The citation for his second MC stated: “Lieutenant Garland displayed throughout the action cool and clear-headed leadership and complete disregard for his own personal safety.”
Transferring to the RAF in 1942, after which he was always known 
as “Judy”, Garland trained as a pilot in Southern Rhodesia alongside the future Rhodesian leader Ian Smith, gaining his wings in August 1942. In May 1943 he joined 208 Squadron equipped with Hurricanes and resting in Iraq after arduous fighting in the North African desert campaign. After moving to Syria, the squadron re-equipped, with Spitfires, and in March 1944 landed in Italy.
On May 4 1944 Garland, now one of the two flight commanders, was shot down by anti-aircraft fire over the Cassino battle area. He was seriously wounded in the leg and suffered burns to his hands and face as he baled out of his burning Spitfire. A squadron pilot saw him parachute behind enemy lines, where he was taken prisoner by waiting German soldiers. They took him to see his aircraft, which had exploded in a farmyard, injuring the farmer. “He was crying,” Garland recalled, “and one of the German soldiers and I grinned at each other over this rather weak behaviour.”
His adjutant wrote: “His loss is keenly felt but we firmly believe that he is safe and that if there is a chance to escape, Judy Garland will do so.” He was correct, but it would be a year before there was any news of him. In the meantime, his father was informed that his son was to be declared dead.
Despite his wounds, Garland made several attempts to escape. Twice he was caught while climbing through a window. The third time, after sliding down a laundry chute, he was captured while trying to saw through a door. He succeeded at the fourth attempt on June 17 1944 after jumping from the window of a hospital train taking him to a PoW camp in Germany.
He headed south, often sleeping rough and sometimes taking refuge with friendly Italian families. In August, while he was attempting to walk from Lake Garda to Cremona, the wound in his injured leg became infected and he had to abort the plan and spend 60 days hiding in a false wall at the end of a barn while his injuries healed. He then continued his journey south and joined the partisans taking part in a major action at Vasto di Sotto in which 78 German soldiers were killed or captured. He continued to fight with the partisans until April when he crossed the lines in the Po valley and met up with US forces.
There were great celebrations on May 4 when he rejoined 208 Squadron having fulfilled the adjutant’s forecast. Soon afterwards he returned to Britain, where he received further treatment for his injuries.
