Al Capone was a stone cold killer – but he wore a pink apron to welcome reporters to lunch

On a freezing January afternoon in 1927, a group of journalists gathered outside a respectable looking house on Prairie Avenue in downtown Chicago and, presumably with some trepidation, knocked on the door. The premises were home to a certain Al “Scarface” Capone who, at just 29, sat at the head of the Southside Outfit, the most ruthless and powerful organised crime gang in Prohibition America. Capone’s enemies had the unfortunate habit of ending up in the hospital, the morgue, or at the bottom of Lake Michigan. To get on the wrong side of him was very foolish indeed. But Capone could also defy expectations, as I discovered while researching my new book, Notorious: History’s Villains and Why They Matter.

And as the journalists stood, stamping their feet in the winter chill, they were stunned when he appeared in front of them dressed in slippers and a pink apron, clutching a wooden spoon. Having invited them in, they were led to a dining room where, over a slap-up meal of fine wines and pasta, cooked by Capone himself, the mob boss held court.

Capone loved to share his opinions on subjects as diverse as baseball, opera, the plight of the poor and the role of “proper history” in public schools. Sounding every inch the populist politician, he declared that he was no villain but a regular guy who gave the public what they wanted in the face of a bad law.

Most of all, he stressed that he did not have time for violence, for the simple reason it was bad for business. By the time the journalists stumbled out into the street several hours later, Scarface had been transformed Cinderella-like into a witty and urbane latter-day Robin Hood. In later life, Capone would regret having courted the press and thus made the fatal error of drawing attention to himself, but from that bizarre press conference in January 1927, he became easily the most famous gangster in the world.

It had all begun very differently. Alphonse Capone was born in Brooklyn on January 17, 1899. The fourth of nine siblings, his parents were Italian immigrants who had sailed to the US, like so many others, in search of a better life. Back home in Salerno, his father, Gabriele, had been a pasta maker but, with a growing family to support, he was obliged to work on construction sites in New York before retraining to become a barber.

Italian migrants experienced significant prejudice in turn-of-the century America and were discriminated against at every level. Opportunities for social mobility were few and the American Dream was about as far out of reach as it was possible to imagine. So while Capone’s parents grafted and prayed and hoped for something better, the odds were stacked against them.

With the exception of his eldest brother Vincenzo, who became a policeman, Capone’s siblings all drifted into crime. Determined to keep their fourth son out of trouble, Gabriele sought to set the teenager up in a shoe-shining business. But the plan backfired when the young lad discovered that there was more money to be made in “protection” than in polishing the footwear of wealthy passers-by.

Soon, he had come onto the radar of Johnny Torrio, an established Brooklyn “godfather” who took a “business-like” approach to crime which greatly influenced his young protegé. Following a brief spell as a bouncer in a Coney Island nightclub where, in a fight with a patron, he received the scars to his face that gave him his hated nickname, Capone tried to go straight. Taking work as a box cutter, working in a packaging warehouse, he met and married a respectable Irish girl called Mae and their only child, Sonny, was born in 1918. But Al’s stab at legitimacy did not last.Soon, he was back in Torrio’s circle.

In January 1920, the United States introduced the Volstead Act which made it illegal to manufacture and sell alcohol in the country. Torrio immediately grasped that Chicago was the perfect place to set up a bootlegging business and invited Capone to come to the city and work for him. Al quickly rose to the top of the Outfit and, when Torrio retired from the operation, following a failed assassination attempt by a rival gang in 1925, he became “Chairman of the Board”.

Being a gangster boss in 1920s Chicago certainly had its hazards. As rival gangs fought a decade-long battle for control of the city’s illicit but lucrative liquor trade, at least 700 people were murdered – most of them in the pay of the gangster bosses. As the head of the Outfit, Capone ordered the execution of scores of rivals and, in doing so, became a target himself.

In one incident, a fleet of cars pulled up outside a restaurant on West 22nd Street where he was eating lunch and emptied 1,000 rounds into the premises. Capone only survived because his bodyguard, Frank Rio, threw him to the ground. On another occasion, rival mobster Joe Aiello put a $50,000 bounty on Capone’s head after the hitmen he had sent to kill him all unexpectedly wound up in the morgue.

By 1928, Capone was, as one contemporary put it, “the most shot-at man in America”. To protect himself, he installed solid steel shutters on the windows of his suite of hotel and was driven about in a customised armoured Cadillac which had 25mm-thick bullet-proof windows. The glass was so heavy, the windows needed a special winching system to be wound up and down.

Undoubtedly his life of crime brought many fringe benefits too, and by the time of his 30th birthday, Capone’s enterprise was turning over an estimated $100million a year (equivalent to $1.3billion 2025). Capone’s payroll was extensive, and he boasted that at least $30million of it was spent on bribing police officers and city officials. Even the city’s mayor, Big Bill Thompson, was in his pocket, and as he and everyone else turned a blind eye to his criminal activities, the good times continued to roll.

Capone’s enormous wealth bought him the finest clothes, diamond jewellery, the company of famous jazz musicians and luxury homes, but it bought him something else as well – the American Dream which had been so out of reach to his parents. He had risen from nothing to become a somebody – and with it came power and respect. Capone was a family man, too. He doted on his wife and child and provided the very best education money could buy for his younger siblings and various nieces and nephews. He never forgot where he came from and gave back to the community.

Noted for his generosity, he would tip well over the odds and was a veritable Santa Claus where the poor and dispossessed of Chicago were concerned. Following the Wall Street Crash in 1929, he set up three soup kitchens and a stall which dispensed free coffee and doughnuts to the jobless. On Thanksgiving, he distributed free turkeys for families who could not afford their dinner. He was also very much aware of the hypocrisy at play, telling journalists: “Crooked bankers who take people’s hard-earned cash for stock they know are worthless would be far better clients at penal institutions than the little man who robs so that his wife and babies may live.”

But as the violence escalated and Capone grew ever more brazen, Chicago’s dwindling band of respectable citizens decided that enough was enough and formed a consortium made up of local businessmen and “untouchable” federal agents including, most famously, the PR-savvy Eliot Ness.

All of them were determined to take Capone down. However, despite what you may have gathered from hit movies like 1987’s The Untouchables, starring Kevin Costner as Ness and Robert De Niro as Capone, it was in fact a woman – Mabel Walker Willebrandt, then serving as Assistant Attorney General – who had the bright idea of pursuing Capone for unpaid federal taxes.

Following the Saint Valentine’s Day Massacre in February 1929, when six members of the rival North Side gang were murdered in cold blood – most probably on Capone’s orders – the net began to tighten. Convicted of tax evasion in 1931, he was sent to prison for an 11-year stretch in 1933. Once incarcerated, it was discovered that he was suffering from syphilis and his health declined rapidly.

In August 1934, Franklin D Roosevelt’s new administration declared war on organised crime and to that end, announced that a new prison facility, for the nation’s most dangerous criminals, would be opened at Alcatraz off the coast of San Francisco. Though Capone had been a model inmate at previous penitentiaries, he was sent there as inmate number 85. Despite the rigours of the harsh regime and attempts on his life by fellow inmates, he made the best of it.

He read the self-help book Life Begins at Forty, taught himself the banjo and even became a member of the prison band The Rock Islanders, who gave concerts to fellow inmates. However, Capone’s mental faculties were rapidly declining and, upon his release in November 1939, he was judged to have a mental age of 12. Having retired to Florida, he lived out his days fishing and died aged just 48 on January 25, 1947, while his doting wife and a nurse tended to him.

Al Capone was a complex figure. Loved by many, feared by others and hated by those whose lives he destroyed, he was certainly no hero, but nor was he a comic book villain.

A complex product of his environment and times, he still shapes the cultural landscape today. But more than anything else, he reminds us that there has always been a dark side to the American Dream – and that those who court the press can very often fall victim to it, too.

• Notorious: History’s Villains and Why They Matter, by Otto English (Welbeck,£20) is out now