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Big Jim Colosimo with his wife, Dale Winter, date unknown.

Zelig Harry Lefkowitz, aka ‘Big Jack’ Zelig, was born in New York City (May 13, 1888 – October 5, 1912). He began his life of crime as a pickpocket at the age of 6. Eventually he joined the Eastman Gang and lent out his talent for violence for a fee.

His rate were quite competitive and were as follows:

• Slash on the cheek with a knife: $1 to $10
• Shot in the leg: $1 to $25
• Shot in the arm: $5 to $25
• Bombing: $5 to $50
• Murder: $10 to $100

(Source: thisblogofours, via )

Giacomo ‘Big Jim’ Colosimo  (February 16, 1878 – May 11, 1920) was an early American Mafia boss who created the Chicago Outfit and led it from 1902 to his death in 1920.  Immigrating from Italy in 1895, he gained power through petty crime and the heading of a chain of brothels. 

Beginning as a small time hood, Colosimo was noticed by First Ward aldermen Michael “Hinky Dink” Kenna and John Coughlin. He worked for them first as a precinct captain and later as their bagman. This provided Colosimo with the political connections that aided him in his rise to power 

Colosimo would later earn another nickname, ‘Diamond Jim’, a name he earned due to his frequent habit of dressing in a white suit with diamond rings, pins and other jewelry. This veneer of success together with his charm and money helped establish a good relationship with many women. He soon entered the world of prostitution and in 1902 he married Victoria Moresco, an established Chicago madame and the two opened a second brothel. Within a few years Colosimo expanded his business to nearly 200 brothels and had made inroads into gambling and racketeering.

By 1909, Colosimo was being seriously threatened by the Black Hand gang in Chicago and he realized he needed help. He brought John ‘The Fox’ Torrio to Chicago from Brooklyn and made him his second in command. Torrio brought with him Al Capone to help out and serve as a bartender and bouncer.

When prohibition went into effect in 1920, Torrio pushed for the gang to enter into bootlegging, but Colosimo refused. In May 1920, Colosimo went out of town to marry his second wife, Dale Winter (he had deserted his wife). After Colosimo returned to Chicago returned to Chicago a week later, Torrio called him and let him know about about a shipment arriving at his cafe. When Colosimo appeared at the cafe to wait for its delivery, he was shot and killed. 

- A coroner demonstrating how Colosimo might have been killed

The initial murder suspect was his new wife Dale, but no one was ever arrested for the murder. It was widely believed that Torrio ordered the killing so that the gang could enter into the lucrative bootlegging business. Torrio reportedly brought in New York associate, Frankie Yale, to murder Colosimo. Al Capone has also been suspected as Colosimo’s assassin.

David Pietrusza