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"Big" Jim O'Leary, Chicago's greatest gambler and the man who held that number for many years, was born into the city's most infamous and unfortunate family. It was Mrs. O'Leary's -- his mother's -- cow who started the Great Fire of 1871 -- or so the story goes. Big Jim was only two at the time, but that event set the course for the rest of his life in the underworld.
After the fire, the family was decimated financially and their reputation in the city was shot, so they moved to the South side stockyards district, where Jim grew up on the rough streets, among the slaughterhouses. With his infamous name, legitimate work was hard to find, and a large chip grew on his shoulder as he aged. In his 20s, he opened a saloon on Halsted St. near the stockyards, soon adding a handbook and other gambling enterprises.
With the profits from that enterprise, he opened the city's most palatial gambling mecca at 4183 S. Halsted, which included a billiards room, several bowling alleys, a saloon, a barbershop, and a sauna. The name "O'Leary" in giant electric letters (pictured below), proudly emblazoned the front door as a sign of Big Jim's pride.
Big Jim was "the man who would bet on anything." He had agents working in every downtown hotel, ready to take wagers on every sporting event imaginable. A daily set of odds quotes was distributed to office employees at the nearby stockyards. Ninety years before Intrade made it fashionable, O'Leary offered odds on the 1908 presidential election (4-to-1 on Taft, 5-to-1 on Bryan).
Big Jim's motto was:
There are three classes of people in this world - gamblers, burglars, and beggars. Nearly everybody gambles. Sometimes it's with money, sometimes it's with time, sometimes it's with jobs. Nearly every fellow is willing to take a chance. Other folks are burglars. They make their lives by stealing. The second-story man, the safe cracker, and the dip are not the only burglars. You'll find a lot of others in offices in the loop. A fellow that won't gamble or steal is a beggar.
Whatever that meant, O'Leary became the top gambler in the city, with a reputation for fair dealing. Chicago's longtime alderman-vice lord, Michael Kenna, said of him, "He was a square shooter. Big Jim never welshed on a bet. He was a good loser and his patrons had confidence in him that he would always pay off if he lost. His home life was ideal."
O'Leary's success attracted unwanted attention, both from rival gambling operations and the police. The resort at 4183 S. Halsted was constantly raided by the cops for twenty-five years, beginning in 1899, but Big Jim was always one step ahead, and though indicted four times, he was convicted for gambling only once, at the age of 53, three years before his death, and was fined $100 for the first offense. In 1906, the Mayor briefly revoked O'Leary's saloon license, but before long, O'Leary "sold" his gambling house to an employee, who reapplied for, and was granted, a new license, putting Big Jim back in business for good. Some of O'Leary's success in evading the police was political: his son, James, Jr., married the daughter of the city's top police inspector. Also, police officers, like most other men, enjoyed gambling, and frequently tipped off O'Leary if a raid was planned.
A bigger problem were rival gamblers. During the gambling wars, Big Jim's place was bombed with dynamite in 1907 (possibly as retribution for the bombing two months earlier at Blind John Condon's place), and twice in 1908. Each time, he rebuilt.
Late in life, O'Leary mused to a reporter about his success: "How much have I cleaned up? I'm satisfied with the results. I've got enough to take a trip around the world when I sell my shop. Then I'm going to settle down in some live little town."
Big Jim never got to do that, as he died in 1925. After his death, the O'Leary gambling house continued to be run by a business partner for a few years, until, somewhat ironically, the place burned down in the second-biggest fire in Chicago history, the 1934 Stockyards fire.
The lot stood empty for a decade, then was occupied by the Burlington Diner (pictured below), built inside an old train car, which was decorated inside in the "pop art" style, with every window a different color. The Burlington advertised "The best coffee in town. We never close." But in the early 1970s, with big demographic changes affecting the old "Back of the Yards" neighborhood, the Burlington did close. The site is now again an empty lot, as pictured at the top.