Sign up for email updates from The Crime and Investigation Network
I accept the T&Cs
Al Capone
Al Capone

Friday 17 Oct 9.00PM

Discover how the St Valentine's Day Massacre of 1929 saw the bloody deaths of six gangsters and the emergence of Al Capone as the godfather of crime.

The biggest gangster of all, he made many people offers which they couldn't refuse. Illegal booze and other rackets were his stock-in-trade; tax evasion was what nailed him in the end.




Many New York gangsters in the early 20th Century came from impoverished backgrounds, but this was not the case for the legendary Al Capone. Far from being a poor immigrant from Italy who turned to crime to make a living, Capone was from a respectable, professional family. His father, Gabriele, was one of thousands of Italians who arrived in New York in 1894. He was thirty years old, educated and from Naples, where he had earned a living as a barber. Hi wife Teresina (Teresa) was pregnant and already bringing up two sons, two-year-old son Vincenzo and infant son Raffaele. The family moved to a poor Brooklyn tenement where Alphonse Capone was born on January 17, 1899.

The young Capone’s home was far from salubrious. He lived in a squalid tenement, little more than a slum, near the Navy Yard. It was a tough place given over to the vices sought by sailor characters that frequented the surrounding bars.

The family was a regular, law abiding, albeit noisy Italian-American clan and there were few indications that the young Al Capone would venture into a world of crime and become public enemy number one.

Certainly the family’s move to a more ethnically mixed area of the city exposed the young Capone to wider cultural influences, no doubt equipping him with the means to run a notorious criminal empire.

It was whilst doing his bar job that Capone received his famous facial scars after gangster Frank Gallucio took exception to a lascivious remark Al made to his sister. Gallucio pulled a knife on the enraged Capone.

But it was Capone’s schooling, both inadequate and brutal at a Catholic institution beset with violence that marred the impressionable young man. Despite having been a promising student, he was expelled at fourteen for hitting a female teacher and never went back.

It was then that Capone met the gangster Johnny Torrio which would prove the greatest influence on the would-be gangland boss. Torrio taught Capone the importance of maintaining a respectable front, while running a racketeering business. The slightly built Torrio represented a new dawn in criminal enterprise, transforming a violently crude culture into a corporate empire. But when he left for Chicago it was a criminal of a completely different breed who would first employ Capone as an eighteen-year-old bartender and bouncer.
>>>
Frankie Yale was originally from Calabria. He built his turf not through astute diplomacy like the ‘gentleman’ Torrio, but on sheer brutality. Yale opened up a bar, the Harvard Inn, on Coney Island and gave the softly spoken Capone his first job and introduced him to violent crime.

Later, Al was forced to apologise to the aggrieved man. The incident was to teach him not only to restrain his temper but also, as boss Yale impressed upon him, how to run a loan sharking, pimping and ‘protection’ business with brutal force.

Despite a brief hiatus when Capone married middle-class Irish girl Mae Coughlin and settled down as a bookkeeper, he was soon to return working for his old boss Johnny Torrio in Chicago. The unexpected death of Capone’s father was a turning point. It is believed that the sudden freedom from parental influence was the reason that he stopped trying to maintain a law abiding, respectable lifestyle.

In 1920 Chicago arrived in Chicago, a corrupt, wealthy city known for its sexual promiscuity and gaming.

When the local big shot "Big Jim" Colosimo was assassinated in his own nightclub, Torrio stepped into his shoes, overseeing the vast empire he had helped to build up. The act of Prohibition simply added to the fortunes gained from whorehouses and gambling dens.

As Capone’s reputation grew he still insisted on being unarmed as a mark of his status. But he never went anywhere without at least two bodyguards. He was even sandwiched between bodyguards when travelling by car. He also preferred to travel under cover of night, risking travel by day only when absolutely necessary.

With his business acumen, Al became Torrio's partner and took over as manager of the Four Deuces - Torrio's headquarters in Chicago’s Levee area. The Four Deuces served as a speakeasy, gambling joint and whorehouse under one roof.

A crackdown on racketeering in Chicago meant that Capone’s first mobster job was to move operations to Cicero. With the assistance of his brothers Frank (Salvatore) and Ralph, Capone infiltrated the government and police departments. Between them they took leading positions within Cicero city government in addition to running brothels, gambling clubs and racetracks.

Capone kidnapped opponents’ election workers and threatened voters with violence. He eventually won office in Cicero but not before his brother Frank had been killed in a shoot out with Chicago’s police force.

Capone had prided himself on keeping his temper under wraps but when friend and fellow hood Jack Guzik was assaulted by a small time thug, Capone tracked the assailant down and shot him dead in a bar. Due to lack of witnesses, Capone got away with murder, but the publicity surrounding the case gave him a notoriety that he had never had before.

After the attempted assassination of Capone’s friend and mentor Johnny Torrio the frail man left his legacy of nightclubs, whorehouses, gambling dens, breweries and speakeasies to Capone.

Capone’s new found status saw him moving his headquarters to the luxurious Metropole Hotel as part of his personal crusade to become more visible and court celebrity. This included fraternising with the press and being seen at places like the opera.

Capone was different from many gangsters who avoided publicity. Always smartly dressed, quiet and with political nous, he set out to be viewed as a respectable businessman and pillar of the community.

Capone’s next mission involved bootleg whiskey. With the help of his old friend Frankie Yale in New York, Al set out to smuggle huge quantities into Chicago. The events would lead to what became known as The Adonis Club Massacre where Capone had Yale’s enemies brutally attacked during a Christmas party.

Capone’s bootlegging whiskey trail from Chicago to New York was making him rich, but an incident involving Billy McSwiggin, known as the "hanging prosecutor", was to prove a major setback for the unassailable gangster.
>>>
McSwiggin was mistakenly shot and killed by Capone’s henchmen during a shoot out between rivals outside a bar. Capone was blamed but once again due to lack of evidence he escaped arrest. However, the murder was followed by a big outcry against gangster violence and public sentiment went against Capone.

High profile investigations against Capone failed. The police therefore took their frustrations out by constantly raiding his whorehouses and gambling dens.

Capone went into hiding for three months during the summer. But eventually he took a huge risk and gave himself up to the Chicago police.

It proved to be the right decision as the authorities did not have enough evidence to charge him. Capone was a once again a free man having made a mockery of the police and justice system.

Ironically, Capone took on the role of peacemaker, appealing to the other gangsters to tone down their violence. He even managed to broker an amnesty between rival gangsters and for two months the killing and violence ceased.

But Chicago was firmly in the grip of gangsters and Capone appeared beyond the reach of the law. Somewhat ironically it was the pen pushers from the tax office who were to pose the greatest threat to the gangsters’ bootlegging empires. In May 1927, the Supreme Court ruled that a bootlegger had to pay income tax on his illegal bootlegging business. With such a ruling it wasn’t long before the small Special Intelligence Unit of the IRS under Elmer Irey was able to go after Al Capone.

Capone left for Miami with his wife and children and bought Palm Island estate, a property that he immediately started to renovate expensively. This gave Elmer Irey his chance to document Capone's income and spending.

But Capone was clever. Every transaction he made was on a cash basis. The only exception was the tangible assets of the Palm Island estate, which was evidence of a major source of income.

Meanwhile, internal infighting between rival gangsters escalated into street violence and frequent hijackings of Capone’s whiskey transports became a big problem.
>>>
Another thorn in the side for Capone was Frank Yale. Once a powerful associate, he was now seen as the main instigator of disruptions to Capone’s whisky business. One Sunday afternoon, Yale met his end with the first use of a ‘Tommy gun’ against him.

Capone also had to deal with rival gangster Bug Moran and his North Siders gang.

They had been a threat for years. Moran had even once tried to kill Capone’s colleague and friend Jack McGurn. The decision by Capone and McGurn to avail themselves of Moran was to lead to one of the most infamous gangland massacres in history – The St Valentine’s Day Massacre.

On Thursday, February 14, 1929 at 10.30am Bugs Moran and his gang were lured by a bootlegger into a garage to buy whiskey. McGurn's men would be waiting for them, dressed in stolen police uniforms; the idea being that they would stage a fake raid. McGurn, like Capone, made sure he was far away and checked into a hotel with his girlfriend.

When McGurn’s men thought they saw Bugs Moran, they got into their police uniforms and drove over to the garage in a stolen police car. The bootleggers, caught in the act, lined up against the wall. McGurn’s men took the bootleggers' guns and opened fire with two machine guns. All the men except Frank Gusenberg were killed outright in cold blood.

The plan appeared to go brilliantly except for one major detail; Bugs Moran was not among the dead. Moran had seen the police car and took off, not wanting to be caught up in the raid.

Even though Al Capone was conveniently in Florida, the police and the newspapers knew who had staged the massacre.

The St. Valentine’s Day Massacre became a national media event immortalising Capone as the most ruthless, feared, smartest and elegant of gangland bosses.

Even while powerful forces were amassing against him, Capone indulged in one last bloody act of revenge – the killing of two Sicilian colleagues who he believed had betrayed him. Capone invited his victims to a sumptuous banquet where he brutally pulverised them with a baseball bat. Capone had observed the old tradition of wining and dining traitors before executing them.



Capone’s activities attracted the attention of President Herbert Hoover who in March, 1929, asked Andrew Mellon, his secretary of the Treasury, "Have you got this fellow Capone yet? I want that man in jail."

Mellon set out to get the necessary evidence both to prove income tax evasion and to amass enough evidence to prosecute Capone successfully for Prohibition violations.

Eliot Ness, a dynamic young agent with the US Prohibition Bureau, was charged with gathering the evidence of Prohibition violations. He assembled a team of daring young men and made extensive use of wire tapping technology. While there was doubt that Capone could be successfully prosecuted for Prohibition violations in Chicago, the government was certain it could get Capone on tax evasion.

In May 1929, Capone went to a ‘gangsters’ conference in Atlantic City. Afterwards he saw a movie in Philadelphia. When leaving the cinema he was arrested and imprisoned for carrying a concealed weapon. Capone was soon incarcerated in the Eastern Penitentiary where he stayed until March 16, 1930. He was later released from jail for good behaviour, but was put on the America’s ‘Most Wanted’ list which publicly humiliated the mobster who so desperately wanted to be regarded as a worthy and man of the people.

Elmer Irey undertook a cunning plan to use undercover agents posing as hoods to infiltrate Capone’s organisation. The operation took nerves of steel and despite an informer ending up with a bullet in his head before he could testify, Elmer managed to amass enough evidence through his detectives, posing as gangsters, to try Capone in front of a jury. With two vital bookkeepers Leslie Shumway and Fred Reis, who had once been in Capone’s employment, now safely under police protection it was only a matter of time before Capone’s days as Public Enemy No. 1 were over.

Furthermore, agent Eliot Ness, angered by Capone for the murder of a friend, managed to enrage Capone by exposing Prohibition violations to ruin his bootlegging industry. Millions of dollars of brewing equipment was seized or destroyed, thousands of gallons of beer and alcohol had been dumped and the largest breweries were closed.






Key Dates
17/01/1899 – Al Capone born. New York.

16/01/1920 – The Prohibition Act is implemented in America.

May 1927 - Supreme Court rules that bootleggers pay income tax.

14/02/1929 – St Valentine’s Day Massacre.

16/03/1930 – Capone first incarcerated at the Eastern Penitentiary.

6/10/1931 - Capone is tried in the Federal Court

17/10/1931 – Capone is found guilty of tax evasion and sentenced to 11 years.

25/01/1947 – Al Capone dies

Key Figures
Frank (Salvatore) and Ralph Capone : Al’s brothers. Both men infiltrated the Cicero government and police department.

Johnny Torrio : Chicago mobster and Capone’s mentor.

Frankie Yale: Mobster, gave Capone his first job at the Harvard Inn, Coney Island. Eventually murdered by Capone.

Billy McSwiggin "the hanging prosecutor" mistakenly shot and killed by Capone’s henchmen.

Bugs Moran: Rival mobster to Capone and intended victim during St Valentine’s Day massacre.

Elmer Irey: Officer at Special Intelligence Unit of the IRS. Investigates Capone’s activities.

Eliot Ness: Agent with the U.S. Treasury Department's Prohibition Bureau. Responsible for bringing Capone to book.


On March 13, 1931, 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.

The grand jury later returned an indictment against Capone with twenty-two counts of tax evasion, totalling over $200,000. Capone and 68 members of his gang were charged with 5,000 separate violations of the Volstead Act. These income tax cases took precedence over the Prohibition violations.

Fearing that witnesses would be tampered with, and having doubts that the six-year statute of limitations would be upheld by the Supreme Court, a deal was secretly truck between Capone’s lawyers and government prosecutors. Capone was to plead guilty to a lighter charge and would receive between two and five years. However, when word got out, the press were outraged and campaigned against what they saw as a blatant whitewash.

The over confident Capone, who believed he would receive less than five years in prison suddenly, became less cocky when he realised that his plea bargain was now null and void.

On October 6, 1931, fourteen detectives escorted Capone to the Federal Court Building. He was dressed in a conservative blue serge suit and without his usual pinkie ring and gaudy jewellery. It was inevitable that Capone’s henchmen procured a list of jury members to bribe, but unbeknown to Capone, the authorities had been aware of the plot.

When Judge Wilkinson entered the courtroom he suddenly demanded that the jury be exchanged with another in the same building. Capone and his lawyer were shocked. The fresh jury were even sequestered at night so that the Capone mob couldn't get to them.

During the trial Attorney George E. Q. Johnson made a mockery of Capone’s claim to be a ‘Robin Hood’ type figure and man of the people. He stressed the hypocrisy of man who would spend thousands of dollars on meals and luxuries but give little to the poor and unemployed. How he asked could Capone possess so much property, vehicles and even diamond belt buckles when his defence lawyers profess that their client had no income?
>>>
After nine hours of discussion on October 17th, 1931, the jury found Capone guilty of several counts of tax evasion. Judge Wilkerson sentenced him to eleven years, $50,000 in fines and court costs of another $30,000. Bail was denied.

In August 1934, Capone was moved from a prison in Atlanta to the infamous Alcatraz in San Francisco. His days of privileges in prison were gone and contact with the outside world, even through letters and newspapers was minimal.

Capone’s health was exacerbated by tertiary syphilis and he became confused and disorientated. His sentence was finally reduced to six and a half years for good behaviour.

After release, Capone slowly deteriorated at his Palm Island palace. Mae, his wife stuck by him until January 25, 1947 when he died of cardiac arrest at age 48.

Richard Bevan












The Crime & Investigation Network is a registered trademark of A&E Television Networks | Privacy Policy | Terms & Conditions | Contact Us | Advertise with Us