

It's 1929 and Chicago is a bloodbath. The city is deep in prohibition, which means the booze peddlers and the bar and nightclub owners are getting filthy rich. And so are, of course, the organized crime groups that run those rackets. This includes the fast becoming infamous Chicago outfit. Chicago's offshoot of the Sicilian mafia's running things back east. Headed up by none other than Al Capone. But Capone, he's got competition. Like Bugs Moran and his Northside gang.

Moran hated Capone as a competitor and because he hated prostitution, which Capone was heavily involved with. And his Northside gang had been fighting a war with Capone's outfit for years, back when it was headed up by Capone's mentor, Johnny Torrio.

There were numerous attempts on each other's lives, and the outfit even managed to take out the two previous leaders of the Northside gang. Moran had just attempted to kill a member of Capone's gang when Capone commits the infamous St. Valentine's Day massacre, when the members of his gang dress up like cops and gun down seven of Buggs' gang after lining them up against the wall. That's the day the Chicago outfit pretty much takes over the city.

And in the decades that come, for honestly the next century pretty much, the outfit grows to become one of, if not the most powerful mafia in the United States. Taking over the entire city, having its tentacles stretch everywhere from police to judges to politicians, well into the 1990s and 2000s even. But back then, Capone is smart enough to know it was time to escape out of town, which he did right before the massacre went down.

He hadn't completely solidified his place as the Godfather though. And when he's out of town, three of his goons take the opportunity to start telling folks that they're the ones now in charge. Capone hears about what's going on. So when he gets back to town, he throws a party for these guys to show his appreciation of all the hard work they've been doing. He invites them to a dinner at a mob-owned casino in Indiana, just across state lines from Illinois.

During the dinner, the three usurpers are seized by Capone's goons and brought out back. Outside, one of Capone's young up-and-comers, a kid with real promise, beats the three to death with a baseball bat. Capone, watching it happen, says, quote, boy, that kid is a real Joe Batters. And the nickname Joe Batters is born. And Joe Batters? He's going to go on to become arguably the most successful American mob boss of all time. This is The Underworld Podcast.

Welcome back to another episode of the Underworld Podcast, where two journalists who have traveled all over the world bring you new episodes of organized crime stories from all over the globe every week. You listen to it, and then advertisers pay us money to pitch their products to you, the listener. And that's just, that's how the world works.

I am one of your hosts, Danny Gold. I am joined as always by Sean Williams, the bane of all of our existences and someone who we are trying to fast track into becoming an influencer. How is that? How's that working out for you so far? Yeah, I mean, people aren't really going to know behind the curtain how much of a bane of your existence I am today. But yeah, that is the nicest intro you've given me for a while. I mean, I'm concerned my face is a bit asymmetrical. I can confuse chimp when I'm doing questions on camera, but yeah.

You know, whatever. If people want to find us on YouTube, I'm going to be doing a lot more video interviews with some really cool people. So check that out.

Yeah. And as always, bonus episodes, interviews, and more, including a weekly international organized crime news roundup that Sean does every week at patreon.com. That's the end of our podcast for $5 a month to help us keep going. You can also sign up on Spotify and at iTunes. Yeah. And I think Danny's brother Noah finally figured out what we couldn't do in over three years and stuck the merch on the various socials as well, even though Facebook seems to be trying to block us at every moment. So cheers, Zuckerberg. But, um,

Yeah, you can check that out as well. Get t-shirts and shit like that. We'll probably have more information on that, I think, in the coming weeks because we're still figuring that part out.

Now, we're actually going to dip into a classic American mafia tale right here. We don't usually do that, but I spent a lot of time in the Midwest this past year on sort of Midwest mafia-related stories. So this seemed a good one to do. But don't worry, the next few episodes are all around the globe. You know, too often this podcast, it's filled with broken dreams and dashed hopes. Meteoric rises that don't last too long. Yeah, and are soon replaced with devastating fails.

Cautionary Tales brought to you by Cautionary Tales as I like to describe it. But every now and then it's good to do an episode that's hopeful, you know, where things work out at least for one guy, but definitely not the bodies, the trail of bodies and their loved ones that he left behind. But that's where we have Tony Accardo, the big tuna.

Yeah, I mean, that doesn't sound quite as cool in my accent. The big tuna just sounds like some Downton Abbey shit. But yeah, this is going to be a cool one. Yeah, I mean, you probably don't know the reference because, you know, you had the worst version of The Office, but that was like a big running joke on the American version of The Office. I'm sure our millennial listeners appreciate that. Antonio Tony Accardo is born in 1906 in Chicago at a parents who had just come over from Sicily.

His parents were no different from tens of thousands of other Sicilians coming to the U.S. at the time, heading for Boston, New York, Providence, other cities, and yes, of course, Chicago. He's one of six, and his dad's a shoemaker, so you know what that means. He's pulled out of school at 14 to get a job, and he starts working. Actually, I don't know if, like, do we know what that means if your dad's a shoemaker? Maybe you have good shoes for

For some reason in my head, I was like, oh, that means he's not going to finish school, which he doesn't. He gets pulled out of school at 14 to get a job. And he starts working as a delivery boy at a grocery store, which is fortuitous because

Because that year just happens to be 1920, right? And what happens in 1920? Prohibition, which is the best thing to happen to organize crime before the invention of this podcast 100 years later. So Young Tone, as a delivery boy, he starts making deliveries because that's what delivery boys do, Sean.

And of course, the hottest business in town and all over Little Italy, where young Tony is working, is selling booze. Yeah, but that's illegal, right? He can't do that. Sounds pretty naughty. It's definitely naughty, but that's where the money is, my friend. Oh, wow. At 16, Tony hooks up with the Circus Cafe gang, which is one of the various local gangs running around Chicago.

These gangs sort of served as like, you know, the minor leagues where more major organized crime groups would scout out the talents, typical farm team stuff. And it's named after the cafe where they would all hang out at.

One of the more prominent gang members is Vincenzo Antonio Gabaldi, who had changed his name to Jack McGurn, and whose nickname is Machine Gun Jack, which is a sweet nickname, and he takes Tony under his wing after seeing Talented Him. So young Tony starts out with pickpocketing, break-ins, and soon graduates to armed robberies.

while also picking up on the other mob rackets like gambling, which was a huge one, and of course, booze. In 1926, Machine Gun Jack, who is, you know, I'd say much more of a badass than Machine Gun Kelly, he promotes Ricardo to be his driver and personal bodyguard. Machine Gun Jack is seen as like a rising star himself, as a hitman, and he's soon recruited by

Al Capone. Capone at the time is head of the outfit. I imagine all my American listeners probably know this, but the outfit is basically the entire Chicago Sicilian mafia. What ends up being different about

Chicago outfit as opposed to the New York mob is that the New York mob is split into five families who divide up New York City. And the Chicago outfit is never divided. And they end up ruling all of Chicago as the sole mafia, which is, you know, Chicago is a major city. It's obviously not as big as New York, but it's not divided five ways and the competition isn't there. So you can only imagine how powerful the outfit grows to be.

During this period, though, the outfit is engaged in multiple bloody feuds with other criminal organizations, over the millions being made in Prohibition and other rackets, which is why they need hitters like Machine Gun Jack and the Circus Gang. Yeah, that's like something out of a DC comic. I mean, you really do got to hand it to the American Mafia. They got their names down pat, right? Not like those chumps from Taiwan last week. I mean, yeah, but also like...

Half the guys were named Bugs. That was their name for a crazy guy, which is not the best nickname. It doesn't strike fear in my heart. These guys, they get a rep as basically the armory in the outfit because they store and distribute the heavy weapons for their various feuds. Capone rules the south side of Chicago but wants to expand to the north side where there's a very lucrative speakeasies and gambling halls.

But the North side is run by Bugs Moran and his mostly Irish gang. Capone is planning for a real war. So he asked machine gun for some more soldiers and he puts on a Cardo who starts out as a lookout, but is soon promoted to being a driver and bodyguard for Capone himself. And then all hell just sort of breaks loose. Shoot arts are happening all over. You know, they got the Tommy guns hanging off the cars and all that. Mobsters are being dropped left and right. 30 are killed in the first four months of 1926. In

In September of 1926, a bunch of mobsters pull up on Capone as he's eating lunch and hundreds of rounds of machine gun fire are sprayed all over the restaurant.

When the gunfire starts going off, Ocardo pushes Capone to the floor, jumps on top of him like Secret Service style or like Furio does. Furio? Furio. Furio does in The Sopranos. And this story turns into like Chicago mob lore. So we don't really know how accurate it is. But what we do know is that Capone is very impressed by the young tone. In 1929, with Capone still battling the Northside Gangsters led by Bugs Moran,

So that's basically also when the St. Valentine's Day Massacre occurs that we just talked about. Seven members of the Bugs Moran gang are killed, and Capone and the outfit basically take over. Segway, as I mentioned, I was interviewing or spending time with some prominent Midwest gangster mafia guys, basically, who are all

One of them happens to love Al Capone. He's in his 70s, and he was trying to tell me that Capone was actually innocent, and it really was just cops who did the massacre, which is definitely not true. Yeah, you got your Swifties, your Capones. I mean, we've got some really weird Mencho reply guys on the YouTube videos as well. Yeah, those guys need to log off. Yeah, I mean, if you're watching Tokyo Vice, a big thing about that is the fanzines they had for the Yakuza guys.

But they rarely murdered people. So there's a lot of fanzines for... I don't know if fanzine is the right word, but online fans of the various cartels, which unless you're in the cartel, seems like a weird thing to be a fan of. But to each their own. We'll find out. We've got Jake Edelstein on the show soon. So we'll ask him about some of that. I think he's pretty into it. Lots of Tokyo stuff, but the cartel stuff just is...

But I guess to each their own, like you like cricket, these guys like cartels. They're both very weird. It is what it is. So yeah, that's when the Joe Batter story happens, right after the massacre. And for the next few years, Ocardo's name pops up in a lot of gangland murders. But of course, Capone doesn't last long. They get him for tax evasion in 1931, and he's replaced by Frank Nitti, who bumps Ocardo up to a captain.

Ricardo then handles all the gambling rackets, which, you know, get a lot more important when Prohibition ends in 1933. Side note, which is, like, why didn't any of these gangsters ever think to get involved in legal alcohol? Like, was it just not as profitable then as it is now? Because I imagine, obviously, it's not as profitable as it was during Prohibition, but, like, how...

How many athletes and actors and rappers have made hundreds of millions of dollars on just terrible booze? Yeah. And why aren't we making any money off terrible booze? We're right here. We're right here.

We should get on that Bud Light train, right? Fuck, man. We've been blowing it left and right. Ocardo, he shows some genius with the gambling. And also, you know, he's pretty chill. He's not flashy. He's not out there like Capone. He gets married. He adopts a kid. He keeps a low-key personal life. A mob historian said that Ocardo had a higher intellectual capacity than most of his contemporaries and saw a bigger picture than, say, someone like Capone, who was essentially kind of just a thug.

He expanded organized crime in Chicago into new ventures. And by the end of the decade, there was nearly 7,500 mob-controlled gambling houses in the city, which is an insane number. But, you know, there's like 15 apps on my phone that I've used for gambling. So I guess it is what it is. How's it going? How's it going? Not so good. Not great. It's actually, it's harder. You think if you just keep winning...

you'll get really rich, but then it's hard to keep winning. That's the top piece of advice there. Then Nitty really bumps him up to the big leagues, which is organized labor, getting involved with the unions. The first target is the union of motion picture projectionists, the dudes who run the film projections at movie theaters. The president of the Chicago local of this union already had his own scam going with kickbacks from theater owners, and if they refused, he would have his union members not show up to work.

Nitti liked this racket he wanted in, but the Irish Union had refused. So Nitti called on Ocardo to take care of this problem. Ocardo was not only a captain in the outfit, but he's also viewed as the chief enforcer.

So he and one of his guys take out the union head with a drive-by shooting in broad daylight, and the union is now controlled by the outfit. You really got to wonder if it's worth standing up to the entire mob just to keep the projectors union going. I mean, I don't know. I don't want to shit on anyone's career, but...

That seems like a pretty bad bet for me. You heard it here, folks. Famed left-wing activist Sean Williams hates unions and wishes they would just give up. I mean, frankly, Sean, I'm appalled at your behavior. I'm apolitical, as we all know. Yeah. We talked a lot about how the mob got involved with unions, I think, in the Murder, Inc. episode, which focused on New York. But let me just simplify it real quick.

Back in the day, the bosses of whatever it was, warehouses, carpenters, whatever it was, construction sites, they would hire thugs to break strikes, right? And soon the strikers themselves started hiring those same thugs to protect them and shake down bosses.

And then, you know, the old saying about letting the mob help you. It's very true. Next thing you know, you've got Teamsters loaning out hundreds of millions of dollars of their pension funds to buy corrupt casinos. But that is a story for another day. And a very simple version of that. But yes, the mob gets really involved with unions. I would say, I don't even know how to specify it, but like 1920s, 1930s, I think around that phase would be pretty accurate.

Nice.

That's a bit close to the bone. Fucking hell. Yeah, I wonder if Dale picks up on that one. Also, are we calling projectionists creatives? Do they get in the crowd? Do they get to wear skinny jeans and shit? I don't think the word creative was invented until like 15 years ago, but maybe, I don't know any modern day projectionists, but maybe they'd call themselves that. I don't know, man. So Nitty and The Outfit, they're looking at Hollywood with their sights set on the international alliance of stage employees.

This is a massive union. It's controlled basically all the unions that had a hand in making movies, from the sound guys to the carpenters on the set to set designers and all that. And California, too, was wide open back then. The outfit then infiltrates enough of these unions that they start making demands from studio heads for hundreds of thousands of dollars in payoffs, which is the equivalent of millions today, or they would just shut down productions and movies.

The studio heads, they see no way out of it. They pay up. And over the next several years, the outfit brings in $2 million just off this racket alone. However, all good things come to an end. And in March 1943, pesky feds indict Needy and his underboss, Paul Rica, and several other mafiosos on charges related to these extortion attempts.

While Ricardo was the guy who kind of did the hit and got them really back into the union game in Chicago, he was still just overseeing the massive gambling operation at this point. He had little to do and almost no involvement in the extortion scheme out west, so he kind of skates by easily. And that's something we'll see he's very good at. He just kind of is always under the radar and always able to stay out of trouble, no matter how big he is.

At that point in 1943, he also has two more daughters. And this is important to note because one of those daughters will be instrumental in launching one of the great mafia NFL dynasties of our time. Oh, cool. I have a question, actually, speaking about staying out of trouble. Like, were none of these guys getting drafted into the war? Did the US have conscription for the Second World War? Because this is like right when especially the Pacific theater is heating up.

They did. I think some of them did. I don't know whether the top guys, Chicago outfit, I'm sure they had ways to get out of it or they were older at that point, but they definitely, cause these guys weren't, they weren't in their, in their teens or in their twenties, I think. Um, but yeah, I mean, I'm pretty sure there are stories of, of mafia guys going off into the war.

or even like, you know, controlling the ports and all that. But I think they were mostly the top guys were in their 30s, 40s. So I don't know if they would be drafted, right? That was always someone in their 20s. Yeah. But honestly, I have no idea at this point. But back to this, a day before those indictments come down about the extortion stuff out West, there's a big meetup of the outfits top brass. And Nitti at this time, he's the boss, but he's in his 50s and in bad health. And has only ever done a few years for tax invasions.

So his underlings, they want him to take the fall to keep the outfit going strong by just sort of taking all the blame. So they give him two choices. Either he takes the fall or they're going to take care of him. It must be nice at that point, just threatening the boss, but I guess they could get away with it. Nitty wasn't interested in going to jail again, so a few days later, he just offs himself, kills himself, and that's it. He's dead.

That was good. You think so? Yeah. Nitty, can we say that? Do you have to say unalive yourself to get past the censors? But yeah, I mean, it seems a little dramatic for like a 15 year sentence, which you could probably get off earlier for good behavior. But maybe he was really sick. I don't know. It just seems a little over the top for me, you know?

But with him now dead, Paul Rica, he takes over as boss, and our guy Tony Accardo is now the underboss. And I got a note here that some mob historians believe that Nitty was always just the front, and that Paul was actually the real shot caller throughout the Nitty as boss era. There might be some truth to this, but we don't really know for sure. And remember, just because Nitty is no longer alive...

doesn't mean Paul is home free on the movie studio extortion case. In October of 1943, he's sentenced to a 10-year prison stint along with several other top outfit figures, leaving only a cardo who takes over as the street boss, acting boss, whatever you kind of want to call it, when Paul's locked up and all the other outfit figures are too. And this happens when he's only 37 years old. So yeah, I guess, you know, when would the draft have been? 41 or 43? Because 41 is Japan. Yeah. Yeah, I mean...

Guy in his mid to late 30s, I don't know if he would have been... I mean, I know men like that were, but probably not early on. I don't know, man. Honestly, I have no idea. I'd be interested to learn more about that. If you're one of our listeners and know more, email us and we'll...

say something about it. Just read it for our own. And we will at least skip it over in the email inbox. Well, no, for our own knowledge. It's good for us to learn stuff too. I'm just really into the problematic stuff you're saying about mental health at the moment, considering the current climate. Maybe he was traumatized by...

watching some TV show or he was sapiosexual and he couldn't get by in jail. I don't know. You never know. I actually, I really wonder back then what the situation was like for bosses in prison with communication. Like it must have taken forever to get any info in or out or was it easier? There's no cell phones, but like...

I don't think they were as strict as they were in terms of communication, but it, I don't know, but it does make sense that he would be forced to relinquish power if he's just out there. Cause you can't make day-to-day decisions, right? When you're in prison the whole time and there's no cell phones.

Paul, though, gets out of prison in 1947, only four years into his 10-year sentence, but Ocardo officially remains boss. And this part's actually kind of interesting, too. It's generally understood that Rika and Ocardo enter in a power-sharing arrangement that would last decades, which is unheard of. Most of these guys refuse to share power with anyone. This sort of thing might come about in conversation, and then someone gets killed right afterwards. So it's really, really rare for something like this to occur.

Rika, he kind of plays the background, but they say that he was kept in the loop on any major mob moves and any murders that were ordered. And he remained extremely powerful in the outfit as basically a senior consultant, while Ricardo ran the day-to-day operations. Again, it's just a really unique situation and pretty much some

Something I haven't heard a lot about in all of organized crime. Ricardo then, he expands his gambling operations into Northwest Indiana. I mean, I wonder if any other non-Americans have this, but I always think about if I had to name all of this 50 states, like which one am I most likely to miss out? And it's probably Indiana. I mean, like they've got the Colts. Is that it? I don't really know anything about that place at all. I'm really sorry to our one listener from Indiana, but is that a big prize for the mob? Northwest Indiana? Yeah.

I mean, I assume so because Chicago is right on that border. Like I said, it's the northeast border. So suburbs and all that. Although the only place right there that I've been to is Gary, Indiana, which I do not recommend at all.

as a tourist destination. Oh, yeah. It's like the worst place in the world. Or any other destination. I think it was one of the most dangerous places in the US 10, 15, 20 years ago. I don't think it's as dangerous right now, but it's still probably not a great place to go. Also, I believe it's where Michael Jackson grew up. Okay. So it's the worst place in the world. I mean, we can just say Indiana sucks, right? I'm sorry if you come from there, but we don't want you listening to the show. We don't want you anywhere near us.

Stop it. I'm sure we have at least a couple dozen listeners out there and we need every listener we can get. I disagree with Sean. Indianapolis is cool, man. I spent some time in Indianapolis a couple days.

And we got the Mannings, right? Everyone loves the Mannings these days. Anyway, Ricardo creates a very corporate style way of governing the outfit with him as the chairman. Then he's got lieutenants all over in charge of different counties and numerous states. Plus he had treasuries. They all had lawyers. He was like a real businessman type, which is interesting because he really does start off as like this brutal hitman thug type of guy who literally beats people to death with baseball bats. But he's a really smart sort of future man

looking at, future looking at, full of ambition, you know, the kind of person that you wouldn't associate with being like, you know, a shit kicker. Throughout the 40s, Ocardo just ramps up the gambling operations. He's placing slots in bars and gas stations and restaurants throughout the territory. They also expand into narcotic smuggling, counterfeiting cigarettes and liquor smuggling.

tax stamps, all that sort of stuff. You know what? I'm being too harsh on Indiana because I just remembered I met a Native American chief at Stonehenge with a bunch of Druids years ago and we smoked a joint. And that guy was ace. So I like Indiana now.

Was he from Indiana? Yeah. Yeah. He was some chief from a reservation there. He was cool. Yeah, because you left that out in the initial. All right. In 1950, we were losing our minds as episode. Look, it's Friday night. What is it? Saturday morning there. You know, bear with us. It'll all be over soon. In 1950, we get one of these Senate hearings, which is, you know, the thing that they used to do at the time. I

I think we've mentioned it in a bunch of other American organized crime episodes we've done. They do it even into the 80s with like Russian and Asian crime groups, but there are these fascinating slices of history at that time. I think the most infamous is the Valachi hearings in 1963, where a former mafioso admits the existence of the mob to everyone, I guess, the general public and all that, who, I guess it was like a known thing for a lot of people in these cities, but it wasn't like a nationally known thing back

then. No, it was like the first time that someone had broken a meta, right? Which is the code of silence ever in public. And he was like spilling all kinds of shit about their rituals and background of people. It's really interesting. I thought, I just looked him up and uh,

He, I thought, oh man, you're going to be dead within a week of this. But he actually killed a guy in prison himself shortly after the hearings and died age 66 behind bars. So must have been a pretty handy street fire. Yeah, I mean, he, because that was back when they actually carried that stuff out and you couldn't just start a podcast after, you know, after you testified, but...

Those hearings, you can find some of them on YouTube when you search for it or in various archival things that are out there on the internet. They're pretty crazy to watch. Imagine...

Now, senators... I mean, it's funny to watch senators interview Mark Zuckerberg or the TikTok guy, but watching them interview killers that are... It would be pretty amazing. I mean, I can't wait for a Michael Francesi podcast with an AI Joe Valachi that's going to be great next year. Or just even now, like...

some, some 85 year old Senator, just like asking some 17 year old Bronx drill rapper, like what's going on and seeing how they interacted would be incredible. We should make that happen. That should be one of our goals for, for the next year. But this, this, this is like one of the first committees. I think it's a Cavalier. I don't know if I'm spelling the same guy's name, right?

He's the senator that chaired it. And usually these just consist of senators asking mob guys questions and the mob guys just completely refusing to answer. But they usually do come with witnesses that do end up talking, and it leads to the general public kind of getting a sense of these things. So at this point, Ocardo is the head of the outfit. He's considered one of the most powerful mob bosses in the country, and rightfully so. And the committee was a traveling one, so they went from city to city holding these hearings.

So Tony Ocardo and most of the top underlings, they vanish when these guys get to Chicago. Tony goes to Mexico, but the committee just like waits him out. And six months later, he finally testifies. And he, of course, refuses to answer anything and pleads the fifth a bunch that

The two findings from the committee is that there are two big organized crime groups, one in New York and one in Chicago. Whole lot of other smaller ones probably, but I don't think they really get too much into that. With the hearings, Tony gains a sort of new visibility, but he's still very cautious with the press. He acts like a gentleman with reporters. He tries to be as low-key as possible, which with all that, it's actually a very good strategy that I'm surprised more people in his position don't do.

He adopts another child at this time, still keeps it low key. He fishes, he golfs, he even enjoys wintering in California. He did have one indulgence though, which is they initially live in like a modest house as family. But in the mid fifties, he upgrades to just a giant mansion that costs $150,000 in Chicago suburb, six bedrooms, indoor bowling alley, indoor pool, which is, you know, pretty tight.

Yeah, I mean, I know 150K is probably like $50 billion these days, but six bed, pool, bowling alley. I mean, you know, can you get that nowadays for a few hundred grand? I'm not going to stop eating avocados, basically. So.

Yeah, screw the police. Northwest Indiana, you can get a house like that. Oh, yeah. Well, I'm never going to step foot in that shithole, but yeah, maybe somewhere else. So he catches a little bit of flack from the outfit because he would constantly preach to his underlings to be low profile, but sometimes they're stacking cash and just kind of ball out a little bit. But just to emphasize how low profile he kept, this is a quote from the Press and Sun Bulletin paper in 1961.

Capone was well known as a matinee idol. Ricardo, by design, could walk through Chicago's Loop tomorrow at high noon and not be recognized by one out of 100 people. And later in the same piece, Ricardo was the head, the absolute head of the Capone mob.

Capone was powerful, but Ocardo's power exceeds that of the feudal lords of old. That's a good line. Also, I mean, I'm just going to call BS on the matinee idol line. Capone was a tough guy, but he looked like a thumb, man. The guy's TikTok game would have been shocking. I don't think they mean it like that. I think they just mean it in terms of not how good looking he was, but in terms of the attention that he got or could get wherever he went. You know, like he was...

Like the John Gotti of back then. In 57, Ricardo steps aside as boss to become the consigliere of the organization. And Sam Giancana is anointed the new boss and the person now responsible for running the day-to-day operations. But again, he still has to get all the major moves and hits approved by Paul and by Tony. I like how I call them by their first names, like we're just buds. Like, yeah, Paul and Tony. They had to approve everything.

Now, there's two competing narratives when it comes to this move based on contradictory sources. The first is that with this newfound publicity and, you know, Ocado describes as heat, specifically from the IRS, he wants to lower his profile even more in Giancana, who is his protege, takes over as boss. But in reality, it's more of a front while Ocado and Rica remain the true powers of the outfit. The second narrative is that Rica actually demoted Tony and Ocado was unhappy with the decision, but it

but accepts it. And in this telling, Giancana is Rica's protege. I tend to believe the first narrative that Ocardo himself decided to step away due to IRS investigations, which, you know, he does end up at a trial for tax evasion in 1959.

But they'd been in this power-sharing agreement for like 15 years, and Ricardo saw Rica move more into the shadows and maintain his power and money. So he probably thought it looked like a really good idea, a safe idea. And I actually doubt that Rica would demote him, even if he had the power to do so, which we don't know that he did after such a successful partnership that's lasted this long. And Rica had great respect for Ricardo. According to a 1984 Chicago Tribune article, he said of him...

Ocado had more brains for breakfast than Capone had in a lifetime. You don't get lines like that in newspapers these days, and we are

way poorer for it. I mean, I guess your New York Post days, you must have had some bangers there, right? Yeah. Yeah. You could print quotes like that, but yeah, man, it was a better time. And Tony, at that point, he seems to step back at the right time because in 1958, he's called to DC for yet another Senate hearing where he takes the Fifth Amendment 170 plus times. And then in 1959, they're both charged with tax crimes. Really?

Rika gets convicted and serves 27 months in jail or prison, I guess, if it's 27 months. And Tony Accardo is charged with filing false tax statements because, and get this, his fake job is being a beer salesman. And on his tax forms, he deducts his car as a business expense, which...

It's hilarious when you think about it because he's like a top guy at the outfit who's been making millions of dollars for close to two decades now, but he couldn't resist just deducting his car as a business expense, which is classic and just kind of shows you how these guys work. Like wherever they could finagle a dollar out of the government, they would just do it. Ricardo's convicted. He's sentenced to six years, but before he ever sets foot in a cell, he wins an appeal for a new trial. And his lawyer argues that all these negative stories in the press, they taint the trial.

During the retrial in 1962, his lawyers are really well prepared. He's found not guilty and he gets off. He still doesn't like the attention from the press or law enforcement and some internal pressure from the outfit kind of gives him a hard time too. So he moves away from his mansion back into a smaller house. Rika gets arrested for tax stuff again in the 60s and he's in his 60s. So he basically takes a backseat

Giancana is the boss now anyway, and he's like Capone or, you know, God, he was flamboyant out there dating pop stars, having JFK killed, trying to kill Fidel Castro, all that sort of stuff. But also just being watched closely by the feds who really start upping their wiretap game around this time period. And through these wiretaps, we gain a little bit of insight into the relationship between Ricardo and Giancana.

Yeah.

He ain't worth it, mate, is how it would go down. Yeah, I mean, it's good advice. I mean, that's the kind of guy that he was, right? He's cool. He's calm. He's collected. Basically like me and the opposite of Sean, who is fiery tempered and just full of rage. He's just a spicy, spicy man. Genuinely true. Yeah.

By then, Giancana, he's getting a rep for making bad... I like it's just now it just devolves into jokes between me and you at each other expenses that no one in the audience even cares about a little bit. I am actually going to smash some of this equipment up after the recording. So I'll send some pics. By then, Giancana, he's getting a rep for making bad decisions and being irrational.

Also, like me and Sean. And the Fed surveillance is just getting to him. He actually sues the FBI in 1963 saying they were violating his rights by harassing him and invasion of privacy and all that. And there were, there's tons of stories about illegal wiretaps back then. He even hires a film crew to film the FBI while they're following him and he shows it in court.

Either way, the outfit folks, including Ricardo, they're just getting tired of his behavior. And I got to say, I'm working on a separate project that deals with some pretty violent members of the outfit up through the 70s, 80s, and 90s. And those guys, man, they just had a habit of killing each other all the time for little slip-ups. It really seems...

like a very dangerous and psychotic and unforgiving group on a level that other American mobs were. And other American mobs were pretty brutal. You know, when you see everything that happened, like, you know, with Goodfellas and all that, not the movie, but the book that it's based on and everything, like it really was a lot of friends that just were killing their friends for various little things. Even with that, when you read about the outfit and went on there, it takes it to another level of brutality. Yeah.

So Giancana, moving on. So Giancana, who was also not distributing some funds to outfit members who needed it, guys who were on the lam or whatever else it was. So he's starting to ruffle feathers with people whose ruffle feathers lead to you getting murdered. In 1965, Giancana, he's in another one of those Senate hearings. He gets bagged for contempt for a year.

Ricardo Enrique immediately replaced him as boss with Joey, Joey Doves Ayupa. Joey had actually got a start in the outfit back in the 1920s by being a driver for Ricardo. And when Ricardo was named captain, he elevated him to his crew. So these two go way back.

When Gene Conn is released a year later, Ricardo and the senior leadership, they've had enough. So they basically exile him to Mexico due to his high profile and unsettling behavior. Like I did with Sean in New Zealand after a few too many stories from the Berlin club scene. We were getting out of him back in 2022. I mean, getting exiled to Mexico. That's I can think of worse things in life than that. But I don't know. Maybe you just wanted to just really love killing people. So it wasn't for him.

Especially back then, man, like the glory days of Acapulco. But in 1972, Paul Rica dies. He leaves Ocado all alone as the ultimate authority in the outfit. Side note, this is an amazing Ocado story. To highlight once again how publicity-averse that he was, there were two Italian professional wrestlers who came to town and they wrestled as a mafia-inspired tag team called the Sicilians. And Ocado...

persuaded them to drop the gimmick because he didn't like it. I mean, obviously today that would never happen because Vince McMahon, he's more of a psychopath than a mafia boss, so they would have to back down. He tells them what to do. While in exile, Giancana opens up gambling operations on cruise ships in Guatemala and Iran somehow. However, he doesn't send any money back to the outfit, which makes Ricardo pissed off and other top outfit members, they're not too happy with it.

In the early 1970s, the Senate starts investigating the CIA illegal operations, which include the Giancana Castro assassination conspiracies that we talk about on the Marcello episode from a few months back. And the Senate, of course, they want to hear from him. Yeah, you guys should, if you haven't listened to that one, go back. It's what, like six, seven episodes ago, exploding cigars, mobsters left in trash cans. It's great, especially because I think I was recording it at 530.

5 a.m. in a P&G hotel room. So my performance, as it is today, is absolutely incredible. So Giancana, you know, he gets sent back from Mexico to testify. He returns back to Chicago in 1974 with the church committee, which is what it was called. That's expecting to get going in 1975.

But as we talk about in that episode, he's gunned down in his home by someone who was close to him. News articles immediately theorized that he was taken out maybe by the CIA. Was it because the outfit was scared that he was going to talk? And we get the probable real answer in a quote from a 1977 New York Times article. Mr. Giancana was killed because he tried to reassert his authority in Chicago after a 10-year absence.

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The 1970s is also when the outfit gets involved in Vegas, where they end up making some good money. Vegas always had this mob presence going back to like Bugsy Siegel, Moe Dallas out of Cleveland, Kansas mobs, Milwaukee mobs, Florida, all the mob families that had casino investments at one time or another for a few reasons. The first is that Vegas was an open city, meaning no mob had claimed to it and everyone could get their hustles on. And the second was that for a long time, Wall Street, banks, everything was open.

Everyone with money wanted nothing to do with Vegas investments casino-wise because it was seen as improper, too sleazy, too risky. Definitely not like it is now. So a lot of mobs would use their influence, you could say.

with the labor union pension funds to then loan out money to people who are building or taking over casinos in Vegas. If you've seen Casino, you kind of know what it's all about. No, I've never seen it. Were the Indiana mob involved in any of this? It doesn't seem so. I think the Chicago mob dominated the Indiana mob. Oh, yeah, of course. But I'm actually, I'm working on a doc series podcast about some of the guys involved with that particular play, The Argent Enterprise. Yeah, let me rewind a sec to when Chicago and Ocado first really got involved. Yeah.

which was the Stardust Casino. It's a resort. It's being built in the 1950s by a bootlegger turned gaming magnate who previously had mafiotized casinos that went belly up.

Tony makes a secret investment in the Stardust in 1954 among a bunch of other people. The builder actually runs out of money. He gets multiple loans from various other mobsters. That's the first of multiple casinos where Cardo has a piece. The major one, though, is which casino is based on and the Doc Shares podcast I'm doing too. It's the Argent Skim, and that's where the Teamsters Pension Fund, Central State Teamster Pension Fund, gets convinced by the Milwaukee mob with a little help from Kansas City and Cleveland to

to make $90 million worth of loans to a small-time real estate guy named Alan Glick, who buys up four casinos, which the various Midwest mafias own pieces of, and they steal from it off the top with the help of Lefty Rosenthal and with protection of Anthony Spolatro. Those are the characters that...

Bobby De Niro and Joe Pesci play in Casino. Basically, the guys are based off them. Eventually, Chicago gets involved. There's multiple stories of how and when, but most center on a dispute between the various mobs. And Chicago is kind of brought in to be the boss to calm things down and, of course, take a healthy piece of the action for their work doing that. The skim is worth millions of dollars a month, and it ran for years with Tony Accardo in the Chicago outfit getting the biggest taste of the profits and just completely running the show.

So yeah, you could say the outfit is doing really, really well. And they've expanded nationally. And basically, they're the most powerful organized crime organization west of the Mississippi. Maybe even overall, with New York being split five ways. Gene Conn is out. Joey Ayup is in. And Ricardo is just sitting pretty. Maybe even calling a lot of the shots. And by the late 1970s, multiple top outfit members and a number of Chicago mobsters, they purchased homes in Palm Springs, California. According to a 1978 Chicago Tribune article,

The outfit had invested $50 million into Palm Springs and 45 mafia members had homes there, including 32 from the outfit alone. These mobsters included Iupa and a Cardo, which is, you know, kind of hilarious when you think of these guys in this sort of rich retirement community. I guess now it's kind of like a hipster spot as well, but yeah, yeah. Them just having like a, there's a sitcom there, you know, something along those lines. A Cardo basically retires himself.

He spends most of his time in Palm Springs, occasionally flying to Chicago to mediate big disputes and for sit-downs. By this time, his personal holdings include legal investments in commercial office buildings, retail centers, lumber farms, paper factories, hotels, car dealerships, trucking companies, newspaper companies, restaurants, travel agencies.

He's been at the outfit at the top of it for basically 40 years and just has diversified everywhere. He's still a mob guy through and through. And in 1978, when he's in Palm Springs, burglars break into his house. I guess he wasn't there. They ransacked it. They robbed the place. Within a couple of months, seven people that are connected to it are found brutally murdered. So yeah, he could still get things happen, even though he was technically retired.

I mean, this is real good old days if mobsters are running newspapers. I guess that's one way to revive the media industry. I'd be well up for that. But also, I spent a night in Palm Springs once. It's such a nice place. I really enjoyed it. Like robbing a house in Palm Springs back then is like ultimate street gang Russian roulette. So it could be some retired old trust funder or it could be a bloodthirsty like 60 year old gangster. I mean...

You know, I'm down for it. Yeah, imagine they rob that house not knowing who it was. Like, my assumption is they knew who it was and thought they could get away with it. But, uh, just a major, major faux pas there. Yeah. The thing with Ocardo is organized crime bosses who kind of reach the heights like him, they don't retire usually, right? They either get killed as boss, go to jail, or in some rare examples, die from natural causes. I think Meyer Lansky would be one. And I think another one would be, um, the original founder of the Gulf Cartel, Don Juan, I think it is. Yeah, yeah. He's semi-retiree.

But his nephew is a family member who takes over, not other people. So Tony Accardo, he just must have had this ultimate respect in his Chicago outfit. Not just because he wasn't taken out, but because mob guys are notoriously greedy and we got to assume he wasn't still participating at the stage for free. You know, he was getting money because at some point, you know, one of the bosses doesn't tell him just to get the hell out of there or just kill him and take over what was his.

In 1984, he's basically like just a grandpa, you know, like a mall walker. He's hauled before another Senate committee investigating labor racketeering. He says a little bit more, but he's still cited for contempt. Somehow, though, like always, he avoids big trouble. And two years later, when Joey Aipa and a whole bunch of top alpha and other Midwest guys get convicted or forced to plead in the Argent Casino skim trials, he too is kind of somehow not brought down with them.

Ricardo by then, he's barely spent any time locked up. There's also been no major attempts on his life throughout his career as a boss. He's legit retired and living with his daughter and son-in-law in their home. He's got heart disease and he eventually dies of that in 1992 at the age of 86, which, uh, yeah, like massive kudos to this guy. He's got the whole thing going on, right?

Get into real estate, get into legit businesses, keep your head down, don't IG your crimes, like die peacefully in your 80s, rich, absolutely nailed it. Yeah, and that legacy, I mean, that's why many consider him to be one of the most, if not the most successful American mobster of all time, right? It's one thing to be super successful and then get murdered at 45. It's another to be super successful and retire and then die in your home with your family and in your 80s.

I mean, there could be an argument for him being one of the most successful organized crime figures of all time, especially in the age of wiretaps and Ricos and FBI and other countries' equivalents to the FBI. But legacy, he ends the game with a boatload of cash. He didn't live lavishly and diversified like crazy. And how's his family doing today, which is a big question. Are they still wealthy?

They're better than wealthy, Sean. They're in the NFL, the most dominant force in American culture besides Taylor Swift. Maybe tied with Taylor Swift. Yeah, it's the same thing. Yeah, none of his children get into organized crime. His daughter marries an NFL player, making his son-in-law

an NFL player. And then the next generation, his grandson becomes an NFL player. And finally now, his two great-grandsons aren't just in the NFL. They're not just regular players. They're the Bosa brothers who both played defensive end. One's second overall in the draft. The other's taken third overall in the draft. Both were named Defensive Rookie of the Year in their respective classes. Joey Bosa, I think, signed a five-year deal for $135 million in 2020 for the Chargers. And Nick,

was named not only Rookie Defensive Player of the Year, but Defensive Player of the Year in 2022. And before the start of his season, signed a five-year, $170 million contract, which is the highest of any NFL defensive player in history. So yeah, I mean, the Ocado family tree, they're doing pretty well. And yeah,

I mean, my little brother helped me with this paragraph because he's a diehard NFL player, but they're doing good. Do they talk about this much? Because I've even heard of the Bosa brothers, so they're huge. I had no idea they were mob royalty. I assume they don't bring it up often, but if they want to do a podcast, we're here for you guys. Can one of them please take Taylor Swift off of Kelsey so we can get that?

fan base as well. If you want to reach one of the top five or 600 podcasts in the US, like we're your guys. Forget Rogan or call her daddy. Like we're the guys to talk to. So yeah, to recap, all-star NFL great-grandchildren making more money than any modern day criminal in the US could dream of. Probably internationally too, besides like a couple of actual mafia guys in Italy, Gamora guys and cartel bosses and some Asian meth and heroin kingpins. No real jail time.

Semi-retired, not do day-to-day operations, all the stress until he dies like Carlo Gambino. So I think, yeah, the battle between him and Carlo Gambino, he comes out on top and his family is definitely way richer now. Although the Gambinos are doing well from what I understand. But there you have it. The most successful US mobster of all time. Yeah, and I'm going to go off and research making an Indiana Sucks Bulls t-shirt, which I think will do really well. Don't.

Don't start. But yeah, thanks for bearing with us, folks. Until next week. Patreon.com, all the other stuff. ... ... ...

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