Richard Gregory was part of the Argonaut Rowing Club’s junior eight squad as early as 1909, but the highlight of his career came when he represented Canada as part of the men’s coxed eight crew at the 1912 Summer Olympics. The team, consisting of Gregory, Charles Riddy, Phil Boyd, Albert Kent, William Murphy, Alex Sinclair, Becher Gale, Geoffrey Taylor, and Winslow McCleary, was defeated in the opening round by Great Britain’s New College, Oxford squad and was eliminated from the tournament. He continued to row with the Argonauts until World War I, when he joined up with the Canadian Heavy Artillery and served with them overseas. He was injured in France in September 1917 and contracted pneumonia on the journey home. He never recovered fully and died at the young age of 35 in 1920.