Mr. John Robert Gilliss Jr., known to all as Jack, passed away on Nov. 12, 2025, in his home in Cape Charles.
Born on Aug. 31, 1946, to John Robert Gilliss Sr. and Eula Lee Gilliss (Wimbrow), Jack lived most of his life in Chincoteague before moving to Cape Charles in his final years.
Jack graduated from Chincoteague High School and attended the College of William & Mary before graduating from Randolph Macon College in 1969, where he was a proud member of Sigma Phi Epsilon fraternity, serving as social chairman. It was during his college years that Jack met the love of his life, Kathy. They celebrated 56 years of marriage together.
Jack began his career teaching math for 10 years throughout Accomack County while also serving as head lifeguard on Assateague. He later transitioned to the insurance industry as an insurance adjuster and eventually purchased Coastal Adjustment Bureau, where he built a successful 38-year career traveling the roads of the Delmarva Peninsula and accumulating hundreds of thousands of miles along the way.
Jack was deeply committed to his community, coaching Little League, Senior League, and middle school baseball and basketball at Broadwater Academy, where he also served on the Board of Directors for four years. He served for over a decade on the Chincoteague Board of Zoning Appeals.
Jack will be remembered as a beloved husband, father, grandfather, teacher, friend, and coach. He had a passion for quail hunting, fishing, boating, and golf — spending countless hours on the links searching for his game and, on occasion, employing a well-timed foot wedge. Those who knew Jack will fondly remember his gift for storytelling, his quick wit, and his sharp intellect.
In his later years, Jack demonstrated remarkable courage and perseverance as he faced Parkinson’s disease with grace and determination.
Jack is survived by his devoted wife, Kathy; his son, E. Neil Gilliss (Carrington), of Richmond, whose accomplishments were a source of immense pride for Jack; and two cherished granddaughters, Mary Archer Gilliss and Taylor Carrington Gilliss, who were his greatest pride and joy.
A private burial was held on Nov. 15, followed by a celebration of life at the Coach House Tavern in Cape Charles.
In lieu of flowers, gifts may be made to The Michael J. Fox Foundation for Parkinson’s Research, P.O. Box 5014 Hagerstown, MD 21741 (www.michaeljfox.org/give) or the Chincoteague Island Library, 4077 Main St., Chincoteague Island, VA 23336-2407 (www.paypal.com/US/fundraiser/charity/1922649).
Memory tributes may be shared with the family at
www.williamsfuneralhomes.com
Arrangements were by the Williams-Onancock Funeral Home.
