This Old Canaryville Irish Saloon Has Connections to Two Chicago Fires, Chicago Mobsters

A former Canaryville Irish saloon on South Halsted Street, pictured in the Chicago History Museum image above, is jam-packed with connections that reflect several significant moments in Chicago’s history.

James Patrick “Big Jim” O’Leary opened the large saloon and gambling house in the 1890s, which was then located near the old Union Stockyards. Big Jim was the son of Irish immigrants Catherine and Patrick O’Leary – yes, that Catherine O’Leary. She was accused of starting the Great Chicago Fire of 1871. The legend goes that she was milking a cow who knocked over a lantern that started the conflagration, but that story has since been disregarded as a myth based in anti-immigrant prejudice. Big Jim was about two years old at the time of the fire, and he later worked in the Union Stockyards as an adult before opening the saloon. 

The saloon at 4183 S. Halsted St. was “palatial” and a “gambling resort,” says his 1925 Chicago Tribune obituary. Big Jim earned a fortune off of his gambling ventures, and the headline on the Tribune story refers to him as a man “who would bet on anything.” He mostly managed to avoid legal trouble – though the gambling room in the back of his saloon was raided once. Big Jim had connections to some big names in the Chicago gangster scene. According to an article from the Digital Research Library of Illinois History, Big Jim delivered whiskey to Colosimo’s Cafe for Johnny Torrio – an early leader of what would later be known as the Chicago Outfit and mentor to Al Capone. Although O’Leary was never charged, he was also suspected of involvement in the murder of James Colosimo (who was also known as "Big Jim"). In the Tribune obituary, Michael Kenna, an alderman with mob ties, praised O’Leary as a “square shooter…who never welched on a bet. He was a good loser and his patrons had confidence in him that he would always pay if he lost. His home life was ideal.” 

Big Jim died at the age of 56. In 1934, the building that housed the old saloon burned down in a massive fire that began in the Union Stockyards and burned through eight city blocks.