Mrs. O'Leary heirs hoping family antique grandfather clock can find new home

William Lee, Chicago Tribune on Jul 15, 2025

By clicking submit, I authorize Arcamax and its affiliates to: (1) use, sell, and share my information for marketing purposes, including cross-context behavioral advertising, as described in our Privacy Policy , (2) add to information that I provide with other information like interests inferred from web page views, or data lawfully obtained from data brokers, such as past purchase or location data, or publicly available data, (3) contact me or enable others to contact me by email or other means with offers for different types of goods and services, and (4) retain my information while I am engaging with marketing messages that I receive and for a reasonable amount of time thereafter. I understand I can opt out at any time through an email that I receive, or by clicking here

CHICAGO — The towering grandfather clock in the foyer of Paul and Susan Monreal’s soon-to-be former home is far more than a conversation piece. It is a relic from the grand old age of worker’s saloons and packed gambling houses — and it involves one of Chicago’s most well-known families.

The clock is believed to have once resided in the old South Side mansion built by James “Big Jim” O’Leary, famous gambling boss of the early 20th-century Union Stock Yards area and the son of Catherine O’Leary, the most maligned milkwoman in city history.

Paul Monreal is a fourth-great-grandchild of Catherine and Patrick O’Leary, who endured the enmity of Chicagoans after they were wrongfully accused of starting the Great Chicago Fire, which legend said was started by a jittery dairy cow named Daisy.

Since 1994, the intricately carved, 9-foot-tall behemoth has held court in the entryway of Paul and Susan Monreals’ split-level home in New Lenox, where they raised three children. Now empty nesters, the Monreals are downsizing and won’t be able to bring the antique clock to their new home. They are hoping someone will take it and display it for younger generations.

The clock had long been in the possession of Big Jim’s granddaughter, Geraldine O’Leary Ross, known in the family as “Doll,” at her home in Coloma, Michigan.

“When I was about that big,” Paul Monreal recalled, raising his hand to his belly, “I wasn’t allowed to touch it. I know it came from the (O’Leary) mansion. And then when it came from the mansion, it went to Coloma. Outside of Doll, who had it, she never really talked about it.”

The clock was constructed by the Tobey Furniture Co. of Chicago, a cabinet maker and dealer in fine furniture dating back to 1856. The Monreals note the clock’s wood carvings are similar to those found at the mansion, including faces believed to be Catherine O’Leary. The heirloom isn’t trouble-free, Monreal says, requiring winding every month and oiling its wood once every year.

Paul Monreal’s grandmother, Anna Frances O’Leary Monreal, was Big Jim’s granddaughter. She died tragically along with two of her three young children in a house fire started by a defective stove in south suburban Worth Township in 1943. Her eldest child, Edward Jr., survived and his father remarried. Edward Monreal, who was partially raised by his aunt Doll, shared stories of his lineage, but never spoke of the fire that claimed his own family.

“(Paul’s) dad never talked about (the fire),” said Susan Monreal, who grew up with her husband. While the Monreal’s home is mostly packed up, their living room was covered in O’Leary memorabilia from their branch of the family tree, from a framed piece of ash that was supposed to be from the Chicago blaze, to a leather-bound listing from the 19th century featuring all of Catherine and Patrick O’Leary’s children baptized at Holy Family Church. There are scores of newspaper clippings, keepsakes covering several generations and so many photos of relatives, the Monreals don’t know them all.

As with other branches of the O’Leary descendants, the Monreals said they grew up with their own stories of what truly sparked the Chicago fire.

“We were always told,” Susan Monreal said, “that because it was such a drought in Chicago at the time, that all the sidewalks were wood plank and guys from the saloon would come around and when they walked around they would hit their pipes ashes on the building. And that’s what we’ve always been told (about) how the Chicago fire started.”

The clock isn’t only a remembrance of Catherine O’Leary, but also of her son, James Patrick, who made a name for himself outside of the family’s dark shadow. “Big Jim O’Leary had it made,” said Susan Monreal.

Aside from the already extraordinary tale of the O’Leary clan, Jim O’Leary led a life of adventure as a main cog for the city’s infamous gambling operations at a time when gangsters battled over control of the Prohibition liquor trade.

Though he grew up poor, Big Jim built a fortune running gambling and booking houses, poolrooms, an amusement park and his famous two-story stockyards saloon, O’Leary’s, at 4187 S. Halsted St., despite near-constant hounding from police and reform-minded politicians.

“I’ve run every kind of a gambling game,” the famously honest gambler told the Tribune in November 1911. “Every time I heard of a new one, I learned it and tried it. Nobody can say that O’Leary ever ran a crooked game.”

His 33-room, 6,270-square-foot mansion at 728 W. Garfield Blvd., built in 1890 for $100,000, was reportedly built for his mother, who died five years later.

Citing the clock’s sentimental value and craftsmanship, Monreal said it didn’t occur to him to sell it, wanting younger generations to be able to appreciate it as his family has.

“We could sell it, but what’s the dollar value? What’s it worth? Who is it worth (to)?” he said. “Once you start doing that, you’re getting rid of history and after that, it’s pretty much gone. If I can get it in somewhere where people are looking at it and talk about it, if it’s taken care of, well then that’s pretty much what I’d be happy with.”