James Patrick O'Leary
Encyclopedia
James Patrick O'Leary was a gambling boss and saloon owner in Chicago. His parents were Patrick and Catherine O'Leary
Catherine O'Leary
Catherine O'Leary was an Irish immigrant living in Chicago, Illinois in the 1870s. She was married to Patrick O'Leary...

, in whose barn the Great Chicago Fire is believed to have begun.

Biography

O'Leary was born at 137 DeKoven Street
DeKoven Street (Chicago)
DeKoven Street is a street in Chicago, Illinois named for John DeKoven, one of the founders of the Northern Trust Company.The Great Chicago Fire started at 137 DeKoven Street, now numbered 558 West DeKoven, in a barn belonging to Patrick and Catherine O'Leary...

, 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
Long Beach, Indiana
Long Beach is a town in Michigan Township, LaPorte County, Indiana, United States. As of the 2010 census, Long Beach population was 1,179. It is included in the Michigan City, Indiana-La Porte, Indiana Metropolitan Statistical Area.-Geography:...

, an off-track betting
Off-track betting
Off-track betting refers to sanctioned gambling on horse racing outside a race track.-US history:...

 resort, however it soon closed due to bankruptcy
Bankruptcy
Bankruptcy is a legal status of an insolvent person or an organisation, that is, one that cannot repay the debts owed to creditors. In most jurisdictions bankruptcy is imposed by a court order, often initiated by the debtor....

 by the 1880s. As a young man, O'Leary worked at the Union Stock Yards
Union Stock Yards
The Union Stock Yard & Transit Co., or The Yards, was the meat packing district in Chicago for over a century starting in 1865. The district was operated by a group of railroad companies that acquired swampland, and turned it to a centralized processing area...

, 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
Halsted Street
Halsted Street is a major north-south street in the American city of Chicago, Illinois.-Location:In Chicago's grid system, Halsted street marks 800 West, one mile west of State Street, from Grace Street in Lakeview south to the city limits at the Little Calumet River in West Pullman...

, which he designed to include Turkish baths, a restaurant, billiard room, and a bowling alley, as well as the detailed race track
Race track
A race track is a purpose-built facility for racing of animals , automobiles, motorcycles or athletes. A race track may also feature grandstands or concourses. Some motorsport tracks are called speedways.A racetrack is a permanent facility or building...

 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.

In 1904, O'Leary began operating illegal gambling on Lake Michigan
Lake Michigan
Lake Michigan is one of the five Great Lakes of North America and the only one located entirely within the United States. It is the second largest of the Great Lakes by volume and the third largest by surface area, after Lake Superior and Lake Huron...

 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
Union Stock Yards
The Union Stock Yard & Transit Co., or The Yards, was the meat packing district in Chicago for over a century starting in 1865. The district was operated by a group of railroad companies that acquired swampland, and turned it to a centralized processing area...

; in the summer of 1907, Luna Park
Luna Park, Chicago
Luna Park was an amusement park that was in operation in Chicago, Illinois, from 1907 to 1911. Located on the plot of a former picnic grove at the corner of 51st and Halsted Streets, it was owned by an investment group led by boxing promoter James "Big Jim" O'Leary...

, opened with O'Leary as its primary owner. The popular park was in operation for four years before its gates were permanently closed.

O'Leary, who had been delivering whiskey to Colosimo's Cafe under arrangement with Johnny Torrio
Johnny Torrio
John "Papa Johnny" Torrio , also known as "The Fox", was an Italian-American mobster who helped build the criminal empire known as the Chicago Outfit in the 1920s that was later inherited by his protege, Al Capone...

, was suspected of being involved in the murder of James Colosimo
James Colosimo
Giacomo Colosimo , better known as Big Jim Colosimo, was an Italian-American Mafia crime boss who built a criminal empire in Chicago based on prostitution, gambling, and racketeering. Immigrating from Italy in 1895, he gained power through petty crime and the heading of a chain of brothels...

 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.

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

He died on January 23, 1925 in Chicago, Illinois.

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

External links

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