09/04/2026
September 3, 2026
Commission on Chicago Landmarks
Department of Planning and Development City of Chicago
121 N. LaSalle Street, Room 1000
Chicago, IL 60602
RE: Landmark Designation Request for the James O’Leary Mansion at 726 West Garfield Boulevard
Dear Members of the Commission on Chicago Landmarks:
I am writing to you today with an urgent plea to preserve a vital, irreplaceable piece of Chicago’s history: the 1890 James O’Leary Mansion located at 726 West Garfield Boulevard. I strongly urge the Commission to initiate the process of granting this extraordinary property official Landmark status before its physical decay or potential redevelopment erases its rich legacy.
This 6,270-square-foot Renaissance Revival brownstone is far more than just an aging historic home; it is a monument to two of the most infamous and storied figures in our city's history, representing both the ashes of the Great Chicago Fire and the colorful era of early 20th-century syndicate operations.
There are several compelling reasons why the O'Leary Mansion meets the criteria for Chicago Landmark designation:
1. A Direct Link to the Great Chicago Fire and the O'Leary Legacy
The mansion was famously built in 1890 by James "Big Jim" O’Leary for his mother, Catherine O’Leary. Catherine is forever woven into the lore of the 1871 Great Chicago Fire. Though she and her cow were later exonerated by the Chicago City Council in 1997, the stigma and heartbreak followed her for the rest of her life. She lived her final years in this very home before passing away in 1895. The home even features a likeness of Catherine on the exterior façade, and the windows and dormers were architecturally designed to spell out the word "MoM" when viewed from a distance. Furthermore, reflecting the family’s trauma regarding fire, the property is said to be the only private residence in Chicago to boast its own dedicated fire hydrant in the rear alley, installed at James's request to protect his mother.
2. The Era of "Big Jim" O'Leary
James O'Leary was a towering figure in Chicago's underworld and political machine. Known as the "Gambling King of the Stock Yards," Big Jim made a fortune in bookmaking and ran a massive resort across from the Union Stock Yards. The Garfield Boulevard mansion stands as a physical testament to his immense wealth and operations. Remarkably, the property still contains two massive, original walk-in vaults—one on the main floor and one in the basement—where O'Leary reportedly stored his vast cash reserves. Preserving this home offers a tangible look into the syndicate history of the South Side prior to the Prohibition era.
3. Architectural and Historical Integrity
Designed by Zachary Taylor Davis—a prominent Chicago architect—the four-story brownstone is a stunning example of Renaissance Revival architecture. Despite needing cosmetic restoration, the home boasts remarkable structural integrity with 12-foot ceilings, original woodwork, towering doors, 33 total rooms, and its original two-story coach house and carriage stone in the rear. James O'Leary's initials remain proudly carved in the stone out front. Very few homes of this magnitude and pedigree from 1890 remain standing on the South Side, making its preservation all the more critical.
The James O’Leary Mansion is currently in a vulnerable state. It requires significant, specialized restoration to save its crumbling plaster and aging infrastructure. Without the protection and potential incentives that come with Chicago Landmark status, we risk a developer purchasing the land for its lot size, demolishing the structure, and permanently erasing the physical footprint of the O'Leary family from Chicago.
Our city is defined by its stories. The O’Leary Mansion encapsulates the tragedy of the 1871 fire, the immense wealth of the Stock Yards era, and the architectural grandeur of the 1890s in one single address.
I respectfully urge the Commission to review the historical and architectural merits of 726 West Garfield Boulevard and take immediate action to protect it as an official Chicago Landmark.
Thank you for your time, your service to our city, and your dedication to preserving the history of Chicago.
Sincerely,
Zachary Squires
President
Bensenville Area Historical Association
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