Lt. W. H. (Bill) Naylor joined the 2nd Battalion, 48th Highlanders in Toronto and is shown in a 1940 newspaper article as one of the 52 officers of the 2nd Battalion who were training for service in the Second World War. Following training Lt Naylor sailed to England to join the 1st Battalion, 48th Highlanders and was appointed to A Company. In April 1943 a fourth company was created. D Company and Lt Naylor became Platoon Commander of 16 Platoon, just in time for the battalion’s sailing for landing in Sicily on 9 July. In the first significant action in Sicily, at Valguanera, Naylor’s 16 Platoon and Lt Bob Handley’s 17 Platoon, with 18 Platoon providing covering fire, executed a right hook against over 200 dug in Germans on a ridge. Although driven to ground by intense fire the last section of 17 Platoon completed the hook, driving the Germans off the ridge to eliminate the anchor position of the German defence for the town. In November 1943 Naylor returned to England as part of Operation Pouch, to provide battle-experienced officers and NCOs to the Canadians still in England.