Jim O'Leary

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James "Big Jim" O'Leary (c. 1860-January 22, 1925) was an early illegal gambling racketeer in Chicago and formed one of the cities first gambling syndicates.

One of Chicago's early crime figures, James O'Leary was born outside Chicago to Patrick and Katherine O'Leary, the woman who's cow supposedly started the Great Chicago Fire of 1871 [1]. O'Leary began working for local bookies as a teenager eventually opening Long Beach, Ind., an off-track betting resort, however it soon closed due to bankruptcy by the 1880s. O'Leary soon opened another betting parlor on South Halstead Street which he designed to include Turkish baths, a restaurant, billiard room, and a bowling alley, as well as the detailed race track results and other betting information to become one of the countries most prominent resorts by the 1890s.

In 1904, O'Leary began operating illegal gambling on Lake Michigan with the steamship The City of Traverse. However, without police protection, the ship soon went out of business by 1907 due to repreated police raids whenever the ship had docked. O'Leary however, refused to bribe police and instead had his businesses fortified including the construction of an iron and zinc layered oak door to his resort which were supposedly "fire proof, bomb-proof, and police-proof." After Chicago crime lord Michael Cassuis MacDonald's death that same year O'Leary gained exclusive control of gambling operations in Chicago's Southwest Side based in around the Union Stock Yards.

O'Leary, who had been delivering whiskey to Colosimo's restaurant arranged by Johnny Torrio, was suspected of being involved in the murder of James Colosimo on May 11, 1920. Despite his connection, there were no charges brought against him. By the time of his death in 1925, O'Leary had become a millionaire several times over.

[edit] References

Asbury, Herbert. The Gangs of Chicago: An Informal History of the Chicago Underworld. New York: Alfred A. Knoff, 1940. ISBN 1-56025-454-8
English, T.J. Paddy Whacked: The Untold Story of the Irish American Gangster. New York: HarperCollins, 2005. ISBN 0-06-059002-5
Johnson, Curt and R. Craig Sautter. The Wicked City: Chicago from Kenna to Capone. New York: Da Capo Press, 1998. ISBN 0-306-80821-8
"Big Jim" O'Leary Dead". New York Times 23 Jan. 1925