- [Narrator] They were the overlords of Chicago's underworld.

- You shoot one of my guys, I'm gonna shoot two of your guys.

You stab two of my guys, I'm gonna stab three of your guys.

- You can get killed for any number of reasons.

(gun banging) - It was almost like a war.

- [Narrator] But for gangsters willing to risk a bullet, Prohibition-era Chicago was a bootlegger's paradise.

- One of the biggest industries in America had just been declared illegal.

Didn't take a genius to figure out that you could make a fortune.

- [Narrator] Especially for one man who rose to rule a criminal empire.

(soft music) - Al Capone is the prototypical celebrity gangster.

He's bigger than Chicago.

- Around the world, people knew who he was.

You tell somebody you're from Chicago and what do you get?

Oh, Chicago.

(imitates gun banging) (gun banging) (glass shattering) - [Narrator] To some, Capone's a man of the people.

- He was like Robin Hood, right?

Everybody loved him, so nobody would rat him out.

- [Narrator] To others, he's a cold-blooded mobster.

- Al Capone was Public Enemy Number One.

- [Jonathan] He made himself a target.

- [Narrator] And his legacy changed organized crime forever.

- It was the quintessential story of good versus evil, G-men versus gangsters.

But no one is above the law, not even Al Capone.

(cell door slams) - [Narrator] Al Capone's Bloody Business, next on "Chicago Stories."

(lighthearted music) (train clanking) (soft music) Chicago was the bloody epicenter of gang warfare in America in the 1920s.

Deadly disputes over money, territory, and retribution fueled the violence, especially between Chicago's biggest gangs: the North Siders, led by Bugs Moran, and Al Capone's South Siders.

- Different people line up on different sides of that, so it's virtually a citywide gang war in terms of everybody's either wearing blue or gray.

- [Narrator] The bitter rivalry culminated in the Saint Valentine's Day massacre on February 14th, 1929.

(gun banging) Seven men associated with Bugs Moran's crew lined up and gunned down, execution style, in a Lincoln Park garage.

- The crime really shocks America.

And not only that, the newspaper photos are gruesome.

- [Narrator] Assassins dressed as police officers released a hail of bullets.

The reported target, Bugs Moran, missed the hit by minutes.

The grizzly murders made headlines around the world.

Al Capone was never charged.

- He wasn't in Chicago, he wasn't in the garage, and he hired outsiders to do it.

But they weren't even his guys directly.

- [Narrator] But the killing cemented his status as Chicago's undisputed mob kingpin.

- The mythological image is that he's this cigar-chomping, Tommy gun-toting madman who just knocks off anybody who gets in his way.

He's Scarface, he's the supervillain.

- [Narrator] Almost 80 years after his death, Capone remains the country's most notorious gangster.

- If this man is going to all of these pains to make himself the first celebrity gangster and celebrate it and a big shot, it'll be this wonderful deodorant for all of the felonious and nefarious activity that he does.

- Ask anyone around the country today, perhaps even around the world, to name somebody associated with Chicago.

There's a good chance that person might say Michael Jordan or Barack Obama, but there's an equally good chance that that person might, even to this day in the 21st century, say Al Capone.

And that gives you a sense of how much that one individual has become associated with this city, for better or for worse.

(horn blaring) - [Narrator] Alphonse Gabriel Capone was born in Brooklyn, New York, January 17th, 1899, to Italian immigrants Gabriel and Teresa.

- My grandfather had been raised as a Catholic, very traditional Italian-Catholic upbringing.

And he was very hungry for his parents' approval and to please them.

- His family was a solid family, two parents, hardworking, trying to get by with nine kids on a barber's salary.

And like most immigrant families, as soon as the kids could help raise some money, they sent the kids out to do that.

- Papa was the fourth oldest.

And his mother said to him, "I need help, and you're the only one I can count on."

And so from the time he was about 10 years old, that responsibility was something that he took very seriously.

- [Narrator] Capone left school in sixth grade, fell in with local street gangs, and picked up odd jobs to support the family.

- Capone happened into some jobs working at a box factory, working eventually at a place called the Harvard Inn, a saloon on Coney Island.

That was actually a really rough place.

He starts there as a dishwasher, but this is a key moment in his life because he meets some people there who are serious players in the underworld, serious criminal figures.

- [Narrator] People like his boss, Francesco Ioele, an Italian gangland heavy, better known as Frankie Yale.

- He's the one who decides to name this saloon the Harvard Inn because his name is Yale and he thinks that's funny and it sounds like an Ivy League kind of an operation, which it definitely is not.

- [Narrator] At the Harvard Inn, the beefy teenager from Brooklyn graduated to a whole new world of vice and crime.

- But by that time, he was physically imposing.

He was tough, he was not afraid to fight, and so he earned his keep.

- [Narrator] Capone tended bar and met a regular named Johnny Torrio.

17 years his senior, Torrio was already a seasoned gangster who worked closely with Yale.

- And then begins to find himself in a position where he's, you know, doing some more dangerous work for guys like Torrio and Yale.

- [Narrator] Capone was straddling two worlds.

By day, he was an all-American teenager working a dull job in a box factory.

By night, a criminal apprentice.

(gentle music) In the spring of 1918, he fell head over heels for Mae Coughlin, a devoutly Catholic Irish girl.

- He met my grandmother when he was only 18.

They worked together at a box factory in Brooklyn.

And I think it was kind of love at first sight.

- Capone definitely could have gone either way.

He's still an American immigrant's kid who loves America, who loves the sports, loves to run in the streets with his friends.

If the box factory where he worked had offered him a promotion, had offered him a better salary, maybe he stays there.

There's nothing to suggest that he was a psychopath, that he was maniacal, that he had to be involved in criminal activity, nothing like that.

- [Narrator] But by that summer, Mae was pregnant, and money was tight.

- Suddenly, making money becomes a lot more important.

He's got a family to provide for now.

He doesn't have a great education.

He's gonna have to do what he has to do to get by.

- [Narrator] Capone became a father on December 4th, 1918, at age 19.

Weeks later, he married Mae in her family's church.

But their only child, Albert, nicknamed Sonny, was born two months premature, reportedly with congenital syphilis, an STD Capone unknowingly passed to Mae.

- Capone at 18, 19 is a wild man.

He's impulsive, he's taking crazy chances.

He's sleeping with women, he's sleeping with prostitutes.

So he's getting into trouble.

- [Narrator] And plenty of it.

Just four days after Sonny's birth, Capone hit on the wrong girl at the Harvard Inn.

- And the girl's brother comes after Capone, slashes him with a knife three times across the left side of his face, and they were visible forever, and Capone became known as Scarface, a nickname that he, of course, despised.

- [Narrator] Working the bar as muscle for his boss, Frankie Yale, Capone's bravado grew along with his criminal resume.

By then, Yale's buddy Johnny Torrio was working in Chicago as the underboss for his uncle, Vincenzo Colosimo, better known as Big Jim.

- He was the first of that type of gangster.

But what Colosimo really was, everybody thinks gangster, and he was more of a pimp.

- [Narrator] Johnny Torrio recognized talent and saw it in Al Capone.

He offered him a job in Chicago.

The timing couldn't have been better.

- He was wanted for questioning in a murder.

We don't know for sure whether he was guilty or not, but there's plenty of suggestion that he might've been.

So he's living on the edge.

- He was only 20 when he left Brooklyn and went to Chicago and then started sending more money back to the family in Brooklyn, until ultimately he could afford to bring my grandmother and my father out.

- [Narrator] Capone's father, Gabriel, died one year later, leaving Al as the breadwinner for his whole family and Mae's.

- He's suddenly thrust into adulthood, literally scarred by this period in his life.

So, all of a sudden, childhood is over and manhood has begun in the most violent way.

- [Narrator] Capone's surrogate fathers in the mob would step in and shape his future.

- Two big figures who'll play a significant role in his life are "Big Jim" Colosimo and Johnny Torrio, both older men, both people who figured out how to make money illegally.

(light music) - [Narrator] In Chicago, 20-year-old Capone embraced his new bosses, Big Jim and Torrio.

Under their tutelage, Al cut his teeth working for Colosimo in the city's seediest vice district.

- "Big Jim" Colosimo gets involved in prostitution in 1902 on the Near South Side in what was called the Levee District.

And from there, he branches out bigger into prostitution, gambling, some labor racketeering.

- (Clarence) Colosimo's wife, Victoria, is a madam.

Victoria and Jim build an empire where they have hundreds of brothels that they at least have one thumb in.

He could have just been happy at being the husband of a madam and running her business, but he has bigger ideas and bigger dreams.

- [Narrator] Colosimo was already making millions from his brothels, but he also wanted political clout.

The city's biggest pimp capitalized on a partnership with two of Chicago's most corrupt aldermen, John "Bathhouse" Coughlin and Michael "Hinky Dink" Kenna, who ran the red-light Levee District of the South Loop.

- The best investment you could make as a criminal was to buy police, politicians, and judges, and they were cheap in Chicago.

- [Narrator] Coughlin and Kenna were willing to be bought.

In exchange, they named Colosimo their First Ward precinct captain, which provided a veneer of legitimacy, plus protected status from police raids on his brothels.

- Colosimo was probably the most important underworld figure in Chicago before Capone and Torrio took over.

- [Narrator] But police didn't protect him from violent criminals.

Colosimo's brothels and rackets reportedly raked in $50,000 a month at their height, more than 750,000 in today's dollars, making the barrel-chested vice lord a perfect target for a group of deadly Italian extortionists known as Black Handers.

- You'd get this letter unsigned, except maybe there's a black hand print on the bottom saying, "If you don't give us $1,000, I know where a bomb, put in one corner of your building, might do a lot of damage."

- That's when he brought Torrio in.

He was a thinker, he was a businessman.

They killed the people who were trying to extort Colosimo.

- The perfect name for Johnny Torrio was "The Fox."

He was cagey.

He was very, very, very meticulous.

- [Narrator] With his extortionists dead and Torrio's protection, "Big Jim" Colosimo lived it up.

- "Big Jim" Colosimo favored white linen suits and suspenders studded with diamonds.

(bright music) - He was called "Diamond Jim" because not only did he always have a pocket full of diamonds, he'd take them out and play with them.

If you were a big shot in Chicago and you wanted Italian food, you went to Colosimo's American cafe on Wabash.

All the opera singers, all the baseball players, all the prizefighters went there.

- [Narrator] As a measure of gratitude, Colosimo let Torrio run his own gambling joint and brothel, the Four Deuces on the Near South Side, and Torrio assigned Capone to work the door.

- That might have been his job for a while until he found something better.

But Prohibition offered something a lot better.

(light music) (tense music) (bottles shattering) - [Narrator] Prohibition took effect on January 16th, 1920, banning the manufacture, sale, or transportation of alcohol.

Intended to promote moral and social reform, the law instead provided gangsters with their greatest opportunity yet.

- By the time it's enacted, the public sentiment has changed.

The war is over.

(patrons chattering) We wanna celebrate, we wanna have a good time, we wanna cut loose.

You see, you know, women starting to wear these shorter skirts and smoking and drinking in public, and Prohibition suddenly seems like a terrible idea, but it becomes the law.

- [Narrator] Legitimate bars closed their doors overnight, and a lucrative black market of bootlegging took over.

- If not for Prohibition, we never would've heard of Al Capone.

He would've been a bartender, he would've been a janitor, or he would've just gotten into a bar fight and killed somebody and spent the rest of his life in jail.

But there is no Al Capone without Prohibition.

- Chicago was a very, very, very good place to be a bootlegger during Prohibition if you chose to.

Why?

One, it's a hard drinking town.

The average Chicagoan drank three times as much hard liquor as the average American.

The second thing, there's an unparalleled level of corruption and a virtual breakdown of law and order in general in the Chicago area during Prohibition.

- One of the biggest industries in America had just been declared illegal.

You know there's demand.

All you have to do is create the supply.

- Once Prohibition goes into effect, it's still about $5 to produce a barrel of beer, but now you can sell it for $55 or more.

- [Narrator] It was a ticket to easy street and Torrio wanted in, but Colosimo wouldn't budge.

- Johnny Torrio, perhaps more than anyone in Chicago, sees that they could make more money than they've ever dreamed of.

This is like Microsoft, (chuckles) you know, that's the vision he's got.

The cops aren't really standing in their way, the mayor isn't standing in their way.

"Big Jim" Colosimo's standing in his way a little bit because he's the biggest operator in town.

- [Narrator] Big Jim, who had married Torrio's Aunt Victoria, was already in the way.

And then he fell for a songbird and sealed his fate.

- He started running around with a singer by the name of Dale Winter.

And Johnny Torrio, now that this man has very, very unceremoniously divorced his beloved aunt and has taken up with a singer, he owes this man no personal loyalty, and the die is cast.

- You get rid of him, what else is there, right?

So, Colosimo's gotta go.

- [Narrator] Torrio called in a favor from Frankie Yale in New York, his old friend from the Harvard Inn days.

(tense music) On the afternoon of May 11th, 1920, (gun bangs) Yale strode into an office across the street from Colosimo's Cafe and fired a .38-caliber slug into the base of Big Jim's brain.

- And so when the police couldn't find any witnesses to testify about the murder of Big Jim, the newspapers started to refer to this as a case of Chicago Amnesia.

- [Narrator] Rumors surfaced that Capone was in on the hit.

No one was ever charged.

- Shortly after Colosimo's death, Torrio inherits his operation and he soon begins to expand beyond the vice of the era, primarily gambling and prostitution, to include bootlegging.

- [Narrator] Torrio designated Al Capone as his right-hand man.

- It's almost like he was born for this.

And he gets to Chicago as a young man, willing to do anything, willing to try anything, desperate to make money to support his family.

And he's got connection to the guy who may be the most important figure in the Chicago criminal world.

- [Narrator] But the competition for bootlegging was fierce.

- At the start of Prohibition, there were some 12 major bootlegging gangs in Chicago.

- [Narrator] Most worked as allies for either the Torrio-Capone outfit on the South Side or Dean O'Banion's North Siders.

Unlike the East Coast Mafia, most Chicago gangs were ethnically diverse.

- Going back to when Jim Colosimo founded that gang, it was never an all-Italian gang.

The North Side gang was never an all-Irish gang.

There were Poles, there were Jews, there were Germans, a Scandinavian or two.

It's a misnomer propagated by people who don't really know Chicago.

- [Narrator] Though alliances shifted often, Torrio brokered a peaceful coexistence between the factions.

- Torrio was famous for using the phrase, you know, "We don't wanna have any trouble if we can help it."

And I think that's probably where Al Capone learned his own diplomatic skills from.

- He thought there was money enough to go around for everybody, that any kind of conflict over turf or over supplies, really all it did was cut into profit and bring publicity upon what was happening.

- [Narrator] Torrio and Capone patch-worked a vast network of breweries, distilleries, and amateur bootleggers.

- You had people making stuff in their bathtubs.

Imports coming in small boats from Canada.

They were really just trying to get everything they could, any way they could.

- Johnny Torrio ends up setting up a rather complicated operation that's working on multiple levels, and Capone kind of builds upon this foundation.

- [Narrator] They needed manufacturing, transportation, distribution, and an army of accomplices.

- There was so much pure alcohol being produced in Chicago during Prohibition that the Capone gang was not only largely supplying its own needs, but notoriously exporting that to many states, west, south, and even east of Chicago.

(light music) (people chattering) Beer tended in many cases to be produced locally.

Look at the explosion of microbreweries today around this country.

It's not that hard to do it.

So the bootleggers had some people who knew how to make beer, they'd put up some copper kettles, they'd start churning out beer, and they'd keep doing it there until they were raided.

- [Narrator] Though police raids were a constant risk, Torrio and Capone had friends in high places.

And Chicago's mayor, "Big Bill" Thompson, was more than happy to turn a blind eye.

- He was bought and paid for by Capone.

He had a picture in his office of Al Capone.

And then it just trickles down to your leadership, your aldermen, your department heads.

If they're not playing, they're not in those jobs, plain and simple.

- [Narrator] With officialdom in their back pockets, Torrio and Capone cranked up production.

- At the time that national Prohibition went into effect, there were about 60 breweries in the city of Chicago.

They all have to shutter and close down.

But what doesn't go away, the breweries themselves and a lot of the people who worked there and all of the supplies and machinery that were already on hand.

So Johnny Torrio, and then later Capone, began acquiring breweries.

- [Narrator] And Chicago's new booze barons had major transportation advantages that bootleggers in smaller cities didn't have.

- [Paul] Chicago was the center of the railroad industry.

It had access to the Great Lakes.

It had access to industry, also to a fleet of trucks, which were ideal for shipping booze.

- Drinking alcohol was not illegal, but selling it, manufacturing it was.

So, if you could find a way to get it, you were fine to drink it.

So, suddenly there's an enormous incentive for folks who have not much to lose.

- [Narrator] Capone later boasted- - [Voiceover] "I give the public what it wants.

I never had to send out high-pressure salesmen.

(chuckles) I could never meet the demand."

- [Narrator] And the profits rolled in.

In 1924, five years after Capone came to Chicago, the federal government estimated Capone and Torrio's operations brought in a staggering $7 million a month.

- And by that time, he could afford to bring the whole family.

It was a two-family house, but his mother, his other siblings, my grandmother, my dad all lived in the same house.

- [Narrator] The classic Chicago two-flat bungalow on the city's Far South Side was a modest safe haven for Capone's loved ones.

- His business life, his professional life, was outside the home.

And when he came home, it was all about family and sitting at the table.

- [Narrator] But Al was rarely home.

By 1923, the political tide was turning, and a growing chorus of reformers helped push crooked "Big Bill" Thompson out of the mayoral race.

That November, reform candidate William Dever was elected and turned up the heat on vice enforcement.

Capone needed headquarters outside the city, (people chattering) (light music) so he headed west to Cicero, a working-class suburb where virtually every politician with a pulse had a price.

- They welcomed them in Cicero 'cause they knew they were gonna make money.

- He was referred to in some of the newspapers as the "Mayor of Cicero," and Cicero was called "Capone Land."

- [Narrator] Capone set up shop at Cicero's Hawthorne Hotel and equipped it with bulletproof steel shutters.

He stayed for months at a time and ruled the joint with trusted lieutenants, including Jake "Greasy Thumb" Guzik, in charge of payoffs and gambling, Italian prizefighter-turned-triggerman "Machine Gun" Jack McGurn, and Capone's older brothers Ralph and Frank.

- Guys in the Capone gang themselves used to refer to their organization as "our outfit" or "the outfit."

- So those were the monikers that they used, and "outfit" kinda stuck.

- [Narrator] And with Cicero mayor Joseph Klenha in his back pocket, Capone operated freely.

- So freely in fact that, you know, Capone feels comfortable beating up the mayor on the steps of City Hall.

(chuckles) (keyboard clacking) (tense music) - [Narrator] In April 1924, when a reform candidate tried to oust the mayor, Capone terrorized Cicero, using brute force to swing votes towards Klenha.

- He has his men at the polls reminding people who they should be voting for.

And the cops don't like this, and there's a confrontation and shooting breaks out.

- 120 Chicago policemen deputized as county sheriffs, and they were met right at 22nd and Cicero by a gang of gunmen, and they had a shootout and Frank was killed.

- [Narrator] Klenha won his election, but the Capones paid dearly.

- Al brought his brother to Chicago to work with him.

Al thought he was the savior, that he was rescuing his family from poverty.

Now he brings his brother into the business and gets his brother killed.

- Al was deeply disturbed over that, but there really wasn't a hell of a lot he could do.

- [Narrator] And the violence was about to escalate.

- The Genna gang, who were in control of the area around Taylor Street on the Near West Side, they were pushing some of their whiskey into parts of the North Side.

Now, there'd been an agreement put together by John Torrio in 1920 among the various gangs.

We all stay in our own area and we don't go into anybody else's area.

- That kind of led to more or less a kind of code of conduct among the different people involved in the Outfit and among their rivals.

- Well, Dean O'Banion, the North Siders, they went to Torrio and said, "What about the agreement?"

Torrio apparently just shrugged his shoulders like, huh?

The North Siders start hijacking the liquor trucks being used by the Genna gang, and O'Banion himself seems to not only be mad at the Gennas, he decides Torrio is also at fault.

- [Narrator] Furious at Torrio for refusing to enforce the rules, O'Banion set up a double-cross.

- O'Banion and Torrio had joint ownership in a brewery on the North Side that had been going on for several years.

O'Banion comes up with a story he'd like to sell Torrio his half for, like, $500,000.

Except O'Banion has invited the Chicago Police Department there for the closing.

Everybody who's there gets arrested, including Torrio.

And for Torrio, that means a jail term.

And at that point, I think O'Banion is a dead man walking.

- [Narrator] In November 1924, Torrio assembled a hit squad and called in Frankie Yale from New York.

They murdered Dean O'Banion at Schofield's Flower Shop, the North Siders' headquarters, across from Holy Name Cathedral.

- The reason we think of these rivals to Capone as being, you know, blood enemies is because blood does pour.

- [John] They go after John Torrio, shoot him up pretty good, don't kill him.

They try and get at Al Capone, they shot up his car.

- And the police aren't doing anything about it.

There's no investigations, there's no convictions, no charges are filed.

So the message is, you know, you guys shoot it out amongst yourselves, you guys work this out.

- And that then sets off the gang, the big gang war that runs through much of Chicago's history for about the next six years.

(tense music) - [Narrator] But Johnny Torrio, nursing five bullet wounds from the North Siders' payback, wanted no part of it.

- Torrio does something very interesting, you might say, for gangland.

He decides that the best way to go through life is actually alive.

And he does a jail term, and what does he do?

He leaves Chicago, he goes back to New York where he's from, and it's Capone's to run now, but during a hot gang war.

- [Narrator] In late 1925, 26-year-old Al Capone stepped into his new role as the head of what would officially become the Chicago Outfit.

- It is pretty intoxicating, I think, for a person who all of a sudden begins to have a certain amount of power.

I think he liked having the respect, I think he liked having the attention.

- [Narrator] Capone was at the helm in a city divided.

- All the major bootlegging gangs in the city are on one side or the other of that conflict as allies.

(guns banging) - [Narrator] Chicago and surrounding suburbs erupted into a violent loop of retaliatory attacks among rival gangs, each fighting for territory in their smuggling and bootlegging operations.

The bloodbath lasted for six years (gun banging) and became known as the Beer Wars.

(people shouting) (whistle blowing) - It was the number one spectator sport in the city of Chicago.

The public loved to read about that stuff.

- [Narrator] Though experts debate the exact numbers, hundreds of gangsters were killed during the Beer Wars.

Capone was especially good at skirting prosecution: implicated, but never charged for dozens of murders.

- He had about 500 gorillas working for him at that point.

They're not like the corporate world where they have a, you know, an HR department.

The rules are very clear about what you're supposed to be doing and not doing.

And quite often the punishment is they'll kill you if you seriously break the rules.

- [Voiceover] "Those who work for me are kept faithful, not so much because of their pay as because they know what might be done with them if they broke faith."

- But most of the time, he wouldn't dirty his hands.

Why should he?

That's what he pays people to do.

- Capone is America's most notorious criminal to this day.

And Capone acted like, "Yeah, that's me, I do that."

And I think because he carried on with this sense of pride in what he was doing, he does not fit the image of the cold-blooded, maniacal killer.

He combines it with the American dream, the ambition, the desire to be a businessman, to take care of his family.

And when you put those two together, you get this fascinating conflict.

- [Narrator] And Capone carefully cultivated his public image.

- He was known for being very flamboyantly dressed, brightly colored suits, his trademark hat.

He liked to be well regarded, even asking people to call him Snorky, meaning well-dressed.

He was known to travel with members of the media, who would write favorable stories about him.

So he really tried to use that to his advantage.

- All these other bootleggers were saying, "What the hell are you doing?

You're an idiot.

You don't call attention to yourself.

You're making all this money illegally.

Shut up."

But he loved talking to the press.

He loved seeing his picture in the paper as long as they took his picture from the other side.

- He really, really understood the shine, he understood the flash, he understood slogans, he understood sound bites.

- [Voiceover] "I'm a businessman.

I've made my money supplying a popular demand.

If I break the law, my customers are as guilty as I am."

(lively music) - And you can sort of see the logic in it.

Nobody likes Prohibition.

And if you're breaking a law that people don't think should be the law, maybe you're not a criminal after all.

- Criminals are very often gregarious, they have great confidence, but those types of individuals often like to think that they're smarter than everyone else, and so they can't see the danger in talking and talking and talking.

- [Narrator] Capone had perfected living a double life.

(soft music) - He could close a door on certain aspects of his life, and I think he had a willingness to do whatever he had to do, even if it was against the law or was not the way he had been raised, it was breaking moral laws to get to a place where he could be sure that his family was going to be well cared for.

And along the way, he wandered into a very dark place.

- These were people who broke the law, these were people who committed acts of violence, and you don't wanna lose sight of what they actually did in their lives.

(tense music) - [Narrator] By 1927, "Big Bill" Thompson won reelection in Chicago.

With his ally back in the mayor's office, Capone brazenly reestablished headquarters in Downtown Chicago.

First, renting a floor of the Metropole Hotel, then taking over two floors of the Lexington Hotel.

- The practical reason for him, or any infamous person who has a target on them, is to move around a lot and to do so in plain sight.

- Nobody ever really came close to killing him.

Shot himself once on the golf course (laughs) with a gun in his pocket.

It's really remarkable that Capone survived as long as he did, and I think that was 'cause he was careful, he kept bodyguards around him, but also because he tried to avoid conflict when he could.

(lighthearted music) - [Narrator] Some of Capone's Chicago haunts remain to this day.

The Blackstone Hotel Barbershop, marble with no windows, hosted haircuts and Outfit meetings.

And underneath Chicago's L tracks, the Exchequer Restaurant, originally the 226 Club, where patrons sipped liquor in teacups downstairs (cups clinking) and upstairs.

- A hundred years ago, like Al Capone, you could have come up here and enjoyed something off the menu.

Because this was a brothel.

- [Narrator] In case of a raid, the club offered another secret: (door creaks) tunnels.

- Chicago was built on a swamp.

Around the late 1840s, early 1850s, a decision is made to actually raise the city, to lift it up.

You can go all across Chicago and find various subterranean spaces, basements, and sub-basements.

Stories have arisen that these places were used as tunnels that Al Capone used to escape from one place to another.

The Green Mill, for example, in the Uptown neighborhood, it's without a doubt one of Chicago's premier jazz cabarets, dating all the way back to the 1920s.

- If you had to get outta here and you didn't wanna go out on the street 'cause guys are looking for ya, you go behind the bar, you go down the trapdoor.

Then there's a series of tunnels you could go out and you could end up down the block.

- They were already in place before Prohibition even existed.

Because many of them survived to this day, they've become associated with the legend and lore of Prohibition.

- [Narrator] At the Green Mill, Capone reportedly had a favorite booth.

- There'll be people waiting outside, they'll come in, like tourists from Europe or something, and they just come in, "Oh, Green Mill, Green Mill, where'd Al Capone sit?"

Then the bartender's like, "Ah, geez, over there."

- Al Capone really, really loved music.

He was a musician, he wrote songs.

And in his particular era, the musicians that were the most plentiful were African American musicians playing this brand-new genre of music called jazz.

(bright jazz music) - I don't know if it was him or his guys, they kidnapped Fats Waller, a piano player, and used him, like, for some kind of private parties or something.

(cheerful piano music) - According to Mr. Waller, they partied for three solid days, and Fats Waller left with more than $3,000 cash in an envelope.

Probably a really bad headache too.

- Legend that I've heard, he'd have a girl in the room and he wants to, you know, make out and everything, and he'd hire, like, a little combo and they'd be behind a curtain playing music to make it romantic in the room.

(tense music) - [Narrator] By the late 1920s, Capone was filthy rich.

- The federal government estimated that in 1927, the Capone gang's total revenues were $105 million.

- [Clarence] A big part of it goes into the pockets of people who need to be bribed.

Many people within the Chicago Police Department, many judges, many politicians.

- So the Capone gang in total might have had profits around 15 million.

Al Capone's personal income might have been 1, $2 million a year, maybe a little more.

- [Narrator] In today's dollars, that's 15 to 30 million a year.

And Capone blew right through it.

- Al Capone had enormously expensive tastes, from custom-made silk underwear made for him at Marshall Field's to box seats everywhere, to traveling all over the place, to having his own railroad car, his private island resort in Miami.

- I think Al Capone's view of the world was, I got a lot this month and there's gonna be more next month and the month after.

There's always gonna be more.

- He flashed a lot of jewelry, particularly diamonds.

(soft music) And he enjoyed the finer things in life.

Fine automobiles, fine wines, fine food.

- He spent it as fast as he got it.

By his own estimation, he pissed away about $8 million or so in gambling.

He was a degenerate gambler, and he spent on lavish things.

- [Narrator] And he spread the wealth, perhaps strategically.

- He was like Robin Hood, right?

Everybody loved him, so nobody would rat him out.

And I think that's what drove law enforcement crazy, because not only did his granddaughter see that he had a big heart, but he showed it to his neighbors and to his friends and his community, and that's what buys respect, not authority.

- I don't think he genuinely thought that he was a hero or that he was a Robin Hood.

And I think when he sets up the soup kitchen, it's mostly done for public relations purposes.

- And one of the reasons that people who knew him and loved him were able to compartmentalize this guy who was a crazy murderer is because, wow, he's really a nice guy.

- [Narrator] Capone became the world's first celebrity gangster and a household name.

In Hollywood, charismatic gangster types replaced classic leading men, a through line that carried even into modern film.

- They clearly recognized that he was, you know, an iconic figure that we could not necessarily relate to but we were all fascinated by.

- I run this outfit!

Me!

Al Capone!

- What?

- They got the shipment.

- What?

(guns banging) - Hey, lookit.

They got machine guns you can carry!

- Terrible.

- Hey, Johnny.

Look what I got!

- I want him dead!

I want his family dead!

I want his house burned to the ground!

I wanna- - We always have this tension in American society.

Once something becomes familiar, once we turn it into a TV show and a movie, we get to know that version and we forget the truth.

- This whole thing about Al Capone, you know, what's true, what's not true?

What's legendary?

What's fact?

I just go by "The Man Who Shot Liberty Valance" movie.

"When the legend becomes the fact, print the legend."

Because that's what everybody wants.

- [Henchman] Put your mitts up.

- [Narrator] But on February 14th, 1929, Capone's larger-than-life public popularity evaporated.

(guns banging) The St. Valentine's Day massacre sent shock waves throughout the country.

(soft music) The violence ignited public outcry.

Many Americans were no longer willing to turn a blind eye to gangland bloodshed in exchange for access to illicit booze.

- The local authorities, the mayor, et cetera, they don't seem to be able to do anything about this guy.

Some of Chicago's citizens went to Washington, D.C., and said to the president of the United States, "Can you do something about this guy, Capone?

I mean, this is a problem."

- I don't think Capone had anything to do with the Valentine's Day massacre.

We know for a fact that he wasn't there.

He was in Miami when it occurred.

He knew that the FBI and the IRS were breathing down his neck.

There's just no reason to think that he would've ordered this hit.

There's just no logic to it.

- He didn't go in there and shoot those guys himself.

He made sure he was out of town, and he didn't use faces from his men, from his gang, whose faces will be recognized by the North Side gangsters.

But it was definitely a Capone operation.

- But we'll never know for sure because the crime, all these years later, remains unsolved.

- [Narrator] While Capone's involvement has ignited historical debate for decades, after the massacre, newly-elected President Herbert Hoover leveled a mandate: get Capone.

- He wants to send the message that he's going to be tough on crime.

And what better way to send that message, take out the most famous criminal in America.

- [Narrator] Al Capone became Public Enemy Number One.

- And really, once he started to lose control of the public's opinions, that news attention turned negative, and it stayed negative, and that certainly hurt him as he went along.

- [Voiceover] "They've hung everything on me but the Chicago Fire."

- And we know he was never convicted of murder or he was never convicted of breaking the bootlegging laws, although he did it, you know, thousands of times.

- [Narrator] The Feds tapped Prohibition agent Eliot Ness to raid Capone's breweries and distilleries.

Ness and his incorruptible agents did rack up Prohibition charges and cut into Capone's profits.

But Ness didn't mastermind Capone's downfall like books and movies gave him credit for, including 1987's "The Untouchables."

- Eliot Ness gets a lot of attention because he's breaking down doors of breweries and he's calling reporters to come with him and getting his picture taken among the broken bottles of beer.

So he's very good at public relations, but he's not making a dent in the Capone operation.

There's no way to really tie him even to the bootlegging because there's no books.

- [Narrator] Instead, it was a dogged United States attorney in Chicago named George E. Q. Johnson who went to work on a new, yet decidedly less sensational angle, pinning Capone on tax evasion.

- The job falls to the accountants for the IRS.

So U.S. Attorney George Johnson makes the decision that tax charges are the best we can do.

"I'll take it," you know, anything just to get him in jail and to get him off the streets.

(pensive music) - [Narrator] In February 1929, prosecutors got an unlikely break when Capone was subpoenaed from his Florida home, wanted for questioning in a small-time bootlegging charge in Chicago.

- Now, Al Capone's private attorney filed an affidavit with the court from Capone's doctor.

That affidavit said that Capone was too ill to travel and had been laid up in bed for six weeks.

The U.S. Attorney's Office called in the FBI to determine was this true or was Al Capone lying?

- [Narrator] FBI Agents headed to Miami and discovered Capone wasn't laid up.

He was living large, spending his days at the racetrack and on fishing trips.

Capone testified in Chicago three weeks later.

- As he was leaving the courtroom, he was arrested on contempt of court charges.

He did bail out for $5,000, but then he went on two months later to be arrested in Philadelphia on weapons charges with his bodyguard.

So he did approximately one year in a Philadelphia prison.

It was just the beginning of the end for Mr. Capone.

- [Narrator] But hard time was different for Capone than most prisoners.

- Capone had a way of winning over his wardens.

He would let them borrow his car, he would pay them to allow him certain luxuries.

So these wardens, I think they kind of liked Capone and they cut him some favors from time to time.

- [Narrator] Meanwhile in Chicago, George Johnson, aided by an equally methodical accountant named Frank Wilson, worked day and night.

- Frank Wilson is this forensic accountant working for the IRS.

He's got these bottle thick glasses and he looks like a total geek.

But he's a bulldog.

He has been fighting corruption his entire career and he just will not let go until he gets Capone.

- [Narrator] Wilson discovered forgotten gambling ledgers, confiscated from Capone's days in Cicero.

- They're literally, like, just going through boxes.

And they find a guy who was one of the accountants and they put the screws to him.

And they find a couple of ledgers, and they find ledgers that appear to have Capone's name written on them.

- [Narrator] The feds already had eye-popping evidence of Capone's lavish spending.

But the ledgers revealed something new, proof Capone earned at least some income from gambling, yet he paid no income taxes.

Still, Johnson's team was tentative, afraid that the evidence could be too circumstantial to stick.

In July 1931, they offered Capone a plea deal to serve two and a half years in prison.

Capone jumped at the offer.

- It's pulled out from under him, and they go to trial, and everything about this trial smells fishy, like Capone never has a chance.

The jurors that they choose are thrown out.

Some people think that Capone had tainted the jury pool.

And the judge throws them out at the last minute, brings in jurors who had all served on other Prohibition juries and had all voted for conviction.

- [Narrator] As Capone's trial began, a crush of press and curious Chicagoans descended on the courthouse.

It was the trial of the century.

(tense music) (people chattering) 11 days later, Federal Judge James H. Wilkerson handed down Capone's sentence: 11 years in prison.

- At the time, Al Capone was such a huge figure in the Chicago public eye.

Really, it was the quintessential story of good versus evil, G-men versus gangsters.

It's easy to feel as though you have a stranglehold on Chicago and you're invincible, but no one is above the law, not even Al Capone.

- [Narrator] By early May of 1932, reporters flocked to cover Al Capone's transfer from Cook County Jail to the Atlanta Federal Pen.

(people chattering) Two years later, Capone was transferred to Alcatraz, the notorious island prison better known as The Rock.

- [Siobhan] Once that prison was created, they would of course want to populate it with those that the Americans thought were at the top of the public enemy list.

Really, he experienced a much harsher existence than he had at any prison before.

- [Narrator] Capone wrote weekly letters to Sonny and Mae.

- It's addressed to "my dear son."

"Well, son of my heart, here is dear father, who loves you with all my heart and proud to have a son as smart as you are.

Until next week, give Mother a nice big kiss for me, and God bless you both.

Your dear father, Alphonse Capone."

(soft music) - [Narrator] The year after his move to prison- - [Reporter] December 5th, 1933, in a moment, the story.

- [Narrator] Prohibition was repealed.

In Chicago, Frank Nitti would become Capone's successor.

Though violence continued, by 1932, the Beer Wars had ended, and the empire Capone had built virtually controlled organized crime in Chicago.

- And after Capone goes to prison and Prohibition is over, I would say that's when the Chicago Outfit is created.

The Outfit with a capital O only comes into being, it's the Capone gang morphing into The Outfit.

- [Narrator] In failing health, Capone was granted early release in November 1939, suffering from the neurological effects of long-term syphilis.

- You can definitely see that physically he's experiencing a lot of changes, likely mentally as well.

So when you compare where he started, that really is a significant change, more significant than a change you would expect to see in an individual only about a decade apart.

- The usual claims are that when Al Capone comes out of Alcatraz in 1939, his brain is fried.

You know, the syphilis that he caught when he was younger has now gone to where he's got some serious mental health issues, that he's, you know, debilitated.

- [Narrator] But Diane Capone's grandmother disagreed with the usual claims.

- Some people who he'd known in Chicago came to visit him and they thought he was, you know, losing his mind.

One of them said, "He's nutty as a fruitcake," and she was offended.

And Papa's remark to her was, "Let 'em think whatever they want.

It's my ticket out."

As long as they thought he was no longer a threat to them, that he was not going to reveal things or he wasn't going to take back his powerful authority, you know, he felt that it was his ticket out.

- [Narrator] Eight years after his release, and eight days past his 48th birthday, Al Capone died at his Palm Island, Florida home on January 25th, 1947.

Not from syphilis, but from a stroke, compounded by pneumonia.

He was buried in Chicago.

(melancholy music) Capone's larger-than-life mythology grew into a pop culture obsession after his death.

- He's an interesting, compelling person.

When you think of your most well-known figures, in the likes of Babe Ruth, Marilyn Monroe, presidents, he is a primary figure.

- [Narrator] In 2021, auction of the Capone estate, presided over by his surviving granddaughters, drew frenzied attention.

- We had over 1200 people registered for that sale.

It was an experience of a lifetime.

(soft music) The guns were the two highest-grossing items in the sale.

So, that's a very intimate object for him.

And Sonny Capone's items did well.

His wife, Mae Capone's items did well.

That's how powerful he was, that it transcended.

And just to own a piece, there's only so many pieces.

- It was a sense of closure, and it was a blessing to feel that I had somehow shared who he was with the world and would create a different picture than a lot of people held of him.

- If we just think of Capone as this snarling, cigar-chomping madman, well, history doesn't have much to teach us if we just fall back on the cliches.

It's important to not try to exaggerate these figures and not turn them into cartoon characters and to realize that they're real.

- What is clear is not how you feel about the things that he did.

What is clear is that he violated federal statutes.

He committed crimes, and he was forced to pay for those transgressions.

He hurt the populace and there are consequences for that.

- [Narrator] What remains of the Chicago Outfit has nowhere near Capone's high profile.

That may be at least, in part, by design.

- I refer to sometimes the lesson of Al Capone that was learned by many of his successors.

It was keep your head down, keep your mouth shut, stay out of the public limelight, don't call attention to yourself or to the organization, 'cause all you're doing is you're targeting yourself and the organization in the eyes of the authorities.

- [Narrator] Despite its diminished presence, the Chicago Outfit continues to operate just off the radar.

- You can't separate Capone from those who took over the Outfit after him to the Calabrese family to what we're seeing today.

Each one is a building block that builds on the one that came before them.

You see the Bank Secrecy Act, you see RICO.

Those are charges that you could not charge before as part of one big conspiracy, but now, now you can.

That is a huge breakthrough that allows us to really go after organized crime, and really that led directly to the much diminished Outfit that we do see today.

- We focus a lot on what our heroes can teach us, our presidents and our, you know, moral leaders, but we don't think as much about what our anti-heroes can teach us.

The bad guys have lessons to teach us too, and they tell us a lot about who we are as a country.

- He certainly was a very complex man and a man who did a lot of bad things, but he tried to make amends for them and had found peace with God.

- [Narrator] Al Capone remains one of the most prolific gangsters in history, and his legend shows no sign of fading.

- We have no way of knowing how many people he killed.

We have no way of knowing who he ordered killed.

But ultimately, Al Capone might be the definitive Chicagoan because he came to Chicago with almost nothing and he left Chicago before his 35th birthday, he was dead before he was 50, and yet we're still talking about him and what he did in Chicago today.

(soft music) (pensive music) (pensive music continues)