By Tane Beecham

Someone out for a stroll through Hubbard Woods in the early 1900s would have observed many new homes going up as the area became increasingly populated with family-sized houses on manageable lots. One would also have taken note of a very large 10-acre wooded plot of land on the north side of Tower Road, dwarfing much of the subdivided land surrounding it.

Referred to on historic maps as “Dennehy’s Consolidation,” the property was the estate of Thomas C. Dennehy. It was sold to C. A. Hemphill and Associates in 1939, and became the 38 residences of the Forest Glen subdivision.

Walking through Forest Glen now it is difficult to imagine the romance of this once large sprawling estate. Slightly rolling and completely wooded, the land encompassed a large mansion serving as the Dennehy family’s summer residence.

Thomas C. Dennehy acquired the property at 1231 North Avenue (later renamed Tower Road) by 1905, choosing the property as a summer season complement to the family’s glamorous home on Astor Street in Chicago’s Gold Coast. The Dennehy estate burned down sometime during the 1930s.

The Dennehy name, now largely forgotten, was at one time associated with the pinnacles of wealth and prominence in Chicago.

Born in 1858 to a Chicago family operating a successful liquor distributorship, Dennehy entered the family business at age 17. The success of the Clear Springs Distilling Company brought the Dennehys significant wealth and established them as one of Chicago’s most prominent families.

In 1900, at the age of 41, Dennehy married another Gold Coast resident, Virginia Inderrieden, age 26. During the next few years they lived in several Gold Coast residences, finally settling in 1913 on a four-story home at 1549 Astor Street with ten bedrooms and a magnificent ballroom. With the onset of Prohibition in 1920, Mr. Dennehy redirected his business endeavors into commercial real estate.

The Dennehys acquired their Hubbard Woods property with plans to use it primarily as a summer retreat. Thomas and Virginia Dennehy proceeded to raise seven children there – all of whom married into equally prominent families.

Their daughter Josephine married former Prince Nicholas Galitzine of Russia in 1932 and became known as Princess Josephine. Another daughter, Eleanor, married Ralph Isham, son of Northwestern University Medical College founder and owner of the Gold Coast residence known as the Playboy Mansion. A third daughter, Mary, was wed to Hempstead Washburne, son of the former Chicago Mayor also named Hemptead Washburne.

Society pages took note of Dennehy marriages, some of which were held at their Winnetka home, as well as other family milestones. For daughter Mary’s 18th birthday, her father gave her a birthday gift of Chicago real estate worth over $4 million in today’s dollars.

The Thomas C. Dennehy family lived in Winnetka for over 30 years. And while their roots were very much in Chicago, the family personified the historical link between the big city and the small town up north. Society, business, and culture kept them in the city, but in summer their hearts always drew them to Winnetka. ■

Thanks to Dennehy family historian Charles Askins for inspiring and contributing research to this story.