Al Capone: The American Gangster

Al Capone was an American gangster who led a crime syndicate dedicated to smuggling and bootlegging of liquor and other illegal activities during the Prohibition Era of the 1920s and 1930s. Capone began his career in Brooklyn before moving to Chicago and becoming the boss of the criminal organization known as the Chicago Outfit; although, his business card reportedly described him as a used furniture dealer. He was, and still is, the most recognized and influential Mafioso in American history. Both hated and loved by the public, he shared a common dislike with many people in American society at that time; a strong disdain for the temperance movement.

Alphonse Gabriel “Al” Capone was born on January 17, 1899 in the Brooklyn borough of New York City to Italian immigrants Gabriele and Teresina Capone. They landed in New York just in time for the Panic of 1893, which would wrack the country’s economy for years. Gabriel who was a skilled barber and Teresina a seamstress, wisely chose Brooklyn as home in preference to the even greater squalor and density of Mulberry Bend, Manhattan’s Lower East Side Italian colony; not that the depression spared Brooklyn. Unemployment would soon idle one quarter of the borough’s workforce, making it no time for the unskilled. [1] 

The Capones’ lived better than most. Though Gabriel could not ply his trade at first, he avoided the drudgery and extreme low pay of manual labor because he boasted another skill that went with his trade; he could read and write. In Italy, as well as in America, the illiterate expected their barber to read them any letters that came their way. Gabriel’s learning earned him a job in a grocery store until he could gather enough of a stake to open his own barber shop; a storefront in a tenement at 69 Park Avenue. [2] 

Little Al, as he was called, had started school at John Jay, P.S. 7, at 141 York, near the Navy Yard. After the family had moved, he transferred to William A. Butler, P.S. 133, at 355 Butler Street; seven blocks away from Garfield. Until he reached sixth grade, he maintained a B average. He devoted much time and energy to his favorite extracurricular activity, playing hooky. He attended class only thirty-three days of the required ninety. A red-haze temper that would occasionally overmaster him all his life exploded one day, and he hit a teacher who was lecturing him. Sent to the principal’s office, he got a whipping and quit school in embarrassment. He was fourteen at the time, but he was ready to quit anyway as it was practically a family tradition. [3] 

Al made a stab at an assortment of honest jobs; clerk in a candy store and pin boy in a bowling alley. For a while he earned twenty-three dollars a week working in an ammunition factory. He also worked as cutter in a book bindery, following his older brother Ralph, who had worked in the print shop of a newspaper. Apprenticeship for Al Capone’s life’s work, though, arose on the streets. The streets Capone traveled as a young boy was ruled by gangs, or more precisely kid gangs. Members of these kid gangs could not be called gangsters; by today’s standards they would barely qualify as delinquents. Excepting petty pilferage and occasional lunch-money extortion, few engaged in activity anyone would consider downright criminal. [4] 

Al was heavily influenced by gangster Johnny Torrio whom he considered to be his mentor. John Torrio was the thinking man’s criminal. Torrio owned a bar on James Street at the corner of Water. He soon expanded, leasing a rooming house down the block which he filled with prostitutes and a nearby store he converted into a pool hall. Young Al could hardly have avoided absorbing the lesson of someone who had attained money and power without the drudgery that were typically weighed on others. [5] 

Al eventually joined the South Brooklyn Rippers, a junior gang that inducted kids as young as eleven. No reliably authentic details about Al’s activities in his late boyhood and early teens have survived, but he evidently did not stand out or apart. Not many years later, a former Brooklyn kid-gang member remembered him “as something of a nonentity, affable, soft of speech and even mediocre….” [6] 

Al had caught the eye of someone who could exert the most portentous influence possible at that stage. It was Frankie Yale, six years older, who had ushered Al into the Forty Thieves Juniors gang. When Al entered his mid-teens, Yale welcomed him exclusively into the adult gang Five Points headed by Johnny Torrio. Membership in this Manhattan gang showcased his tough scrappiness. “Capone learned all there was to know about extortion and slugging and the rest on the banks of the Gowanus Canal,” says William Balsamo, Brooklyn native and historian of New York crime. Yale was fashioning a complex of enterprises beyond the Harvard Inn: a mortuary; racehorses; prizefighters; another nightspot, the Sunrise Cafe; a line of cigars-all based finally on his main line, strong-arm terror. [7] 

Capone’s job as bartender and bouncer at Yale’s Harvard Inn demanded a certain finesse. The trick was to bounce without alienating, and only to do so after considered efforts to calm and subdue had failed. Ideally, the bounced would recognize themselves as out of line. Capone combined the mass to bounce authoritatively and the intelligence to do it with tact. Capone became Yale’s pupil, favored by invitations after a hard night at the Harvard Inn to sleep over at Yale’s house. That happened frequently enough that Yale’s daughters would show visitors “Al’s room.” Yale had the swagger of a young man, already boss yet still a comer. Inevitably, Capone viewed Yale as a model and a teacher. [8] 

One summer night in 1917 resulted in scarring consequences. Frank Galluccio “Galluch,” a merchant seaman, barber’s assistant, and spear-carrier in the Genovese crime family strutted into the Harvard Inn with his date, Maria Tanzio, and his kid sister, Lena. The sight of Lena set Capone’s glands exploding. Every time his rounds took him past her table he would try to chat with her; Lena snubbed him. Her brother who was half drunk and did not know Capone assumed from his familiarity that Lena did. His kid sister’s growing anger penetrated Galluccio’s alcoholic fog stating, “You know that guy?” Lena then responded:

I never saw him before. He’s got a lotta nerve. He won’t give up, Frank. He can’t take a hint. But I don’t like him; he is embarrassing me. Maybe you could ask him to please stop-in a nice way. [9] 

Capone headed their way again and Galluccio was ready to take him aside like a gentleman: “Hey, mister, please do me favor, okay? She’s my kid sister, you know…” Before Galluccio could speak, Capone leaned over to Lena, and “whispered”-loud enough to startle the party at the next table with heads swiveled in amazement-“You got a nice ass, honey, and I mean it as a compliment. Believe me.” Her brother sprang to his feet. The insult was bad enough; the fact that strangers had plainly heard made it insupportable. “I won’t take that shit from nobody,” Galluccio shouted. “Apologize to my sister now, you hear?” At a moment, Capone’s brain reasserted itself, perhaps kicked in by “sister.” Family meant everything, and its evocation put this customer unarguably in the right. With his most ingratiating and placating smile, Capone turned to Galluccio arms spread wide and palms up and open: “Hey, whatsa matter, pal, a little misunderstanding, a joke, no offense…” “This is no fucking joke, mister,” cried Galluccio. [10] 

Galluccio stood five-foot-six and weighed under 150. Capone looked like a mountain avalanching toward him. The “Galluch” knew he could be badly hurt unless he struck first and quickly, but his punch would never do the job. He clawed his knife from his pocket and lunged as the streets had taught him. One slash started two inches in front of mid-ear, curved four inches down the left cheek to just below the corner of Capone’s mouth; the other two each measured two and a half inches, one on the left jaw, and the other on the neck under the left ear. Galluccio grabbed his sister and date and ran out the door. Someone rushed Capone to the Coney Island Hospital where doctors applied thirty stitches to his face. [11] 

Soon Galluccio heard that Frankie Yale had been asking around for him. Galluccio appealed to Joseph Masseria, overlord of all New York for justice. “Joe the Boss” decreed a sit-down at the Harvard Inn where they agreed that Capone had indeed been wrong and would not be allowed to seek vengeance, while Galluccio had to apologize for his disproportionate reaction-which he readily did, contrite at sight of how he had disfigured Capone. Capone also recognized the justice of the settlement and the dishonor of his scars. He later put out the story that the scars had happened to him in service with the Lost Battalion of World War I. In fact, he had never been called up in the draft. This notable scarring had given him the infamous nickname “Scarface.” [12] 

In 1918 Capone met an Irish girl at a dance and fell in love. She was pretty, slim and tall with a round piquant face and large eyes framed by a helmet of blond hair. Baptized “Mary,” she would be known all her life as Mae, daughter of Michael Coughlin, a construction worker, and the former Bridget Gorman. On December 4, 1918, Mae gave birth. Eighteen days later, Mae’s sister, Kathleen, and James DeVico, an otherwise obscure friend of Capone’s, became godparents to Albert Francis Capone, also known as Sonny. Mae had almost two years on Capone, perhaps an embarrassment to them because each fudged a year of age on their marriage registration. Capone appears in the church records as “Albert,” maybe a mistake, or maybe a typical bit of criminal obfuscation. [13] 

Members of the Anti-Saloon League, founded 1893 in Oberlin, Ohio, sincerely believed everyone would be better off without alcohol. They “looked forward,” one historian has observed, “to a world free…from want and crime and sin, a sort of millennial Kansas….” Their campaign, which quickly enveloped the nation, combined such animating idealism with the most brutal brass-knuckles politics; the league terrorized Congress. In the words of a popular song of the era:

What Have They Got on You, Mr. Congressman? We’ve heard just how those drys, Keep cases on you Congress guys. One “wrong” vote and reports would wing back home broadcasted by the league’s fifty thousand field workers. [14] 

America’s April 6, 1917, entry into the war sanctified the dry cause as patriotism even for the doubting majority. The liquor trade gobbled up enough grain for eleven million loaves of bread a day. The league insisted drunken workers could not turn out war materiel any more than drunk soldiers could shoot straight. Caving in to these pressures, Congress passed a resolution calling for a prohibition amendment to the Constitution and sent it to the state legislatures for ratification in December 1917. On January 16, 1919, Nebraska provided the necessary three-fourths majority by becoming the thirty-sixth state to approve the resolution. The Eighteenth Amendment would become law in one year. [15] 

Meanwhile, the league rammed “wartime” Prohibition through Congress. Until the Eighteenth Amendment kicked in at midnight on Friday, January 16, 1920, the interim law forbade anyone in the United States to make, sell or transport-without a permit-any beverage containing more than one half of 1 percent alcohol. The ban-both permanent and interim-cunningly did not include owning, drinking or buying liquor. The league had been careful not to offend voters or members of Congress; many were notoriously wet in habits no matter how dry they voted. [16] 

Capone was a suspect for two murders in 1919 and was seeking a safe haven and a better job to provide for his new family. Capone relocated to Chicago to help out his Five Points gang mentor Johnny Torrio. Torrio had gone to Chicago to resolve some family problems his cousin’s husband was having with the Black Hand. Torrino had also been summoned there to help out his uncle, Big Jim Colosimo, the city’s leading whoremaster to run his empire. By the time Capone arrived, Torrio was in dispute with Big Jim. Seeing the major financial opportunities that came with Prohibition, Torrio wanted Colosimo to shift his organization’s main thrust to bootlegging; Big Jim was not interested. He had become rich and fat in the whoring trade and saw no need to expand. He forbade Torrio to get into the new racket. Torrio realized that Colosimo had to be eradicated so that he could use Big Jim’s organization for his criminal plans. Together he and Capone planned Colosimo’s murder and sent Frankie Yale and his men from New York to carry out the job. Capone and Torrio meantime would act out airtight alibis [17] .

One of Capone’s duties was to buy trucks for Torrio’s operation-which those in it called “the outfit”-especially after Capone took over. Members used it casually when talking among themselves about their group-“I joined the outfit two years ago”-as they would say “I’m with Capone,” when talking about their affiliation to an outsider. Many in the outfit were involved in transporting beer. For most of them, being part of a gang meant little more than being a truck driver; that was the entry-level job for most. Possible promotion led to muscle and racketeering work. But Torrio relied on few to buy new and used trucks; one was Capone. By mid-1922 Capone already ranked as Torrio’s number two. [18] 

The election of reform mayor William Emmet Dever led to Chicago’s city government putting more strain on the gangster agenda within city limits. Dever’s biographer called him “a dripping Wet who enforced Prohibition. He would tell a meeting of beer-guzzling Germans, “I have never pretended to be, and am not now a Prohibitionist.” But he would have law and order stating, “He would enforce the law to the limit.” Within a month, authorities were raiding places citywide with, wrote a reporter, “unabated enthusiasm,” arresting five hundred in one sweep, 450 in another. Within six months his men had closed over four thousand blatant saloons and some five hundred “soda parlors”-notoriously fronts for selling beers. A significant amount of license revocations were set forth. [19] 

To put its headquarters outside of city jurisdiction and create a safe zone for its operations, the Capone organization muscled its way into Cicero, Illinois. This led to one of Capone’s greatest triumphs; the takeover of Cicero’s town government in 1924. Capone made it clear that he wanted an all-out conquest of the town. He installed his older brother Frank (Salvatore) as the front man with the Cicero city government. Ralph was tasked with opening up a working-class brothel called the Stockade for Cicero’s heavily blue-collar population. Al focused on gambling and took an interest in a new gambling joint called the Ship. He also took control of the Hawthorne Race Track. [20] 

For the most part, the Capone conquest of Cicero was unopposed, with the exception of Robert St. John, the crusading young journalist at the Cicero Tribune. Every issue contained an expose on the Capone rackets in the city. The editorials were effective enough to threaten Capone-backed candidates in the 1924 primary election. On election day things got ugly as Capone’s forces kidnapped opponents’ election workers and threatened voters with violence. As reports of the violence spread, the Chicago chief of police rounded up seventy nine cops and provided them with shotguns. The cops, dressed in plain clothes, rode in unmarked cars to Cicero under the guise of protecting workers at the Western Electric plant there. Frank Capone, who had just finished negotiating a lease, was walking down the street when the convoy of Chicago policemen approached him. Someone recognized him and the cars emptied out in front of him. In seconds, Frank’s body was riddled with bullets. Technically, the police called it

“self defense,” since Frank, seeing the police coming at him with guns drawn, had revealed his own revolver. [21] 

Al was enraged and escalated the violence by kidnapping officials and stealing ballot boxes. One official was murdered. When it was all over, Capone had won his victory for Cicero. Capone’s temper stayed under control for about five weeks. But then, Joe Howard, a small-time thug, assaulted Capone’s friend Jack Guzik when he turned him down for a loan. Guzik told Capone and tracked Howard down in a bar. Howard had the poor judgment to call Capone a “dago” pimp and Capone shot Howard dead. [22] 

While only twenty-five, Al Capone became a prominent figure in Chicago’s organized crime. He wasn’t the only one though. Dion O’Banion owned a thriving florist shop, but was also one of the biggest names in the bootlegging business. Flamboyant but untrustworthy, O’Banion became a thorn in Capone’s side. In one instance, O’Banion killed a man outside of Capone’s Four Deuces gambling joint and the ensuing trial dragged Capone into unwanted attention. O’Banion also set up Torrio to be arrested by the police. He had promised Torrio he would move to Colorado if Torrio agreed to buy O’Banion’s Sieben Brewery. O’Banion took the money and left while the police were waiting to raid the brewery. Torrio went to jail and O’Banion kept the money. The Brewery was eventually shut down permanently. [23] 

O’Banion met his end while preparing a floral arrangement in his shop on November 10, 1924. He was a consummate hand shaker and on that day three known gangsters came in the shop. Thinking they were there to pick up flowers for the funeral of another prominent gangster, he went to shake their hands. One of them pulled O’Banion off balance and six shots rang out. While there was a great deal of speculation concerning the triggermen, no one ever went to trial over the murder. It did leave O’Banion’s territory wide open for Capone to move in, but also made powerful enemies of O’Banion’s friends. These friends included Hymie Weiss and Bugs Moran. [24] 

Over the next two years, Moran and Weiss would fail in over a dozen assassination attempts against Capone. On January 24, 1925, Torrio was returning to his apartment at 7106 South Clyde Avenue from a shopping trip with his wife Anna. Walking from his car towards his apartment building, Weiss and Moran opened fire. They shot Torrio in the chest, neck, right arm and groin, but miraculously the elderly man survived. The true miracle came about when one of the men-reportedly Moran-held his gun to Torrio’s head and pulled the trigger only to hear the click of an empty firing chamber. This incident made Torrio consider quitting the game. After recovering, Torrio pleaded guilty and was sentenced to nine months in jail for the Sieben Brewery raid. During his jail sentence Torrio informed Capone he was planning on leaving Chicago and turning his vast empire over to Al stating, “It’s all yours Al. Me? I’m quittin’. It’s Europe for me.” Torrio then moved to Italy with his mother and wife. [25] 

Shortly after he took over Johnny Torrio’s empire, it was clear that his new status had changed Al Capone. He was a major force now in the Chicago underworld. To underscore his rise in the world, he moved his headquarters to the Metropole Hotel. His luxurious suite of five rooms cost $1,500 per day. He went from near obscurity to cultivated visibility. Capone became visible at the opera, at sporting events and charitable functions. He was an important member of the community: friendly, generous, successful, supplying a throng of thirsty customers. In an era where most of the adult population drank bootleg alcohol, the bootlegger seemed almost respectable. [26] 

In the spring of 1926, Capone’s run of good luck hit a snag. On April 27, Billy McSwiggin, known as the young “hanging prosecutor” who had tried to pin the 1924 death of Joe Howard on Capone, met with an accident. A bootlegger named Jim Doherty picked McSwiggin up by car at his father’s house. Doherty’s car broke down and they hitched a ride with bootlegger “Klondike” O’Donnell, a bitter enemy of Capone. The four Irish lads went on a drinking binge in Cicero with O’Donnell and his brother Myles and ended up at a bar close to the Hawthorne Inn where Capone was having dinner. O’Donnell’s cruising around in Cicero was a territorial insult. [27] 

Capone and his henchmen, not realizing that McSwiggin was in the bar with Myles O’Donnell, waited outside in a convoy of cars until the drunken men staggered out. Then out came the machine guns and McSwiggin and Doherty were dead; Capone was immediately blamed. Despite the blot on McSwiggin’s integrity for keeping company with bootleggers, sympathy was with the dead young prosecutor. There was a big outcry against gangster violence and public sentiment went against Capone. While everyone in Chicago knew that Al Capone was responsible, there was not a shred of proof and the failure of this high-profile investigation to return an indictment was an embarrassment to local officials. Police took out their frustrations on Capone’s whorehouses and speakeasies which endured a series of raids and fires. [28] 

Capone went into hiding for three months. Reputedly some 300 detectives looked for him all over the country; in Canada and even Italy. He initially found refuge in the home of a friend in Chicago Heights and then, for most of the time, with friends in Lansing, Michigan. Those three months in hiding made an indelible mark on Al. He began to see himself as much more than a successful racketeer. He believed he was a source of pride to the Italian immigrant community; a generous benefactor and important fixer who could help people. His bootlegging operations employed thousands of people, many of whom were poor Italian immigrants. While much of this was just his ego getting larger, Capone had real leadership abilities and was very capable of extending those talents into areas that were beneficial to the community. He seriously thought of retiring from his life of crime and violence. [29] 

On July 28, 1926, he returned to Chicago to face the accusations of murder. It turned out to be the right decision because the authorities did not have sufficient evidence to bring him to trial. For all the public uproar and efforts of the law enforcement groups, Al Capone was a free man. The people of Chicago were tired of reading about gang violence and the newspapers fanned their anger. Capone held a highly publicized “peace conference” in which he appealed to the other bootleggers assembled there to tone down the violence. He made his point stating, “There is enough business for all of us without killing each other like animals in the streets. I don’t want to die in the street punctured by machine-gun fire.” At the end of the meeting, an “amnesty” had been negotiated which accomplished two key things; first, there would be no more murders or beatings and second, past murders would not be avenged. For more than two months thereafter, nobody connected with the bootlegging business was killed. [30] 

In May of 1927, the Supreme Court made a decision that Manny Sullivan, a bootlegger, had to report and pay income tax on his illegal bootlegging business. Just because reporting and paying tax on illegally-derived revenues was self-incrimination, it was not unconstitutional. With the Sullivan ruling, the small Special Intelligence Unit of the IRS under Elmer Irey was able to go after Al Capone. [31] 

Unaware and uninterested in Manny Sullivan or Elmer Irey, Capone became more compulsively extroverted and expansive. He indulged heavily in his two big passions; music and boxing. He became close pals with boxermJack Dempsey, but given the concern over fixed fights, the friendship had to be very discreet. Always an opera lover, Capone expanded his patronage to the jazz world. With the opening of the Cotton Club in Cicero, Al became a jazz impresario, attracting and cultivating some of the best black jazz musicians of the day. Unlike so many other Italian gangsters, Al did not seem to have the deep-seated racial prejudice and he gained the trust and respect of many of his musicians. Al extended his generosity and personal concerns to everybody who worked for him, black or white.

Al spoke to reporters:

Public service is my motto. Ninety percent of the people in Chicago drink and gamble. I’ve tried to serve them decent liquor and square games. But I’m not appreciated. I’m known all over the world as a millionaire gorilla. [32] 

Capone biographer Laurence Bergreen described the way Capone inserted himself into the lives of those he knew:

He came to dominate them 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. [33] 

The exposure was becoming a real nuisance. When he left for a trip to the West Coast, he had police surrounding him at every station. Los Angeles’ toughest detective said “We have no room here for Capone or any other visiting gangsters whether they are here on pleasure tours or not.” When Capone came back from the West Coast he found himself surrounded by six Joliet policemen with their shotguns aimed at him. Capone stated, “Well, I’ll be damned. You’d think I was Jesse James. What’s the artillery for?” In Chicago, the police made things as uncomfortable as possible by surrounding his house and arresting him at the slightest provocation. [34] 

Capone left for Miami where the weather was much better than the Chicago winter, but the reception by the local community was chilly. He, Mae, and Sonny rented a house for the season and started to look for a permanent residence. Over the coming months he would invest a small fortune in redecorating his new palace in Miami, securing it like a small fortress with concrete walls and heavy wooden doors. [35] 

The Palm Island estate came to the attention of IRS Intelligence Unit watchdog Elmer Irey. He chose Frank J. Wilson to head up the job of documenting Capone’s income and spending. The job was monumental; despite Capone’s lavish spending everything was transacted through third parties. Although Capone had incredible wealth, every transaction was on a cash basis. The major exception was the very tangible assets of the Palm Island estate, which was evidence of a major source of income. [36] 

George Emmerson Q. Johnson, a member of the Scandinavian “old boy’s network” in the Midwest, was appointed U.S. attorney for Chicago. Johnson targeted Capone with unbridled passion. In the spring of 1928, the violence preceding the April primary election began to escalate out of control. It was not clear who was orchestrating all of this violence, but this time the targets were not gangsters, but U.S. Senator Charles Deneen, a reformer and a judge. The unabashedly corrupt Mayor Bill Thompson was presumed responsible since the victims were people who opposed him, but Al Capone who was still in Florida, was the scapegoat.

While Mae Capone spent the spring of 1928 on an extravagant decorating spree Al dedicated himself to establishing himself as a legitimate citizen of Miami. In spite of the outward show of respectability, Al quietly made plans to solve pressing problems caused by his old boss Frankie Yale. The liquor supply deal that Capone and Yale had negotiated was experiencing too many hijackings, which Capone believed Yale had initiated. [37] 

Al called six of his Chicago partners to Florida to figure out how to handle the problem with the powerful Yale. Capone biographer John Kobler:

Toward midafternoon on July 1, a Sunday, Frank Yale, his jet-black hair and dark skin set off by a Panama hat and light-gray summer suit, was drinking in a Borough Park speakeasy when the bartender called him to the phone. What he heard sent him hurrying out to his car parked nearby. A few minutes later on Forty-fourth Street a black sedan crowded him to the curb; bullets from a variety of weapons-revolvers, sawed-off shotguns, a tommy gun-nailed him to the seat. The tommy gun was the first ever used to kill a New York gangster. [38] 

In the summer of 1928, Capone made his headquarters in the once highly respected Lexington Hotel, occupying two floors of the large and imposing structure. He lived like a potentate in his six-room suite with a special kitchen for his catered meals. Secret doors were installed so that Capone could escape undetected if the need arose. It was clear to Capone that Prohibition would not last forever, so he began to diversify into the rackets. A Chicago business newspaper reported:

A “‘racketeer’ may be the boss of a supposedly legitimate business association…Whether he is a gunman who has imposed himself upon some union as its leader, or whether he is a business association organizer, his methods are the same; by throwing a few bricks into a few windows, an incidental and perhaps accidental murder, he succeeds in organizing a group of small businessmen into what he calls a protective association. He then proceeds to collect what fees and dues he likes, to impose what fines suit him, regulates prices and hours of work…Any merchant who doesn’t come in or doesn’t continue to pay tribute, is bombed, slugged or otherwise intimidated. [39] 

Like in the bootlegging business, Capone ran into the same old antagonist Bugs Moran. Moran had tried twice to murder Al’s friend and colleague Jack McGurn. When Capone went to Palm Island for the winter, Jack McGurn went to visit him in early February to discuss the enduring problems with Bugs and his North Siders gang. Neither McGurn nor Capone ever thought that the planned assassination of Bugs Moran would be an event that would be notorious for many decades to come. Capone was lolling so lavishly in Florida, so how could he be held responsible for the murder of a bootlegger. Machine Gun” McGurn was given complete control of the hit. [40] 

McGurn put together a first rate team of out-of-towners. Fred “Killer” Burke was the leader and was assisted by a gunman named James Ray. Two other important members of the team were John Scalise and Albert Anselmi who had been used in the murder of Frankie Yale. Joseph Lolordo was another player, as were Harry and Phil Keywell from Detroit’s Purple Gang.

McGurn’s had a bootlegger lure the Moran gang to a garage to buy some very good whiskey at an extremely attractive price. The delivery was to be made at 10:30 A.M. on Thursday, February 14th. McGurn’s men would be waiting for them dressed in stolen police uniforms and trench coats as though they were staging a raid. [41] 

McGurn wanted to be far away from the scene of the crime. He took his girlfriend and checked into a hotel; establishing an airtight alibi was uppermost in his mind. At the garage, the Keywells’ spotted a man who looked like Bugs Moran. The assassination squad got into their police uniforms and drove over to the garage in their stolen police car. Playing their part as police raiders, McGurn’s men went into the garage and found seven men, including the Gusenberg brothers who had tried to murder McGurn. [42] 

The bootleggers, caught in the act, did what they were told; they lined up against the wall obediently. The four assassins took the bootleggers’ guns and opened fire. The men slumped to the floor dead, except for Frank Gusenberg who was still breathing. To further perpetuate this charade, the two “policemen” in trench coats put up their hands and marched out of the garage in front of the two uniformed policemen. Anyone who watched this event believed that two bootleggers in trench coats had been arrested by two policemen. The four assassins eventually left in the stolen police car. [43] 

It was brilliantly executed except for one small detail-the target of the entire plan, Bugs Moran, was not among the men executed. Moran was late to the meeting seeing the police car pulling up just as he neared the garage; he took off, not wanting to be caught up in the raid. It didn’t take a genius to figure out that the target of the cleverly organized assassination attempt was Bugs Moran and the most obvious beneficiary was Al Capone. Even though Al Capone was conveniently in Florida and Jack McGurn had an airtight alibi, the police, the newspapers, and the people of Chicago knew who was responsible. The police couldn’t arrest Capone without any evidence. McGurn was smart enough to marry his girlfriend Louise Rolfe, better known as the “blonde alibi,” who could not testify against her new husband. All charges against him were dropped. No one was ever brought to justice for the spectacular assassination. [44] 

The publicity surrounding the St. Valentine’s Day Massacre, as it was famously named, was the most that any gang occurrence had ever received. And it was not only local publicity; it was a national media event. Capone ballooned into the national conscious and writers all over the country began books and articles on him. Bergreen saw the massacre as endowing Capone with a grisly glamour:

There had never been an outlaw quite like Al Capone. He was elegant, high-class, the berries. He was remarkably brazen, continuing to live among the swells in Miami and to proclaim love for his family. Nor did he project the image of a misfit or a loner, he played the part of a self-made millionaire who could show those Wall Street big shots a thing or two about doing business in America. No one was indifferent to Capone; everyone had an opinion about him. [45] 

Capone reveled in his new found celebrity status and used Damon Runyon as his press agent, but the damage of all that publicity had been done. He attracted the attention of President Herbert Hoover. “At once I directed that all of the Federal agencies concentrate upon Mr. Capone and his allies,” Hoover wrote. In the beginning of March, 1929, Hoover asked Andrew Mellon, his secretary of the Treasury, “Have you got this fellow Capone yet? I want that man in jail.” [46] 

Evidence was mounting that two of his Sicilian colleagues were causing Capone problems. Kobler describes the famous scene in which Capone met the problems head on:

Seldom had the three guests of honor sat down to a feast so lavish. Their dark Sicilian faces were flushed as they gorged on the rich, pungent food, washing it down with liters of red wine. At the head of the table, Capone, his big white teeth flashing in an ear-to-ear smile, oozing affability, proposed toast after toast to the trio. Saluto, Scalise! Saluto, Anselmi! Saluto, Giunta! [47] 

Capone had observed the old tradition; hospitality before execution. The Sicilians were defenseless because they left their guns in the checkroom. Capone’s bodyguards lashed them to their chairs with wire and gagging them. Capone got up holding a baseball bat.With both hands he lifted the bat and slammed it down full force. Slowly and methodically, he struck again and again breaking bones in the man’s shoulders, arms and chest. He moved to the next man and when he had reduced him to mangled flesh and bone he went on to the third. One of the bodyguards then fetched his revolver from the checkroom and shot each man in the back of the head. [48] 

The St. Valentine’s Day Massacre catalyzed the government forces against him. Herbert Hoover pressured Andrew Mellon, the Secretary of the Treasury, to spearhead the government’s battle against Capone. Mellon commissioned a two-pronged approach to get the necessary evidence to prove income tax evasion and to amass enough evidence to prosecute Capone successfully for Prohibition violations. Once the evidence was collected, the Treasury agents were to work with the U.S. Attorney, George E. Q. Johnson to initiate prosecution of Capone and the key members of his organization. [49] 

The man charged with gathering the evidence of Prohibition violations was Eliot Ness who began to assemble a team of daring young agents like him. The biggest effort was led by Elmer Irey of the IRS Special Intelligence Unit who redoubled his ongoing efforts shortly after Hoover’s mandate. While there was doubt that Capone could be successfully prosecuted for Prohibition violations in Chicago, Mellon felt sure that with the Sullivan ruling would penalize Capone on tax evasion.

Capone went to a movie in Philadelphia and when he exited two detectives were waiting for him. Capone was arrested and imprisoned for carrying a concealed weapon. In mid-March of 1930 Capone was released from jail a few months early because of good behavior. A week later Frank J. Loesch, the head of the Chicago Crime Commission, put together a Public Enemies list which was headed by Capone. Capone who wanted to legitimize himself as a contributing member of the community was now Public Enemy Number One; he was enraged, humiliated and thoroughly insulted. [50] 

As 1930 drew to a close Capone embarked on a major publicity campaign. He opened a free soup kitchen for the people who had been thrown out of work by the deepening Depression. The soup kitchen served three free meals a day. It was carefully calculated to rehabilitate his image and to ingratiate himself with the workingman who had come to regard him as another unimaginably wealthy and powerful tycoon. The kitchen didn’t melt his enduring problems though. [51] 

Eliot Ness was becoming increasingly successful at finding and shutting down Capone’s brewing business. He and his Untouchables had impressively documented thousands of Prohibition violations that would be used against Capone if the tax case failed. Millions of dollars of brewing equipment had been seized or destroyed; thousands of gallons of beer and alcohol had been dumped; and the largest breweries were shut down. Wiretaps on Capone’s lieutenants revealed how bad things were getting. The mob had to cut back its graft and payments to the policemen. Beer had to be imported from other areas to supply the speakeasies that used to buy Capone’s beer. Trouble escalated when they raided a gigantic operation that was supplying 20,000 gallons a day. [52] 

A federal grand jury met secretly on the government’s claim that in 1924 Al Capone had a tax liability of $32,488.81. The jury returned an indictment against Capone that was kept secret until the investigation was complete for the years 1925 to 1929. On June 5, 1931, the grand jury met again and returned an indictment against Capone with twenty-two counts of tax evasion totaling over $200,000. A week later, a third indictment was returned on the evidence provided by Ness and his team. Capone and sixty-eight members of his gang were charged with 5,000 separate violations of the Volstead Act. The income tax cases suddenly took precedence over the Prohibition violations. [53] 

Capone was facing a possible 34 years in jail if the government completely won its case. On October 17, 1931, after nine hours of discussion, the jury completed its deliberation and found Capone guilty of some counts, but not all counts of tax evasion. The following Saturday Judge Wilkerson sentenced Capone to eleven years, $50,000 in fines and court costs of another $30,000. Bail was denied and Capone would be led to the Cook County Jail to await eventual removal to a federal penitentiary. [54] 

The New York Times reported:

Capone tried to smile but the smile was bitter. He licked his fat lips. He jiggled on his feet. His tongue moved in his cheeks. He was trying to be nonchalant, but he looked as if he must have felt –ready to give way to an outburst of anger. It was a smashing blow to the massive gang chief. His clumsy fingers, tightly locked behind his back, twitched and twisted. [55] 

Capone then continued by looking at Ness:

Well, I’m on my way to do eleven years. I’ve got to do it, that’s all. I’m not sore at anybody. Some people are lucky. I wasn’t. There was too much overhead in my business anyhow, paying off all the time and replacing trucks and breweries. They ought to make it legitimate. [56] 

Initially, Al was a prisoner at the U.S. Penitentiary in Atlanta and quickly became its most famous prisoner. There were charges almost immediately that he was living “like a king.” His cell was lavished with decorative décor and he had more socks, underwear and sets of sheets than the other prisoners. He maintained these extravagances by virtue of a hollow handle in his tennis racket in which he secreted several thousand dollars in cash. In 1934, Attorney General Homer Cummings took over the prison on Alcatraz Island to warehouse dangerous and intractable criminals. In a radio address, Cummings explained that “here may be isolated the criminals of the vicious and irredeemable type so that their evil influence may not be extended to other prisoners.” [57] 

In August of 1934, Capone was sent to Alcatraz. His days of living like a king in prison were gone. Capone would run nothing on or from Alcatraz; he wouldn’t even know what was happening outside. There would be no smuggled letters or messages; all incoming letters were censored then retyped by guards with prohibited subjects omitted, which included the faintest whiff of business or the doings of former associates. Censors excised the mention of current events; no newspapers were allowed; magazines had to be more than seven months old. At best, prisoners could write one letter a week, rigorously censored, and only to their immediate family members. Family members had to write the warden for permission to visit. They made no physical contact; they sat on opposite sides of a plate of glass. [58] 

Capone had contracted syphilis as a very young man through his sexual liaisons with prostitutes. He was advancing into the tertiary stage called neurosyphilis. At that time the antibiotic Penicillin was available, but it was not scientifically recognized to be successful in treating syphilis. By 1938 he was confused and disoriented. Al spent the last year of his sentence, which had been reduced to six years and five months for a combination of good behavior and work credits, in the hospital section being treated for his medical condition. He was eventually released in November of 1939. For his remaining years, Al slowly deteriorated in the quiet splendor of his Palm Island palace. On January 25, 1947 he died of cardiac arrest at age 48 with his grieving family surrounding him. [59] 

In his short forty-eight years, Capone had left his mark on the rackets and on Chicago. More than anyone else, he had demonstrated the folly of Prohibition; in the process he also made a fortune. Beyond that, he captured and held the imagination of the American public as few public figures ever do. Capone’s fame should have been fleeting, a passing sensation, but instead it lodged permanently in the consciousness of Americans. On December 5, 1933, the ratification of the Twenty-first Amendment to the constitution repealed the Eighteenth Amendment which enforced Prohibition. Some believe Capone would have been an average noble citizen, potentially a bar owner, if the Prohibition had never been enacted. His life story continues to intrigue and fascinate many even till this very day.