Remembering Charles “Charlie” Gwynne ’64

Born in Cranston, Rhode Island, Charlie was the son of Arthur W. Gwynne II and Patricia (Gallagher) Gwynne. After graduating from Providence Country Day School in 1964, he went on to attend the United States Military Academy at West Point, graduating in 1969. Commissioned in the infantry, Charlie served 21 years in the U.S. Army, including command of a rifle company in Vietnam at just 24 years old. He earned the Bronze Star Medal and the Combat Infantryman Badge for his distinguished service. He later earned a master’s degree in International Relations from the University of Maryland.

Upon retiring from the Army as a Lieutenant Colonel, Charlie returned home to PCD in 1991, joining the Mathematics Department and quickly becoming a beloved teacher, advisor, and coach. In 1994, he succeeded Bob Dickerman as Athletic Director, a position he held until his retirement in 2007. During Charlie’s tenure as AD, Country Day enjoyed a period of athletic success across multiple sports and leagues, a reflection of his steady leadership and personal competitiveness. 

At PCD, Charlie was admired for his intelligence and humility – qualities that inspired students and colleagues alike. He was particularly gifted at helping students navigate the challenges of adolescence, often using his keen sense of humor to put things in perspective. His 2007 Commencement address remains fondly remembered for both its wisdom and, in true Charlie fashion, its side-splitting humor. A standout athlete during his own years at Country Day, Charlie remained a true sportsman throughout his life: an avid golfer and bowler, and a lifelong supporter of Boston’s professional teams.

Charlie was predeceased by his beloved wife, Ann M. (Anderson) Gwynne, and is survived by his children Jennifer M. Gwynne (Sean), Jamie G. Nostrant ‘94 (Christopher), and Charles S. Gwynne Jr. ’95 (Kelley); his grandchildren Jordan, Stratford, Caiden, Charles III, and Henry; and many nieces and nephews.

Charlie’s legacy at PCD and beyond endures in the countless lives he touched – as a soldier, educator, mentor, and loyal friend. 

A visitation with family will be held at Caughman-Harman Funeral Home – Lexington Chapel, located at 503 North Lake Drive, Lexington, SC 29072, on November 23, 2025, from 3:00 pm to 5:00 pm.  Calling hours and then an interment ceremony at the Rhode Island Veterans Memorial Cemetery in Exeter, Rhode Island will be held at a later date. In lieu of flowers, contributions to the American Cancer Society would be appreciated.