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Thursday, Mar 12, 2026 – Posted by Isabel Miller

* The Beverly Review’s South Side Irish Parade Guide profiles Sen. Bill Cunningham’s great-grandfather…

One of essentially the most fascinating, colourful and essential early Irish-American Catholics who moved to the Ridge was James Dominic “Yank” Cunningham, who began the industrial district alongside 111th Street in Mt. Greenwood. […]

“The place my great-grandfather opened, like a lot of pubs of that time, was a social and cultural center for immigrants,” stated Bill. “In the 1890 census of Chicago, 80 percent of the population of the city was immigrants or the children of immigrants. They went to the local pub to find a job or find a room to live in, to get their local news and share stories. They built up life around a tavern.”

Yank Cunningham developed a friendship and dealing relationship with James “Big Jim” O’Leary, the son of Catherine and Patrick O’Leary, in whose barn the Great Chicago Fire of 1871 is claimed to have began.

Big Jim O’Leary, born in 1863, was referred to as “the king of gamblers” in Chicago, the “man who would bet on anything.” He was identified for being very sincere, and his patrons had confidence that he would all the time pay up if he misplaced. His involvement in a playing operation was an indication that it will be run pretty and truthfully—even when it was unlawful. […]

“I like to think that my great-grandfather and grandfather would have gotten a real kick out of the idea that one day one of their descendants would hold public office,” stated Bill Cunningham, “because when they first got out here to the Ridge, they weren’t very welcomed by the people who held public office.”

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