A series of successful raids by Commandos and partisans hurt the Germans, and in May 1944, a more ambitious attack by British and Yugoslav personnel was planned on the German-held Yugoslav island of Brac. It was here that Jack Churchill’s amazing luck at last ran out. The operation required attacks on three separate hilltop positions, dug in, mutually supporting, protected by wire and mines, and covered by artillery. Several Allied forces would have to work in cooperation. One of these, a reinforced Commando unit plus a large contingent of partisans, Jack Churchill would lead himself.
While partisan attacks on the main German position got nowhere, 43 (Royal Marine) Commando went to the attack on the vital hill called Point 622. Pushing ahead in clear moonlight through wire and minefields, 43 Commando carried the hilltop but was forced to fall back with heavy casualties. Churchill now sent 40 Commando—also Royal Marines—in against the hill, and led them himself, playing the pipes. The leading troop went in yelling, shooting from the hip, and overran the German positions on 622.
But between casualties on the way up the hill and more casualties from very heavy German fire on the top, Churchill quickly found himself isolated with only a handful of defenders around him. There were only six Commandos on the hilltop, and three of those were wounded, two of them very badly. “I was distressed,” said Churchill with memorable understatement, “to find that everyone was armed with revolvers except myself, who had an American carbine.”
Still, the little party fought on until the revolver ammunition was gone and Churchill was down to a single magazine for his carbine. A German mortar round killed three of his little party and wounded still another, leaving Churchill as the only unwounded defender on the hilltop. It was the end. Churchill turned to his pipes, playing “Will ye no come back again” until German grenades burst in his position and he was stunned by a fragment from one of them. He regained consciousness to discover German soldiers “prodding us, apparently to discover who was alive.”
Long after the end of the war, Churchill was pleased to hear that the German account of the fighting for the hill described his lonely piping as “the doleful sound of an unknown musical instrument.”
Jack Churchill would play his pipes one more time, at the funeral of 14 Commandos who died on the slopes of Hill 622. He and his surviving men escaped killing by the Gestapo under Hitler’s foul “commando order” through the chivalry of one Captain Thuener of the Wehrmacht. “You are a soldier, as I am,” the captain told Churchill. “I refuse to allow these civilian butchers to deal with you. I shall say nothing of having received this order.” After the war, Churchill was able to personally thank Thuener for his decency and to help him stay out of the merciless hands of the Russians.
Churchill was flown to Sarajevo and then on to Berlin, there apparently being some thought that he was a relative of Winston Churchill. There is also a story that on leaving the aircraft, he left behind a burning match or candle in a pile of paper, producing a fire and considerable confusion. During the inquiry that followed, Churchill innocently told a furious Luftwaffe officer that the army officer escorting Churchill had been smoking and reading the paper on board the aircraft.
Churchill spent some time in solitary confinement, and in time he ended up in Sachsenhausen concentration camp. That infamous prison was only one more challenge to Churchill, however, and in September 1944, he and an RAF officer crawled under the wire through an abandoned drain and set out to walk to the Baltic coast. Their luck was not in, however, and they were recaptured near the coastal city of Rostock, only a few miles from the sea. In time, they were moved to a camp at Niederdorf, Austria.
Here, Churchill watched for another opportunity to escape, keeping a small rusty can and some onions hidden in his jacket in case a sudden opportunity should present itself. On an April night in 1945, it did. The chance came when the camp’s lighting system failed. Churchill seized the moment and walked away from a work detail, disappearing into the darkness and heading for the Alps and the Italian frontier. Liberating vegetables from Austrian gardens and cooking them in his tin can, he walked steadily south. Keeping off the roads, he crossed the Brenner Pass into Italy and headed for Verona, some 150 miles away.
On the eighth day of his escape, hobbling along on a sprained ankle, Churchill caught sight of a column of armored vehicles. To his delight, their hulls carried the unmistakable white star of the United States Army. He managed to flag down one vehicle and persuade the crew that in spite of his scruffy appearance he was indeed a British colonel. As he later told his old friend and biographer, Rex King-Clark, “I couldn’t walk very well and was so out of breath I could scarcely talk, but I still managed a credible Sandhurst salute, which may have done the trick.”
Churchill was free but frustrated. The European war was almost over, and he had missed much of it, including the chance for further promotion and perhaps the opportunity to lead a Commando brigade. Nevertheless, hope sprang eternal. “However,” he said to friends, “there are still the Nips, aren’t there?”
There were. And so Churchill was off to Burma, where the largest land war against Japan was still raging. Here, too, however, he met frustration, for by the time he reached India, Hiroshima and Nagasaki had disappeared in mushroom clouds, and the war abruptly ended. For a warrior like Churchill, the end of the fighting was bittersweet. “You know,” he said to a friend only half joking, “if it hadn’t been for those damned Yanks we could have kept the war going for another 10 years.”
The abrupt departure of Japan from the war was a distinct disappointment to Churchill, especially since he had risen to command of a Commando brigade in the Far East. Still, there were other brushfire wars still smoldering, and in November 1945, he reported home from Hong Kong, “As the Nips have double-crossed me by packing up, I’m about to join the team v the Indonesians,” who were by then casting covetous eyes on Sarawak, Borneo, and Brunei. British and Commonwealth troops killed or expelled the invaders, but Jack missed this little war as well.
By the next year, he had transferred to the Seaforth Highlanders and was looking forward to jump school, where, at 40, he qualified as a paratrooper. He took a little time off in 1946, this time for the movies. Twentieth Century Fox was making Ivanhoe with Churchill’s old rowing companion Robert Taylor and wanted him to appear as an archer, firing from the wall of Warwick Castle. Churchill took the assignment, flown off to the job in an aircraft provided by the movie company.
Though Jack Churchill might have thought that he was through with war, he was not. After World War II ended, he qualified as a parachutist, transferred to the Seaforth Highlanders, and later ended up in Palestine as second-in-command of 1st Battalion, the Highland Light Infantry. And it was there, in the spring of 1948, just before the end of the British mandate over that troubled land, that he again risked his life for other people.
Those were dangerous days, with much blood—Jewish, Arab and British—shed by Arab terrorists and by Jewish radicals, notably the so-called Stern Gang. On a day in May a Jewish medical convoy—ambulances, trucks, and buses—was ambushed by Arabs on a narrow street in Jerusalem, not far from a small HLI detachment at a place called Tony’s Post. Churchill rushed to the site in a Dingo, a small armored car. This one had its turret removed for repair, but it gave him a semblance of protection at least.
Accurately assessing the potential for mass murder by the Arab terrorists, he radioed for two Staghounds, heavy cannon-armed armored cars, and these were diverted from convoy protection and dispatched to him. It would take time for the armored cars to reach him, however, and while they were on their way, Churchill acted. He drove down to the beleaguered convoy in a large armored personnel carrier covered by the only escort available, an open-topped Bren gun carrier and a small police armored car armed with a machine gun. Leaving his tiny convoy and swinging a walking stick, he walked calmly into the open and down the road to the convoy.
Marching into the teeth of the battle around the convoy, he must have been quite a sight. Since he had just come from a battalion parade, he was resplendent in full dress: kilt, glengarry bonnet, red-and-white diced stockings, Sam Browne belt, and white spats. And as usual he later made light of this extraordinary cold courage: “I grinned like mad from side to side,” he said afterward, “as people are less likely to shoot at you if you smile at them … [that] outfit in the middle of the battle, together with my grinning at them, may have made the Arabs laugh because most of them have a sense of humor. Anyway, they didn’t shoot me!”
Churchill spoke to the occupants of one bus and offered to drive his big armored personnel carrier down to the convoy and make as many trips as necessary to evacuate the patients and their medical personnel. He warned those at the convoy that there might be casualties when they moved to the British vehicle, and one of the Jews asked whether he would not first drive off the Arabs. He patiently explained that he could not; there were hundreds of Arabs and he had only 12 men.
After a discussion with one of the doctors, as Churchill stood in the open, his offer was refused. “Thank you very much but we do not want your help. The Haganah (the Jewish defense force) will save us.” Churchill walked down the convoy repeating his offer, but was uniformly refused. By now one of Churchill’s men had been mortally wounded, and he ran back to his vehicles and sent them out of harm’s way. Returning to Tony’s Post, he supported the Jewish convoy with small arms fire until Arab gasoline bombs and rifle fire destroyed the Jewish vehicles and most of their passengers. The Haganah had not arrived to save them after all, and 77 Jews died in the narrow street.
Later, Churchill engineered the evacuation of some 700 Jews—patients, staff, and students—from the university and hospital atop Jerusalem’s Mount Scopus. Churchill made an early run up Scopus in his jeep accompanied by Eli Davis, the deputy medical director of the hospital.
Here is how Davis later told the story: “Major Churchill told me there was slight chance of getting through … because the Arabs saw the British meant business. He agreed to make the trip up to Scopus and invited me along. The Major took a Jeep and his driver. I sat while he stood in the Jeep twirling his stick. He looked as though he were on parade in London…”
Jack Churchill never changed, never lost his flair for the unusual, not to say the flamboyant. In his later years, passengers on a London commuter train were often startled by seeing an older male passenger rise, open a window, and hurl his briefcase out into the night. The passenger would then leave the car and wait by the train’s door until it stopped at the next station. It was Churchill, of course, enjoying his little gesture and reasonably sure that his fellow passengers could not know he had thrown the case into the garden of his house. It saved him carrying it home from the station.
Who were the badasses of history you haven't heard of?
Check out our all-time list of
The Men & Women Who Turned the Tide of War
In later years, Churchill served as an instructor at the land-air warfare school in Australia, where he became a passionate devotee of the surfboard. Back in England, he was the first man to ride the Severn River’s five-foot tidal bore and designed his own board. He finally retired from the army, with two awards of the Distinguished Service Order, in 1959. He went right on working, now as a Ministry of Defense civilian overseeing the training of Cadet Force youngsters in the London District. One of his old friends wrote later that Churchill liked the job not only because of his association with the enthusiastic cadets, but also because the job gave him an office in Horse Guards at Whitehall, and a window from which he could watch troopers of the Household Cavalry mounting guard in a courtyard below him. He was older now, but still the warrior.
Churchill and his wife Rosamund could spend more time together now, and they used part of it sailing coal-fired steam launches on the Thames River between Oxford and Richmond, Churchill decked out in an impeccable yachting cap and Rosamund giving appropriate sailing orders to her husband. Churchill was also well known for his intricate and accurate radio-controlled models of ships, mostly warships of course, all so carefully engineered and built that they were much sought after by collectors.
Churchill passed away peacefully at his home in Surrey in the spring of 1996, but he left a legacy of daring that survives to this day. One respected publication dealing with the Commandos features large color drawings of Commando uniforms, insignia, and weaponry—and one of the illustrations is of Mad Jack Churchill, complete with claymore.
Jack Churchill was one of that rare and happy breed for whom war is their element. That does not mean that he did not hate the suffering that war caused; it was simply that he thrived on the excitement and relished the chance to achieve and excel. His whole philosophy was pretty well summed up by a couplet he scribbled on a postcard he sent to a friend, a card whose face bore the regimental colors: “No Prince or Lord has tomb so proud / As he whose flag becomes his shroud.”
He might have been describing himself.
Below, the fox terrier ‘Salvo’ prepares for a drop over England. Military dogs played a key role in morale and companionship throughout the war.
Thanks to technological advances and local help, a Wehrmacht Pioneer was finally located and laid to rest years after Operation Barbarossa.
Emperor Julian ‘The Apostate’ sought to emulate Alexander the Great’s conquest of Persia, but Shapur II’s Savaran cavalry proved his undoing.