“Big” Jim O’Leary was a gambler & racketeer in early Chicago, he is credited in forming one of the cities first gambling syndicates and for having a rags to riches story.
James O’Leary was born to parents Patrick and Katherine O’Leary. Katherine O’Leary is rumored to be the woman who’s cow started the Great Chicago Fire of 1871. Both Mrs. O’Leary & the cow were exonerated in 1997. After the fire, the O’Leary’s moved to the South Side of Chicago & the Back of the Yards neighborhood.
James O’Leary start working for local bookies as a teenager and eventually opened a bookie office of his own in Long Beach, Indiana, it was an off-track betting establishment but by the 1880’s James had to close the business due to bankruptcy. He then took up employment in the Union Stock Yards where he would be given the name “Big Jim”
O’Leary soon opened a saloon on South Halstead Street which included a Turkish baths, a restaurant, billiard room, and a bowling alley. Big Jim would post detailed race results and other betting information near the entrance to the Union Stock Yards. O’Leary’s would become one of the biggest, if not the biggest gamblers in Chicago, he had a reputation for being fair and honest, according to Michael “Hinky Dink” Kenna a longtime Chicago Alderman, “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.”
By 1904 O’Leary began operating illegal gambling on a boat on Lake Michigan, a steamship named The City of Traverse. But by 1907 this business venture would shut down as O’Leary refused to pay police any bribes to stay in business and his boat would be raided everytime it docked.
Big Jim O’Leary had a simple philosophy in life “There are three kinds 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.”
Big Jim O’Leary died of natural causes in 1925, he had become a millionaire several times over during his lifetime.