Bugs Moran: The Notorious Life and Legacy of the Chicago Gangster Who Became Al Capone’s Biggest Rival

`Sprightly swing music spills across the dimly lit club. The grayish curtains of cigarette smoke part every once in a while to reveal a sparkling stage and tables upon tables of patrons, some incurably inebriated and others high on the fast-paced nightlife. Fabulous flappers in shimmery cocktail dresses and stylish feather headbands throw their hands up and stomp their feet to the addictive beat on the dance floor. Smartly dressed men, their hair neatly parted and slicked back, toss fistfuls of dice onto the plush green baize of the craps tables. Some hover over roulette wheels, staring intently at the spinning flashes of silver, while others finger their playing cards as they sip on tumblers of whiskey, eyeing both the river and the tower of tokens next to them.

Frisky tunes, chic fashion, and American gambling are nostalgic, rose-tinted images most choose to project when visualizing the Roaring Twenties, but the other side of the coin brought an uninviting, much harsher reality that most would prefer to sweep under the rug. The first real estate bubble was on the brink of bursting, and progress was evident, but painfully slow, which gave way to yet another era of violent riots, lynchings, and other forms of oppression imposed on minorities.

Then, of course, there were mobsters. Remove the silk three-piece suits, burnished Tommy guns, and obscene stacks of cash from the equation, and one would be left with limp, bullet-ridden bodies either slumped over their steering wheels or sprawled out like broken rag dolls on the floors of public establishments, the walls painted with blood spatters and shattered glass littered about. These, they say, are the lucky ones, for their corpses, though laid out as a public message, provide the deceased's loved ones with some form of closure. Over the decades, dozens involved in this deadly game disappeared altogether, never again to see the light of day.

One of the most infamous of the gangsters during this era was George “Bugs” Moran, who bore all the qualities of a stereotypical 20th century mobster. They didn’t call him “Bugs” for nothing, as the man was a vindictive, ticking time bomb who unleashed hell upon anyone who dared cross him. One of the most prolific career criminals of his time, he was convicted and incarcerated at least three times before his 21st birthday. George was a seasoned gunman (so much so that he was eventually crowned the “father of drive-by shootings”), an expert rum-runner, and the fearsome head of one of the most prominent gangs in all of Chicago.

It was these activities and his gang’s most prominent rivalry that have ensured Bugs Moran remains a household name today. On February 14, 1929, members of his North Side Gang arrived at a warehouse on North Clark Street in Chicago, only to be approached by several police officers. The officers then marched them outside up against a wall, pulled out submachine guns and shotguns, and gunned them all down on the spot. A famous legend is that one of the shot men, Frank Gusenberg, dying from 14 gunshot wounds, told police that nobody shot him. Though Gusenberg’s statement is probably apocryphal, nobody opened their mouths.

Nobody was ever convicted for the “Saint Valentine’s Day Massacre,” the most infamous gangland hit in American history, but it’s an open secret that it was the work of America’s most famous gangster, Al Capone. Indeed, “Scarface” has captured the nation’s popular imagination since Prohibition, managing to be the most notorious gangster in America while living a very visible and high-profile life in Chicago. Bugs and Scarface had hated each other for over a decade, and, though he narrowly avoided it, Bugs was supposed to be the main target.