Robert Cahoon Diamond DFC MBA was born in Gladstone, Manitoba and raised in British Columbia. On May 21, 1942, Diamond enlisted in the RCAF in Vancouver. He took air crew instruction at training schools in Canada and on July 23, 1943, he graduated as a pilot from No. 3 Service Flying Training School in Calgary, Alberta.

After arriving in the UK, Diamond received his pilot officer commission in May 1943. He was eventually posted to No. 432 Squadron flying Halifax bombers from a base in Yorkshire, England. On the night of October 9, 1944, on their 34th and final mission before being repatriated to Canada, Diamond's Halifax bomber and his crew were assigned to bomb oil refineries in eastern Germany near the city of Bochum. They had dropped their bombs and had turned to head for their home base when one of the squadron's planes just metres above Diamond's old Halifax, dropped its bombs down on them by accident. One bomb ploughed right through the fuselage less than a metre from where Diamond manned the controls. Thankfully, the bomb did not detonate, so the plane was not instantly destroyed. But the rudders were disabled and Diamond fought to keep the plane in the air.

While flak from German guns pounded the sinking plane, the crew parachuted out one by one as Diamond heroically kept the plane from spinning out of control. On its final dive near the city of Duisburg, Diamond managed to kick out an emergency panel beneath his pilot's seat and launch himself from the plane. When Diamond and the crew landed, they were captured by Germans and survived nine months in prisoner of war camps until the spring of 1945 when the European war ended.

Diamond received the Distinguished Flying Cross (DFC). His crew credit Diamond's heroic behavior for saving their lives. After returning to Canada at the end of WW2, Diamond finished his degree at the University of British Columbia and before joining the permanent RCAF, married his wife Joan. He and Joan had four children including two sons named Michael and Brad. He obtained his MBA degree in 1961 at the University of Western Ontario, London and retired form the military with the rank of lieutenant colonel.