James Patrick O'Leary

From Wikipedia, the free encyclopedia
Jump to: navigation, search
This article is about the gambler. For the politician, see James A. O'Leary.
James O'Leary
Born 1869
Chicago, Illinois
Died January 23, 1925(1925-01-23) (aged 56)
Chicago, Illinois
Other names "Big Jim"
Occupation Gambling czar, amusement park manager
Criminal status Deceased
Spouse(s) Annie McLaughlin
Children 2 sons, 3 daughters
Parents Patrick and Catherine O'Leary

James Patrick O'Leary (1869 - January 23, 1925) was a gambling boss and saloon owner in Chicago. His parents were Patrick and Catherine O'Leary, in whose barn the Great Chicago Fire is alleged to have begun.[1]


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, Kathleen O'Leary, 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.[2]

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 repeated 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; in the summer of 1907, Luna Park, opened with O'Leary as its primary owner. The popular park was in operation for four years before its gates were permanently closed.[3]

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.[4]

O'Leary married Annie McLaughlin, whose family lived in the cottage next to the O'Learys at the time of the fire.[5] The couple had five children, two sons and three daughters.[2]

He died on January 23, 1925 in Chicago, Illinois.[2]


  1. ^ Pierce, Bessie Louise (1957, rep. 2007). A History of Chicago: Volume III: The Rise of a Modern City, 1871-1893. Chicago: University of Chicago Press. p. 4. ISBN 978-0-226-66842-0.  Check date values in: |date= (help)
  2. ^ a b c Kelley, John (January 23, 1925). "O'Leary, Who Would Bet on Anything, Dies". Chicago Tribune. 'Big Jim' O'Leary, as he was known to thousands of followers of the turf, died early last evening at his residence...his death was unexpected. 
  3. ^ Duis, Perry (1998). Challenging Chicago: Coping with Everyday Life, 1837-1920. Champaign, IL: University of Illinois Press. ISBN 0-252-02394-3. 
  4. ^ Merriner, James L. (2004). Grafters and Goo Goos: Corruption and Reform in Chicago, 1833-2003. Carbondale, IL: Southern Illinois University Press. p. 84. ISBN 0-8093-2571-3. 
  5. ^ "Centennial Eve Reveals Truth of Great Fire". Chicago Tribune. 1903-09-23. 

Further reading[edit]

  • 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

External links[edit]