At Hong Kong on the morning of the 19th of December 1941, a company of the Winnipeg Grenadiers to which Company Sergeant-Major Osborn belonged, became divided during an attack on Mount Butler, a hill rising steeply above sea level. A part of the company led by Company Sergeant-Major Osborn captured the hill at the point of the bayonet and held it for three hours when, owing to the superior numbers of the enemy and to fire from an unprotected flank, the position became untenable. Company Sergeant-Major Osborn and a small group covered the withdrawal, and when their turn came to fall back Osborn, single-handed, engaged the enemy while the remainder successfully joined the company. Company Sergeant-Major Osborn had to run the gauntlet of heavy rifle and machine-gun fire. With no consideration for his own safety he assisted and directed stragglers to the new company position, exposing himself to heavy enemy fire to cover their retirement. Wherever danger threatened he was there to encourage his men.

During the afternoon the company was cut off from the battalion and completely surrounded by the enemy, who were able to approach to within grenade throwing distance of the slight depression which the company was holding. Several enemy grenades were thrown which Company Sergeant-Major Osborn picked up and threw back. The enemy threw a grenade which landed in a position where it was impossible to pick it up and return it in time. Shouting a warning to his comrades this gallant Warrant Officer threw himself on the grenade which exploded, killing him instantly. His self-sacrifice undoubtedly saved the lives of many others.

Company Sergeant-Major Osborn was an inspiring example to all throughout the defence which he assisted so magnificently in maintaining against an overwhelming enemy force for over eight and a half hours, and in his death he displayed the highest quality of heroism and self-sacrifice.

John Robert Osborn was born in Norfolk England on the 2nd of January 1899. He served in the First World War as a seaman in the Royal Naval Volunteer Reserve and saw action at the Battle of Jutland in May 1916. At the end of the war he moved to Saskatchewan where he farmed for two years at Wapella. He then worked with the maintenance division of the Canadian Pacific Railway in Manitoba where he married and had five children. He joined the Winnipeg Grenadiers in 1933 and was called to active duty on the 3rd of September 1939. At forty-two years of age he was the second oldest VC recipient in the Second World War. Company Sergeant-Major Osborn has no known grave but his name appears on the Hong Kong Memorial. His medal is on display at the Canadian War Museum in Ottawa.