John Winters

John Francis “Jack” Winters passed away peacefully at the age of 94 while walking to a family dinner party at the Ishnala Supper Club in Baraboo, WI. Born in Andover, Massachusetts, Jack was the youngest of seven children in a lively Irish Catholic family.

Known affectionately as “Rumples” (short for Rumpelstiltskin), Jack carried from boyhood a rare blend of wit, warmth, and curiosity. Gifted with both the gab of a storyteller and the voice of a singer, he once aspired to be a writer—but his true calling was the art of human connection, guided by humor, empathy, and an irrepressible zest for life.

Jack served proudly and achieved the rank of a Petty Officer Third Class in the U.S. Navy as an aerographer, stationed in Newfoundland. After his service, fate intervened at a Greek restaurant in Washington, D.C., where he met Lucille Carol Philipps of Mineral Point, Wisconsin—the love of his life and his lifelong partner through joy and heartache, song and silence, purpose and grace.

A craftsman of the printed word, Jack worked at McArdle Printing Company in Washington, D.C., and Wells Printing in Madison, Wisconsin, before founding Darwin Printing with his friend Ron Darga. What began as a modest venture grew into a remarkably successful business, achieving returns that would rival even the most seasoned investors—an enduring testament to Jack’s vision, discipline, and quiet entrepreneurial spirit.

In his long and wondrous journey amid family, friends, and the world at large, Jack came to understand life is both comedy and tragedy—woven together in ways that deepen the heart. Jack and Lucille endured unthinkable sorrow, surviving the loss of three beloved sons—Jim, Ted, and later Rick. Through the long arc of grief, they found strength in one another and in the enduring bonds of family. With time, healing found its quiet way back home, to family and to himself.

Jack was a man of song and spirit—a poet with a playful soul. He could turn an ordinary moment into a melody, transforming conversation into laughter and laughter into love. At Christmas, dressed as Santa, he serenaded his children and grandchildren with songs he wrote himself—his heart open, his joy contagious.

Jack’s life was a journey of continual growth—a path defined by his willingness to question long-held beliefs, to change when wisdom called for it, and to laugh at life’s little mysteries, like why he could never hit a four-iron to save his life. He leaves behind a legacy not only of laughter and insight, but of presence—a reminder that genuine connection is life’s most enduring art form.

He is survived by his wife Lucille, sons John and Bruce; grandchildren John Francis, Kenneth, Ryan, Brady, and Samantha; and great-grandchildren Elin, Josselin, Lynnie, Athena, and Artemis.

A Mass of Christian Burial will be held at Our Lady Queen of Peace Catholic Church, 401 S Owen Dr, Madison, on Friday, October 24, 2025. Visitation will start at 10 am, followed by the church service at 11 am.  Following the church service, family and friends will have an opportunity to gather together to share memories and honor his legacy.

Jack’s spirit lives on in every story told, every song remembered, and every moment of kindness shared. His was a life fully lived, and a soul deeply loved.

To view this obituary and leave a memory, please visit: www.ryanfuneralservice.com.

Ryan Funeral Home & Cremation Services
Verona Chapel
220 Enterprise Drive
608-845-6625