Obituary published on Legacy.com by Leonard Memorial Funeral Home & Cremations - Glen Ellyn on Jan. 22, 2026.
Gerard Skipwith Wolf, 78, passed away peacefully on January 18, 2026, in
Carol Stream, Illinois. Born on November 24, 1947, in
Pittsburgh, Pennsylvania, Gerard lived a life marked by deep devotion to family, a passion for sailing and nature, and a steadfast commitment to service and community.
Gerard's early years took him from Pennsylvania to Illinois, where he graduated from Hinsdale Central High School. He went on to earn his bachelor's degree from John Carroll University in Ohio and later completed a master's degree at DePaul University in Chicago. His academic journey reflected his lifelong love of learning.
An ROTC graduate, Gerard served with distinction in the U.S. Army in Germany, where he directed inland waterway logistics. His time on the Rhine River merged his sense of duty with his affinity for the water. It was during this time that he met Barbara, a schoolteacher for the children of service members. Their meeting marked the beginning of a partnership that would span more than five decades.
Gerard and Barbara were married for 52 years and built a loving home together. They raised two daughters: Lindsey DeKuiper (Brad), whose children Grant, AJ, and Elliott brought Gerard immense joy; and Susan Stott (Aaron), whose children Evelyn, Harrison, and William were also cherished deeply by their grandfather. Gerard is also survived by his brother Greg Wolf (Laurie) and many nieces and nephews.
He was preceded in death by his parents Dan and Margaret Wolf; his sister Denilee; and his brother Daniel "Red" Wolf.
A skilled sailor with an enduring love for Lake Michigan, Gerard was an active member of the Chicago Yacht Club for many years. He completed an impressive 40 Chicago to Mackinac Island races-each one a testament to his perseverance and seamanship. His contributions extended beyond competition: as founding chairman of the Chicago Yacht Club Leukemia Cup Regatta, Gerard helped raise over one million dollars for the Leukemia & Lymphoma Society (now known as
Blood Cancer United). He also served on the club's board of directors, offering leadership rooted in integrity and vision.
When not on the water, Gerard could often be found immersed in a good book. His daughters fondly remember weekends spent with him reading in his recliner-quiet moments that spoke volumes about his thoughtful nature.
Nature held a special place in Gerard's heart. His favorite retreat was Good Hart, Michigan-a serene haven where he spent countless evenings on the porch under starlit skies, listening to the gentle sounds of the lake. At his cottage nestled deep in the woods, he found peace unlike any other.
Those who knew Gerard remember him as a loving husband and father who believed deeply in people's potential. He was kind-hearted yet driven-a man who chose words carefully but never hesitated to share stories that inspired laughter or reflection.
Gerard Skipwith Wolf leaves behind a legacy of love, hard work, adventure, and quiet strength. May his memory bring comfort to all who knew him and continue to inspire those whose lives he touched.
Memorial service February 21, 2026 at 11:00am at Glen Ellyn Covenant Church, 277 Hawthorne Blvd.,
Glen Ellyn, IL 60137.
In lieu of flowers, please make a donation in honor of Gerard to the
Blood Cancer United (previously known as
Leukemia And Lymphoma Society) at https://bloodcancerunited.org.
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