Herbert Philip Crabb was born in Donisthorpe, Leicestershire, England on January 8, 1889. He came to Canada in 1904 as a boy of fifteen and settled at Borden, Saskatchewan. In 1907, after a few years of farm work he joined the staff of the Bank of Commerce in Radisson, Saskatchewan. In 1912, he went to Winnipeg, Manitoba and worked for the real estate firm of Stephenson and Field. In April 1915, he enlisted in Winnipeg in the Canadian Remount Depot of Calgary. In May he went to France with Canadian 3rd Echelon Headquarters. In January 1917, Captain Crabb transferred to the Royal Flying Corps and received flying training in Christ Church, Oxford. He was then posted as a flight instructor and after qualifying for service in the R.A.F., he became wing examining officer with the 26th Wing, R.A.F. at Cambridge. Towards the end of the war (1918), he was training instructor at Fowlmere, Cambridge, on Handley Page bomber aircraft.

In July 1919, he returned to Winnipeg and became a member of Stephenson, Field, and Crabb. It was at Fowlmere that he met Doreen Simons, who was a transport driver with the W.R.A.F. She came to Canada in 1921 and they were married in Winnipeg when he was 32 years old. In 1923, Crabb formed his own firm, Crabb and Company Ltd., with himself as president. He later formed the Crabb Construction Company, which built many of the larger homes in Winnipeg. He was also president of Moss Products Ltd. and General Discounts Ltd. He eventually sold Crabb and Company in 1953 and was then self-employed in the investment business. During the Second World War, he became commanding officer of the 112th City of Winnipeg Squadron from 1937 to 1939. He mobilized the squadron for active service. Every officer and 95 percent of the men volunteered for active service. In December 1939, Crabb transferred to Air Force Headquarters in Ottawa with the rank of squadron leader, going to the Directorate of Manning. He was promoted to wing commander and deputy director of Manning in March 1940, and director in November 1941 with the rank of group captain. He was later second in command of No. 4 Air Training Command at Calgary and then commanding officer of No. 9 Bombing and Gunnery School at Mont Joli, Quebec.

In the summer of 1944, at the age of 55, he returned to Winnipeg. Crabb served for many years on the Assessment Board of the City of Winnipeg and was also regional director for the Dominion Department of Labor. One of his main interests was the development of Canadian aviation. He served as a commissioner of the St. James – Winnipeg Airport Commission. He was a founder-member of the Aviation League of Manitoba, the Aviation League of Canada, and the Winnipeg Flying Club. Along with Bill Straith and Air Vice Marshall John Sully, Group Captain Crabb located and founded the airport in Winnipeg. He was later chosen to investigate the death of young Frederick J. Stevenson (1896-1928) who was killed in a flying accident in Northern Manitoba. On his return he suggested using the name Stevenson Field which is now Winnipeg James Armstrong Richardson International Airport. He was a member of the Winnipeg Gyro Club since its organization in 1920 and the Wartime Pilots’ and Observers’ Association. He was President of the St. George’s Snowshoe Club, and the Winnipeg Real Estate Board and a member of the Manitoba Club, St. Charles Country Club, Motor Country Club, and the Winnipeg Winter Club Group. Captain Crabb died in Winnipeg on May 5, 1966 after suffering from a series of strokes. He was survived by his wife, Doreen, and his son, John Philip Crabb.