AL CAPONE

A Life From Beginning to End

Copyright © 2018 by Hourly History.

All rights reserved.

 Table of Contents
Introduction
How Capone Became Scarface
Taking Over Chicago
The Press Takes on Capone
Silencing His Detractors
The Murder of McSwiggin
Public Enemy Number One
Taking Down Capone
Holed up in Alcatraz
The Last Days of Al Capone
Conclusion
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 Introduction
The most infamous gangster of all time came into this world as a tiny bundle
of his mother and father’s joy on January 17, 1899. The son of Italian
immigrants, Alphonse Gabriel “Al” Capone began his life in Brooklyn, New
York. His roots were modest, with his father Gabriele cutting hair for a living
and his mother Teresa sewing gowns. Capone shared his parents with eight
siblings—Vincenzo (who later changed his name to Richard), Raffaele,
Ralph, Salvatore, Ermina (who died at age one), Ermino, Albert, Matthew,
and Mafalda.
The big Italian family did their best to survive as they eked out a modest
existence in their little home on 95 Navy Street, in the bustling downtown
Brooklyn of turn-of-the-century New York City. Even back then Brooklyn
was filled with more than its fair share of hustlers, gangsters, and runners of
illicit commodities of all kinds, and perhaps it is not too surprising that
young, impressionable Al Capone would fall into a life of crime.
Nevertheless, as Capone grew up, he initially showed quite a bit of promise
as a student, giving his family the luxury of thinking that his good marks
would allow him to rise above his surroundings. But although Capone made
good grades, he had a penchant for breaking the rules. At the age of 14, this
rule breaking would come to a head when he came to blows with one of his
teachers, punching her in the face. The resulting expulsion from school
marked the end of Al Capone’s formal education, but his internship with the
streets of New York City was just beginning.
 Chapter One

How Capone Became Scarface

“I’ve got nothing against the honest cop on the beat, the kind you can’t buy.
You just have to have them transferred someplace where they can’t do you
any harm. But don’t ever talk to me about the honor of police captains or
judges. If they couldn’t be bought they wouldn’t have the job.”

—Al Capone

Al Capone first entered into the life of crime by hooking up with bands of
petty, local crooks such as the Bowery Boys and a gang referred to as the
Junior Forty Thieves. Most of the gangs of New York were not very
organized at this point in time and focused primarily on small-time hustling
and robbery. The most powerful local gang of the day was the Five Points
Gang from Manhattan.
It was in this atmosphere that Capone came under the attention and
employ of a local crime boss and Five Points associate named Frankie Yale.
Yale had been involved in several protection rackets in which he demanded
bribes from several businesses in order for them to safely function on his turf.
It was from these proceeds that Frankie had opened up a bar in Coney Island
called the Harvard Inn. Under the auspices of taking a job at the Inn, Capone
began his tutelage under Frankie Yale. On the official level, Capone worked
at Frankie’s bar as a bartender and sometimes bouncer, but in reality, he was
being groomed in all the inner workings of the New York criminal world.
In 1917, 18-year-old Al Capone, while working as a bouncer at the
Harvard Inn, provoked an incident that would gain him a nickname that
would stick with him for the rest of his life—“Scarface.” Capone in the
decades after the incident would float stories that he received the scars in the
trenches of World War I, although he never actually served. Perhaps he
preferred those tales of heroism to what had actually happened. In reality,
Capone was working the doors of the bar one night when a pretty girl caught
his eye. According to legend, Lena Galluccio was a vivacious, dark-haired
Italian girl with a stunning figure, and young Capone apparently couldn’t
keep his eyes off of her. The only trouble was she was also the sister of local
gangster Frank Galluccio who had a reputation for fierce retribution to those
that offended him. But that didn’t stop Al from trying his luck.
As Lena’s brother and company proceeded to drink themselves into
oblivion, Capone kept trying to find reasons to go to their table in order to
smooth talk her. But as she continued to ignore his advances, Capone’s
charm turned to coarse harassment. And when Capone got the bright idea to
offer up to her the unsolicited compliment, “You’ve got a nice ass, honey,”
big brother Frank had finally had enough. Face red with rage, Frank
Galluccio abruptly stood up and shouted, “I won’t take that shit from nobody!
Apologize to my sister now, you hear?”
It is a bit unclear as to exactly what happened next, but Galluccio later
claimed that rather than apologize Capone had charged at him, and in an
effort to defend himself, the drunken Galluccio pulled out a pocket knife and
slashed Capone across the face three times. This apparently stopped Capone
in his tracks as he doubled over, clutching his face that was now spraying
blood all over the dancefloor. Galluccio, sobering up from the grisly sight,
then quickly fled the scene with his entourage in tow. It is said that if it
wasn’t for the quick-thinking actions of the staff at the Harvard Inn, Capone
might have died that night. But as it were, they bundled up his bleeding
wounds in fresh towels and sent him off to the nearby Coney Island Hospital
to get treated.
Several stitches later, the bleeding had ceased, and Capone would forever
marked with the nickname “Scarface” which he so despised.
 Chapter Two

Taking Over Chicago

“A crook is a crook, and there’s something healthy about his frankness in the
matter. But any guy who pretends he is enforcing the law and steals on his
authority is a swell snake. The worst type of these punks is the big
politician.”

—Al Capone

After his first major altercation with another gangster, it is said that Al
Capone longed for revenge against Galluccio. But after an intervention of
senior mobsters, the two were made to make amends. Galluccio was
prompted to apologize for the damage he had inflicted while Capone was
made to pledge that he would not seek retribution. In an amazing show of
forgiveness in the criminal world, the two decided to let bygones be bygones.
This forgiveness was apparently genuine since Capone, even after becoming
one of the most powerful kingpins of the underworld, never sought
vengeance against Galluccio. The truth is, it didn’t take him long to see how
wrong he had been in his own actions. As strange as it may sound for a career
criminal, Capone would come to respect family values. In this sense, despite
the wounds he had received, he could only admire Galluccio for standing up
for his sister.
On December 30, 1918, with his family values still front and center, now
19-year-old Al Capone married his girlfriend Mae Josephine Coughlin. Less
than a month prior, the couple had already had a son whom they had named
Albert Francis “Sonny” Capone. Even as a young man, Capone was a firm
believer in marriage and determined that his son have a married mother and
father. So although Sonny had been born out of wedlock, when the
opportunity came to Capone, he jumped at the chance to tie the knot.
Shortly after his marriage to Mae, Capone, at the behest of mobster
Johnny Torrio, was asked to try his luck in Chicago. This transfer from New
York to Chicago wasn’t an easy one, but nevertheless Capone appreciated the
opportunity to make a name for himself in the windy city. Along with his
criminal enterprises, Capone soon became a regular in the Chicago nightlife,
routinely drinking and patronizing brothels. It was from the latter that Capone
is said to have become infected with syphilis, an illness that would plague
him for the rest of his life. Nevertheless, he continued to make progress
during his tenure in Chicago, buying a small house in the city in 1923.
During his first few years in Chicago, Capone presented himself—of all
things—as a boxing promoter. But it wasn’t boxing that this New York
transplant was promoting; in reality, Capone had become second in command
of a Chicago Outfit headed by Johnny Torrio (who had taken over after the
previous crime boss, “Big Jim” Colosimo, had been murdered—a murder
which some believe was carried out by none other than Al Capone). Here
Capone put his New York street smarts to use as a negotiator and deal maker.
He actually sought to end the rampant skirmishes between various Chicago
crime syndicates by creating treaties between the groups.
Primary among these agreements were efforts to get Chicago’s North
Side Gang to cooperate with the growing influence of the Genna brothers,
who were allies of Torrio. The North Side Gang, led by local tough guy and
bootlegger Dean O’Banion, wasn’t about to let the Genna brothers’
encroachment on their turf go unchallenged. O’Banion did not like what he
saw as Torrio’s favorable treatment of the Genna brothers, and due to his lack
of cooperation, Torrio and Capone plotted to have him killed—a plot which
led to O’Banion’s assassination at his flower shop in October of 1924.
As tough as O’Banion was he apparently had a penchant for flowers, and
besides his various criminal operations he ran a legitimate flower shop in
which he spent a lot of time. Due to this successful shop, as was often the
case with mob bosses, O’Banion could present himself as a legitimate
businessman if only he could leave his criminal dealings behind. But, as was
almost always the case, he was not willing to leave his lucrative albeit illegal
side business—at least not in this life. The flower shop he was so fond of
would turn into the crime scene of his murder; he was said to have been
clipping chrysanthemums at the time he was gunned down.
O’Banion’s death would instigate bursts of intermittent gang warfare on
the Chicago scene over the next few years. In addition, the new mayor of
Chicago elected in 1923 made it his solemn duty to crack down on Capone
and Torrio’s South Side Gang, unlike his predecessor who had been in the
gang’s pocket. But even in the middle of this storm, Capone was determined
to right the ship in his favor, setting up a new base of brothels, speakeasies,
and gambling dens in the town of Cicero, a Chicago suburb. Soon enough, he
had high-ranking Cicero officials on the gang’s payroll, finally providing
them with the political influence they desired. One of Al’s brothers, Salvatore
“Frank” Capone, was instrumental in this takeover of Cicero, dealing with the
town council on the gang’s behalf.
As the 1924 election approached in Cicero, Capone needed to make sure
that his corrupt mayor, Joseph Z. Klenha, stayed in power. So, when the
Democratic candidate pledged to crack down on Capone’s criminal
enterprise, he was determined to put the would-be mayor out of business. On
April 1, 1924, when election day arrived, Capone and his goons embarked
upon a massive campaign of their own—a campaign of voter intimidation
and bribery to ensure that the hard-line candidate would not get elected, and
one favorable to Capone and his cronies would. To call it voter intimidation
is almost an understatement since voters were not only intimidated but
directly assaulted and, in some cases, even murdered. These brave citizens
stood up for their constitutional right to vote in an election that was,
according to the Chicago Tribune, “marked by shootings, stabbings,
kidnappings, and other outlawry unsurpassed in any previous Cook County
political contest.”
Even though Capone’s candidate Klenha would end up being re-elected,
Capone did not completely get away with these antics. When the police
finally responded, a gun battle erupted, and Capone’s brother Frank was shot
and left for dead in the middle of the road. The angst then culminated in an
orchestrated assassination attempt on Capone in January of 1925. Capone
survived the attempt unscathed, motivating him to take a much more
proactive approach to his personal security from this point forward. His boss
Torrio experienced a similar incident just a little over a week later when he
was the victim of a shooting while at the mall. It was on his hospital bed
while he was attempting to nurse back his health that Torrio made the
decision to hand over the reins of Chicago mob power to Al Capone.
Al Capone was only 26 years old when he was suddenly nominated to be
the most powerful gangster in all of Chicago. This position meant that he
would take control of all the bootlegging operations and protection rackets.
This role allowed him the chance to use increasing amounts of force in order
to get what he wanted. This was demonstrated by the fact that local alcohol
brewers that refused to do business for him were often attacked, in many
cases even bombed. The businesses that refused Capone’s so-called
protection were likely to meet the same fate. It is said that over one hundred
people lost their lives in these attacks in the 1920s alone.
As well as being ruthless, Capone was known to be a rather dapper don,
often wearing the finest of suits, the best hats, and the shiniest of shoes. He
was absolutely obsessed with his public image. Even though it was far from
the truth, Capone always presented himself as an upstanding citizen and
businessman. Whenever he was questioned about his dealings, some of his
patent responses were, “All I do is satisfy a public demand” and “I am just a
businessman, giving the people what they want.”
 Chapter Three

The Press Takes on Capone

“This American system of ours, call it Americanism, call it capitalism, call it
what you will, gives each and every one of us a great opportunity if we only
seize it with both hands and make the most of it.”

—Al Capone

In the height of his heyday in Chicago, Capone made his base of operations
in nearby Cicero, Illinois after his successful infiltration of the town council.
This location provided him enough detachment to create a safe haven in
which his growing group of enemies would not be able to reach him very
easily. Nevertheless, they tried. At one point, one of his chauffeurs who
frequently made the trip between Cicero and Chicago was found murdered,
apparently the victim of an egregious incidence of torture.
As the attempts on his life and the lives of his associates continued
unabated, Capone determined to increase his security at all cost. One step he
took during transits between his base in Cicero and trips to Chicago and other
important cities was to buy out the whole train car. He would have himself
and his compatriots buy all train tickets to ensure that no-one would be able
to catch them off-guard. They would also use assumed names when checking
into hotels in order to keep their adversaries off of their trail.
Meanwhile Capone sought to reinvent his image. Instead of just being
seen as a two-bit crook, he tried to present himself to the public as a Robin
Hood type figure through his generous donations to certain charities and
public trusts. He even became a kind of champion of the anti-prohibition
movement through his public advocacy of repealing the law as well as his
private sales of illicit liquor.
But the affection he garnered from the public would not last for long as
Capone’s reputation for brutal violence increased. He also received quite a
blow to his persona after an investigative report blew the lid on one of
Capone’s major operations, a brothel on the edge of suburban Cicero, Illinois.
The reporter on the scene was the editor of Cicero Tribune newspaper, a 21-
year-old named Robert St. John. It was a riveting story in which an
undercover St. John took down the testimony of several prostitutes, crafting
an in-depth exposé of the whole enterprise. As Robert St. John would later
recall his experience, “One night I put on shabby clothes, emptied my
pockets of all identification and set out. The place was a square, unpainted
frame building two stories high and the size of a small Armory. I entered
through a room large enough for one table and a miniature bar. This was not
a drinking establishment. What was served at the bar was near beer,
obviously designed to discourage any interest in lingering longer than
necessary in this antechamber.”
St. John then goes on to say, “The ground floor of the main building was
a large room, its four walls lined with wooden benches. A client coming from
the bar took a seat on a bench just to the left or right of the bar door. The
procedure from then on was obvious at a glance. A girl wearing only the two
most essential feminine garments would come down from upstairs, enter a
large waiting room through a door in the far wall, make a slow circuit of the
room, greeting anyone she already knew, and then would go back upstairs,
accompanied by the man who occupied the spot on the bench just to the left
or right of the far door.”
St. John’s description of the inner workings of the seedy establishment
continued, “Little conversation was taking place. Traffic moved rapidly. It
took about half an hour to get from entrance to exit. In that time nearly one
hundred different girls would each have made two appearances. When a man
had worked his way to a place by the exit door, he had the privilege of
leaving with the next girl going upstairs or, if he had taken a fancy to some
particular female employee during the half hour, he could wait for her.”
St. John continued to hang out at the brothel until he found someone he
thought he could trust enough to discreetly interview for the paper. As he
explains, “During the half hour of waiting I studied the faces of hundreds of
girls. I finally found one whom I thought perhaps I could trust. She was older
than the others and looked intelligent. I waited for her. One paid the five-
dollar fee just before going upstairs where there were at least one hundred
small rooms. The girl’s name was Helen. I had brought ten-dollar bills with
me, and handed her one as soon as she had locked the door. Stumblingly I
explained that I was a ‘writer.’ I had come here only to get ‘material.’ Would
she be willing just to talk to me for the next fifteen minutes? I was lucky in
the choice I made. She answered every question I asked with what seemed
like honesty.”
It was through this helpful Helen and a few other girls that St. John was
able to compile an incredibly extensive report on the whole operation. This
report wound up in the Tribune’s very next issue and was flying off the
newsstand as a bestseller when the sensational typeset finally reached the
angry eyes of Al Capone. From this day forward, St. John would be a marked
man for his efforts to expose the kingpin’s underworld dealings. But with the
cat out of the bag about Capone’s bordello, the damage had already been
done.
The story inspired a group of concerned denizens of Cicero, at the behest
of a few members of the clergy, to form the West Suburban Citizens’
Association. Led by Reverend Henry C. Hoover, this group of citizen
vigilantes were determined to remove the illegal establishments that had been
creeping up in suburban Chicago. The group’s first line of action was to
directly petition Cicero police chief, Theodore Svoboda, to shut the brothel
down. All of these concerned citizens were then promptly paid a bunch of lip
service that something would be done, but no further official action was
taken. Disgusted, members of the group decided to take measures of their
own and actually raised $1,000 to pay off a rival gang to do the job for them.
Police corruption of greater Illinios was apparently so bad that local citizens
had to pay criminals in order to stop the actions of other criminals.
The committee had discreetly deposited the money into the accounts of
members of O’Banion’s old gang, now led by Hymie Weiss, a young man
who had become a personal enemy of Al Capone. Weiss’ gang promptly set
the bordello on fire, and an infuriated Capone woke up the next morning to
hear that his brothel had been burnt to a crisp. Although the North Side Gang
was at least polite enough to commit their arson in the early morning hours
when no-one was around, Capone and his men were not going to take such
things lightly. But instead of going after Weiss’ gang, or even the ones who
put them up to it, Capone unleashed full retribution upon a certain editor of
the Tribune newspaper, Robert St. John.
.
 Chapter Four

Silencing His Detractors

“My rackets are run on strictly American lines and they’re going to stay that
way.”

—Al Capone

It was just a couple days after the North Side Gang burned down Capone’s
Cicero brothel that his own outfit sought retribution against the one person
they perceived to be the catalyst of it all. Robert St. John was taking his
morning walk when he was intercepted by a carload of Capone’s thugs.
Leading the charge was none other than Al’s brother Ralph Capone. One of
the men was armed with a gun, and another had nothing more than a bar of
soap in a sock that he wielded over his head like a medieval flail. It is said
that there were actually police eyewitnesses on the scene but, demonstrating
the unbelievable corruption of Chicago, these cops just sat back and watched.
Not daring to lift a finger against the thugs who helped make their payroll,
the police were not so innocent bystanders to the whole ordeal.
The general narrative of what happens next is a little odd because
according to most reports, this besieged editor completely negated the fight
or flight response by engaging in neither. Instead of running or putting up a
fight, Robert St. John is said to have flung himself to the ground and curled
himself up in a ball, feebly attempting to shield his head with his hands as he
let this gang of thugs mercilessly beat him within an inch of his life. Perhaps
St. John believed that the police stationed nearby would be of assistance and
was waiting for them to intervene, but this was obviously not the case. No-
one lent a helping hand, and the beating didn’t stop until St. John was
unconscious, bleeding on the pavement.
Eventually the gangsters decided that the job had been done and jumped
into their car and fled the scene. It was only after the assailants made a clean
getaway that St. John was rushed to the emergency room. He would spend
several days in the hospital recovering, and the only positive of the
experience was that when he was checking out to receive his hospital bill, he
found that an anonymous person had already paid it for him. Was this a
Chicago citizen concerned about the brutality and disgusted by the
corruption, wishing to do good in the face of evil? Perhaps this was the
theory that the battered newspaper editor assumed was true when he first
received word of his anonymous creditor. But any such belief was dispelled
when the attending clerk mentioned that the donor had a deep and long-
running scar across his face. It was none other than Al Capone who footed
the bill for Robert St. John.
It may seem bizarre for someone to order someone else to be mercilessly
beaten and then turn around and pay their medical expenses, but this was the
twisted mind of Al Capone at work. After going out of his way to lend
corporal punishment to a newspaper writer who wrote a unflattering story
about him, it was Capone’s way of showing he had no hard feelings. Capone
in his own sick way wished to be a nice guy, and even after forcibly
correcting his detractors, he wanted to continue to project his nice guy image.
But the fact that Capone paid his after breaking his bones certainly wasn’t
going to sway Robert St. John. As soon as he got out of the hospital, he
marched right down to the police station and demanded that his assailants be
prosecuted to the fullest extent of the law. However, the police were even
more determined to display the full extent of their corruption and steadfastly
refused to be of any assistance. It was only after badgering them for several
hours that the police agreed to meet with him the following day to see about
starting the process of pursuing the assailants. As instructed, St. John
dutifully showed up at the station the next day and upon his arrival was
directed by the police chief to an empty room and told to wait. Shortly
thereafter the door opened, and none other than a fedora-wearing Al Capone
walked through.
Capone was not there to intimidate, however, and if he didn’t come right
out and apologize he launched into his own warped version of being an
apologist for his actions. Minimizing his role in St. John’s assault, he
explained to him, “I’m an alright guy—sure I got a racket. So’s everybody.
Most guys hurt people. I don’t hurt nobody. Only them that get in my way.”
This was the rationale that nice guy Capone was attempting to convey to
Robert St. John. As long as he didn’t get in Capone’s way with newspaper
stories that he found unflattering, he would stay on Capone’s good side. He
then sought to sweeten the deal as he always did—through bribery.
Pulling out his wallet like he did so many times before in front of corrupt
cops, politicians, and even clergy, Capone started thumbing through hundred-
dollar bills. He then acknowledged that he was indeed the one to pay for St.
John’s medical expenses and he wanted to give further compensation for his
pain and suffering. But unlike corrupt Chicago officials, St. John refused to
be bought. Without taking a dime, he stormed out of the room, leaving
Capone and his cash behind. But not everyone was immune to Capone’s
sway, and soon enough Al Capone was the owner of the Cicero Tribune,
having finally found a way to silence Robert St. John.
Hymie Weiss, Capone’s rival and nemesis, would also soon meet his end
when he was shot and killed by a Chicago gangster outside O’Banion’s
flower shop in October of 1926.
 Chapter Five

The Murder of McSwiggin

“When I sell liquor, it’s called bootlegging; when my patrons serve it on
Lake Shore Drive, it’s called hospitality.”

—Al Capone

In late 1925, the Capone family decided to spend the Christmas holidays in
Al’s old stomping grounds of New York. But this wasn’t just a sight-seeing
tour—the trip also had the ulterior motive of the health of Sonny Capone, Al
and Mae Capone’s seven-year-old child. Sonny had apparently developed a
bad ear infection and was in desperate need of corrective surgery. Capone
was determined to have his son treated by the best surgeons NYC had to
offer. The operation was successfully performed on Christmas Eve without a
hitch, but the young Capone would always have partial hearing loss in that
ear for the rest of his life.
With his son’s condition taken care of, Capone began to see to some of
his other dealings in the city, and by Christmas Day he was paying a visit to a
gangster hangout he often frequented in his youth called the Adonis Social
Club. The club was traditionally the hangout of Italian mobsters, but on this
night a rival Irish group led by gangster Richard Lonergan was on the scene
causing a bit of trouble for the establishment. Lonergan and his thugs had
apparently been intimidating customers and yelling obscenities at staff for
much of the night when Capone and his crew arrived around two o’clock in
the morning. Capone would later claim that his arrival was a coincidence, but
the events that transpired next seem to be far from chance.
As soon as Capone and his subordinates arrived, someone in the club
dimmed the lights, and as if right on cue, tables were flipped up for wooden
shields, and gunshots erupted in the darkness. Lonergan and his
troublemakers were riddled with bullets. The only one to escape was
Lonergan’s associate James Hart, who had to quickly crawl out of the club—
his lower legs shattered by bullets—to avoid further gunfire. Police later tried
to question Hart as he was the only surviving witness, but as was often the
case, the universal gangster code of silence prevented him from spilling the
beans to authorities, and he refused to testify. As a result, Capone once again
got away with murder, and by January 1926, he was back in Chicago to
celebrate the brand-new year, none the worse for wear.
At this point Capone’s reign over Chicago seemed unshakable. He had
corrupted and controlled nearly all of greater Chicago, and no-one seemed
too motivated to curtail the threat that he posed—that is until a popular
assistant state’s attorney by the name of William H. McSwiggin turned up
dead. Even in the corrupt atmosphere of Chicago, McSwiggin, at only 26
years old, was known as a no-nonsense prosecutor who had successfully
pursued a string of high-profile cases. His crime fighting came to an end
however on April 27, 1926, when a friend of his named Tom Duffy took
McSwiggin over to Cicero for a night of drinking. McSwiggin, nicknamed
the “Hangman Prosecutor,” was a straight-laced lawman, but he was also
known to take a few swigs of his preferred beverage on occasion as well.
On this particular night, McSwiggin ended up going to a popular hangout
called the Pony Inn. After several rounds of beer, McSwiggin and his friends
left the bar only to be caught in a burst of gunfire from a passing car.
McSwiggin sustained multiple gunshot wounds and was rushed off to the
hospital where he passed away the next day. After so many had looked the
other way for so long, the city of Chicago was filled with a sense of righteous
indignation at the word of the passing of this respected attorney, and a
thorough investigation was demanded.
It didn’t take long for investigators to pick up a trail that led right to Al
Capone. Capone was taken in for questioning, but as usual he denied all
charges. At one point he is recorded to have told his questioners, “I didn’t kill
McSwiggin—I liked the kid.” As the investigation progressed, it became
clear that Capone gangsters were indeed behind the bullets of the drive-by
shooting that killed McSwiggin, but the findings seemed to indicate that the
murder was actually an accident. As often happens with rampant gang
violence, it appears that McSwiggin and his friends were not the intended
targets but were caught in the crossfire of gang warfare. Nevertheless, with
the city’s rage and indignation intact, authorities were energized enough to
conduct several raids on Capone’s establishments. It was actually during one
of these raids at Capone’s Hawthorne Smoke Shop that investigators picked
up a piece of evidence that would one day put Capone in prison.
So, what did they find? Details of Capone’s plots? Capone’s hit list? They
never found anything quite so incriminating, but the documented evidence
that they did find would eventually be enough to put Capone away regardless
—not for murder, but for tax evasion.
 Chapter Six

Public Enemy Number One

“I’ve been accused of every death except the casualty list of the World War.”

—Al Capone

For most of 1928 you might think that perhaps Al Capone was on an
extended vacation. For starters, it was in 1928 that he forked over $40,000
(equivalent of around $560,000 in 2018) to purchase a 14-room mansion
getaway in Palm Island, Florida near Miami Beach.
But it wasn’t all fun and games in the sunshine state, because in the midst
of vacationing that year Capone’s son Sonny took a turn for the worse. His
ear infection had returned with a vengeance, and he had to receive emergency
treatment from the Capone family physician. Once again Sonny went through
a successful surgery, and the infection went into remission, but an ear
infection was apparently not the only thing that his attending physicians were
worried about. The doctors in his care also insisted that the boy be tested for
syphilis. Not only that, they suggested that Capone’s wife Mae be tested as
well.
The family doctor had heard it through the grapevine that Al Capone in
the past had been seeing a mistress who in later years had come down with
full-blown syphilis and was concerned that this dreaded illness had long ago
been passed to his wife and child. Fortunately for Sonny and Mae, they
proved to be completely free of the malady. Although not tested at the time,
Capone himself would not prove to be as lucky, famously finding himself
completely ravaged by the disease in his last years of life.
The fact that his physician was worried about the illness makes it clear
that Capone’s extramarital dalliances were well known. It is said that Mae
was, of course, well aware of them too, but she and her husband came from a
time and place that taught them to minimize such things as being irrelevant to
the state of their matrimony. For the Capones, being faithful had nothing to
do with sex; for them, a faithful marriage meant financially taking care of the
family and treating each other with respect, which Capone is said to have
done in spades. He is remembered as treating his wife with the utmost
reverence. For the Capones, his flings with showgirls were trivial and
meaningless as long as all privilege and priority were given to his wife.
Besides the brief crisis of his son’s returning illness, Capone spent most
of the time at his Floridian estate in luxury. He also spent it plotting and
planning. It is said that Capone, wishing to shake up his rivals back in
Chicago—especially one of his enemies, North Side gangster Bugs Moran—
concocted the infamous St. Valentine’s Day Massacre from this sunny locale.
Carried out on February 14, 1929, this bloody valentine delivered courtesy of
Capone took no prisoners. On that day a group of Capone’s hitmen strong-
armed seven members of the North Side Gang.
Apparently lured to a warehouse through subterfuge and deception, the
duped gangsters believed they were there to receive an illicit shipment of
stolen liquor. Capone then staged a fake raid in which some of his gangsters,
dressed as police officers, stormed into the building and had all the North
Siders stand up against a wall. Normally when such surprise raids did
happen, even if gangsters were arrested all it took was a few bribes to corrupt
officials, and the mobsters were out the very same day. So, these career
criminals didn’t flinch and were ready to cooperate with the police and go
through the motions. But this, of course, was no ordinary arrest, and the
uniformed men before them unfortunately were not Chicago police officers.
After being lined up against that warehouse wall, before they even knew
what hit them, the North Side mobsters were all shot execution-style right on
the spot. The gunmen fled the scene, and only one of the victims managed to
survive long enough to talk to police. But even in the throes of death, when
asked who shot him, he maintained the mob’s code of silence. When asked,
“Who shot you?”, bleeding and riddled with bullets, this survivor made the
statement, “No-one shot me.” This lone survivor of the St. Valentine’s Day
Massacre passed away a short time later, taking his stifled testimony with
him to the grave.
In frightening his opponents and forcing them into silence and
submission, the mission was a success. But after the hit, Al Capone faced a
public outcry that was even louder. As a result, a grand jury was formed
against Capone, and he was ordered to testify before them on the best charges
they could trump up at the time—violation of the federal prohibition laws. In
1929, the prohibition of alcohol was still in force, and it was well known that
Capone’s main bread and butter was through the sale and distribution of
illegal alcohol. Capone delayed his court appearance, however, citing his
poor health. When he finally did decide to show up in court on March 27,
1929, FBI agents apprehended Capone shortly after leaving the courtroom.
Incredibly, even though his crimes were well known, the only thing the FBI
could officially charge him on was contempt of court for missing his previous
court appearance.
In May 1929, Capone was given a sentence that was enhanced by the fact
that he was found carrying a gun on his person, giving him a stint in jail that
lasted until March of 1930. Shortly after he regained his freedom, the
Chicago Crime Commission had him listed as “Public Enemy Number One.”
But even though Capone was viewed as such a threat to the interest of the
public, he could only be brought into custody on the flimsiest of charges—
something that was repeated in Miami, Florida in April of 1930 when he was
arrested on vagrancy charges. Capone then made the mistake of claiming that
his guards had not given him food and water. These complaints did not grant
Capone any better treatment; instead, he was accused of lying and
subsequently charged with perjury.
After being released from his latest round of petty criminal sentences,
Capone was once again charged with contempt of court in February of 1931.
He ended up being sentenced for six months but kept himself out of jail due
to the appeals process. In the constant barrage of minor charges, it was as if
they were trying to kill the kingpin through a death of a thousand papercuts.
The final breakthrough to take Capone down, however, wouldn’t come from
grand juries, the police, or the FBI—it would come from the IRS.
 Chapter Seven

Taking Down Capone

“Every time a boy falls off a tricycle, every time a black cat has grey kittens,
every time someone stubs a toe, every time there’s a murder or a fire or the
Marines land in Nicaragua, the police and the newspapers holler ‘Get
Capone!’”

—Al Capone

The idea that crime bosses could be taken down for their failure to pay taxes
on their illicit gains was the brainchild of the then acting Assistant Attorney
General Mabel Walker Willebrandt. She rightly understood that though crime
bosses were obviously making a lot of money from their illegal dealings,
none of them had ever filed their taxes as any legitimate money-making
citizen would. It was then that she realized that all of these usually
untouchable mobsters could be easily brought down by this one glaring fact.
At this point, there was already precedent for it since in 1927 the highest
court in the land, the Supreme Court, had decided in the case of United States
v. Sullivan that criminally earned money was still indeed subject to income
tax. Formulating their plan, the IRS then created a task force to look into
Capone’s financial dealings. The main evidence that they had to come up
with was documented proof of Capone’s financial worth. After looking into
the matter, they found a rather easy means of proving Capone’s finances.
Although Capone kept no records of his earnings, it was discovered that his
attorney had already made entreaties to come up with ways for Capone to pay
taxes. Although these talks never amounted to anything, Capone’s lawyer
was on the record stating that Capone had made over $100,000 during the
years 1928 and 1929. This was the smoking gun, right there in black and
white print was Capone’s own attorney signing off on the fact that Capone
had untaxed income for 1928 and 1929.
From this alone, Capone was charged and convicted of income tax
evasion in 1931. At first it appeared that Capone would be allowed to plead
guilty in order to gain a reduced sentence, but such talk was quickly
dismissed. Capone was instead handed an 11-year sentence and was ordered
to pay over $215,000 in back taxes. After all of the times Capone had dodged
the bullet, both physically and financially, his failure to file taxes had hit him
where it hurt.
In May of 1932, at the age of 33, Capone was made to face the music and
was sent to serve his sentence at a federal penitentiary in Atlanta, Georgia.
The crime boss was determined to make the best of it, and it is said that as
soon as he arrived he began to barter and enter into negotiation to gain as
many privileges in prison as he could. It is said that he was even able to buy
off a couple of prison guards to serve as his own personal security. He also
received what for prisoners’ constituted luxury goods, such as his own
furniture and special bedding for his cell. Capone even managed to get his
cell equipped with brand new carpet on the floor. He was allowed to have a
radio so that he could keep up with current events, which was indeed quite a
rare privilege.
Out of fear that Capone was corrupting the officials at the Atlanta jail just
as he did the authorities of Chicago, prison officials quickly decided to
shuffle Capone off to a little-known, new prison called Alcatraz. Situated on
an island off the coast of San Francisco, this prison was considered both
corruption and escape proof. Here Capone would no longer be able to use his
force of personality to get his way—he would just be another number on the
cellblock. In many ways, if Capone’s reign as crime boss had any real
termination point, it could probably be found behind the walls of this
infamous island prison.
 Chapter Eight

Holed up in Alcatraz
“I have spent the best years of my life giving people the lighter pleasures,
helping them have a good time, and all I get is abuse, the existence of a
hunted man.”

—Al Capone

At first, when Al Capone the great gangster from Chicago stepped foot on
Alcatraz, his fellow inmates looked upon his nearly six-foot, 250-pound
frame with a mixture of fear and awe. They expected Capone to be ruthless
and to start calling the shots in the facility in short order. But Capone had
other things in mind.
Number one, he realized that Alcatraz was far different than any mainland
prison. Alcatraz—which began its life as a military installation before being
converted into a prison—was a law unto itself. Here, no matter who you
were, if you showed the least amount of resistance, the guards would beat
you back into shape. The military precision of Alcatraz was absolutely
ruthless. There would be no cajoling or bribing. Secondly, Al Capone
realized that his only real recourse to shortening his sentence was to get out
on good behavior and this meant following the rules. Sure, some of the felons
that were serving life sentences had nothing to lose, but Capone could be out
in a matter of a few years if he played his cards right.
It was for these two reasons that inmates at Alcatraz saw a very different
Al Capone begin to take shape. Following his guards’ orders to the letter, he
became a model inmate. His first prison job was in the library putting away
books—a simple job, one that he very much enjoyed. During the course of
his work, he became an avid reader. Although he had nothing more than a
sixth-grade education, Capone put it to use reading as much as possible. He
was especially enthralled by travel guide type books about faraway places.
He would read about these vistas and dream about visiting them. He also read
up quite a bit on politics, with records indicating that he once checked out a
book entitled Looking Forward, which outlined then-President Franklin
Delano Roosevelt’s plan for the future of America. Al Capone in his own
strange way always viewed himself as a patriot, and his criminal enterprise he
simply viewed to be a by-product of the same capitalist system that Roosevelt
championed.
When it came time for Al Capone’s Confidential Work Report, his
immediate supervisor at the library wrote up a glowing account of the time he
put in. He noted Capone as being “friendly, pleasant, energetic, and faithful.”
His only complaint was that Capone—apparently channeling some vestige of
his crime boss past—was occasionally a bit too headstrong. He was found
often making recommendations about the work that should be done, when
such advice was not warranted. But all in all, his supervisor wished to keep
on Capone for the long haul.
Capone was, however, eventually rotated to another work detail—this
time he was recruited out of the soft confines of the library and into the
miserable, hot, and back-breaking service of the prison laundry room. Under
the hellish conditions of this hard labor, tempers often flared, and Capone
soon found himself the target of other agitated inmates. Early on, he was
attacked by a fellow prisoner, and although he did not fight back, he was
punished just as much as the attacker. For simply being beaten up by another
inmate in an unprovoked attack, Capone was automatically locked up in
solitary confinement. He would spend a little over a week in the dank
darkness that the denizens of Alcatraz referred to as “the hole.”
In this empty, silent void, Capone’s only stimulus from the outside world
was the metal food tray routinely dropped through his door for meals.
Although it only lasted a week, it is said that Al Capone would come out of
his confinement a changed man. The experience broke his will, shattered his
spirit, and left him much weaker, both physically and mentally. As a result,
he was left much more vulnerable to attack than ever before, as was
demonstrated on June 23, 1936, when Capone was attacked in the laundry
room once again, except this time with a pair of scissors. Inspired by the idea
of making a name for himself by taking down Al Capone, this crazed inmate
launched a murderous assault on the former crime boss. As a result, Capone
received several deep puncture wounds in his chest and back. He also
received several lacerations on his arms and hands as he attempted to fend off
the attack. Even worse, a piece of one of the scissor blades had broken off in
the skirmish and embedded itself deep into Capone’s thumb.
After being rushed to the hospital, the wound to Capone’s thumb was the
most serious since it was in such a precarious position, and physicians had to
show great care to remove it. There was also the fear that the scissors may
have been contaminated with something prior to the attack leading to
concerns that the wounds would become infected. To avoid this, Capone was
made to stay in the hospital for several days as his body had several doses of
tetanus shots pumped into it.
It turned out to be a slow and daunting recovery for Capone whose
general condition had already been weakened by the advanced stage of
syphilis from which he was suffering. After his initial release from the prison
hospital, the hospital doors would become a revolving door for him, with
Capone frequently coming in and out for treatment of various ailments. And
so his condition would remain until he was finally let out on parole for good
behavior and released from Alcatraz on November 16, 1939.
 Chapter Nine

The Last Days of Al Capone

“I’m a kind person, I’m kind to everyone, but if you are unkind to me, then
kindness is not what you’ll remember me for.”

—Al Capone

Shortly after his release from prison, Al Capone was placed under the care of
physician and syphilis specialist Dr. Joseph Moore and received treatment at
Union Memorial Hospital in Baltimore, Maryland. He would ring in the New
Year of 1940 from his hospital bed. After he was thoroughly examined by the
medical staff, it was determined that his syphilis had advanced considerably
during his time in prison. Further psychological tests indicated that his mind
had diminished to the point of Capone having the mental capacity of a seven-
year-old child. It remains unclear how accurate such pronouncements are, but
after treating Capone, the same doctor indicated that by the time he left the
hospital in March, just a couple of months later, his treatment had managed to
improve Capone’s cognition to that of a 14-year-old.
No matter how the professionals quantified it, Al Capone’s mental state
had definitely taken a turn for the worse. He was known to spout random
gibberish and was often violently angry at the slightest of provocations—
especially when he was confronted by people he did not know. It was for this
reason that the doctor suggested that the Capone family hire a strong male
nurse to serve as a companion and helper, to chaperone Capone throughout
the day in order to stabilize his condition and prevent outbursts. The Capone
family politely declined this entreaty for a few reasons: First, they couldn’t
afford the extra expense, they were strapped for cash as it was. And second,
they figured they had enough relatives to lend a helping hand without
bringing outsiders into the fold. After making this quiet determination, Al
Capone was checked out of the hospital without incident, and to show her
gratitude for the care that he was given, his wife Mae had two weeping cherry
trees planted on the hospital grounds. It was her gift, but it was officially
signed off as a donation from Al Capone.
In the middle of March, the Capone family then piled into the car and
drove directly to their estate in Florida. At first things seemed fine, but
shortly after Capone’s arrival, what the doctor had warned them about came
to fruition—Capone had violently attacked someone. It was no doubt
fortunate that the victim of Al’s anger was his own brother Ermino,
nicknamed “John,” since the family was able to quickly brush off the incident
out of consideration for Capone’s best interest. But they knew full well that if
this had happened to someone outside of the home, it wouldn’t be taken so
lightly. If a stranger had been the recipient of such an attack, it wouldn’t take
long for the police to be involved.
The family had to be very careful with Capone not to set him off; for this
reason, they were quite upset when Capone’s brother Ralph offered to take
him to Chicago to meet up with old friends. In Capone’s mind, this meant
that he was returning to his role as leader of the Chicago mob. Of course, in
his mental state, this was impossible. But after being told by his brother of a
possible return to his old stomping grounds, it was all Capone would talk
about. It seems that Ralph realized his mistake after the suggestion and
backtracked on his plan for the trip. But it took much soothing and coaxing to
get Capone to take his mind off of the trip once it had been mentioned.
With much work and effort, by March of 1941, the family had managed
to bring some stability to Al Capone’s life. He had calmed down considerably
at this point and could actually hold meaningful conversations with those
around him. But even so, he still had considerably odd bouts of behavior
much of the time, including many occasions in which Capone seemed to act
as if he were speaking to people who were not there. Capone allegedly later
revealed to those that would listen that he was speaking to the people he had
killed. As to the discussions that the former mob boss was having with these
murdered souls, Capone confided that he was explaining to them “why they
had to die.”
One bright spot during these dark times came on December 30, 1941,
when Capone’s son Sonny got married. On this day that coincided with his
own mother and father’s wedding day, Sonny wed his long-time girlfriend
Diana Ruth Casey. Despite fears to the contrary, Al Capone was on his best
behavior for the event. He was in a good mood, his mental faculties were
surprisingly sharp, and he even managed to display his old charm for the
guests. For a moment the family was even tempted to think that Al Capone
had been cured—he had returned to his old self.
Shortly after their marriage, Sonny and Diana would have back-to-back
children, four girls in total. These granddaughters would prove to be the
greatest joy of Al Capone’s life in his last few years. He and his wife
showered the grandkids with affection, and they returned the favor, lovingly
referring to their grandpa as their “paw paw.” It was pretty obvious to anyone
who witnessed it that Capone had finally left the thought of returning to his
criminal enterprise behind. With the birth of his granddaughters, he had
officially entered into a new phase of his life. He was a family man now and
loving every minute of it.
Even the FBI, who doggedly conducted surveillance on Capone’s every
move since his release from prison, couldn’t help but take note. In official
reports they remarked upon happy family gathering after happy family
gathering at the Capone residence, with one agent making the official
comment that Capone and his family had an “extremely close bond.” In the
end, it was a bond that only death would break.
 Conclusion
After his return from prison it was soon discovered that Capone had immense
difficulty sleeping in the large master bedroom of his Florida estate. His time
in prison cramped in a small cell had made him to where he could only sleep
if he was ensconced in similar conditions. Most nights Capone preferred to
sleep on a single bed in a small backroom of the house. He did on occasion
join his wife in the master bedroom, however, and on January 21, 1947, it
just so happened that Capone chose to sleep in the same bed as his wife Mae.
On that particular night, Mae was jarred awake to hear her husband gasping
for air beside her. Right away she intuitively knew that Al was in serious
trouble, perhaps even breathing his last breaths.
As he struggled, she desperately attempted to soothe him back to a
normal state, but his difficulty persisted. She then gave him a glass of water,
but after trying to drink it he merely started choking on the fluid, making his
condition even worse. Mae then began to scream for the rest of the household
to wake up and help her as Capone began to go into convulsive fits. His
physician was quickly called and arrived as soon as he could, reaching the
Capone residence around five o’clock in the morning. Thankfully the doctor
was able to give Capone some medication that calmed his condition and
allowed him to finally catch his breath.
A couple of days after the incident first occurred, on January 23, Capone
was fully awake and seemingly making a complete recovery. But just as the
family thought that his recovery was assured, they were informed that
Capone had developed a case of acute pneumonia. He was immediately given
oxygen and other medications deemed to be helpful, but none of it seemed to
give him permanent relief. Despite the best efforts of his family and
physicians, Capone’s life began to persistently fade shortly thereafter.
Al Capone quietly passed away on January 25, 1947. The official cause
of his death was listed as bronchial pneumonia. After his death, arrangements
were made for his funeral and burial to take place in his adopted home of
Chicago. His family must have realized that Chicago and Capone were
forever intertwined, and there could be no other way. Initially, Capone was
buried at Mount Olivet Cemetery but for reasons that still remain unclear, a
few years out from this internment, his remains were removed and transferred
to Mount Carmel Cemetery in Hillside. Here, in his final resting place, Al
Capone, the man who so ruthlessly ruled Chicago, has a gravestone with
three simple words, “My Jesus Mercy.”
The families of his victims may not all feel quite so forgiving or merciful,
but perhaps in the end even the twisted and corrupt soul of Al Capone found
some sort of atonement. Both in prison and his time as a virtual recluse on the
outside, he certainly had a lot of time to think about what he had done. And
in his last days, the man who so often defended his actions by saying what he
did was “just business” seemed to have finally had his guilt catch up to him.
He was, after all, often seen having imaginary conversations with people he
had killed. In the final chapter of his life, perhaps Al Capone who was so
famous for his wheeling and dealing in gangland had worked out one final
treaty, one last negotiation, and attained some form of clemency for himself.
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