Background
His father served in the Highland Light Infantry in World War I from 28 May 1915 to 9 August 1916, when he was discharged due to illness.
His father served in the Highland Light Infantry in World War I from 28 May 1915 to 9 August 1916, when he was discharged due to illness.
Winning was educated in Troon, Ayshire, and apprenticed at a shipping company.
He migrated to Java as a young man to work on a plantation. Upon the outbreak of war in 1940, he enlisted in the Australian forces and fought against the Japanese in the New Guinea and Bougainville campaigns. After the war, he returned to Java, where he continued to manage one of the plantations.
He was murdered there by anti-European rebels in 1950.
In 1926, at age 19, he traveled to Batavia, planning to settle in the Dutch East Indies. As a young man, Winning managed an estate owned by the Anglo-Dutch firm Pamanoekan en Tjiasemlanden in Java.
In September 1940, Winning traveled to Sydney to enlist in the Australian Imperial Force (AIF). After being accepted on 9 September, he was posted initially to the 1st Cavalry Training Squadron.
Upon completion of his training, he was promoted to temporary warrant officer, and, in December 1941, was commissioned lieutenant and transferred to the 4th Independent Company.
Promoted captain in March 1942, he left for Portuguese Moresby in April with the 2/5th Independent Company, which was later renamed the 2/5th Cavalry (Commando) Squadron. The company flew to Wau, New Guinea that May and, as part of the Kanga Force, began patrolling the tracks leading into the Bulolo Valley, from which they could harass the Japanese. Winning was widely respected among his men, earning the nickname The Red Steer.
The Red Steer is also the name given to the wild brush fires that blaze across the outback, a useful tool against squatters and intruders.
He led the Salamaua Raid, the first offensive land action against the Japanese in World World War II, on 29 June 1942, in which at least 100 Japanese soldiers were killed. The raid also captured Japanese equipment and documents.
Described as a copybook action for its diligent scouting, meticulous planning and audacious, Winning, then a captain, led multi-pronged attack against a Japanese force 10 times the attackers" strength. The 2/5th returned to Australia in May 1943 for additional training, and in November Winning transferred to the 2/4th Commando Squadron as second-in-command.
The unit deployed near Finschhafen, in New Guinea, for operations against the Japanese on the Huon Peninsula.
After a brief trip to Australia in February 1944, he was sent to the Far Eastern Liaison Office in April. On 8 July he was promoted to major and given command of the 2/8th Commando Squadron. They trained at Lae in New Guinea before deploying to Bougainville.
The unit engaged the Japanese several times near the Jaba River and in the area north of the Buin Road.
Following the war, he left the service on 26 September 1945, and awarded the M.B.E. in 1947. He resumed his work as a planter, managing an estate for P&T after the war.
On 2 or 3 December 1950, he was shot by terrorists while driving from the plantation he managed to Subang.