cover of episode The Rise and Fall of Al Capone

The Rise and Fall of Al Capone

2023/7/26
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This program is presented solely for educational and entertainment purposes. It contains mature adult themes. Listener discretion is advised. It's October 5th, 1931, and Alphonse Capone glides into the federal courthouse in downtown Chicago. He wears a tailored mustard suit and is flanked by his personal bodyguard. The courthouse can't help but stare.

Al smiles at the jurors as he passes them by. Since his cushy plea deal was rejected back in June, Al's team has worked hard to line the jury's pockets with $1,000 bills or show up unannounced to their homes and charm them by other means. Al confidently takes his seat, surrounded by three of his well-paid attorneys.

At the bench, a bushy-browed Judge James Herbert Wilkerson appears. It's he who, to the shock of everyone, had rejected Al's guilty plea to tax evasion two months prior. "No one is to bargain with federal law," he had stated, and he isn't done bringing Al down to size. Wilkerson looks out over the crowded courtroom. He calls the bailiff to the bench.

Judge Edwards has another trial commencing today, he tells the bailiff, but loud enough for the court to hear. Go to his courtroom and bring me his entire panel of jurors and take mine to him. Al's face is tactfully neutral. The mighty man sits still in his chair as the jurors file out. But betraying him, the first beads of sweat begin to appear on his forehead.

Al Capone, the most notorious gangster in history. In the 1920s, he had the entire city of Chicago under his thumb. His criminal empire encompassed gambling, prostitution, and bootlegging, fueling a campaign of violence the likes of which the United States has never seen before or since.

But he wasn't invincible. And his plummet from grace was just as mighty as his ascent. Capone was a legend in his own time, to use the cliche. He understood that fame can help make you bulletproof. He provided soup kitchens for the homeless. He bought milk for all the schoolchildren in Chicago.

But ultimately, it doesn't detract from the way Capone made his money. There was a determination to get rid of Capone. Capone just didn't see the disaster that was coming his way. In this episode, we speak to historians and enthusiasts to understand the trajectory of Al Capone's life and legacy, how his unique qualities led to both violent triumph and crippling failure.

You're listening to Forbidden History, the podcast series that explores the past's darkest corners, sheds light on the lives of intriguing individuals, and uncovers the truth buried deep in history's most controversial legacies. This is The Rise and Fall of Al Capone.

Alphonse Capone was born in New York City in 1899 to Italian immigrants Gabriel and Teresa. His father was a barber and his mother a seamstress. They brought Al up to better himself through hard work and education, and he did prove to be a fast learner, but he was also a brawler, and during sixth grade, a fight with his teacher led to him leaving school for good.

For a first look into his early life is author and historian Tony McMahon. Al Capone was undoubtedly a very clever child and apparently very good with numbers, but he preferred life on the streets to life in the classroom. And he seems to have balked at rules and any attempt by teachers to control him. And on one occasion, a female teacher struck him and he struck her back. And that was basically the end of his education.

His father tried to put him back on the straight and narrow by setting him up with a shoeshine business. But despite his best intentions, this proved to be Al's gateway into a world of crime. It was while shining shoes that Al observed a gang extorting protection payments from local businesses, and it inspired him to try the same thing, albeit on a smaller scale.

He took protection money from the other shoeshine boys and employed two of his older cousins as heavies. Al's cousins were bigger than him, but crucially, not particularly intelligent. Employing people heavier but not cleverer than himself was to be a model that he followed for the rest of his life. But more specifically, his efforts brought him to the notice of Frankie Yale and Johnny Torrio.

Torrio in particular saw potential in the young Al Capone and started using him to run money.

Capone's natural ability when it came to numbers, and his scrappy violent nature, saw him rise to the top of the pile. Now a teenager, Torrio gave him an insight into more and more of his other businesses, from prostitution to extortion. Capone's responsibilities came to encompass visiting Torrio's brothels and collecting the money they earned, and he may well have started using the prostitutes himself.

With women and sex available to him, he indulged from a young age. To explain further is author and historian Hallie Rubenhold. Al Capone had a huge appetite for women and a huge appetite for sex. And he wasn't especially particular. It was just really any woman, anytime, anywhere, Al was game.

But towards the end of 1917, while working as a laborer in a box factory, he met a young woman who was working in the timekeeping department. She was called Mary Josephine Kauflin, better known as May, and she would go on to become one of the most important women in Al Capone's life. On the face of it, May and Al had nothing in common. She was a cool, calm, collected woman, two years Capone's senior.

He, a young tearaway who was always getting into one scrape or another. She lived in a lovely terrace house on a nice street. He lived above his father's barbershop in an area little better than a slum. She was of an Irish background. He, of Italian descent. So it shouldn't have worked.

But despite their obvious differences, they became very close, much to the disdain of her mother, who thought him totally unsuitable due to his Italian background.

Despite this, they fell very much in love. And May fell pregnant.

On December 4th, 1918, she gave birth to Albert, nicknamed Sonny. And almost a month later, Al and May got married. So Capone had a legitimate job, a loving wife, and a new baby. But on the other hand, he was a small-time crook in the criminal underworld of Torrio and Yale. So which way was he going to go?

Well, in November 1920, his father died, and so he found himself the man of the house with a family to provide for. Crime simply paid better. Johnny Torrio and Frankie Yale took Al on full time, but Torrio then moved to Chicago to work for the crime boss Big Jim Colosimo. Chicago, being larger than Brooklyn, had more opportunities to make money.

and a new source of illegal income was just opening up. In January 1920, the 18th Amendment came into force, which made the production, transportation, and sale of alcohol illegal. This ushered in the era of prohibition. But as you might imagine, people still wanted to drink. All that was needed was for someone to supply it, and the heavy hitters of organized crime stepped in.

It's ironic that prohibition, with all its moral motives, that it was going to improve American people, what it actually did was gave a huge opportunity to organize crime. Because as the name organized crime suggests, they could organize criminal activities better than anybody else. So you ended up

with floating warehouses, these ships that were essentially liquor stores, giant liquor stores off the coast, you know, beyond three miles so they could operate legally. And the distribution of the liquor and the production was all run by organized crime. So the result of prohibition was it put a lot of money into a lot of bad people's pockets. Capone worked for Frankie Yale in New York until an incident forced him to relocate to Chicago and work for Torrio.

On the streets of Chicago is Craig Alton, who runs Untouchable Tours, Al Capone-themed history tours of the city. He got into a little trouble in Brooklyn, New York. The Italian mob had asked him to rough up an Irish guy who'd been reneging on paying back a betting debt. Al beats the guy almost to death. And now the Irish mob wants the Italian mob to hand Al over for vengeance. Unfortunately, he had no choice. He had a new wife and a baby.

He had to get out of Dodge. And the only person that he knew outside of New York was Johnny the Fox Torrio, Papa Johnny to him. And Johnny was working here at Colosimo's Cafe for his uncle, Big Jim Colosimo. This was the classiest nightclub in Chicago and actually had a mechanical floor that came out of the basement with a live jazz band on it and all the dancers.

Enrico Caruso, Zazu Pitts, Charlie Chaplin, Sophie Tucker, Mae West, all the big names of the 20s would come to Colosimo's cafe to be seen by all the other big names. And Al Corse came here to be bodyguard for Colosimo himself. He was having problems with a group called the Black Hand. This was a Sicilian extortion ring. He would pay them off, they would want more, pay them off, want more, and finally

Colosimo asks Johnny Torrio, his nephew, to go ahead and just pay him off once and be done. Johnny goes there and kills all of them.

And now he needs a bodyguard. Colosimo needs a steady bodyguard. It was a great first job, you know. He was a fancy dresser, and this was the part. On the other hand, in his spare time, he also worked as a bartender and a bouncer at one of Colosimo's clubs called the Four Deuces, which was right down the street here. So Al would stand out in front here. You know, he was always a fancy dresser. He had a big gravelly voice, and he would rope guys into the place. Come on in, come on in, hey.

"Hey, first drink is on me. Come on in, come on in." And sure enough, you know, they'd slip you a drink with a couple of drops of knockout drops, you know? You get a few belts in you, they take anything of value from you and then throw your body underneath the L-tracks. - Mysteriously though, after only less than a year of working for Colosimo, Colosimo was assassinated.

It has been since theorized that Al himself pulled the trigger to make way for his mentor Torrio to dominate Chicago. Working at these establishments, however, Al felt at liberty to indulge in what they had to offer. Despite being married to May, he proved unable to resist the charms of the women he encountered.

-Al Capone was not faithful to May, and he even had an affair with a 15-year-old prostitute of Greek descent and made her dye her hair blonde 'cause he had a thing about blonde women.

May found out about this, and to make a point, she turned up at Sunday lunch at Al Capone's mother's house with her hair dyed blonde. And Capone just seems to have said, "Oh, that looks nice." You know, kind of nonchalant response. But May, curiously, kept her hair dyed blonde for the rest of her life. What may seem like a contradiction, at heart, Al was a family man, and providing for them drove everything he did.

Prohibition era in Chicago was proving incredibly fruitful as the gangs came up with more and more novel ways to smuggle booze to the people who wanted it. So of course, one of the questions that everyone wants to know, how did you get beer during Prohibition? You know, big, heavy commodities that were hard to get around, easily recognizable. So here's how they got away with it. Beautiful places here like the old Schoenhofen Brewery,

When Prohibition goes into effect, 1,700 workers were out of a job. This was a huge complex, the sixth largest brewery in the nation at the time. During Prohibition, they got a permit from the U.S. government to produce a near beer. Technically, it was beer made the old-fashioned way. It's going to be boiled off the alcohol until it was less than one half of one percent.

Capone would have them put it into barrels and then take those barrels and ship them to all of his speakeasies across Chicago. Get it inside the speakeasy, and then once all the doors were locked, his guys would come by later in the day, usually with veterinarian syringes for horse or for cattle.

They would fill that up with 180 proof pure alcohol and then right through the bung they would inject it to give it the punch that the guys were buying it for. And literally he used this method all the way through the 1920s because it was never illegal until it was inside and already locked up.

is a perfect way to get around it. Capone and Torrio ruled through a reign of violence. They targeted and assassinated the leaders of other crime organizations in the city and took out anyone who dared to assault their crew. Chicago's mayor, William Dever, began to target their speakeasies.

Johnny Torrio ordered Al and his brothers to move all their brothels, speakeasies, and gambling dens to the Chicago suburb of Cicero, where Al paid off the local Republican council members.

In 1924, at the primary elections, the Democrats mounted a serious challenge against his paid-off politicians. So, Al's brother Frank unleashed a wave of terror on the city, even placing gangsters with shotguns at polling stations to make sure people voted correctly. The Chicago Police Department decided to intervene and sent 70 plain-clothed officers to Cicero in order to stem the violence.

Although this had little effect on the election, it had a massive one on Al. At one polling station, a patrol car spotted one of Al's known associates, Charlie Vachetti, a man they didn't recognize, and Al's brother, Frank. What was to unfold would turn Al's world upside down.

Franco, Fischetti, and the other fella are standing here in front of the hotel when a big car pulls up. It's an unmarked squad car. In those days, they didn't really look too different than anybody else's.

Four guys step out, and sure enough, shots are fired. Frank was the first one killed. Frank Capone was killed. And when he went down, he had three shots out of his pistol that had been fired. This was huge. You know, being Al's younger brother, they were very close. The funeral was held at the home on South Prairie Avenue. Al's mother, you could just imagine. You know, she was absolutely a wreck.

150 cars were in front of the casket at the funeral. $20,000 in flowers. And all these people, of course, in the old days, always circled by your house. You can just imagine car after car after car after car for 15, 20, 30, 40 minutes as the whole neighborhood watched in front of the Capone mansion there. Capone's political puppets had won the election, but victory had come at a terrible price.

Frank's death was unexpected and devastating. It made headlines in the city of Chicago, but Al himself was not really in the public eye. All that was about to change.

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Towards the end of 1925, Johnny Torrio retired and left control of the outfit to his protege, Al Capone. Al moved his headquarters back to the heart of Chicago and set about building his empire. And he was building on fertile ground.

Prohibition hadn't lessened people's desire for a drink, it had turned it into an exciting form of rebellion. And drinking was coupled with an equally rebellious form of music: jazz. As the world's foremost jazz musicians gravitated towards the speakeasies and clubs of Chicago, Al Capone found himself one of the country's principal patrons of the jazz scene.

Jazz being predominantly performed by African American musicians didn't sit well with some in racially segregated America. But Al, perhaps due to his own immigrant background, couldn't care less. He simply wanted the best entertainment for his club patrons. Historian Dominic Selwood to tell us more. Prohibitionary America was still heavily segregated.

But Capone was above all a businessman. Artists like Louis Armstrong were active in Chicago at the time, and Capone was very happy to have them in his clubs because it made good business sense for him. Capone seems to have had something of a progressive streak. He seems to have treated African-American musicians on equal terms and was regarded as something of a patron of the jazz age.

Capone had really hit the big time and began to pay great attention to the way in which he was perceived by the public. Working with friend and journalist Harry Reid, the pair fashioned Capone's public image so that he was seen not as a gangster, but as a businessman.

Harry Reid gave Al Capone PR tips. He was like a kind of a spin doctor to the gangster. And Capone took the advice. You know, he talked to the press but avoided politics. He went to baseball games and stood there taking the evasion of the crowd. And he'd turn up at City Hall, you know, acting as if he was an elected politician, even though he was nothing of the sort. And on his way, he'd be giving racing tips to people in the streets and, of course, even giving them advice on fights he knew were rigged. And this sort of

The commutative result of this was that Capone was regarded by people in Chicago as something of a working class hero. You know, that he was one of them, that he'd made it. And so they liked him. Al became something of a celebrity, and the whole world talked about him. He would flaunt his wealth by festooning himself with diamonds and jewelry, and would order a dozen custom-made suits at a time, costing nearly $70,000.

When it came to the color of his clothing, he would wear lime green, yellow, lavender. Nothing seemed beyond the boundaries of taste. He was a gift to the eager newspaper paparazzi.

Capone was a real showman and he loved to flaunt his wealth. He was really attracted, for example, to diamonds. He had an extraordinarily large diamond pinky ring. He also had diamonds on his belt buckle. Even in his house, his billiard table and pool cues were diamond studded. Al became fixated on his image and found every way to disguise his unruly past. Once, back in New York, in his

In his side job at the Coney Inn on Harvard Island, he had an altercation with a gangster, Frank Galluccio, something Al would never forget.

Al made rather a crude comment to Frank about his sister, and Frank didn't take it well. He responded by slashing Al across the face with a blade. This left Al with permanent scars that earned him the nickname Scarface. Al Capone absolutely hated the scars on his face. And, you know, he'd give the unscarred profile when he was being photographed and even resorted to having his face powdered in order to hide these kind of unsightly scars

the unsightly evidence of his previous street fights. He was a guy who wanted people to like him. Even as a child, you know, people did like him. He would go out of his way that you liked him. On the other hand, as we say in Chicago, if Al liked you, he took care of you.

If he didn't like you, he took care of you." Al was a hit with the public, and his organization was growing rapidly. By 1926, the outfit's gross income was nearly $1.5 billion per year in today's money. But in his private life, things weren't so simple. May was diagnosed with syphilis, which she probably caught from Al himself, who refused to be tested.

On top of that, their child, Sonny, a rather frail boy with poor hearing, who always seemed to have one illness or another, was having a hard time at school. Capone, the man who could order deaths on a whim, found himself powerless to help. So here was a man who, you know, murdered people with a drop of a hat, didn't think anything of it. And yet he had this very...

intense, loving relationship with his son, who he wanted to protect sort of from the truth of what he was doing, but also from the world because he saw Sonny as very vulnerable. He was hard of hearing, he was partially deaf. And Al, it was like Al channeled all of the love that he had into this boy and into his relationship with this child.

But because his professional life was one encounter after another with rival gangs, he didn't see much of him. In fact, Al spent much of the second half of the 1920s in one hotel or another, and security was at the forefront of his mind. In 1928, he moved his HQ to the Lexington Hotel, where his security turned it into Chicago's answer to Fort Knox.

Capone's real headquarters was on the fourth and fifth floor of the Lexington Hotel, which he'd had completely kitted out just for him and his crew. There was a special lift to take people up to his private area. He'd had chairs specially built with bulletproof reinforced backs. There were traps, there were escape tunnels. This was the command HQ for the Capone crime syndicate. It's no exaggeration to say that Capone murdered his way to the top.

You know, murder was part of his business strategy. And so when you murder people, people want to murder you too. And the sort of people he murdered were definitely going to come after him. So he was constantly aware of his security, constantly knowing that he could never drop his guard. So he was always surrounded by this entourage of heavies. While he lived under the constant fear of his safety, the rewards were certainly worth it.

By 1929, Al Capone was 30, and his personal net worth was over $150 million in today's money. To explain why he was so successful is his biographer, Jonathan Eyge, speaking from one of Capone's old haunts, the Green Mill.

Capone was a legend in his own time, to use the cliche. He was celebrated and he fascinated people because he broke the law. And because the law was so unpopular, all of the morals were kind of tossed on their heads. Here's a guy who says, "I'm breaking the law, but I'm giving the people what they want." The law banning alcohol was incredibly unpopular. So somebody who breaks that law can be popular. I think he was very smart about certain things. I think his great brilliance was actually in marketing and publicity. He knew how to sell himself

And that's why he's the most famous criminal of his time and maybe the most famous criminal in American history, because he understood that celebrity was a powerful tool for a businessman, something we all understand today, something even politicians are recognizing. Capone understood that fame can help make you bulletproof and fame can help sell whatever products you're trying to sell. In his case, he was trying to sell booze, but he was also trying to improve his image. He wanted to be seen as a legitimate businessman.

So he was likable. He was able to survive in this business a long time, keep it going because he was smart about bribing public officials. He was smart about delegating the violent acts. He was definitely no dummy. With his new fame and success, Al felt invincible. But in February 1929, with his ego perhaps a little too big, he was to go too far.

Designed to take out rival gangster Bugs Moran, Al would put out a hit that would undo all that good publicity. The event became known as the St. Valentine's Day Massacre.

and it exposed him for who he truly was. Capone now wanted to seize control of his bootlegging activities. And the way he conceived of doing that was to launch a fake police raid where Capone's operatives dressed as police officers and lined up some of Moran's people against a wall, notionally to search them. But at a signal,

Machine gun fire was released. They were all killed. Chicago and prohibition-era America were used to a degree of gangster violence associated with prohibition and the illegal trade around it. But the St. Valentine's Day massacre plumbed a new depth and to a large degree started to turn the American public against Capone and his like. And it played out on the front page of newspapers with these horrible shots of

of blood spilling from these men's heads. And the government began to really push to try to do something about this violence that was sweeping the cities of our country. That's when Capone's image began to change, and the government played a big part in changing that image. The Valentine's Day Massacre raised the stakes. The government really felt like they had to make an example of Al Capone.

They had to send a message that this kind of violence was not going to be accepted anymore. And President Hoover, Herbert Hoover, decided that the best way to do that was to use Capone, to go after Capone, send a message, because he was the most famous criminal in America, maybe in the world. If you can take down Capone, you send a message to all Americans that prohibition is going to be enforced. The laws are the laws and nobody is going to get away with crime anymore. So he became obsessed with getting Capone.

But nailing Al Capone was not going to be easy. He kept his hands scrupulously untainted from his crimes, and people feared the consequences of testifying against him. He failed to take this new threat seriously. But one woman was determined to find a way.

Mabel Walker Willybrand was a truly extraordinary lady. She started life as a schoolteacher, but through studying in night school, she taught herself law, got qualified as a lawyer, became a prosecutor and ended up as the Assistant Attorney General. She was the one who realized that it was never going to be possible to prosecute Capone for his bootlegging and his prohibition crimes because nobody would testify against him.

So instead she turned to the fact that he was always flashing his money. This was something he clearly had a lot of. So she went against him for income tax evasion and that's how she got him.

Capone had always used a mixture of terror and charm in order to get his way, and also had judges, politicians, police on his payroll. And I don't think he fully appreciated that the tide was starting to turn. There was a determination to get rid of Capone. Capone just didn't see the disaster that was coming his way.

Capone's lawyer, Mattingly, made a very serious tactical mistake, which is that he admitted how much money Capone owed in tax and offered to pay it back. But once the sum was out there, it was a noose around Capone's neck. At the trial in October 1931, Capone was only convicted of five counts, but it was enough to see him handed an 11-year sentence.

Capone didn't lose sleep about investigations against him. So when Mabel's trial against him finally succeeded, he was in deep shock and bewildered that somebody had managed to bring him down. By the end of the month, he was shipped off to Cook County Jail. From there, he went to the Atlanta Penitentiary, but he was suspected of continuing to run the outfit from prison.

So, in August 1934, Capone was transferred to the recently opened federal facility of Alcatraz.

I think it's fair to say Al Capone had a miserable four and a half years on the rock, as it was called, Alcatraz. I mean, visiting hours were very short. He was a very sociable man. He wanted to see his family, didn't get to see them very much. And he didn't exactly hit it off with the other prisoners. I mean, there's an incident where he's stabbed with a pair of barbershiers, and the only thing he's got to defend himself with is his own banjo from his band.

And to cap it all, he's going down with syphilis and it's eating into him and it's reducing him really to the sad, pathetic individual that he'd become at the end of his life. As falls from grace go, Al's was a pretty spectacular one. The man who had once ruled Chicago now found himself living in a 9x5 concrete cell.

In 1936, he was stabbed by a fellow inmate, and while the incident left him with only minor wounds, it served as a grim reminder of just how far he'd fallen. Two years later, he had a serious mental breakdown. In 1939, in such poor health, he was moved from Alcatraz to a hospital in Baltimore.

He was soon paroled, after which he retreated to his Palm Island villa in Miami Beach. While there, he was visited by family and old associates under the watchful eye of the FBI. But due to his syphilis, he was not particularly lucid and would ramble at length about communists and his old rival, Bugs Moran.

Capone was eventually released from Alcatraz into hospital, and from there he was sent home to die. He had very serious syphilitic dementia. Doctors examining him at the time said he had the mental age of a 12-year-old. In 1945, Al Capone became one of the first civilians to be treated for syphilis with penicillin. But it was too late.

His health declined still further, and on January 25th, 1947, a week after his 48th birthday, he suffered a stroke and cardiac arrest, and died. But with Al's death, a legend was born. He would become immortalized in film and television, which would, to an extent, glamorize him and the times in which he lived.

You get the impression, really, that Chicago is rather conflicted about the legacy of Capone. I mean, a former mayor, Richard Daley, went out of his way to demolish buildings that had anything to do with Capone, and you won't find a plaque commemorating the St Valentine's Day massacre for obvious reasons. But nevertheless, the gangster tours continue, the memorabilia's for sale, so no matter how much the city would like to cut its link with Capone, he's there omnipresent.

Al Capone's success as a gangster was truly lightning in a bottle. With Prohibition leaving an economic vacuum in which organized crime could prosper, Al had the right charm, brains, connections, and appetite for violence to make himself king. In a decade where the media was first taking root, Al's fixation with his image gave the hungry tabloids a shining star.

But being on top leaves a long way to fall. Al's obsession with women and his pride to not get himself tested led to his brutal demise under syphilitic dementia. His inflated ego blinded him to holes in his defense right up until the fatal blow.

From his humble beginnings on the streets of New York, to his peak as the undisputed King of Chicago, to finally dwindling into a withering recluse, the rise and fall of Al Capone is a captivating cautionary tale. What was it like to be a prisoner like Al Capone in the infamous Alcatraz Federal Prison?

For a deep dive into the lives of its notorious inmates and its high-profile escape attempts, listen to our extra episode, Forbidden Fruit, available soon on all your favorite podcast platforms.

This is an audio production by Like A Shot Entertainment. Presented by Bridget Lappin. Executive Producers Danny O'Brien and Henry Scott. Story Producer Maddie Bowers. Assistant Producer Alice Tudor. Thank you for listening.