Today’s fun read
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 the most interesting, colorful and important early Irish-American Catholics who moved to the Ridge was James Dominic “Yank” Cunningham, who started the commercial district along 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,” said 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 working 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 said to have started.
Big Jim O’Leary, born in 1863, was called “the king of gamblers” in Chicago, the “man who would bet on anything.” He was known for being very honest, and his patrons had confidence that he would always pay up if he lost. His involvement in a gambling operation was a sign that it would be run fairly and honestly—even if it was illegal. […]
“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,” said Bill Cunningham, “because when they first got out here to the Ridge, they weren’t very welcomed by the people who held public office.”
Go read the rest.
- Amalia - Thursday, Mar 12, 26 @ 2:29 pm:
there was a place at 111th just west of Western, Red’s. Family that owned it, Cunningham. Part of the family? total high school hangout.