James Patrick O'Leary

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This article is about the gambler. For the politican, see James A. O'Leary.

James Patrick O'Leary (1869 in Chicago, Illinois - January 23, 1925 in Chicago) was a gambling boss and saloon owner in Chicago. His parents were Patrick and Catherine O'Leary, in whose barn the Great Chicago Fire began.

O'Leary was born at 137 DeKoven Street, the house in which his parents lived and which would see the start of the Chicago Fire two years later. He had a sister, who married James Ledwell.

O'Leary began working for local bookies as a teenager eventually opening Long Beach, Indiana, an off-track betting resort, however it soon closed due to bankruptcy by the 1880s. As a young man, O'Leary worked at the Union Stock Yards, where he acquired the nickname "Big Jim." By the early 1890s, however, he had left the Stock Yards to open a saloon on Halsted 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, near the entrance to the Stock Yards. He also started operating a pool hall and book parlor from the back of the saloon. One of the leading gambler barons in Chicago, O'Leary was known for taking bets on everything from presidential candidates to the weather.[1]

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 Cassius 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 Cafe under arrangement with 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.

Despite numerous raids by police, he was only found guilty of gambling once during his thirty year career. There was a perception that O'Leary, along with gambling bosses Mont Tennes and "Hot Stove" Jimmy Quinn, controlled the Chicago Police.[2]

O'Leary married Annie McLaughlin, whose family lived in the cottage next to the O'Leary's at the time of the fire.[3] The couple had five children, two sons and three daughters.[1]

[edit] References

  1. ^ a b Kelley, John (1925-01-24), “O'Leary, Who Would Bet on Anything, Dies”, Chicago Tribune 
  2. ^ Merriner, James L. (2004). Grafters and Goo Goos: Corruption and Reform in Chicago, 1833-2003. Carbondale, IL: Southern Illinois University Press, 84. ISBN 0809325713. 
  3. ^ “Centennial Eve Reveals Truth of Great Fire”, Chicago Tribune, 1903-09-23 

[edit] Further reading

  • 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 January 1925
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