This trophy was established in 1973 by the Royal Canadian Air Force Association to commemorate Gordon R. McGregor, who served in the Second World War and made outstanding achievements in the field of air transportation in Canada.
McGregor earned his private pilot’s license in 1932 and won the Webster Trophy in 1935, ‘36 and ‘38, awarded to the best amateur pilot in Canada. At 39, McGregor became the oldest fighter pilot and the top-scoring Royal Canadian Air Force ace to serve in the Battle of Britain, with six German aircrafts destroyed, seven probables and eight damaged.
In April 1941, he was promoted from Squadron Leader to Wing Commander. Noticed for his leadership and managing skills, McGregor was given various command posts in the Pacific zone following the Japanese attack on Dutch Harbor, Alaska. In 1944, he was recalled to England to prepare for the invasion of Normandy. Led by McGregor, No. 216 Wing was the first unit to base itself permanently on the continent after D-Day. In the months that followed until the final victory, his wing was the most successful.