Gerard Hillsman

Gerard "Gerry" Charles Hillsman of Glenview passed away peacefully on Sunday, September 28, 2025, at the age of 91.
Gerry was born to Otto and Frances Hillsman, raised in Rogers Park, and studied at St. Margaret Mary School and Loyola Academy before attending the University of Notre Dame as an Air Force Reserve Officer Training Corps (ROTC) cadet. Upon his 1955 graduation from Notre Dame, Gerry proposed to Carole Ann Eastman of Evanston, his beloved high school sweetheart, with his school ring. That June, Gerry was commissioned a second lieutenant in the U.S. Air Force. Upon receiving deployment orders the following fall, Gerry and Carole were married in nine days' time before his deployment to Okinawa, Japan. Carole joined him shortly thereafter in Okinawa, where their oldest child, Mary, was born. After returning to the States several years later, children Jean, Rich, and Peter arrived in steady succession, with Stephen, the caboose, arriving five years later.
A CPA by trade, Gerry led the accounting firm his father had started, Otto Hillsman & Company, before merging with Clifton Gunderson (now CliftonLarsonAllen), where he was a long-time Partner. He also served as the long-time Treasurer of the ND Club of Chicago, and then as President, and loved cheering on the Fighting Irish as a season ticket holder, like his father before him.
Gerry and Carole were active parishioners of St. Martha Catholic Church and School in Morton Grove, where they raised their family. For many years, Gerry and Carole spent their summer weekends hosting their children and grandchildren along the shores of Magician Lake in Sister Lakes, Michigan, where each of them had spent childhood summers.
After Carole's passing in 1998, Gerry became a committed volunteer for Meals on Wheels and never missed a lunch with his pals, the "ROMEOS," Retired Old Men Eating Out, made up of fellow Notre Dame classmates. In 2000, he married Mary Lourdes O'Toole, a widow with a large family of her own. Together they traveled, spent some winter months each year on Captiva Island in Florida, and spent a great deal of time attending the many family-related celebrations that came with rapidly expanding families.
Gerry's love of his family-particularly sitting in a crowded room filled with his grandchildren and great-grandchildren, taking in all the shenanigans, laughter, and chatter-was clearly his heart's delight. He particularly enjoyed the hilarious Hillsman "White Elephant" gift exchange, the highlight of every annual Christmas gathering.
Gerry is preceded in death by his wives, Carole Hillsman and Mary Lou O'Toole, as well as his sister Virginia Keleher and brother William. He is survived by his five children, Mary (Brian Weberg), Jean (the late Timothy) Ferrara, Rich (Teresa Hedden and the late Linda), Peter (partner Richard Blasey), and Steve (Kathleen); sister, Rosemary Whitmore; 14 grandchildren; 19 ½ great-grandchildren; and 1 great-great-grandchild, all of whom will dearly miss him. He is also survived by Mary Lou's children, John, Mark, Matthew, Patrick, and Margaret, and Mary Lou's many grandchildren.
The entire Hillsman family extends its sincerest gratitude to the staff at North Shore Place who cared for Gerry so devotedly for the past year.
Gerry was an active parishioner at Our Lady of Perpetual Help Church in Glenview for over 35 years, where a memorial visitation will be held on Monday, October 13th from 9:15 a.m. until his memorial mass at 10:00 a.m. Our Lady of Perpetual Help Church is located at 1775 Grove St. Glenview, IL 60025. In lieu of flowers, donations to Misericordia Heart of Mercy at 6300 N. Ridge Ave. Chicago, IL 60660 are appreciated.
To access the live stream of the funeral mass, click https://vimeo.com/event/5424429/embed/e9356ffdb1
To send flowers
to the family or plant a tree
in memory of Gerard Hillsman, please visit our floral store.