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View from the USA: Partners in crime

History and Hollywood have long been fascinated by the world of gangsters, but are we going too far in glamourising their dastardly deeds?

View from the USA: Partners in crime
Aaron Millar. Illustration: Jacqui Oakley

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Al Capone was the ultimate celebrity gangster. People loved him. He opened soup kitchens, homeless shelters, fans gave him standing ovations on the streets. Everyone was bought — the press, the politicians, the police — but everyone was happy. And why not? He was the life and soul of the party; the only man with a bottle in a city desperate for a drink. “When I sell liquor, they call it bootlegging,” he famously said. “When my patrons serve it on silver trays on Lake Shore Drive, they call it hospitality.”

That’s my kind of gangster. If I had a shred of toughness, if I’d been in more than one proper fight my entire life, that’s who I’d want to be when I grow up. 

Why is that? We don’t glamourise Ted Bundy, and kids don’t run around pretending to bury bodies on the moor. Why are gangsters so different? I’ve come to Chicago, the one-time home of the man they call Scarface, to find out. 

First, let’s set the scene: it’s the Prohibition-era 1920s — and the idea has backfired. Instead of sobering the nation up, enforced teetotalism has driven the nation to find their booze from disreputable sources, and a whole generation of gangsters is born. 

I take a crime tour of what was once the most drunken and debauched of all the great Prohibition cities (and I mean that as a compliment), and find out about Vincent ‘The Schemer’ Drucci, who once plotted to steal the Crown Jewels from the Tower of London; George ‘Bugs’ Moran, one of the pioneers of the drive-by shooting and Paul ‘The Waiter’ Ricca — surely the most banal nickname in the history of organised crime. 

Then there’s John Dillinger, part of a gang who robbed banks, murdered 10 people, staged three jail breaks. He bathed his fingers in acid to erase his prints, had plastic surgery in a (failed) bid to evade capture, and ended up lording it in Chicago with stacks of stolen loot. But the good times didn’t last long. Down a dirty alley, by the side of the Biograph Theater, I saw where Dillinger was shot dead by the Feds in full public view. Were the onlookers horrified? No, they ripped the clothes off his corpse as souvenirs and women dipped their handkerchiefs in his blood. To this day, memorials mark the spot where he fell; there’s even a John Dillinger Died For You Society, which meets every year on the anniversary of his death.

If Dillinger was Johnny Depp (2009’s Public Enemies), Capone was Brando: the godfather of godfathers — “a gangster unicorn sprung from a rainbow of bullets,” as my crime guide, John Tampin, describes him. His star shone across the city. I stopped for drinks at The Green Door Tavern — one of the city’s many speakeasies during Capone’s day.

I listen to jazz at the Green Mill Cocktail Lounge, a legendary venue where Capone’s favourite table still stands near the booths on the north wall; and end up in the basement of what’s now Harry Caray’s Italian Steakhouse, where a tunnel once used by Capone’s gang to run liquor through the sewers was recently discovered. 

As I’m about to leave, a photograph on the wall catches my eye: Capone at a ball game. He’s all smiles and charm, but in the stands behind him are five men staring at the photographer with dead eyes filled with violence. It’s a sight that chills me to the bone. 

That’s when it hits me. The gangsters may be glamorous but the violence is real. At the end of the tour, we stop at the scene of the 1929 Saint Valentine’s Day Massacre, Chicago’s bloodiest gangland hit, when Capone’s men lined up seven members of a rival gang against the wall and opened fire with submachine guns. I see the photos: blood, like dark shadows, oozing onto the pavement. 

We caricature gangsters; we give them affectionate epithets, like boxers. But the only difference between gangsters and serial killers is one does it for power and the other does it for pleasure — and power turns us on. Perhaps that’s the real lesson. When we glamourise their violence we’re complicit in it. They may be the killers, but we have one finger on the gun. Guess I’m not growing up to be a gangster, after all.
choosechicago.com  chicagocrimetours.com

Published in the September 2018 issue of National Geographic Traveller (UK)