James Ford Gregory II

James Ford Gregory II passed away unexpectedly on October 15, 2026, at the age of 80. Jim was born on September 7, 1946, in Cheverly, Maryland. Jim lived and worked in Maryland until his retirement when he moved to the Hilton Head area of South Carolina.

Jim had a distinguished retail automotive career for 40 years where he served as General Manager. Jim’s passion was spending time on the Chesapeake Bay with Barbara on their boat, Solitude. Jim and Barbara developed many lifelong friends while boating. Jim enjoyed traveling, especially on their annual trip to Puerto Vallarta which they took for the last 18 years as well as on their Regent Cruises to Europe and the Caribbean.

Jim built a life centered on family, work, service and community. Jim was known for his kindness towards others and found joy with his family. He was incredibly proud of his three sons.

Jim leaves behind his wife of 37 years, Barbara Anne Kautzman Gregory, three sons and their families, James Ford Gregory III (spouse Traci Gregory and children Dylan and Kenzie Gregory), Andrew William Gregory (children Alexandra and Ryan Gregory) and Matthew Benjamin Gregory). He was preceded in death by his father and mother James Ford Gregory and Mary Alice Gregory.

Jim’s legacy will be continued in the lives of all who loved him.

To honor his wishes, Jim was cremated and a celebration of life will be held at a later date.