John Reed Prosser, 83, of Winchester, Virginia, passed away peacefully on Friday, October 9, 2026, at the Winchester Medical Center.
Born on August 13, 1943, in Washington, DC, John was the son of the late U.S. Army Captain Cortland Reed Prosser and Marie DeHaven Prosser. As part of a military family, he lived many places, including a few years in France, and learned to make new friends easily. Back in Winchester for high school, he became a basketball star at James Wood High School, where he graduated in 1961. He continued to play basketball for the Virginia Military Institute, where the team made national headlines by upsetting Lefty Driesell’s Davidson College team on the way to winning the 1964 Southern Conference Tournament Championship and advancing to the NCAA Tournament. His senior season he earned All Southern Conference honors. He graduated from VMI with a Bachelor’s degree in English in 1965 near the top of his class before earning his Juris Doctor degree from Washington and Lee University School of Law in 1968.
After his studies, he joined the Judge Advocate General’s Corps of the U.S. Army, where he honed his legal skills advocating for soldiers stationed in Germany. He returned to Winchester after he was honorably discharged at the rank of Captain from the Army in 1973 to enter the private practice of law. He served on many local boards and committees, including the Winchester City Council. He continued to practice law until he was appointed Judge for the 26th Judicial Circuit Court of Virginia in 1997. He retired from the Court in 2011. For the rest of his life, he was an avid golfer and sprint car fan. He was a long-time member of Braddock Street United Methodist Church.
He is survived by his best friend and wife of 45 years, Shirley; his daughter Tracy Prosser and her husband Grover Leech, of Cobden, Illinois; and his son Reed Prosser, Reed’s wife Claire, and their children Anna and Jack, all of Winchester.
A memorial service will be held at Braddock Street United Methodist Church on Wednesday, October 21, 2026, at 11:00 am with Pastor Jason Duley officiating.
In lieu of flowers, donations can be made to the VMI Keydet Club at P.O. Box 932, Lexington, VA 24450.
