cover of episode 160: Al Capone & the End of Prohibition

160: Al Capone & the End of Prohibition

Publish Date: 2024/7/15
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near you. That's the letter K, the number 12.com slash HTDS. K12.com slash HTDS. It's about 1030 on a cold, gray, windy, and slightly snowy Thursday morning, February 14th, 1929.

Yes, Valentine's Day. And we're at 2122 North Clark Street, Chicago, Illinois, at a garage known as SMC Cargage Company, where one man after another enters, dusts the snow from his thick overcoat, then makes his way to the hot coffee. By the way, those are custom overcoats. Much like their shirts, their suits. What can I say? Bootlegging has its perks, especially when you're a part of George Bugs Moran's gang.

In fact, let me fill you in on Buggs, his operation, and this meeting while his boys are still preoccupied with getting a cup of joe. A thief, a safecracker, and a man with a temper so hot they call him Buggs. George Buggs Moran was running with Dino Banyan when Prohibition first took off and was happy to get in on the bootlegging game.

This newest illicit gig sure paid off, but soon these mostly Irish Chicagoans on the city's north side found themselves in a turf war with the Italian gangsters on the south side. As the 1920s progressed and each side suffered losses, Buggs rose to the top of his game. That left him as the lone rival to the Windy City's most notorious celebrity bootlegger, the South Side's Al Capone. And at this point, there's no end to their war in sight.

In fact, today's meeting might be due to gang violence. While many will later say that the gang is gathered at the garage waiting on a boosted truck transporting Capone booze, it's also possible that this is a meeting of Bugs' best to discuss a recent assassination attempt. Either way, I suppose we'll never really know. But whatever the subject of this meeting, Bugs has not shown up yet.

Right now, the seven men waiting in this frigid, furnace-lacking garage consist of: Five full-on gangsters, all Bugs' boys. A sixth is a young optician named Reinhard Schwimmer, just a friend of the gang who likes to feel tough and live a dangerous life vicariously through them. And finally, John May. See the dark-haired fella in the coveralls, cranking a wrench? The lone guy not in a suit? Yeah, that's him.

Once a safecracker, John now works for a steady 50 bucks per week as Bugs' mechanic. And I'd say that gets us up to speed. Let's get back to that hot and bitter black coffee. The seven men, five gangsters, the wannabe, and the mechanic are still waiting for Bugs. They chat, they sip their coffee. Then finally, the shop's back door opens. But it isn't Bugs. It's two cops with shotguns.

The boys in blue holler at the seven garage dwellers to line up against the wall. Bugs' boys comply without a worry in the world. This can't be a real raid. Their boss pays the right people in the Chicago PD, and handsomely at that. Trusting that this is all for show, so these policemen can write some fake report, the gangsters don't even bother to reach for the guns tucked in their custom coat pockets. Everyone simply puts their hands in the air and faces the garage's brick wall.

The cops begin patting the 7 down, searching for weapons. Yeah, that's a snub-nosed 38. The officer tosses it to the ground. Sure, whatever. On with the show. But now that the gang is disarmed, the cops let two or three other men into the garage. Reaching inside their thick, long overcoats they produce, good god, those are two Thompson submachine guns!

One of these great war-inspired weapons is loaded with a 20-round stick magazine. The other with a 50-round drum. A mid flashes in smoke. One unknown gunman sprays his .45 caliber bullets left and right, while another gunman wielding a shotgun shreds the optician with a blast of buckshot. In a matter of seconds, the 50-round drum is empty and all seven men facing the wall are filled with lead. Six are on the ground, while one's collapsed in a chair.

Ah, but some are still breathing. Time to pull out the other Tommy gun. Blood seeps from Joe's head and body. His coveralls soaked in his own blood. But it's a fair speculation that he's still drawing breath because now the second shotgun is put to use. The left side of the mechanic's head disappears as his brains spray across the garage floor. The murderers walk out the same way they came in, through the back door.

The men in the long overcoats step outside with their hands in the air while the two cops, or at least the men in police uniforms, keep weapons trained on them. A show indeed. Keeping up the appearance of an arrest. The whole group of four or five climb into a black Cadillac and drive off. Welcome to History That Doesn't Suck. I'm your professor, Greg Jackson, and I'd like to tell you a story.

When a neighbor meanders over to SMC Cartage Company, he finds six bloodied dead bodies and one bullet-ridden blood-soaked man crawling for the door. That man is Frank Gusenberg. He's rushed to the hospital, but dies within a few hours without ever naming his assailants.

That said, Bugs, who only survived because he saw the fake police car pull up to the garage and stayed outside, thinking he was avoiding a simple raid, knows who did it. Confidently, the Northside gangster says, "Only Capone kills like that." It was a hit unlike any other that shocked the entire nation and will forever be remembered as the St. Valentine's Day Massacre.

Today, we wrap up the tale of Prohibition with the tale of one of its most notorious gangsters, Chicago's Scarface, the one and only Al Capone. We'll begin with his early life in Brooklyn as the son of Italian immigrants pursuing the American dream.

But Al, we'll soon find, has his own idea of the American dream. One outside the rule of law, in the gangster underworld where extortion, murder, and, as of his 21st birthday, which is the day prohibition begins, bootlegging. We'll follow this infamous mobster as he acquires his scars, moves to Chicago, and rises to the top of the Windy City's mafia, that is, the outfit.

We'll witness his wrath, his bootlegging wars, his godlike power. But finally, see how the mighty fall as Al learns the hard way that there are indeed only two things certain in life, death and taxes. So, ready to close out Prohibition with one of its best dressed and most murderous mobsters? Then let's get to it. And our tale begins back at the turn of the century. Rewind.

On January 17, 1899, Italian immigrants Gabriele and Teresa Capone welcomed their fourth son, Alphonse Gabriel Capone, into their two-room apartment at No. 69 Park Avenue in Brooklyn, New York. They live in an Italian neighborhood, but on its fringe, which allows their kids to interact not only with Italians, but Germans, Irish, and Eastern Europeans, all hoping to live out their American dream.

Perhaps that early taste of New York City's melting pot is part of why Alphonse doesn't cling to old world ideas or identities. That's likely part of why he doesn't answer to Alfonso, preferring the Americanized version of his name: Al Capone. As an adult, he'll be the first to remind you that "I'm not Italian. I was born in Brooklyn." By 1907, the still-growing Capone family has relocated to a street called Garfield Place, and Al is already a force to be reckoned with.

He's a quick learner. Unlike many young Italian New Yorkers, Al speaks fluent English. He has a knack for numbers, but an even better knack for cutting class. While not in school, the young Brooklynite holds odd jobs, working at a candy store, setting pins at a bowling alley, and so on. But he's also bonding with a teenager named Frank Nito, later to be known as Frank Neaty. Frank sees Al's potential and adopts him as an informal mascot for his gang, the Boys of Navy Street.

Al's dad, Gabriel, that's right, he too Americanizes his name, doesn't like this at all. His oldest son, Vincenzo, has disappeared to God knows where and his next two oldest boys, Ralph and Frank, have already departed from the straight and narrow. So no, the hair-cutting father doesn't like seeing his fourth son in a gang and in fights. Not giving up hope though, Gabriel gives Al a shoeshine box and tells him to get to work.

But as the young shoeshine spits and polishes, he observes the nearby protection racket of the first godfather of Brooklyn, Don Batista Balsamo. And Al loves it. Modeled after the Don, the young teen sets up a small crew known as the South Brooklyn Rippers and begins to shake down fellow shoeshines. The more well-established Balsamo organization kicks them off the street, but the underworld is starting to take notice of Al's abilities.

Now about 16, the Brooklyn native catches the eye of the Italian-born Five Points gang leader, Johnny Torrio. Al adores the gangster, affectionately calling him "Johnny Papa." Meanwhile, Johnny appreciates how good Al is with numbers. As the mentor spends more time in Chicago helping his cousin Victoria's husband, Big Jim Colosimo, with, uh, business, he leaves his mentee with quite a bit of responsibility back on the East Coast.

In fact, Johnny connects Al to Frankie Yale out at Coney Island, where business is less refined and brute force is the favored way to solve problems. It's an early evening on an unspecified day in 1917. The 5'10", burly yet nimble Al Capone is bartending at Frankie Yale's Harvard Inn at Coney Island, New York.

Given its Ivy League name, you might think this tavern is filled with students, but no. It draws more dock workers and low-life criminals. Not that Al minds the crowd. As a bartender, he's known to socialize with the clientele in more ways than one. It's here that he contracts the disease that he'll battle for the rest of his life: syphilis. Anyhow, on this particular night, a 5'6" man, maybe 150 pounds soaking wet, enters the establishment.

Slim yet tough, this is Frank DiLuccio. He saunters in with his sister Lena on one arm and his girlfriend on the other. Girl crazy Al's attention is piqued. He brushes by and murmurs something to Lena but gets no response. But the rebuffed bartender makes another pass. Reportedly, Al says to her, "You got nice ass, honey. And I mean it as a compliment, believe me." Now, Frank's a little drunk. Who knows what he actually heard, but that doesn't matter.

No one speaks in such a degrading, dishonorable way to his sister. Frank breaks his beer bottle on the table, then lunges it out. The sharp shards of the swinging, slicing, drunken customer's glass bottle carve into the bartender's left cheek before adding two smaller slashes farther down the jaw and neck. Frank and his entourage hurry out of the Harvard Inn. No one stops or follows them.

Everyone is too busy trying to stop the blood gushing out of Al's face and getting him to the nearest hospital. About 30 stitches later, Al is left with the disfigurement that leads to his notorious nickname, Scarface. But oh, does he hate the scar and the moniker. Al takes to cocking his hat and using talcum powder to hide and soften the scars. He'll also later claim that he received the wound while fighting as one of New York's heroic Lost Battalion Doughboys during the Great War.

I trust you remember their harrowing tale from episode 142. Talk about a stolen Valor lie. Though employed at a box factory, most of Al's income is now the result of his gangster gigs with Johnny "Papa" Torrio and Frankie Yale. Meanwhile, he begins courting the green-eyed, fair-skinned, brown-haired Irish descent and Brooklyn-born Mary Josephine Coughlin, better known as May. Al loves her musical laugh, her wide smile marked by an overbite.

He finds this girl from Brooklyn's Red Hook neighborhood beautiful and their personalities match quite well. But May's mother sees Al for the rising gangster that he is. She forbids her daughter from marrying him. Even when May becomes pregnant, the marriage can't happen until after the baby is born. On December 4th, 1918, the soon-to-be Capones have a son, Albert Francis Capone, aka Sonny. Thanks to his father, Sonny will deal with the side effects of congenital syphilis his whole life.

But with his birth, Al and May can wed. Four weeks later, on December 30th, they tie the knot. Throughout 1919 and 1920, Al works full-time with Johnny Torrio who, between New York troubles and Chicago opportunities, has relocated to the Windy City permanently. His young protege follows. Something else follows around this time too: the passage of Prohibition. On January 17th, 1920, the same day that national Prohibition goes into effect,

Al Capone turns 21 years old. By that May, his mentor, Johnny Papa, is running Chicago's Outfit, as the mafia is known here. How'd that happen? Well, his predecessor and dear cousin, Big Jim Colosimo, who didn't want to get into bootlegging, got whacked by an unknown gunman. Some say it was the work of Frankie Yale, but insufficient evidence and all that.

It's sad, but wouldn't you know it, pro-bootlegging Johnny Torrio has found the inner strength to push through his grief and take over his dead cousin's criminal empire. Meanwhile, Johnny Papa has Al Capone managing the outfit's flagship brothel and gaming house, the Four Deuces, so-called for its address of 2222 South Wabash Avenue. This is where Al's first schemes that actively avoid government agencies begin, though it's not much different from what he did in Brooklyn.

collecting prostitutes' earnings, keeping the books, and ensuring premises stay clean and run smoothly. One year later, in 1922, Al buys a two-story brick house for $5,500 at 7244 South Prairie Avenue, where his family will live for the rest of their lives. By 1923, the whole Capone family, minus Al's missing oldest brother, of course, is in Chicago. Al also gets a new nickname,

snorky, which means swell or sharp dresser. It's well-deserved. The gangster owns over a dozen double-breasted custom five grand a piece suits and in all sorts of bright colors like lime green, yellow, and lavender. His dark overcoats are made of cashmere and camel's hair. His custom-made fedoras are pale gray.

Chicagoans joke that anyone who dons a fedora in this color would get arrested since it's so closely tied to Al. His diamond tie pins, cufflinks, and belt buckles sparkle amidst his neon fabric backdrops. When asked what he does for a living to afford all of this grandeur, Al quips, "'I'm a property owner and a taxpayer in Chicago.'" In April 1924, Al's gangster brother Frank dies in a shootout with plain-clothed Chicago police.

And did Frank start the gunfight mistaking them for members of the heavily Irish North Side gang? Could be. Gang warfare is rampant in Chicago at this point, and it only gets worse when the outfit takes out the North Side gang leader Dean O'Banion that November and Jaime Weiss takes over. Not even the outfit's more diplomatically-minded Johnny Torrio is safe. George Buggs Moran and his shotgun-wielding North Side accomplices nearly kill him in January 1925.

They leave Johnny scarred and shaken. So shaken that he wants out. It's an unspecified day, March 1925. Johnny Torrio is in his Lake County jail cell in Waukegan, Illinois, where he's doing nine months for operating a brewery. But this isn't your typical jail cell. It's furnished with luxurious rugs, chairs, and a cozy bed. It's protected by bulletproof steel mesh blinds and rotating deputy sheriffs.

Honestly, it's a reprieve. The North Side gang can't get him in here, but Johnny can't count on that forever. That's why he's looking forward to today's visit with his protege, Al Capone. The husky, well-dressed gangster steps into the boss's cell, where Johnny and his lawyers are already waiting. Al sits down, and Johnny likely says something along the lines of a previous statement that, "I am getting too prominent for my own good."

Perhaps Johnny tells Al of his plan to move back to Italy here. Perhaps that's later. We don't know exactly how the discussion goes, but when the Brooklyn native walks out of his dear Johnny Papa's cell, all the brothels, cabarets, gambling houses, breweries, and distilleries, not to mention the power, control, and nearly unlimited funds, all belong to 26-year-old Al Capone.

I'll spare you the gruesome details, but over the next year, Chicago sees murder after murder as the Jaime Weiss-led and heavily Irish North Side gang does battle with the South Side's Al Capone-led Italian outfit. Frankly, the Windy City's carnage is so awful that the gangster engagement is soon compared to the recent great war with the moniker, the Bootleg Battle of the Marn.

Al is so worried about his safety that eight bodyguards travel everywhere with him, and a New Yorker article claims these guards are protecting a, quote, double-walled fortress of meat, close quote. Wanting to prove to increasingly suspicious law enforcement that he is, in fact, a law-abiding citizen, Al lets it be known in July of 1926 that he's planning to turn himself over to the police to prove that they have nothing on him.

On the 28th, police find him standing at the Indiana-Illinois border. The crime boss says, I understand you boys are looking for me. Back in Chicago, the feds take Al to the criminal court's building where he denies any connection to any recent gang murders. The skeptical judge throws Al in jail for the night, but during his hearings the next day, the prosecutors fail to produce any evidence. The judge has to dismiss all charges.

On September 20th, 1926, Jaime Weiss sends a parade of cars to Al's Hawthorne Hotel headquarters in Cicero, Illinois, where they blow a thousand rounds in the most terrifying drive-by shooting ever. Incredibly, the only casualties are a few wounded in the windows. No one dies. Though insulted and filled with thoughts of revenge, Al takes a page out of Johnny Papa's book and attempts a peace conference at the Hotel Sherman that October.

Ah, but it fails, leaving Al convinced that the only way to end the bootlegging battle is by killing Jaime. He gives the task to an old Brooklyn buddy, Frank Needy. At approximately 4:00 PM, October 11th, 1926, Jaime pulls into a parking lot kitty corner to a flower shop north of Chicago's Holy Name Cathedral.

Exiting the car and walking across the street, the Northside gang leader is chatting away with his associates when the rain of machine gun fire and shotgun blasts come pouring down from a window of a nearby building at 740 North Street. Jaime never knew what hit him.

Al Duck's responsibility for ordering the hit in the boldest of ways, by publicly denouncing it. The young outfit boss calls a press conference. He tells reporters, I'm sorry Weiss was killed, but I didn't have anything to do with it. I knew I'd be blamed for it, but why should I kill Weiss?

With various crime bosses reeling from Jaime Weiss's death, Al decides to hold another peace conference. The South Side leader forces Jaime's replacement, Bugs Moran, to join. To everyone's surprise, it's a success. Old territorial borders from back when Johnny ran the outfit are reinstated, and the Capos make a promise to resolve all future differences non-violently. After the conference, Al tells a Herald and Examiner reporter, "'I believe it's peace to stay,'

I know I won't break it, and I don't think they will. I feel like a kid, I'm so happy. When the meeting was over, I called up my wife and told her. She cried so she couldn't talk to me. I'm going home to sleep now after I have a couple of beers. That's my celebration. I don't drink as a rule, but the lid's off tonight. But even as he breaks bread and imbibes with his rival bootleggers in a celebratory feast of ghouls, as the press dubs it, Al knows better.

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way to run your household, customized to your family's needs, and the easy way to raise financially smart kids. Get started with Greenlight today and get your first month free at greenlight.com slash Spotify. Peace to stay. It's fair to say that Al Capone wants that.

In 1928, the Italian Southsider explains that he's, quote, tired of gang murders and gang shootings. It's a tough life. You fear death at every moment. And worse than death, you fear the rats of the game who'd run around and tell the police if you don't constantly satisfy them with money and favors, close quote. But push comes to shove. Al prefers the risk of death or prison to giving up what he's got.

By this point, Al is, to quote his first biographer, Fred Passley, the John D. Rockefeller of some 20,000 anti-Volstead filling stations. Close quote. No one knows exactly how much Al is earning, but those close to him estimate it's roughly $30 million per year. How else can he afford to make $100,000 bets at the tracks? You heard that number right. The man is an absolute gambling addict who lives for the thrill.

So, Al takes stronger measures to protect himself. As 1928 continues, he moves the outfit's headquarters to the well-outfitted Lexington Hotel. With basement tunnels connected to other buildings on South Michigan Avenue, Al's ten-room suite on the top floor, only accessible through one specific freight elevator, naturally, has gorgeous views of Chicago's South Side. His bulletproof-backed chair sits in front of a long mahogany table.

On the wall behind his desk are two steel engravings, one of George Washington, the other of Abraham Lincoln, and between them hangs a portrait of Chicago's crooked mayor, Big Bill Thompson, or of Al himself. Reporters never agree on which man it is. And Al is right to worry about snitching rats. The recently appointed U.S. attorney for the Northern District of Illinois, a man with gray hair and wire-framed glasses named George E.Q. Johnson,

wants to take Al down. The same can be said of Prohibition agent Elliot Ness. Only in his mid-20s, Elliot takes Prohibition even more seriously than that sharp middle part in his thick brown hair. And even though U.S. District Attorney George Johnson's witnesses keep mysteriously disappearing or dying, he's encouraged as one of Al's distant acquaintances lets it slip that the outfit boss hasn't paid taxes on his illegal income.

That matters because the Supreme Court declared last year that even illegal income is subject to taxation. So, the feds begin tracking down Al's closer pals. Maybe they're guilty of tax evasion. Maybe they can be flipped against Al. Either way, it's a win. Al's feeling the heat. And I'm not just talking about sunbathing at his gorgeous Florida estate.

He needs to take care of enemies, and as we know from this episode's opening, it's the following Valentine's Day in 1929 that the mafioso sends his cop-dressed boys to take out the North Side gang's Bugs Moran. While they don't get Bugs, the seven-man slaying is so gruesome that, to quote Deirdre Baird's Al Capone, "If all the years of previous bloodshed were added up, they still could not compare with the magnitude of its effect on public consciousness."

Nor is the massacre proving worth the trouble. Though it essentially wiped out the North Side mob, tougher competitors are emerging. Watching things play out from New York, Charlie "Lucky" Luciano describes Chicago as "a real goddamn crazy place. Nobody's safe on the street. So much for Peace to Stay." Worse still, the Peace to Stay gangster is facing internal threats. So, he takes them out.

It looks like Al arranged last year's hit on his old friend, Frankie Yale. And he won't sit idly after hearing that three of his most trusted men, some of those who carried out the St. Valentine's Day massacre, are plotting a coup to kill him and take over the outfit. In Al's eyes, it's time to make an example of these traitors. It's the evening of May 7th, 1929. We're at a restaurant in Illinois or Indiana.

Alas, sources conflict, as is so often the case in underworld history. But wherever this place is, the table is being set. Al Capone is hosting a dinner in honor of his three finest killers. The murder twins John Scalise and Albert Anselmi, and the new Unione Siciliani president, Joseph Hapto Giunta.

Arriving at the restaurant, our three honorees are escorted into a private back room. A wine cork pops and everyone sits down to enjoy a delicious Italian meal of spaghetti, chicken, and all the fixin's. Al sits at the head of the table. He smiles at the three men as everyone eats. It's a lovely meal. As the waiters carry the last of the dishes out of the private dining room though, Al's bodyguards quietly lock the door. The outfit leader rises.

He calmly bows to his guests, but then his demeanor shifts. He curls his famously fat lips and sneers. "This is the way we deal with traitors." Some say the three guests of honor are tied to their chairs. Perhaps, perhaps not. Either way, Al's bodyguards hand him a baseball bat, which the large and powerful gangster swings at Joseph's head and body repeatedly.

Blood oozes from his cracked skull and down his body as he slumps over. The murdered twins scream and plead for mercy, but it's no use. Imitating the great Bambino who's hitting a homer in St. Louis this very same night, Al cracks at John's head.

Terrified, Albert begs, "Not me, Al. Honest to God, Johnny, it was his idea, his and Joe's. Believe me, Al, I wouldn't." Al doesn't even wait for the man to finish talking before crashing the bat on his head over and over. The next day, all three men's beaten, disfigured, and repeatedly shot up bodies are found on an isolated road just over the state line in Indiana.

Given all of this horrific bloodshed, perhaps it's time to take another swing. Sorry, terrible wording. Perhaps it's time to try the whole peace thing again. It's about a week later, in mid-May 1929, that Atlantic City's Enoch Nucky Johnson allegedly arranges for the nation's crime bosses to meet. Now, as established in the last episode, it's possible this meeting never happened.

But regardless, a crime confederation is formed around this time and those at the top of the criminal food chain want Johnny Torrio running the Windy City. Yes, fleeing Benito Mussolini's fascism, Al's old mentor is back from Italy. Now, this won't come to anything. Johnny Papa isn't interested in a full-fledged return, but Al gets it. His fellow gangsters don't love him. Joe Aiello has offered 50 grand for his ad.

So, like Dear Johnny Papa years ago, Al's thinking that the solitude of a jail cell is the answer. On May 16th, 1916, he and loyal bodyguard Frankie Rio are arrested for carrying guns at Philadelphia. Naturally, the arresting cops are friends of the outfit boss, just doing his bidding. Al gets more time than intended. He's sentenced to a year in prison and soon transferred to Pennsylvania's Eastern State Penitentiary.

Still, the gangster lives large as his loving wife, May, sends his mattress, bedding, a radio, silk pajamas, hand-tailored suits, all the comforts one can imagine. Al's released early, on St. Patrick's Day, March 17th, 1930, for good behavior. But that's not the end of his legal woes. No, it's just the beginning.

One month later, on April 17th, Al and his lawyer, Lawrence P. Mattingly, meet with the head of the Chicago Internal Revenue Office, Mr. C.W. Herrick. And heads up, this conversation and its follow-up letter become important later on. So listen carefully. C.W. tells the gangster and his lawyer, "'I think it is only fair to you to say that any statements which are made here, which could be used against you, would probably be used. I want you to know your rights.'"

Now, you might think that any good lawyer would usher his client out of such a meeting if possible. But Lawrence and Al stay put. So, CW goes on. "How long, Mr. Capone, have you enjoyed a large income?" Al answers, "I've never had much of an income. A large income." This annoys CW. He clears his throat and continues, "I will state it a little differently. An income that might be taxable." The gangster isn't having it. "I would rather let my lawyer answer that question."

The lawyer replies, "Mr. Capone owes some tax and Mr. Capone wants to pay it. Normally, that would be a great answer, but the feds aren't so interested in payment this time." Five months later, on September 30th, 1930, Al's lawyer makes an even worse mistake. He sketches out Al's income in writing.

Quite literally everyone knows this number is ridiculously low and clearly not true. But this letter proves that Al has taxable income.

income on which he has refused to pay taxes thus far. Meanwhile, that December, Elliot Ness is promoted as a lead prohibition agent. He and his team stick out because, well, they're not corrupt.

Much of Chicago's elite shun them for doing as directed by President Herbert Hoover and going after the outfit boss, which leads Charles Schwartz to write a piece in the Chicago Daily News comparing Elliott and his team to those at the bottom level of India's caste system, known as the Untouchables. Thus, their famous moniker, Chicago's Untouchables. Elliott thinks the name is a joke, but U.S. District Attorney George Johnson loves it. It's a mark of incorruptibility.

But even as the Untouchables tear into the outfit, doing work that produces an indictment of Al for more than 5,000 prohibition violations, George isn't sure that he can make any Volstead Act-related sins stick in court. The bespectacled U.S. District Attorney knows how much people hate prohibition. Better to stick to the tax issues then. But even there, Al can just bribe juries and can convince witnesses to change their stories or simply make them disappear.

So, when, in May 1931, he receives a visit from Al's lawyers. At this point, Thomas Nash, Michael Ahern, and Albert Fink, George listens to their proposed plea bargain. The men land on two and a half years in prison. Happy enough with this deal, George goes to Judge James A. Wilkerson, who is presiding over Al's case. Now here's where it gets tricky. James never explicitly says that he'll approve the deal.

But George leaves the judge's chambers with the impression that everyone is in agreement and he relays that back to Al's lawyers. The indictment is served on June 5, 1931. Al allegedly has an income of $1,038,654.84 for which he owes $215,080.48 in taxes.

Newspapers think the estimates are too small, but now, Al is prepared to show up in court, plead guilty, do his two and a half years in prison, perhaps pay a fee, then go free and move on with his life. On Tuesday, June 16th, Al saunters into the courtroom in a yellow suit. He replies guilty to each of the indictments. It's all over in less than five minutes, but then the judge says he needs more time to consider the sentencing.

Al can't help but feel disconcerted as the weeks pass. It's Thursday morning, July 30th, 1931. Dressed in a dark green suit and straw boater hat, Al Capone is walking down the hall in Chicago's gorgeous Beaux-Arts U.S. courthouse. Newspapermen are everywhere. They know today's the big day: Al's sentencing. They ask the outfit boss how he feels.

Al stops, turns to them, and answers, "I'm a little nervous. After all, I'm only human." Fair enough. The judge hasn't told anyone his plans either. But there's nothing more to say as Al steps into federal judge James Wilkerson's courtroom. With a steely-eyed look, the dimpled-chinned judge opens the proceedings. Al chews gum furiously, trying to calm his nerves. U.S. District Attorney George Johnson rises.

As he explains the two and a half year deal, Judge Wilkerson cuts him off. - A plea of guilty is a full admission of guilt. The power of compromise is not vested in the court, but is conferred by Congress on other governmental offices. If the defendant asks leniency, he must be prepared to answer all proper questions put to him by the court. - Whoa, not what Al or his lawyers expected, nor Elliot Ness.

In the room and watching the proceedings, the usually reserved prohibition agent will never forget how much he wants to stand up and cheer in this moment. It's now past two in the afternoon. The courts just returned from a recess. Al taps nervously on the table as his lawyer, Michael Ahern, attempts to salvage the deal. We felt particularly after District Attorney George Johnson had obtained the approval of the Secretary of the Treasury that his recommendation would be approved of by the court. Judge Wilkerson isn't having it.

Michael starts to respond, but the judge cuts him off.

Tempers flare as Al's lawyers fire back. If the court would follow the recommendation of the district attorney as made, and if we could have the assurance of the court, suppose the court does not agree with that. Now, it is for the court to determine the degree of guilt, as I said this morning. It is for the court to determine the seriousness of the offense. The court will listen, as I said this morning, to the recommendation of the district attorney. The

Al hustles out of the courtroom, pushing his way through the crowd.

The following morning, the hearing ends with the mafioso withdrawing his guilty plea. The July 1931 hearing was an embarrassment for both the prosecution and the defense. But the trial moves forward. Amid preparations, someone gets word to the prosecution and Judge James Wilkerson that Al has already bought off likely-to-be-selected potential jurors numbers 30 through 39. And yet, without further explanation, the judge tells the prosecution not to worry.

Dressed in a blue serge suit and a white and brown tie, all brought together with a white handkerchief and diamond-studded gold chain, Al takes his seat in federal Judge James Wilkerson's Chicago courtroom at 10:00 a.m., October 6th, 1931. Across from the gangster sits U.S. District Attorney George Johnson in his less flashy, muted gray flannel suit and usual gold-rimmed glasses. Judge Wilkerson, of course, is at the bench. It's now time for the potential jurors to enter.

But, the judge announces that he's swapping panels with another justice in another courtroom. The prosecution smirks. Al grimaces. Both know. That means his bribed jurors are gone. This will be a fair trial after all. Al's lawyers, Michael Ahern and Albert Fink, make all sorts of blunders. They fail to recognize when a testimony references an incident that should be inadmissible because the statute of limitations has expired.

They contradict each other and their own witnesses. When Michael compares Al's tax evasion to the Boston Tea Party, the bemused judge presses the lawyer to expound on this alleged philosophical alignment between his gangster client and the colonial protesters. Michael bombs, answering, No, I don't know what it is. On October 8th, the letter Al's former lawyer, Lawrence Mattingly, wrote, estimating the gangster's back taxes, is brought in.

Al's current attorneys protest, saying, a lawyer cannot confess for his client. The judge overrules, allowing the Mattingly letter, as it's called, but informing the jury only to consider it as proof that these statements were made, not as proof that those statements are true. Still, pretty damning evidence. On October 16th, the defense makes its closing arguments.

Albert Fink speaks for two and a half hours. Capone is the kind of man who never fails a friend. He was loved by his followers. Open-handed, generous, a man a bookmaker would trust with a $10,000 bet. This does not fit with the government's picture of a miserly effort to evade income tax. A tin horn or a piker might try to defraud the government, but not Alphonse Capone.

Pounding his fist on the jury rail, Michael calls the government's case weak and his client a saint. Why does it seek to convict him on such meager evidence? Because Capone has grown into a mythical Robin Hood whose name is bandied all over the nation. The next day, October 17th, George Johnson makes his closing arguments. Although Al looks the part of Robin Hood in today's green suit, the bespectacled U.S. District Attorney is prepared to shred that image.

In his pinched, greedy voice, George bellows out, "Let us see how the halo of mystery and romance fits upon the brow of this defendant. Does he ever appear in a reputable business? Did he keep any records such as an honest citizen keeps? Was there a single instance of contact with reputable business except when he purchased his Florida home?" The jury begins its deliberations. They arrive at a verdict later that night. Al returns immediately to the court.

He smiles, sits, and mops his brow with a silk handkerchief. The jury foreman hands some papers to the bailiff. He in turn passes them to the court clerk. The clerk reads, We, the jury, find the defendant not guilty as charged in indictment number 22852. Al grins.

The clerk continues, and we find the defendant guilty on counts 1, 5, 9, 13, 18, and not guilty on 2, 3, 4. The clerk reads several other not guilty counts, but Al's already crestfallen. The gangster lowers his gaze as his lawyers approach the bench. It's a confusing verdict. In short, the jury has found him guilty of failing to file tax returns, but not guilty of tax evasion.

He's found guilty of one charge in one year, but not the same charge in another year. Even the prosecution is unclear. But no one's confused about the time Al could serve. Between three felonies and two misdemeanors, he's looking at a possible 17 years. It's October 24th, 1931.

Al Capone is back in Judge James Wilkerson's Chicago courtroom for his sentencing. The purple-suited, soon-to-be-incarcerated gangster stands, though slumped and despondent, as Judge Wilkerson reads his offenses and their potential penalties.

The judge declares, "It is the judgment of the court in this case that on count one of the indictment, the defendant is sentenced to imprisonment in the penitentiary for a period of five years and to pay a fine of $10,000 and to pay all costs of prosecution." Al takes this stoically. It's what he expected. But hey, five years isn't bad. And if all the other sentences run concurrently, he can live with that. But that's not what Judge Wilkerson pronounces.

He goes on to explain that Al will serve two of his three felony sentences and one misdemeanor concurrently, but not so for the remaining felony and misdemeanor. Thus, the judge concludes, "The result is that the aggregate sentence of the defendant is 11 years in the penitentiary and the fines aggregating $50,000." Taken aback, defense attorney Albert Fink asks, "Eleven years, did you say?"

The judge answers firmly. "Yes." "Can't you have the misdemeanor counts run first, your honor?" "No, the order will stand." And with that, the hearing is over. A handcuffed Al is practically dragged to the elevator as he yells, "I'm not through fighting yet!" Reporters flock to the gangster, begging for a quote, to which he more calmly responds, "Well, I'll get a lot of time off for good behavior." Thus falls Chicago's most notorious gangster.

President Herbert Hoover sums up what most of the nation is thinking when Al is sentenced. Quote, it was ironic that a man guilty of inciting hundreds of murders, and some of which he took a personal hand, had to be punished merely for failure to pay taxes on the money he had made by murder. Close quote. Yet, so it was. And perhaps it's a silver lining that the feds caught Al on tax evasion and not bootlegging, because the end of prohibition is near.

No constitutional amendment has ever been repealed. But a little over a decade since its passage, the 18th is running out of fans. Here's how it's gone down. The Association Against the Prohibition Amendment began the fight in December 1920.

The AAPA argued that the federal government was overreaching on individual liberties and states' rights, though many Americans questioned its founders' real motives, as they also talked about legal, taxable alcohol as a great way to cut other taxes. But that questioning didn't mean that the general public wasn't already having second thoughts in the early 1920s.

Even in 1922, a Literary Digest poll suggested that 40% of Americans wanted to modify the National Prohibition Act, aka the Volstead Act, and that 20% wanted to repeal the 18th Amendment. In 1926, a similar Newspaper Enterprise Association poll found that the first sentiment had doubled. 80% of Americans wanted Prohibition modified or repealed.

Rabbi Morris Lazaran's 1926 poll of 122 members of the Central Conference of American Rabbis supports that too. Historian Marnie Davis sums up the result, quote, Nearly every rabbi from every region asserted that only two groups seemed to favor prohibition. The first was evangelical Christians, or as a rabbi from Trenton, New Jersey described them, pious, long-faced religious fanatics who are looking for a kick out of life in some future world.

The second group was bootleggers, for whom prohibition had turned out to be a windfall. Close quote. Yes, opinions changed quickly. Like that of nationally known dry Pauline Slavin, the first female board member of the Republican National Committee. A former advocate of prohibition, Pauline's watch to New York so thoroughly disregard prohibition as she switched sides in 1929 to found the Women's Organization for National Prohibition Reform.

and she was hardly the only woman making this 180. The organization will grow to nearly 1.3 million by 1933. Oh, and let's not forget that the Great Depression has begun. Suddenly, the Association Against the Prohibition Amendment's idea of replacing the income tax with taxed booze is sounding pretty good. In 1931, the same year that Al goes to the slammer, the 11-member Wickersham Commission releases its findings on Prohibition.

To President Herbert Hoover's satisfaction, the enforcement-focused commission does not want to repeal the 18th Amendment. Just modify it. During the 1932 presidential election, Democratic candidate Franklin D. Roosevelt takes advantage of Prohibition's waning popularity. He lends support to the financial benefits repeal could bring. Pauline crosses the partisan line. The Republican woman and her powerful Women's Organization for National Prohibition Reform endorses Franklin.

In February 1933, about one month before President-elect FDR's inauguration, Congress begins debating the 21st Amendment. Section 1 is the most important part. Quote, the 18th article of amendment to the Constitution of the United States is hereby repealed. Boom. That's the clincher. But this isn't a liquor-free for all.

Section 2 clarifies that states aren't forced to legalize booze. Rather, this amendment is making the regulation of alcohol once again a state issue. Section 3 sets a seven-year time limit on ratification, as was done with the 18th, and specifies that the several states must ratify by convention, not their state legislatures. This is done to try to dampen the outsized poll dries have in state legislatures.

On February 14th, 1933, Democratic Senate Minority Whip Morris Shepherd holds a one-man filibuster to try to keep prohibition alive. For over eight hours, the Senate waits out the gentleman from Texas, then votes 63 to 23 in favor of repealing prohibition. The House votes in favor of repeal as well, 289 to 121. By February 20th, the proposed amendment is out to the states.

Michigan becomes the first state to ratify on April 10th, while Utah has the honor of pushing it across the finish line as the 36th state to ratify on December 5th. Thus, with the support of two-thirds of both houses of Congress and three-fourths of the several states, the 21st Amendment becomes a part of the U.S. Constitution, thereby repealing the 18th. After 13 years, 10 months, and 19 days, Prohibition is dead.

One can only imagine what the jailed former bootlegger Al Capone thinks when Prohibition is repealed. His cell in Atlanta's U.S. Penitentiary isn't nearly as swank as his Eastern State Penitentiary set up a few years ago, and these guards aren't going to give him a sip of that newly legalized booze. In 1934, he's moved to a new federal penitentiary on an island just off the San Francisco coast. Yes, the soon-to-be infamous Alcatraz Prison.

But only five years later, Prisoner 85, as Al is known, is released. No, not for good behavior. The former gangster's lifelong battle with syphilis is finally catching up to him as it attacks his brain. On February 5th, 1938, he has what newspapers call a quote-unquote berserk breakdown. The volatile crime boss needs psychiatric help, better than he can get on this prison island.

On November 16, 1939, Al Capone, who's paid all his fines and taxes, is released from Alcatraz. He's served a total of seven years, six months, and 15 days. Al goes to Baltimore for treatment before retiring to his white-walled 25-room secluded Palm Island estate in Biscayne Bay, Miami. The famed Chicago mobster never returns to the city he tormented.

In 1946, doctors declare that his declining mental state is that of a 12-year-old child. A sad state of affairs, particularly as his oldest brother, Vincenzo, reappears in the 1940s. Turns out that he's been going by the name Richard James Two-Gun Hart while working as, get this, a prohibition agent. Oh, the irony. But family reunions aside, the end is near for Al.

It's 3:30 AM, January 21st, 1947. May Capone wakes with a start in her Palm Island home. Awakened by the sound of her husband Al's labored, snore-ridden breathing, she pokes at him, managing to wake Al just enough to attempt a sip of water. But it's no use. Al gurgles, unable to swallow. Then he begins to convulse. May's screams wake the rest of the house.

Dr. Phillips, who's been treating Al since his prison days, is called. The doc arrives to find his patient's limbs spazzing, pupils dilated, and jaw dead set. A cocktail of medications helps Al relax as the Italian gangster's Catholic parish priest, Monsignor Barry Williams, administers last rites. But then, Al seems okay. By January 23rd, the seizures have stopped. He's mostly conscious. The paralysis has dissipated.

He's able to sit up in bed and speak with his mother, wife, son, and siblings who have all rushed to be by his side. Dr. Phillips administers a few more tests. Even though Al is looking better, he's coughing. Bronchial pneumonia has set in, and that's no good. The Brooklynite becomes one of the first non-military recipients of the new antibacterial drug called penicillin. Yet, neither the penicillin nor other medications are doing the trick. It's now two days later,

Early in the day, January 25th, Al's brother Ralph steps outside the family's tropical Florida home to tell the clambering newspaper men that Al has "just about one chance in a thousand of pulling through." Later that day, at 7:25 p.m., with no warning whatsoever, the famed mobster of Chicago, the Italian-American, Brooklyn native best known to the public as Scarface, Al Capone,

draws his last breath. He was 48 years old. Despite the many problems they've had over the years, the family is distraught. Mae collapses immediately. She's inconsolable. The family won't allow the doctor to autopsy his brain. Ten days later, on February 4th, 1947, Al's buried next to his father in Chicago's Mount Olivet Cemetery.

In a few years' time, his remains, his fathers, and uncles are all moved to Mount Carmel Cemetery in the neighboring town of Hillside. We've come to the end of two intertwined tales. The tale of Al Capone and the tale of Prohibition. Let's wrap them up one at a time. In a very real way, Al Capone is an extension of the story of Ellis Island that we heard in episode 118. His parents were turn-of-the-century Italian immigrants who came to New York in hopes of achieving the American dream.

Now, we've already established that the law-abiding Capone parents were devastated to see three of their boys, Ralph, Frank, and Al, become gangsters. Yet, in a dark and twisted way, and without offering excuse, the hard streets of New York convinced these boys that their best path to the American Dream was outside the law. That's how Al saw himself. Following the American Dream by providing wanted services.

To quote him, "All I ever did was to sell beer and whiskey to our best people. If people did not want beer and wouldn't drink it, a fellow would be crazy for going around trying to sell it." A fascinating justification from a man whose bootlegging wars in Chicago killed upwards of a thousand people, hundreds by his personal order and dozens by his own hands. And yet, generations of Americans have, to some degree, come to admire Al.

Much like Western gunslingers, none of us would ever really want to encounter, Hollywood films, novels, and daydreams of beating the system have all helped to make prohibition's most deadly gangsters some of America's most celebrated icons. This remains the case to this day, long after their prohibition heyday has disappeared. That brings us to the conclusion of our other tale, prohibition. And what do we make of this national experiment with banning alcohol?

Let's start by pointing out that it did succeed in convincing Americans to drink less. Significantly, in fact, consumption per adult dropped well over 50% during Prohibition. That said, it is as Dan Okrent so bluntly puts it in his book, Last Call, quote, in almost every respect imaginable, Prohibition was a failure, close quote.

To note some of those shortcomings, prohibition launched organized crime into a new stratosphere of success, eroded respect for the law as illegal booze flowed everywhere, from the small town speakeasy to the halls of Congress and even the White House. Poor Assistant Attorney General Marble Willebrand had the dubious job of trying to enforce prohibition while half or more of the Harding cabinet flaunted it. While it saved some lives from excessive drinking, prohibition cost other lives.

Illegal, unregulated hooch led to deadly alcohol poisoning and well, then we get back to the bootleg wars. Finally, we come to the greatest irony of prohibition. Once it's repealed, new state regulations permitting but limiting the sale of alcohol actually make it harder for Americans to get a drink than it was during the free-for-all bootlegging speakeasy-loving 1920s. You heard that right. Alcohol is harder to get your hands on after prohibition.

And so, as Americans raise John Barleycorn from the dead, like Lazarus, though perhaps a well-regulated at the state level Lazarus, we close another chapter in the United States story. But we aren't done with the 1920s yet. From Hollywood to sports, this decade still has a little more roaring to do before the big crash to come.

History That Doesn't Suck is created and hosted by me, Greg Jackson. Episode researched and written by Greg Jackson and Riley Neubauer. Production by Airship. Sound design by Molly Bach. Theme music composed by Greg Jackson. Arrangement and additional composition by Lindsey Graham of Airship. For a bibliography of all primary and secondary sources consulted in writing this episode, visit htbspodcast.com.