O'Leary, Richard Edwin "Dick" (April 23, 1934 April 4, 2022) age 87, passed away on April 4, 2022, at his home in Naples, FL. Born in Pittsburgh, KS and raised in central Illinois, Dick was the oldest child of Bernice Wheeler O'Leary and Edwin J. O'Leary. Dick joined the Naval ROTC at 17 and graduated from the University of Illinois at age 20. There he met the love of his life, Ann Matthews of Salem, IL. A master of efficiency, Dick graduated, was commissioned as an officer in the U.S. Navy, and was married, all in one day. Thus began their 67-year marriage, during which Ann and Dick followed his ambitions to 7 states and over 20 addresses, including their final homes in Naples, FL and Jackson, WY. The O'Leary children were born on submarine bases in CT and HI. After completing his active duty Dick enrolled at the U of I School of Law, working simultaneously as Assistant Dean of Men. His corporate career took him from Monsanto in St. Louis and New York to Studebaker Worthington and Onan in Minneapolis, to virtual stints at KHD and Porsche. In 1984 he ventured into business on his own, establishing H Enterprises International Inc. with several partners to acquire Waldorf Corp. Over time HEII acquired companies ranging from construction materials distribution (Brock White) to industrial equipment to toys (Manhattan Toy). Dick's greatest pride was providing productive employment for the thousands of people he employed over his career. He never retired, serving as Chairman of HEII until his death. Scary to some, respected by all, Dick always characterized himself as "warm hearted and loveable." He was generous with his expertise and the fruits of his labors, serving on the boards of Artis Naples, the Teton Music Festival, and the National Museum of Wildlife Art. Richard O'Leary was preceded in death by his parents and his sister, Patricia O'Leary Hutchings. In addition to his wife Ann, he is survived by his sister, Jeanne O'Leary Shapira of Naples, FL; his children, Lynn O'Leary Piéron (Olivier Piéron) of Portola Valley, CA and Richard Douglas O'Leary (Nora Quinlan O'Leary) of Edina, MN; his 5 grandchildren, Rémy O'Leary Piéron (Kirsten Gardner) of North Bend, WA, Luc O'Leary Piéron (Stephanie Schultz) of San Rafael, CA, Annie Q. O'Leary Mills (Henry Mills) of Chicago, IL, Kathleen Quinlan O'Leary of Minneapolis, MN and John Quinlan O'Leary of San Francisco, CA; and one great-grandchild, Gloria Cynthia Piéron. In lieu of flowers the family suggests memorials to the Neighborhood Health Clinic of Naples, FL or the charity of your choice. Memorial gatherings will be held at the Moorings Park Clubhouse in Naples, FL at 3:30 on Friday, April 8 and at the Minikahda Club in Minneapolis, MN on Friday, May 27th.

Published on April 7, 2022