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Home » Other Mafia Families » The Chicago Outfit – Wiseguys of the Windy City

The Chicago Outfit – Wiseguys of the Windy City

by The Other Guy
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The City of Chicago holds a special place in gangland and always has! The Windy City and the Chicago Outfit has been at the very core of organized crime in this country since the first days of Prohibition. 

Chicago, the town of Cicero, illegal bootleg booze and bathtub gin, Alphonse “Scarface Al” Capone, Frank “The Enforcer” Nitti, George “Bugs” Moran, and the St. Valentine’s Day Massacre are virtually synonymous with the early development of organized crime.

In fact, the very thought of Chicago most often conjures up images of machine-gun-toting gangsters and gangland murders.

The most infamous, of course, was the historic St. Valentine’s Day Massacre when seven of Bugs Moran’s Irish gang got theirs in that damp garage that early morning back in 1929 from Capone’s boys.

It’s just the way it is! The Chicago Outfit was a formidable bunch of racketeers and gangsters. Their iron-clad control over the city of Chicago and its outer territories is legendary.

The Chicago Outfit – Beyond Just Chicago

The Chicago Outfit’s reach extended to California and Hollywood itself, Las Vegas and Reno, Nevada, and its strip of world-famous casinos as well as a near 100 percent “domination” of every labor union that functioned within the Windy City

Not just the locals but right into the highest levels of the internationals themselves.

The City of Chicago
The City of Chicago

Prime examples of this are the Hotel, Restaurant & Bartenders Union, and the Laborers & Hod Carriers Union International, which were based in Chicago giving The Outfit control over those unions.

Chicago is the borgata that allowed all the other borgatas around the country to infiltrate the locals in their respective areas. It is the way of Cosa Nostra – to share the wealth and spread around the influence of each Family in order to strengthen the overall brotherhood.

They also held influence and operated in Arizona, Wisconsin, and other nearby states. Because the Chicago Outfit was the dominant Family in the midwest territories, they more or less held sway over many smaller Families and ran what amounted to a “second” small Commission from the later 1960s forward.

They kept in constant touch and communication with the larger Luciano/Genovese Family in New York City and worked in tandem with the New York Families in setting policy and enforcing the same.

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