Kevin Leonard Winton Healey was born on 4 August 1909 at Paddington. He enlisted on 3 January 1940 at Victoria Barracks, describing his occupation as a commercial traveler. Assigned to 2/3rd Infantry Battalion he embarked for Egypt only a week later. Here he received training and was promoted to acting corporal on 7 May; he underwent further training at the Middle East Weapons Training School in September and was promoted to Sergeant in December 1940.
He fought in both the Battle of Bardia and the Battle for Tobruk.
On 18 January 1941 he was promoted to warrant officer class 2 and in mid-March 1941 his battalion was embarked for Greece. WO2 Healey was wounded in action a month later in April, receiving a shrapnel wound to his back. Healey, who had previously trained as a pathologist, remained conscious and watched his own operation. As the Australians were retreating to Valos, Healey was traveling in a truck when his convoy was targeted by Stukas. A New Zealand officer suffering from shell shock leapt from the truck, Healey followed him and was wounded by a Stuka bomb. He was captured by the Germans and transferred to Kokkinia POW Hospital. In December he was sufficiently recovered to be transferred to Stalag XXA in Torun (Thorn) in central Poland.
He made a radio set in prison and traded 100 cigarettes to a German pilot for a single earpiece, which enabled him to listen in secret to the BBC, keeping his fellow prisoners updated on war news. Here he spent the remainder of the war, involving himself in sporting activities, and fostering health and fitness amongst his fellow internees.