Background
Bennett (who was always known as Gordon) was born in Balwyn, Melbourne, on 15 April 1887, to George Bennett, a South African-born school teacher, and his Australian-born wife, Harriet.
Bennett (who was always known as Gordon) was born in Balwyn, Melbourne, on 15 April 1887, to George Bennett, a South African-born school teacher, and his Australian-born wife, Harriet.
He was the sixth of nine children and attended Balwyn State School, where his father taught, and then Hawthorn College as a teenager having been given a three-year scholarship. While at Hawthorn, he did well at mathematics and in 1903, as a 16-year-old, after completing a competitive examination he was accepted into the AMP Society to train as an actuary. In May 1908, just after he turned 21, Bennett volunteered to serve in the Militia, Australia's reserve military force, joining the 5th Australian Infantry Regiment as a "recruit officer".
Between the wars he was a highly successful accountant, director of important corporations, and a member of government boards. He rose from colonel in the militia reserve in 1921 to become the youngest major general on the active list in 1939. Cocky Bennett was loudly critical of the regular army and especially of British officers (Keegan, Who Was Who, “Bennett”). After heading a training depot until the summer of 1940 he took over the 8th Div, the third to be formed in Australia during WWII. One of his brigade groups went to Malaya in early Feb 1941: Bennett himself reached Singapore on 15 Aug 1941 with the rest of the division minus one brigade group. When Yam-ashita began his Malayan campaign a year later, Bennett's 8th Div consisted of the 22d and 27th Bdes under H. B. Taylor and D. S. Maxwell. Bennett took command of “Westforce” in NW Johore as the Japanese moved down the western side of the peninsula. Using Maxwell’s brigade plus the 8th, 22d. and 45th Indian Bdes, Bennett had some success against crack troops of the Japanese 5th and Imperial Guards Divs during the period 15-18 Jan 1942 before being ordered to withdraw.
On Singapore Island Cocky Bennett commanded the Western Area, where the Japanese main effort began on 8 Feb 1942. Five days later he was among those advising Percival. to surrender. With other Australian officers, Bennett escaped to Johore in a sampan, and on 26 Feb 1942 he reached Batavia in an oceangoing junk. Cleared of misconduct and promoted to lieutenant general in Apr 1942, Bennett headed the 3d Corps, which absorbed Australia's Western Command. But the general never got another field command and after continued criticism for leaving Singapore he returned to private life in 1944. A postwar court of inquiry ruled that Bennett should have surrendered with his troops.