James Stephen Chiles

James Stephen Chiles (Steve), 80, passed away peacefully at the Western Reserve Masonic Community in Medina, Ohio, on Dec. 4. Born in San Rafael, Calif., and raised in Baltimore, Md., he was a beloved husband, father, and dedicated pilot. Steve lived a bold yet humble life, loved his wife and family quietly yet deeply, and played and worked with wide-ranging curiosity, intellect and passion which inspired his family and others. He is survived by the love of his life and wife of 59 years, Judith (Jett), whom he met in college. Their enduring bond was a testament to their deep love and commitment. This love took them on many adventures literally around the world, through their love of cruises and boating. He was a proud father to son, Stephen, and daughter, Kara, who will forever carry his legacy of devotion and kindness. As a doting grandfather "Cap" cherished his grandchildren Taylor Holland, Connor Chiles, and Nicola Chiles, as well as his three great-grandchildren, who brought him immense joy.
Steve spent 34 years as a pilot with United Airlines, before retiring as Captain, and after serving as a Green Beret in the U.S. Army 101st Airborne, and flying border patrol for U.S. Customs in San Antonio, Texas. His love of aviation continued in retirement as a proud owner of a V-Tail Beach Bonanza, from the Spruce Creek Fly-In community in Port Orange, Fla. He and Judy made Florida their home for the last 25 years, where they became fixtures at their favorite seafood spot and doted on their beloved dog, Teddy, who passed in January.
Having gone blind in the last years of his life, Steve suffered from not being able to see his loved ones but was always ready for a spirited conversation on a range of topics. Described as a "renaissance man," he could talk technology, world politics or cinema with equal ease. Steve's memory will be forever cherished by his wife, children, family and friends. His life was a testament to the importance of love, tenacity, and hard work, pursuing one's passions and creating lasting memories. He will be deeply missed, but his spirit will live on in the hearts of those who knew and loved him. "Ti amo."
Steve will be interred after a memorial service with full military honors at Ohio Western Reserve National Cemetery. Online condolences and memories may be shared at www.waitefuneralhome.com.