In New York, it’s well known that there are Five Families behind the majority of organized crime. In Chicago, there is only one. The Outfit.
An organization that emerged thanks to the cooperation of several separate groups running the ‘Black Hand’ extortion scheme, they went on to become one of the most feared groups of Casino Mobsters in history.


At the start of the 1900s, Italian immigrants arrived en masse in Chicago. With no jobs, they needed a way to make money. They brought with them the “Black Hand” scheme – a mode of extortion practiced extensively in Italy. Residents would be threatened, and unless they paid up, they’d be beaten. The threatening letters received were signed using an inky black hand.

Many of these ‘Black Hands’ groups were independent – but over time, various organisations joined forces – and when they came together, they also started to run, and control, other illicit and illegal activities.

Giacomo “Big Jim” Colosimo was a brothel keeper who had managed to win the respect, and the fear, of the Chicago underworld. His organization was the very beginning of the Chicago Outfit – but as is often the case in this game, it wasn’t long before he was ousted, and someone else was sitting in his seat.

When Prohibition came into force in 1919, Big Jim’s nephew Giovanni “Papa Johnny” Torrio tried to persuade him that the liquor business was where the money was – but Big Jim could not be convinced. Torrio had a simple solution for this problem – he had his uncle killed.


The Outfit’s entry into the beer market marked the start of one of the bloodiest episodes in mob history. They already controlled the city’s South Side, but they had their eyes on the Gold Cost – and that was ruled by the North Side Gang. In 1924, they gunned down the leader of the North Side Gang in his own flower shop. There was – of course – retaliation. Attempts to return the favour and take down Torrio failed, but those attempts also shook him. He decided to retire – and handed control to a man who has since become one of the most notorious mobsters in history. Al Capone.

Under Capone, the Outfit’s fortunes soared – but the war raged on. In 1929, Capone came up with a plan he thought would cripple the North Siders On the 14th February he sent his men to gun down seven key North Siders in a garage they owned.

Known as the “St Valentine’s Day Massacre”, the attack got so much press that the city had no option but to announce a crackdown on organised crime. Capone was jailed in 1932. Not for murder, but for tax evasion – the only charge anyone could make stick – he was sent to prison.


In 1933, Prohibition ended – and The Outfit had no choice but to turn their attention to other enterprises. Racketeering, Prostitution, and most notably – gambling.

Under the leadership of Frank “The Enforcer” Nitti and his deputy Paul “The Waiter” Ricca, the organization moved into LA, Missouri, Wisconsin and Vegas. In Vegas they took casinos by force from New York’s five families – and siphoned off the majority of the profits, sending the cash back to Chicago.

Even with law enforcement constantly on their back, a string of indictments and a number of high profile deaths didn’t affect the organization itself – no sooner was one leader gone, had another emerged to take his place.


During the 60s and 70s The Outfit controlled almost all of the illegal activity in the West of the US – and had worrying ties with law enforcement agents and government officials at all levels. One lieutenant (Sam ‘Momo’ Giancana) reportedly tried to arrange Fidel Castro’s assassination at the request of the CIA, as well as at one time seeing a woman that President Kennedy was sleeping with – such was the extent of their integration into the corridors of power.

It was during the mid 80s that The Outfit’s power began to wane – with Las Vegas going legit, Labor Unions purging the gangsters from their ranks, and several federal trials successfully sending huge numbers of mobsters to prison.

In 2007, things got even worse, thanks to an FBI operation nicknamed ‘Family Secrets’. The bureau had managed to turn several “made men” against the Outfit. Their testimony led to the indictment and imprisonment of 14 of The Outfits most powerful figures – including the leader of the day, James “Little Jimmy” Marcello.

The Outfit have been much quieter recently on the national and international front – but rest assured, they’re still running the show back in Chicago. Given their historic tenacity – they probably always will be.

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