The Chicago Fire's Other O'Leary
On the evening of October 8, 1871 a fire broke out in the back shed of Catherine and Patrick
O'Leary's property at 137 W. DeKoven Street. As the fire spread it almost burned down the entire city, and Mrs. O'Leary and a cow were forever joined together. It seems appropriate then that the Chicago Fire Department Training Academy stands on the site where the Great Conflagration began.
2009 /Images & Artwork: designslinger]
James Patrick O'Leary was 2 years old when the fire occurred. "Big Jim" grew up and
became one of Chicago's more prominent saloon keepers, bookies, and gambling house owners. He has been called the city's first gangster. By the time he built this house in 1901, on Garfield Boulevard at Halsted Street, Catherine O'Leary's son was a millionaire. Officially, and for the record, he gathered all that money through the legal ownership of a commission brokerage business.
The architect of O'Leary's 33-room manse, Zachary Taylor Davis, also designed
Chicago's original Comiskey Park, home of the White Sox and Wrigley Field, home of the Cubs.
Catherine O'Leary died in 1895 in her Halsted Street home, located just around the corner
from the future site of her son's mansion. She was hounded by the press until the very end. James fathered 7 children, accumulated even more money, and died a wealthy man in 1925. Although the infamous O'Leary cottage is long gone, (it actually survived the Great Fire unscathed, but was torn down and replaced with a stone and brick row house a few years later) James lives on in the J O and L monogram inscribed on an oval medallion on the building's front porch.
Posted by designslinger at 10/8/2009 2:06 AM 
Categories: Architecture,History
Tags: Catherine O'Leary gambling gangsters James O'Leary Chicago mansions
Categories: Architecture,History
Tags: Catherine O'Leary gambling gangsters James O'Leary Chicago mansions
Wow, this building brings back memories. I love the structure and the history behind it.
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It's quite a story.
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