Lt Jack Pickering joined “A” Coy 1st Battalion, 48th Highlanders CASF in Sicily as a reinforcement officer during the last week of July 1944.
Without a 48th background, he sensed he was severely handicapped, with the challenge to prove himself that much sharper. He noted his platoon’s speculative regard; after a while one man elected himself spokesman: “Sir,” he said, “What were you in Civilian life?” He wished that his reply could sound more warlike: “A school teacher,” he said. There was a prolonged silence; not a man said a word. A little later, Lt. Pickering overheard the spokesman rendering a gracious judgment: “Now, let’s be fair, fellows; at least it’s better than another stockbroker.” He would serve with the Battalion until the end of hostilities and commanded his platoon in every major action through Sicily and Italy, including the Lamone Crossing where his actions were recognized through the award of the Military Cross. In Holland he was appointed as Intelligence Officer. Dileas records the events of his last action of the war when on the afternoon of 8 May near Wilp he accompanied LCol Don MacKenzie to recce a new position for the Battalion Tactical Headquarters (Tac) when a German shell landed near them. Lt. Pickering was wounded and shaken, but as he reached to his hands and knees he saw the Colonel was motionless. He crawled to him. As bits of earth were still pattering back to earth from the explosion, he heard him say painfully: “See where I’m hit, Jack. The Colonel had been so terribly injured internally, he died with the one sentence, and before the dust had fully settled from the shell burst. The Colonel had been so terribly injured internally, he died with the one sentence, and before the dust had fully settled from the shell burst.