Gary's father was a career soldier, who served with Princess Patricias Canadian Light Infantry from 1950 to 1975. Their family lived in Calgary, Griesbach Barracks in Edmonton, Toronto, Germany and finally back to Calgary where his father retired from the military. The family lived in Germany from 1969 to 1972; there Gary's history obsession took deeper root and he gained an appreciation of foreign cultures. Graduating from high school in 1971, he began working for the air force in Baden Soellingen with hopes of joining the air force. However, government funding cuts meant there were few opportunities available. Although he hoped things might change, they did not and he abandoned that goal four years later.

Gary's grandfather served with Lord Strahcona's Horse in WW1 and it was he who first stoked his grandson's life long interest in military history. During the Korean War, Reginald, Gary's father, fought at the Battle of Kapyong in April, 1951 and he also encouraged his son's passion for history.