Episode #224 - What's True About Al Capone? (Part III)

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Hey everyone, Sebastian here.

Before we get going today, I just wanted to let you know that today's episode is going to be a bit more violent than the average episode of Our Fake History.

I know this whole Capone series has been pretty bloody, bloody, but part three is especially gruesome.

There will be descriptions of murder that may be disturbing for younger listeners.

I know a lot of you out there like to listen to this show with your kids.

This one might not be great depending on how old those kids are.

So please use your discretion.

With that said, enjoy the show.

Have you ever heard the story of how Elliot Ness died?

You've heard of Elliot Ness, the Chicago-born prohibition agent that's been celebrated in pop culture as the man who brought down Al Capone.

In fiction, he is the Dick Tracy to Capone's big boy, the incorruptible super cop who managed to bring law and order to a city that had long since given up on on such quaint notions.

This is a man who has been portrayed on screens big and small by the likes of Robert Stack and Kevin Costner.

But how did he meet his end?

Did he go down in a hail of machine-gun bullets raiding the last of Chicago's alky cooking joints?

Was he taken out by a hit called in by one of Capone's successors?

Or did he die peacefully as a fetid elder statesman of American law enforcement?

Well, according to one story, in 1957, Elliot Ness read the final draft of his own memoir and immediately dropped dead.

The book, which had been ghostwritten by the sportswriter Oscar Okey Fraley, was called The Untouchables, and within two years it would make Elliot Ness a household name but in 1957 ness was not a famous man he was a struggling business owner living in obscurity in a small pennsylvania town when he was introduced to his eventual collaborator aki fraley the writer admitted that he had never heard of elliott ness

in this way fraley was like most people in the mid 50s only the most dedicated students of prohibition era Chicago might have had some familiarity with Elliot Ness, but otherwise, he had been largely forgotten.

But as the two men got to know each other, it became clear to Fraley that Ness had lived a remarkable life.

In particular, his memories of his days as a Chicago Prohibition agent struck Fraley as amazing fodder for a book.

Not only was Ness keen to tell his stories, he had also kept a a small personal archive of newspaper clippings from the early 30s that helped flesh out the tales.

The men would spend hours together with Ness using scraps of old Chicago papers to help jog his memory of certain events.

He also created stacks of handwritten notes filled with half-remembered anecdotes from 25 years past.

This all struck Fraley as a good start,

but he was always eager to find something a bit more juicy.

So he pushed Ness to dig deeper and try to remember things that might be of interest to your typical paperback crime enthusiast.

This led to long nights where Ness's office manager, Dorothy Williams, would be tasked with typing up Ness's latest batch of hand-scrawled notes.

According to a 2017 magazine piece by the writer Matthew Pearl, Dorothy's husband Lou was often present at these typing sessions, and he had a few sneaking suspicions that not everything his wife was typing was 100% accurate.

He would sit, quote, nearby, admonishing, Elliot, now you know that didn't happen.

End quote.

It also seems that Fraley took his own liberties with Ness's tales.

In one letter between the men, Fraley wrote, quote, I did a hell of a lot of research to check facts and figures, but don't get scared if we stray from the facts once in a while.

We've got to make a real gangbuster out of this thing.

And after all, we have literary license, end quote.

Just how much literary license was taken in the creation of The Untouchables is still being debated today.

We are told that when Elliott Ness finally read the finished product, he was deeply unsettled by how distorted and unlike his real life The Untouchables had turned out.

The stress caused a massive heart attack and he died right there.

on his kitchen floor.

Aki Fraley would later tell the Miami Herald that he had had been in the room when it happened, saying that after the two had reviewed some proofs for the book, Ness, quote, keeled over right next to me, end quote.

So, was Elliot Ness killed by his own fake history?

Was the man we have celebrated as the only honest cop in a corrupt town shamed to death by his own self-aggrandizing lies?

How's that for irony?

But here's the thing.

Our main source for this story, ghostwriter Oscar Aki Fraley, was a liar.

We know for a fact that he was not in Elliot Ness's house on the day that he died.

Fraley just said that he was because it made a better story.

Now, it is true that Ness died within a few weeks of having received the final draft of The Untouchables from Fraley.

We also know that Ness had been diagnosed with valvular heart disease a few months before his untimely death.

But did he put the book down and then immediately drop dead?

That we do not know.

Aki Fraley certainly presented it that way, but he also didn't frame it like Elliot Ness was suffering from pangs of conscience, because that would have made Fraley look bad by association.

Instead, he suggested that reliving the dramatic moments of the 1930s put too much strain on Ness's weakened heart.

But there's no doubt that The Untouchables is an unreliable text.

The question is just how unreliable, and who should take the blame for the excesses in literary license?

Well, here our sources differ.

As Matthew Pearl explains, when it comes to the final months of the book's creation, there are different accounts of exactly what went down.

He explains, quote, accounts diverge.

Some have Ness trying to back out of the book, furious that Fraley was twisting the facts.

In others, Ness, though uncomfortable, went along willingly because he was desperate to have the book succeed.

Still others insist that Ness was the driving force behind any embellishments in the Untouchables narrative.

End quote.

Was the Untouchables unreliable because a desperate Elliott Ness had fed his ghostwriter a more exciting version of the facts?

Or had the ghost writer fluffed up an interesting but bloodless memoir?

The jury is still out on this question, but it's worth knowing that Oscar Fraley was known to lie about things big and small.

He not only lied about Ness's death, he lied about having a college education, and had a colorful catalogue of tales from his days as a beat reporter, all of which were likely made up.

On top of that, he often lied about his personal life, deceiving people about how many times he had been married and how many children he had.

Honestly, as soon as you dip into the biography of Oscar Fraley, you find a pretty slimy character.

Now, that doesn't mean he should be blamed for all the historical inaccuracies in The Untouchables, but you know, I think it's important context.

What's clear is that if Elliot Ness had lived just two years longer, he would have seen his public reputation completely transformed.

The forgotten prohibition obscurity was about to become an American legend.

When the book was finally published in 1957, its historical accuracy was taken at face value.

The Untouchables became a surprise bestseller and reinvigorated public interest in the Prohibition era and Al Capone.

Then, in 1959, just two years after its release, The Untouchables was picked up by ABC and was adapted for for television.

Originally conceived as a two-part televised movie, The Untouchables eventually became a regular series, starring the square-jawed Robert Stack as Elliott Ness.

In its four-year run from 1959 to 1963, it became one of the most watched shows on American television.

At its best, the TV show was only loosely tethered to the source material of the book, and as the series progressed, it became increasingly unmoored from any historical reality.

But it did a lot to burnish the reputation of its protagonist.

Elliot Ness was now one of the best-remembered American lawmen of the 1930s.

This reputation would get another shot in the arm in the 1980s when The Untouchables was made into a hugely successful Hollywood film directed by Brian DePalma, Kevin Costner played the unflappable Elliott Ness, while Robert De Niro gave a scenery-chewing performance as Al Capone.

But since the release of that film, there's been a huge reappraisal, not just of the film's historicity, but also of the source material from which the movie was adapted.

The film's producer, Art Linson, has gone so far as to say, quote, I don't see this as history.

It's like an opera trying to let you have a sense of feeling, the horror of gangsters, and the romance of gangsters, the love-hate relationship.

The affection was for the mythology, end quote.

So, the movie was pure myth.

But what about the source material?

Well, when asked about the veracity of the original book, David Mammet, the celebrated screenwriter behind the script for The Untouchables, said, quote, I don't believe anything anymore, end quote.

Clearly, David Mammet had got the message from a growing group of Prohibition-era historians who had become increasingly vocal in their dismissal of Ness and Fraley's book.

Some argued that far from being Al Capone's chief nemesis in Chicago, Elliot Ness had little to do with putting away the notorious gangster.

Many of the historians whose work I've used for this series are openly dismissive of Ness.

Luciano Iorizzo calls him a, quote, great pretender, and Deirdre Bear shrugs him off as a gloryhound who chased publicity but ultimately did little to end Capone's career as a gangster.

In 2014, there was a short-lived campaign to rename the ATF headquarters in honor of Elliott Ness.

But this was quickly swatted down by many who argued that his historical reputation had been hugely distorted.

When asked about the proposal, Prohibition historian Daniel Aukrant said it was, quote, ridiculous, naming a building after him for his role of getting Capone?

You might as well name it after Batman.

End quote.

Ah, you know, I love it when historians get sassy.

So, was Elliott Ness a total fraud?

Well, not so fast.

There are some who believe that we have over-corrected in our appraisal of Elliott Ness.

In the 2019 book, Scarface and the Untouchable, writers Max Allen Collins and A.

Brad Schwartz argue that The Untouchables should not be completely discarded as a historical text.

While admitting that the authors certainly took liberties in their presentation, they point out that much of the book is backed up by Chicago newspaper reports from the era.

Perhaps Ness deserves some credit after all.

The untouchable pendulum has swung once again.

So, what's the average fan of history supposed to do with all of this?

How do we right-size Elliot Ness' place in the Capone story?

Well, we should start by unpacking the violent pinnacle of Al Capone's career as a Chicago gangster.

In 1925, Al Capone became the head of the Southside gang formerly run by his mentor, John Torreo.

But being at the top of his outfit didn't necessarily make him the crime king of Chicago.

To get there, a lot of blood needed to be spilled, and a lot of myths needed to be made.

Can we get a clear picture of Capone's time at the top?

And who should really get the credit for his ultimate fall?

Let's see if we can find out today on our fake history.

Episode number 224, What's True About Al Capone, Part 3.

Hello, and welcome to Our Fake History.

My name is Sebastian Major and this is the podcast where we explore historical myths and try to determine what's fact, what's fiction, and what is such a good story.

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This week, we are concluding our look at the life of Alphonse Capone and the many legends that surround his career in crime.

This is part three in a three-part series.

So if you've not heard the first two parts, then I strongly suggest that you go back and give them a listen now.

In the first part, I looked at the early life of Al Capone and did my best to debunk many of the myths about his scrappy childhood on the streets of Brooklyn.

We also spent some time exploring the conflicting tales about his distinctive facial scars.

As Capone got involved in the gang of John Torreo, we took some time to explain the start of Prohibition and the reasons why Chicago became such a hotly contested territory for bootlegging gangs.

In part two, we dove into the Torreo gang's move from Brooklyn to Chicago and the growing profile of Al Capone within the organization.

His tenure as the manager of the four-story saloon, gambling den, and brothel known as the Four Deuces quickly made him one of John Torreo's most important lieutenants.

Capone's importance only grew as the Torreo gang moved into the Chicago suburb of Cicero, Illinois.

As you heard, it was in the lead-up to the infamous 1924 Cicero municipal elections that Al Capone first started to become a media figure.

Critical stories in the local papers were countered by favorable coverage in gang-affiliated publications.

The Cicero elections ended up being a travesty characterized by voter intimidation and all-out fraud by the Torreo-Capone gang, who used whatever means necessary to get their slate of paid-for officials elected.

The haphazard attempt of 70 hastily deputized Chicago police officers to restore order only resulted in chaos and the shooting death of Al Capone's brother, Frank.

From there, we explored the outbreak of the Chicago Beer War.

This multifactional struggle between Chicago's gangs saw the breakdown of John Torreo's attempt to create something like an illegal alcohol cartel.

As gangs like the little Italy-based Jenna gang started pushing out of their traditional territory, Torreo did nothing to make them adhere to the rules of his cartel.

This upset the powerful Northside gang leader, Dean O'Banion.

As you heard, violence between the Capone Torreo gang and the Northsiders ramped up after O'Bannon sold John Torreo the Siebens Brewery, even though he knew it was about to be raided and permanently closed.

This resulted in the arrest and conviction of Torreo on a bootlegging charge.

A few months later, Torreo struck back, assassinating Dean O'Bannon in his Northside flower shop.

This predictably resulted in a wave of gang violence and attempts on the lives of both Al Capone and John Torreo at the start of 1925.

Both men would survive those assassination attempts, but Torreo, who was hospitalized as a result of multiple gunshot wounds, decided that he was ready to retire as the head of the Southside outfit.

The reins of power were passed to Al Capone, but the violence in Chicago was just getting started.

So let's check back in with Big Al in 1925 and see if we can make some sense of the chaotic rounds of killing the Chicago papers dubbed the Beer Wars.

One of the questions that's been at the heart of this series is: what kind of a person was Al Capone?

Now, that might seem like a ridiculous question to ask about a known murderer.

In the last episode, I spent quite some time underscoring the fact that a bar full of people witnessed Al Capone shoot a man at point-blank range.

This is just one of many potential killings carried out by Capone personally.

This is to say nothing of the roughly 200 murders experts believe that he either explicitly ordered or condoned as collateral damage during his time as the head of the Southside Outfit.

And yet, despite those chilling facts, there's still a narrative out there that Al Capone wasn't such a bad guy.

In the introduction to their book, Scarface and the Untouchable, Max Collins and A.

Brad Schwartz accuse many contemporary biographers of glorifying Al Capone, or at least dulling the edges of his most savage acts.

Collins and Schwartz specifically criticize one of the key sources that I have been using in this series, Deirdre Baer's 2016 biography of Al Capone.

In their opinion, Baer's focus on Capone's family life and the use of Capone relatives and descendants as sources gives the impression that at heart Al Capone was a committed and loving family man.

Now, to defend Deirdre Bear,

I don't think she really shies away from the difficult facts of Al Capone's life, nor does she make any glib moral judgments.

The truth seems to be that among his family, Al Capone is remembered as a doting father, a fun uncle, and a fiercely loyal son.

Now, his marriage was another story altogether, and Baer does not paper over all the upsetting complexities of that situation.

But if you only knew Al Capone as the householder living on Prairie Avenue in the south side of Chicago, you might get the impression that he was an upstanding citizen.

This fits with a large body of lore concerning Al Capone's kindness and generosity.

Baer points out that there are many stories told in Chicago about Al Capone helping people in need.

Now, most of these stories cannot be confirmed.

However, Baer does put some stock in one particular heartwarming anecdote.

We're told that one cold Chicago night, Al Capone was sitting in a restaurant.

While having his dinner, he was approached by a shivering newsboy, who asked the well-dressed man if he would consider buying a paper from his large unsold pile.

Capone did him one better.

He bought the entire stack from the kid, paying him the equivalent of several weeks' salary for a typical working man.

Then he told the stunned kid to go home, get warm, and give all of the money to his mother.

Then he made the kid promise that the next day he would go to school and that he would keep going to school every day after that.

Bayer points out that although this tale sometimes gets blown out to mythological proportions in the retelling, the basic facts of the story have been confirmed by a handful of eyewitnesses.

There are many other stories like this, with Capone taking pity on someone in a hard-luck situation and helping them out with some cash or setting them up with a job.

These stories raise the question, just how cynical were these public displays of generosity?

There's no doubt that Al Capone was deeply concerned with his public image and that these conspicuous acts of kindness helped his reputation.

But Deirdre Bear thinks that there may have been a genuinely charitable side to Al Capone.

She writes, quote, certainly he flashed wads of money in public and loved the adulation and the positive publicity it brought him.

But there was also the upbringing he got from good and decent parents who taught him that the Italian and Italian-American way was to show quiet generosity to those who needed it.

In his case, the generosity was often flamboyant and on a grand scale, but it was still sincerely given.

End quote.

Now, here's an interesting question.

Is pointing out the kindness of a murderer an ethical thing to do?

Does it distract from the morally reprehensible side of his character?

Does it encourage the audience to soften their judgments?

Ask yourself right now, how are you feeling about Al Capone?

Does knowing that he was a loving father and that he was generous to the poor change your assessment of him?

Should it?

Just something to chew on before we dive back into the bloodier side of this story.

After the attempted assassination of John Torreo in January of 1925, Capone's gang entered a near-constant state of war with the Northside gang for the next four to five years.

After the flow shop killing of Dean O'Banion, the Northsiders came under the leadership of one Jaime Weiss,

another nearly legendary Chicago gangster.

All of the biographers comment on two things about Weiss, his intelligence and his fearlessness.

Few knew it at the time, but Weiss had been diagnosed with terminal cancer in the mid-1920s, which might help account for his willingness to put his own body on the line during many of the Beer War's fabled shootouts.

You might remember from the last episode that Jaime Weiss had been one of the gunmen who nearly killed John Torio in front of his Chicago home.

But as I've mentioned before, this conflict was not quite as simple as the north side versus the south side.

In the mix, there were at least a half a dozen other gangs whose alliances shifted throughout the conflict.

Now, it would be very easy to get lost in the weeds of this, so I'm going to be giving you a fairly straightforward overview of the beer war.

If you are curious about every twist and turn, every ambush, every double cross, then I recommend the book Al Capone's Beer War by historian John Binder.

But to give you a sense of just how deadly this conflict was, in 1925, the city of Chicago averaged one gang-related murder every day of that year.

Now, our first big casualty of the beer war was the once formidable Jenna gang.

The Little Italy-based gang was headed by the six Jenna brothers, all originally from Sicily.

As you might remember, the Jenna's had been one of the first gangs to upset the criminal equilibrium in Prohibition-era Chicago.

By attempting to push their their booze in Northsider territory, they had started a conflict with the gang that would result in a slew of killings.

By the end of 1925, three of the six Jenna brothers would be dead, and the other three would flee Chicago for Sicily.

Now, the Jenna killings are usually pinned on Jaime Weiss and various Northsider-aligned gunmen.

However, some biographers like Max Collins and Luciano Iorizzo suspect that Capone-hired gunmen may have been involved in at least one of these killings.

Now, why would Al Capone go after his erstwhile allies?

Well, the Jennas had been a persistent source of trouble for Capone and his gang.

They also controlled a lucrative bit of Chicago territory and operated an impressive network of illegal stills.

The Jennas also controlled the powerful Sicilian social club and mutual aid society known as the Unione Siciliana.

This was one of those once benevolent societies that had been transformed into a criminal enterprise by racketeers.

The Chicago Unione Siciliana boasted 40,000 members in 1925.

So controlling it meant exerting control over a huge constituency in Chicago.

With the Jennas out of the way, Capone was able to make his own hand-picked candidate the head of the Union.

Now, Capone couldn't actually take the position for himself because he was not Sicilian.

But with the installation of the puppet president, Capone was able to absorb most of the Jenna's former operations.

This meant that by 1926, Capone had more or less amalgamated all Italian organized crime under one umbrella.

That was until a gangster named Joe Aiello challenged this situation, but more on him a little later.

1926 would prove to be one of the most eventful years in the broader conflict between Capone's Southside gang and Jaime Weiss's Northsiders.

Shootouts between the gang members became regular occurrences.

Bodies were dropping all around Chicago and her suburbs.

Now for the sake of summary, one only needs to look at the rap sheet of one of Capone's key gunmen in this period.

The enforcer, known as machine gun Jack McGurn, was listed by the Chicago Police Department as the chief suspect in 18 gangland killings between February of 1926 and December of 1928.

And that was just one guy.

One of the more daring attacks came in September of 1926, when a small battalion of Northsiders attacked the Hawthorne Hotel, Capone's Cicero headquarters.

Reports tell us that the Northsiders pulled up in front of the suburban hotel in eight cars.

They then shot blanks out of their Thompson submachine guns to hopefully scare people out of the hotel once it seemed like they were out of ammunition.

The men then reloaded with real bullets and proceeded to spray the place with over 1,000 rounds.

While a number of people were wounded, amazingly, no one died.

This may have been because by 1926, the Hawthorne Hotel had become something like a gangland fortress, decked out with bulletproof doors and shutters on the windows.

Capone also kept a house in Cicero that was similarly fortified, complete with a subterranean tunnel that went from the main building to his garage.

There, he could get into what became his signature vehicle, a seven-ton, bulletproof armored Cadillac.

The windows of the car were made entirely from bulletproof glass, and the back window was designed to be lowered so a gunman could shoot at anyone tailing the car.

Now,

I gotta say, this is the real comic book villain stuff here.

The fortified houses and the armored car would become a big part of the Al Capone myth.

These are the details that many people really focus on when they discuss Al Capone because they're colorful.

If you were buying an Al Capone action figure, you would probably want to get the armored car for him to ride around in.

But again, I think I should ask, is this detail a distraction?

By telling you about Capone's armored car, am I glamorizing him?

Does it make the violence seem cool?

At the very least, I think the question should be asked.

The attack on the Hawthorne Hotel was answered a month later with a targeted hit on Northside leader Jaime Weiss.

Once again, the venue for the hit was the Northside Flower Shop once operated by Dean O'Banion.

A small crew of Capone assassins, likely among them Machine Gun McGurn and Capone's childhood friend, Frank Nitty, laid in wait for Weiss, targeting him from a machine gun nest set up in a neighboring building.

It took weeks to finally catch Weiss in a vulnerable spot, but on October 11th, 1926, he was spotted walking towards the flower shop with an entourage of bodyguards.

When Weiss came in range, he was shot dead on the street.

Now,

the weirdest thing is that in the midst of all this death, Capone was giving interviews.

At the peak of of the gangland violence, Capone was astonishingly accessible to journalists.

Now, of course, this helped him muddy the waters.

After the death of Jaime Weiss, he was quoted in a Chicago paper saying, quote, I'm sorry that Jaime was killed, but I had nothing to do with it.

Why should I kill Weiss?

End quote.

Now, few people seemed to buy these obfuscations at the time.

The Chicago chief of detectives was quoted saying, quote, Capone knows why, and so does everybody else.

He had Jaime killed, end quote.

Capone seems to have realized that he needed to get ahead of the increasing bad press that came in the wake of Jaime Weiss's murder.

So in early 1927, he orchestrated one of his more remarkable publicity stunts.

He invited a group of reporters to his family home on Prairie Avenue in Southside Chicago.

He greeted them wearing a pink apron and waving around a wooden spoon that he had been using to whip up his mother's famous spaghetti sauce.

Capone then cooked the gathered journalists' dinner and served them some high-quality Italian wine smuggled into the country and saved for such an occasion.

Over the course of the meal, he insisted insisted that he had never harmed anyone in his life, and in fact, he was disgusted by the gang violence that had engulfed Chicago.

If he had ever been involved in bootlegging, well, he was now completely retired from the game.

He just wanted to live a quiet family life and pursue his second-hand furniture business.

Now, reading about this now, this seems like an obvious ploy.

I mean, the pink apron seems especially on the nose.

But it kind of worked.

Those reporters who came to his house that day were now predisposed to write sympathetically about Al Capone.

For months after the meal, those journalists used quotes in their story that they gathered that night from Al Capone.

They often wrote that Capone was deeply opposed to gang violence.

They helped soften his image.

It was at this time that Al Capone also started actively paying journalists and editors working at the big Chicago papers.

One of the most prominent of these was the editor of the Chicago American, Harry Reed, who started giving Capone public relations advice.

According to Deirdre Bear, Reed coached Capone to, quote, talk as often as he could to the pressed, but steer clear of Chicago politics, end quote.

And so it was that Capone started talking regularly to reporters, always denying any wrongdoing and expressing sympathies for the families of dead gangsters.

And he often told jokes when the opportunity presented.

This was paired with a street-level charm campaign that I alluded to earlier.

Not only would Capone generously give money to the homeless, poor, and destitute, he was also a favorite of Chicago doorman, who he tipped lavishly.

According to the investigative reporter Gus Russo, Capone also, quote, gave writers and complete strangers tips on fixed fights and horse races, end quote.

This little kindness was especially clever because it made the person getting the tip complicit in one of the softer sides of Capone's criminal enterprise.

Capone would hook up the little guy with a tip on a hot horse and then give him a wink and tell him not to tell the cops.

This brings us to Al Capone's celebrity era.

The gang fighting of 1925 and 1926 had made Capone's gang more powerful than ever.

Then, in 1927, there was a big change in Chicago city politics.

The reform-minded mayor of Chicago, William Deaver, who cracked down on Chicago bootlegging, was defeated in the mayoral election by Big Bill Thompson.

Now, Chicago truly has one of the most wild political histories of any major American city.

The sheer number of overtly corrupt politicians in that town truly boggles the the mind.

And I mean no shade to the listeners in Chicago right now.

I have a lot of love for your city, but you have to admit that Chicago municipal politics has historically been a pretty wild ride.

So just understand that I do not speak lightly when I say that Big Bill Thompson may have been one of the most corrupt mayors in the history of Chicago.

He's easily in the top three.

In 1927, he ran on a platform of making Chicago a wide open city.

Under Big Bill, prohibition would not be enforced.

As you might expect, Big Bill was getting all sorts of kickbacks from many of the city's organized crime figures, including Al Capone.

Once Big Bill Thompson came back to City Hall, it became a little bit easier to be a public-facing gangster in Chicago.

In those years, Capone became a fixture at Chicago sporting events.

He loved baseball and liked to attend games for both the Chicago White Sox and the Chicago Cubs.

He was a conspicuous presence when he came into the ball diamond, and on a few occasions, he was given a standing ovation by the Chicago crowd.

Capone also rarely missed a boxing match of any consequence being held in Chicago and was often cheered when he appeared ringside.

The Capone public relations campaign really seemed to work, especially among working-class Chicagoans.

Capone also became good at getting people who were close to him to ignore the unsavory side of his character.

Biographer Lawrence Bergreen describes it like this, quote, He came to dominate people not by shouting, overwhelming, or bullying, although the threat of physical violence always loomed, but by appealing to the inner man, his wants, his aspirations.

By making them feel valued, they gave unstintingly of their loyalty, and loyalty was what Capone needed and demanded.

In the volatile circles through which he moved, it was the only protection he had from sudden death.

The highest compliment other men could pay Capone was to call him a friend, which meant they were willing to overlook his scandalous reputation that he had never been a pimp or a murderer.

⁇

It was in these years that Capone relocated his headquarters to the Southside Lexington Hotel, the same hotel that would later embarrass Geraldo Rivera.

But he also started looking beyond Chicago.

In 1928, he bought a lavish mansion in Miami Beach, much to the chagrin of many locals who were non-plussed that a notorious gangster was setting up shop in their sunny Florida community.

But through a similar campaign of bribery and charm that had worked well for him in Chicago, Capone was eventually accepted in Florida as well.

But the gang wars were still raging.

Capone had emerged as the dominant gang leader in the city, but there were still many that wanted him dead.

Despite his public profile, he lived in constant fear of assassination.

Writing for The New Yorker, the reporter Alva Johnston explained in 1928 that Capone, quote, surrounds himself with eight men selected for thickness of torso, who form an inner and outer ring about him when he appears in public.

They are tall and he is short, a precaution against any attempt to aim at him through the spaces between their necks.

For Al's protection, the eight men wear bulletproof vests.

Nothing smaller than a field piece could penetrate his double-walled fortress of meat.

⁇

Capone may have been famous, but he was also trapped inside a fortress of meat.

But in 1929, just as Al Capone reached the full height of his power, public opinion would shift drastically.

Two particularly brutal and dramatic gangland killings would remind the people of Chicago just how vicious the beer wars truly could be.

This would be the start of Capone's decline and fall.

So let's pause here, and when we come back, we'll look at one of the best remembered gang murders in American history, the St.

Valentine's Day Massacre.

From nineteen twenty-six through nineteen twenty-nine, Al Capone steadily consolidated his gang's control over Chicago.

He was increasingly dominant, but his rule was far from uncontested.

Despite occasional truces, those years were marked by ongoing violence between Capone's outfit and various smaller Chicago gangs looking to challenge his growing empire.

This included what remained of the Northside gang.

After the death of Jaime Weiss, the gang was briefly helmed by one Vincent Drucci before he was slain by a Chicago police officer.

The gang then came under the control of longtime Northsider and one of Johntorio's would-be assassins, George Bugs Moran.

Bugs was so nicknamed because his cohorts thought him to be a little buggy or a little crazy.

It's been debated how much that reputation was played up for effect, but there's no doubt that as leader of the Northsiders, Moran was aggressive.

In January of 1929, he provocatively allied himself with Joe Aiello, a Sicilian crime boss who had formed a powerful new gang out of the remnants of the former Jenna gang.

Between 1927 and 1929, Aiello had made countless attempts to kill Al Capone.

at one point offering a $50,000 reward for anyone who could manage to eliminate the big guy.

But in all cases, Capone's fortress of meat had not failed him.

At least half a dozen would-be Aiello hitmen were killed by Capone's enforcers between 1927 and 1929.

However, when Aiello teamed up with Moran, they were able to successfully take out an important Capone ally.

This was the president of the Unione Siciliana, through whom Capone wielded influence in Chicago's Sicilian community.

When this man was killed, Joe Aiello now had an opportunity to move into the Unione.

This motivated Capone to move against the challengers to his power, and he started with Moran.

Or at least, most people think that he did.

On the night of February 14th, 1929, a group of seven Northside-affiliated men were waiting to meet with Moran in a gang-owned garage.

Suddenly, two men wearing Chicago police uniforms burst in.

Assuming that this was a meaningless show raid, the seven men did nothing to fight back.

When the supposed officers told them to line up against one of the garage's brick walls, they obeyed.

Once they were lined up, two other men in plain clothes came into the garage equipped with Thompson sub-machine guns.

They then proceeded to spray the assembled men with bullets.

The whole operation lasted only about five minutes.

Most of the men died instantly, with one managing to survive for a number of hours before finally succumbing to his wounds on the way to the hospital.

The killing would be remembered as the St.

Valentine's Day Massacre, and it's not an exaggeration to say that it changed the way crime in Chicago was perceived.

Now, it might seem amazing, given just how much death we've already cataloged in this series, that this one gangland murder managed to move the needle of public opinion so dramatically.

As I already said, from 1924 to 1929, gangsters were killed more or less daily in Chicago, and the general public had become fairly numb to this.

Some even thought that it was a good thing.

The reporter Alva Johnston described this attitude in his 1928 New Yorker piece, explaining, quote, The argument ran as follows.

If you prosecute gangsters for killing one another, they may stop killing one another.

This would interfere with nature's method of keeping down their numbers, and they might grow to such a multitude as to become a grave menace to the rest of the population.

End quote.

Using this callous logic, the death of a gangster could be read as a net good for the community.

But the killing on February 14th was too gruesome to be ignored.

The fact that seven people had been killed all at once was legitimately shocking.

The newspapers of the day turned this killing into one of the biggest media events of the 1920s.

The crime was given front-page coverage across the United States and in many foreign papers.

The stories usually ran with gruesome photos from the crime scene, paired with even more explicit descriptions provided by the Chicago reporters.

Capone biographer Lawrence Bergreen even gets poetic when describing its impact, writing, quote, newspapers across the country devoted an unprecedented amount of space to coverage of this mass murder of seven men, and in the process sold millions of copies.

The event impressed itself into the consciousness and the history of the nation like a dark fly in amber, end

The Chicago Herald and Examiner declared that, quote, Chicago gangsters graduated yesterday from murder to massacre, end quote.

And that word, massacre, is what stuck in the public consciousness.

This clearly demanded a response, and soon even the President of the United States, Herbert Hoover, was weighing in on Chicago gang violence.

The eyes of the federal government were now trained on Chicago, and that would change everything for the city's best-known gangster.

Now, when all of this went down, Al Capone was far away from Chicago, attending a hearing in Miami, answering questions about his finances at a Dade County courthouse.

It was a rock-solid alibi, attested to by court records.

As such, there has been no way to conclusively prove that Al Capone was behind these audacious killings.

But pretty much everyone who studies Prohibition-era Chicago agrees that even if Al Capone did not personally plan the attack, he would have needed to give his blessing for it to take place.

It was likely designed as a hit to take out Bugs Moran, and in this sense, it was a total failure.

The killers burst into the garage before Moran had arrived that night, likely mistaking one of the men inside as the Northsider boss.

When Moran got there, he noticed what looked like a police vehicle out front of the garage and quickly got himself as far away as he possibly could.

In the aftermath, Moran would leave Chicago altogether, and what was left of the once mighty Northside gang would wither away.

Despite the fact that seven men had been machine-gunned, the St.

Valentine's Day massacre was a bit of a mixed bag as a gang land hit.

Two of the dead men weren't even really gangsters.

One was a mechanic who did work for the Moran gang, and the other was a former optician who enjoyed the thrill of hanging out with bootleggers.

While the public often had little sympathy for the deaths of known gangsters, these men were a different story.

This meant that just as Capone was about to finally emerge victorious from the beer wars, he was now losing the public relations war that had begun back in 1924.

The bad press got only worse about four months later, when the bodies of three former Capone associates were found dumped roadside in rural Indiana.

Two of the men had been former Capone assassins, John Scalise and Albert Anselmi, nicknamed the Murder Twins.

The other victim was Joe Ginta, a man many believed Capone had wanted as the head of the Unione Siciliana.

Three Capone men dead in a ditch.

Was this a revenge killing for the St.

Valentine's Day massacre?

It was unclear.

But soon a rumor started circulating that Al Capone had personally killed these men when he got wind of a double cross.

And this has gone down as one of the most repeated bits of Al Capone lore.

The story goes that the murder twins and Ginta had been plotting with Capone's last significant rival, Jo Aiello, to snatch the Union Siciliana from his grasp.

When Capone caught wind of this treachery, he devised a particularly dramatic revenge.

We're told that he threw a lavish banquet at one of his more out-of-the-way hotels, just outside of Hammond, Illinois.

The party was to be held in honor of Ginta, who had been tapped as the next president of the Unione Siciliana.

For most of the night, everything seemed normal.

The men ate, drank bootleg champagne, and smoked while Capone chatted amiably with his guests of honor.

When the table had been cleared of dishes, Capone stood up and strolled behind the still sitting Scalis and Selmi and Ginta.

One of his bodyguards then passed him a baseball bat, and Capone allegedly said, quote,

this is how we deal with traitors, end quote.

He then proceeded to beat the three men to death in front of the gathered banquet guests.

This story has often been retold as the ultimate example of Al Capone's savagery.

Those of you who have seen the 1987 movie The Untouchables might remember the banquet scene as one of the movie's more memorable moments, with Robert De Niro's Al Capone grimly wielding his bat after giving a speech about enthusiasms.

But

did this ever actually happen?

Well, the experts are deeply divided on this question.

Almost everyone I have read has a different take on the baseball bat story.

Luciano Iorizzo accepts it out of hand.

Jonathan Eag, the author of Get Capone, argues that it's a total myth that first appeared decades after the fact in 1975.

But Collins and Schwartz, authors of Scarface and the Untouchable, have pushed back on that, pointing out that most of the details can be found in the Chicago Tribune and the New York Times within a few days of the killing, and the more elaborate baseball story was circulating in print within a year of the murders.

Somewhere between those two positions, we have Capone sleuth Mario Gomez, who argues that Al Capone almost certainly had the men killed, but a close examination of the men's autopsy reports shows that their wounds were consistent with being shot at close range with.38 caliber pistol.

They did not seem to have been beaten with a bat.

So, in his estimation, Capone killed the men, but didn't beat them with a bat.

Does that distinction really matter?

Well, maybe, because people seem fascinated by the baseball bat of it all.

So, who knows?

I wish I could give you a straight answer on this one, but the truth remains deeply unclear.

As for the insurgent Joe Aiello, he went into hiding while continuing to orchestrate attacks against Capone, but he couldn't hide long.

Within a year, he was located and machine-gunned in the street by Capone's assassins.

All of this meant that by the end of 1929, it was considerably harder for Capone to make the case that he was simply a misunderstood businessman.

The image of the softie making spaghetti in his pink apron was replaced in the minds of many Chicagoans with that of a calculating killer orchestrating massacres.

Capone himself was likely feeling the heat, which might explain why he was arrested in Philadelphia that year on a weapons possession charge.

He would end up serving a year-long sentence in Pennsylvania in connection with this arrest.

Now, given how uncharacteristically reckless this arrest seems, many biographers speculate that Capone purposely allowed it to happen to hopefully get some of the heat off his back while the St.

Valentine's massacre was still being investigated.

If that was his strategy, it did not work.

When he emerged from prison in 1930, he found that the Hoover administration was motivated to put him right back behind bars.

So, let's take one more break.

And when we return, we'll see how Capone's reign as the crime king of Chicago was finally ended.

The campaign that brought down Al Capone ended up taking the form of a two-pronged attack.

One prong came from the Bureau of Internal Revenue, and the other from a small team of prohibition agents working under the auspices of a specially appointed United States attorney.

The second team was originally headed by one one Alexander Jamie, but in December of 1930, the leadership of the team passed to his 27-year-old brother-in-law, the former Treasury agent Elliott Ness.

Now we have finally come to the question of who ultimately brought down Al Capone.

As I mentioned in the introduction, The publication of The Untouchables in 1957 and its adaptation into a popular TV show led to the belief that Elliott Ness had been instrumental in destroying Capone's criminal empire and securing his criminal conviction.

But the deeply inaccurate pop culture version of Elliott Ness and the Untouchables led to a bit of a reaction and possible over-correction from Capone experts.

For instance, in her 2016 biography of Capone, Deirdre Baer devotes barely a paragraph to Elliott Ness.

She writes him off as, quote, a publicity-seeking federal agent who sought the limelight as much as Capone did, end quote.

However, she does admit that his team did, quote, serious damage to the outfit's income and profit, end quote.

Authors Max Collins and A.

Brad Schwartz push back at Bayer's dismissal of Ness in their book, specifically drilling into what that serious damage actually entailed.

When Ness was empowered by the federal government to aggressively investigate and disrupt Capone's bootlegging operations in Chicago, he did so by targeting Capone's network of illegal breweries.

This involved a complex surveillance operation where beer delivery and empty keg retrieval trucks were carefully monitored.

This, paired with a series of telephone wiretaps, led them to a keg cleaning plant, which I find kind of fascinating because it demonstrates that at the height of Capone's beer-running operations, the gang insisted on a certain level of hygiene.

From this cleaning plant, the kegs were then traced back to hidden breweries and stills all over the city of Chicago and the surrounding area.

This led to a series of well-publicized raids that sometimes involved Ness and his team busting through doors with a custom-built battering ram affixed to one of their vehicles.

Now, these raids were all over the Chicago papers, but didn't really make the news beyond Illinois.

Elliott Ness was a bit of a local phenomenon.

But what about that nickname, The Untouchables?

Was that really used at the time?

The answer is yes.

One Chicago journalist named Charles Schwartz, who wrote for the Chicago Daily Press, took to calling Ness and his team the Untouchables, thanks to their reputation for refusing gang bribes.

The journalist apparently got the idea for the name after reading contemporary articles that were being run about Gandhi's campaigns for independence in India.

These articles often came with descriptions of the so-called untouchable lower caste people in that country.

In fact, the first article about Ness and his team that used the nickname The Untouchables ran on the same page as a story about Gandhi.

So the nickname was definitely real and not just something that was cooked up by Ness and his biographer in 1957.

Over the course of six months in 1931, the Untouchables managed to cost Al Capone's outfit something like $9 million

in lost facilities and potential income.

That would be roughly $178 million

today.

Ness's raids were also conducted in a way that caught as many illegal brewers in the act as possible.

This was key, as it allowed Ness to build a case for criminal conspiracy conspiracy that he hoped would ultimately get Capone a serious prison sentence.

But the truth is that Ness's work on getting a case made for criminal conspiracy ultimately didn't matter in Capone's eventual conviction.

So, the untouchables were a thing, and they definitely put a dent in Al Capone's criminal empire.

But they didn't bring him down, so to speak.

The evidence collected by Ness and his team wasn't really used at Al Capone's trial.

It should also be noted that once Capone was imprisoned, the exploits of Elliot Ness very quickly faded from public memory.

This is part of the reason why the mythical untouchables were able to emerge so dramatically in the late 1950s.

Very few people remembered the real story.

Capone was ultimately dethroned as the most powerful organized crime figure in Chicago thanks to the efforts of agents from the Bureau of Internal Revenue, later known as the IRS.

You see, in 1927, a Supreme Court ruling had set the precedent that income gained through illegal means was still subject to income tax.

Al Capone was obviously living a lavish lifestyle, but he was not filing federal income tax returns.

So it was that a team of internal revenue agents headed by Elmer L.

Iyri started the long process of secretly investigating Capone's income and expenditures.

Now, this was harder than it might sound, as Capone was very good at hiding his money.

He technically showed no income.

He signed no checks.

He didn't even have a bank account.

It was easy enough to demonstrate that Capone spent lavishly, but it was harder for the team to determine what his actual income was.

To build a case against Capone, it took a multi-year investigation that carefully monitored Capone-controlled businesses.

Iri's team used dozens of wiretaps to help document the likely ins and outs of money in the Capone operation.

Even then, by the time the case came to trial, investigators only felt comfortable prosecuting Capone for missed taxes on $165,000 of yearly income.

We know now that that was only a tiny fraction of what Capone was actually making.

But they only felt confident that they had evidence for that much smaller amount.

Now, the ins and outs of Al Capone's tax evasion trial are fairly convoluted, so I'm going to do my best to keep this simple.

Forgive me if I miss something that you think is significant.

But here's what you should know.

In 1930, Al Capone's older brother Ralph was successfully convicted of tax evasion, which ultimately led to a relatively short two and a half year prison sentence.

Interpreting this as a shot across the bow, Al Capone's lawyer contacted one of the IRS investigators currently working on the Capone file and told him that his client wished to resolve his tax situation.

Now,

Capone's lawyer seems to have thought that he was brokering a deal in what would ultimately be a civil case.

He believed that if he declared a certain amount of income for Capone, that would form the basis of an eventual settlement.

He thought that Capone would pay a fine and would likely avoid even his brother's short sentence.

This proved to be a disastrous miscalculation.

The Bureau of Internal Revenue weren't just trying to get some money out of Al Capone.

They were working at the direction of the President of the United States to secure as substantial a conviction as they possibly could.

So, when Al Capone's attorney gave the investigators a letter declaring $100,000 of yearly income, he inadvertently handed them a piece of evidence that would be used in a much more ambitious tax evasion case.

Now, this move by Capone's attorney is still viewed with a lot of confusion by the experts.

His choice to voluntarily declare an obviously falsified yearly income seems like an unforced error.

There's even been some speculation that Capone's attorney may have been turned by the feds and was actively undermining his case from the inside, but there's little evidence of that.

You see, it's important to understand that Capone's case was totally unusual in the world of tax evasion cases.

The modern American income tax had only been in place since 1913.

Before the 1930s, disputes over the non-payment of income tax were usually settled in hearings out of court.

Only rarely did a tax evasion case make its way to criminal court.

In cases where someone was convicted criminally, the sentence was usually a fine.

Only in the most extreme cases would someone get jail time.

And then it was almost never longer than three years.

For instance, Ralph Capone only ended up serving his two and a half year sentence after he refused to pay a settlement that was made for $4,000.

If Ralph had just ponied up, he would have never gone to jail.

It's highly likely that Al Capone's lawyers thought a similar arrangement could be made for their client, except he would have the good sense to actually pay the fine.

Capone's people underestimated just how badly the federal government wanted their client to go to jail.

With the letter from Capone's lawyer in hand, the feds moved quickly against the gangster.

In June of 1931, a federal grand jury indicted Capone on twenty two felony counts of income tax evasion and two misdemeanor charges of failure to file.

Now, at the outset, it looked like the whole thing was going to be settled in a plea bargain.

The prosecution knew that they didn't have a particularly strong case, resting as it did on the letter from Capone's attorney, which could be ruled as inadmissible considering how it was obtained.

So, the prosecution and the defense worked out a plea deal, whereby Capone would plead guilty to a lesser slate of charges and would end up serving no more time in jail than his brother Ralph.

But, in a surprise move, the judge in the case, James Wilkerson, decided that he was having none of this.

In a move rarely seen, he announced that he was not bound by the plea deal and insisted that the trial would move ahead.

It is quite unusual for a judge to reject a plea deal, but Judge Wilkerson was a man on a mission.

Capone was allowed to revoke all his guilty pleas, and the trial went on as though the plea bargain had never happened.

This had the effect of completely wrong-footing Capone's defense team, who had not really prepared a proper defense because they thought they were going to plea out.

From there, you could argue that Al Capone's trial was a total miscarriage of justice.

The judge was clearly biased against the defendant.

Not only did he reject the plea deal, Judge Wilkerson went out of his way to switch the jury panel at the last minute with people from rural Protestant areas who largely supported prohibition.

Now, to be fair to the judge, this was done partially because of a tip that Capone was attempting to bribe members of the jury from urban Chicago.

But this was still a sly move from a sitting judge.

Wilkerson also deemed the controversial letter from Capone's attorney to be admissible evidence, even though it was provided in the context of a plea deal.

In legal circles, this choice is still considered controversial.

Finally, the prosecutor's evidence demonstrating Capone's yearly income was fairly thin.

In recent years, this trial has been used as the basis for many mock trials, and consistently, when modern courtroom standards are applied, Capone is almost always acquitted.

Now, I'm not saying that Al Capone did not deserve to face judgment.

Personally, I think he did.

But this trial was a bit of a farce.

In the end, the jury handed down a somewhat confusing verdict.

They found Capone not guilty on most of the 22 counts on which he was indicted.

However, he was found guilty on three of the tax evasion charges and the two counts of failing to file a return.

With just those five convictions, Judge Wilkerson proceeded to throw the book at Al Capone.

He was given 11 years hard time and was fined $50,000 plus an added $30,000 for court costs.

It was the harshest sentence ever handed down in a tax evasion case to that point in American history.

It was completely without precedent.

After Al Capone was convicted, it effectively ended his time as the head of the Southside Outfit.

His time at the top had been fairly short.

His most devastating move against his most implacable enemies, the St.

Valentine's Day Massacre, ultimately brought on more heat than he could handle.

Capone was first taken to the Cook County Jail before being transferred to the Atlanta, U.S.

Penitentiary.

During his medical examinations for his admittance to the penitentiary, it was discovered that he was infected with both syphilis and gonorrhea.

While the gonorrhea was treatable, the syphilis was already in its late stages.

It's deeply unclear exactly when Capone was first infected, but it was likely in the early 1920s, perhaps even before he left Brooklyn.

A lifetime of unprotected sex with sex workers had caught up with him.

Deirdre Bair's research has also discovered that Capone infected his wife with the disease, but she sought treatment as early as 1925.

Capone himself never sought treatment, and as such, sealed his fate.

By the time he was properly diagnosed, little could be done.

Being a celebrity prisoner also proved to be more of a curse than a blessing for Capone.

While some inside were eager to offer America's best-known crime boss protection, other prisoners resented his his elevated status and complained that he was getting special treatment.

This contributed to Capone being moved to Alcatraz, the newly opened maximum security prison in the San Francisco Bay.

There he would have a strange second act as one of America's most notorious yet beloved prisoners.

His good behavior in Alcatraz was such that he was given the opportunity to play banjo and even joined the Alcatraz inmate band known as the Rock Islanders.

And honestly, that's not a bad name for an Alcatraz band.

So, if you happened to be a guard or an inmate in Alcatraz between 1934 and 1939, you were getting semi-regular concerts from the Rock Islanders that featured the best-known criminal in world shredding the banjo.

But in 1938, the doctors at Alcatraz determined that Capone's disease had entered his brain, and from there, his mental decline was precipitous.

He was paroled in November of 1939 after his ever-devoted wife, May, made an appeal to the court based on Capone's declining mental state.

He would live out his final days at his Miami mansion, which May had managed to keep despite the federal liens on most of the family's assets.

There he would decline steadily for the next seven years.

By 1946, a doctor determined that his illness had progressed to the point where he had the mentality of a 12-year-old.

In 1947, complications from the disease led to a stroke and then cardiac arrest.

When Capone died, he had just celebrated his 48th birthday.

When reading about the final days of Al Capone, there's a certain pathos to the whole situation that can't help but elicit some sympathy.

There's also something almost mythological about his ultimate fate.

Greek myth, in particular, is filled with stories of once powerful men undone by time, hubris, or the justice of the gods.

Capone in Florida can be seen like the hero Jason of the Golden Fleece at the end of his life, despondent, defeated, and leaning on the wreck of his former boat, the Argo, before the prow falls off and ultimately crushes him.

When you hear the stories of an increasingly childlike Al Capone playing banjo in Alcatraz, there's an instinct to go, aw,

was he really all that bad?

All the images of Capone wearing his pink apron, giving gambling tips to eager well-wishers, and buying all the papers from a poor newsie come flooding back.

But perhaps we should also remember him destroying the democracy of Chicago and its surrounding towns.

We should remember the daily murders that plague Chicago during the height of his power.

We should remember him trafficking human beings.

Even if the notorious baseball bat story is ultimately a myth, we should not forget that he shot a man six times in the face in front of a crowded bar.

Capone was very gifted at appearing magnanimous, warm, even cuddly.

In his final years, there's also something genuinely pitiable about him.

But we shouldn't forget the whole picture.

Al Capone may have been America's most

evil banjo player.

Okay,

that's all for this week.

Join us in two weeks' time when we will explore a new historical myth.

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