James E. Gillespie Sr.

James E. Gillespie Sr. obituary, Chicago, IL

James E. Gillespie Sr.

James Gillespie Obituary

Obituary published on Legacy.com by Tohle Funeral Home on Nov. 18, 2025.

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James E. Gillespie Sr. ObituaryJames E. Gillespie Sr. Age 89. Fellow of Casualty Actuarial Society (FCAS). Beloved husband for 65 years of Josephine (nee McManamon of County Mayo). Loving father of James Jr. (Carol) of Chicago, Thomas (Debbie) of Huntley, Mary Ann (Timothy) Nolan of Palos Park, Patrick (Rose Anne) of Chicago, John (Rebecca) of Chicago, Daniel (Krista) of Chicago, Michael (Katie) of Chicago and the late Nancy.
Dearest grandfather of Timothy (Jennifer) Gillespie, Anthony (Kathleen) Gillespie, Katie (Jake) Biros, Caitlyn Mary (Marty) Cassidy, Eileen Ann (George) Jensen, Erin Maureen Gillespie, Catherine Gillespie, Daniel Gillespie, Robert Nolan, Patrick Gillespie, Elizabeth Nolan, Gavin Gillespie, Ryan Gillespie, Molly Nolan, Collin Gillespie, Quinn Gillespie and Owen Gillespie. Great-grandfather of Timothy Gillespie, Evan Gillespie, William Gillespie, Arden Gillespie, Shannon Gillespie, Sarah Gillespie, Anthony Gillespie Jr., Bridget Biros, Jack Biros, Avery Ann Cassidy, Maeve Josephine Cassidy, Beau Thomas Cassidy and Haven Mae Jensen. Devoted son of late John and Anne (nee Hayes) Gillespie of Chicago. Dear brother of the late William (late Mickey) Gillespie of Ohio, late John "Jack" (late Mary) Gillespie of Naperville and his twin brother the late Reverend Thomas Gillespie of California. Survived by many nieces, nephews, cousins, and great friends.
James was a lifelong, northside Chicagoan who attended Saint Edward Grammar School, the Old Saint Patrick High School and the University of Illinois Navy Pier and Champaign campuses. Three generations of the Gillespie family called Lowell Avenue in North Mayfair Park home for over 90 years. James was a true Diehard Chicago Cub and Illini fan.
James successful career in Actuarial Science continued for over forty years with CNA Insurance, Montgomery Ward Signature Group and Zurich American where he officially retired as Vice President.
James will be dearly missed by all that were fortunate enough to have known him.
Visitation Friday January 7th from 3:00 PM to 9:00 PM and Saturday January 8th 9:00 – 10:00 AM from TOHLE FUNERAL HOME 4325 W. Lawrence Ave. to ST. EDWARD CHURCH 4350 W. Sunnyside, Mass 10:30 AM. Interment Maryhill Cemetery. In lieu of flowers donations to the Juvenile Diabetes Foundation, St. Jude Children's Research Hospital, Lurie Children's Hospital or GiGi's Playhouse appreciated. Info 773-685-4400 or tohlefuneralhome.com
To plant a beautiful memorial tree in memory of James, please visit our .
James E. Gillespie Sr. Age 89. Fellow of Casualty Actuarial Society (FCAS). Beloved husband for 65 years of Josephine (nee McManamon of County Mayo). Loving father of James Jr. (Carol) of Chicago, Thomas (Debbie) of Huntley, Mary Ann (Timothy) Nolan of Palos Park, Patrick (Rose Anne) of Chicago, John (Rebecca) of Chicago, Daniel (Krista) of Chicago

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Tohle Funeral Home

4325 W. Lawrence Avenue, Chicago, IL 60630

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