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Big Jim O'Leary, Sporting Gent

One of Chicago's leading gambling house proprietors around the turn of the 20th Century was Big Jim O'Leary (who, incidentally, was also the son of "Mrs. O'Leary," she of Chicago Fire infamy). His resort was renowned for its lavish and sumptuous furnishings, first-rate accomodations and, apparently, for its fortress-like construction. From Herbert Asbury's The Gangs of Chicago: An Informal History of Chicago's Underworld:

   In 1911, when he (O'Leary) talked of retiring and tried to sell his Halsted Street (gambling) house to Cook County for an emergency hospital, O'Leary told a newspaper reporter that he had never paid a dollar for protection. "I could have had all kinds of it," he said, "but let me tell you something. Protection that you purchase ain't worth nothing to you. A man who will sell himself ain't worth an honest man's dime. The police is for sale, but I don't want none of them."
   Big Jim always boasted that his resort, with its massive iron-bound oaken door, steel plates in the outer walls, and inner walls of heavy oak covered with zinc, was "fire-proof, bomb-proof and police-proof." It did resist several attempts to burn it, and bombs planted near it during the gamblers' war of 1907 caused no damage, but the police frequently managed to gain an entrance by battering down the outer doors with axes and sledgehammers. Occasionally they arrested some of O'Leary's customers and bookmakers, but usually Big Jim was ready for them. Once when a detachment of policemen swarmed into the house they found the poolroom bare of all furniture except a plain kitchen table, at which sat an old man devoutly reading a prayer-book.
   On another occasion O'Leary loaded his inner walls with red pepper, and when the police struck their axes into the zinc they were so blinded that for most of them hospital treatment was necessary. The eyes of three were so inflamed that they were off duty for a week.

Though he was a generally deplorable character, you still have to admire his brazenness and his ingenuity.

November 14, 2005 in Books, Chicago Observations | Permalink

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