John Crosby Holloway

John (Jack) Crosby Holloway, 92, passed away on December 23, 2025. He was born in Savannah Georgia on February 27, 1933 to John T. Holloway and Catherine R. Holloway. He loved his Georgia peaches. He was a 1952 graduate of Granby High School in Norfolk VA. Jack married Cynthia Stevenson in 1955. He joined the Air Force after high school and they lived in Texas where he served in the Air Force playing in the band. He served from Sept 1952 – Aug 1956. He played Taps for over 200 military funerals. They moved to Leesburg after his discharge. Jack worked as a dispatcher for the Florida Highway Patrol for 4 years. He continued his affiliation with the Patrol working as an auxiliary trooper for over 28 years. He worked with his parents for many years at the Leesburg Western Auto. He later operated his own company, Holloway Garage Doors. He sold his business and retired in 1998. After retiring, he worked as needed for Cecil Clark Chevrolet transporting vehicles. Jack was a long-time member of Morrison United Methodist Church. Jack joined the Leesburg Masonic Lodge in 1961 and served as The Worshipful Master in 1968 following his father who was Master of the Lodge the previous year. He was a long-time member of the Benevolent Protective Order of Elks and served as the Exalted Ruler of the Leesburg Lodge from 1977-1978. He was also District Director for the state from 1987-1991. Jack enjoyed taking road trips on his motorcycle, camping, going to the mountains, photography, ham radio and CB radio, and slot car racing. He was predeceased by his wife of 70 years, Cynthia. Jack is survived by son Michael (Barbara) of Fruitland Park, daughter Susan of Minneola, grandson Kevin (Heidi) of Winter Springs, grandson Brandon (Kristi) of Apopka, 6 great grandchildren and brother Don Holloway of Richmond VA. In lieu of flowers, contributions can be made to Harry-Anna Investment Fund in Umatilla FL. Visitation will be on Wednesday Dec 31 from 1030-1130 at Beyers Funeral Home in Leesburg followed by a graveside service at noon at Hillcrest Memorial Gardens. Please join the family at Jack’s house after the service. 4331 Magnolia Ave.

John Crosby Holloway

February 27, 1933 - December 23, 2025