Share This Article

Everyone loves a great escape. In the civilian world even the nastiest criminal gets our grudging respect for busting out. And prisoners of war, enemies as well as allies, are doubly admired for seeking freedom. After all, it’s their job: To escape is part of the devotion to duty that got them captured in the first place.

A true warrior never gives up, seeing imprisonment as a challenge that can drive him to seemingly impossible achievements—like those described in the following escape accounts.

Some escapes have become legendary despite being failures. The renowned World War II “Great Escape” from Stalag Luft III, immortalized in the eponymous 1963 film, actually resulted in the brutal execution of 50 of the 76 escapees, 73 of whom were recaptured. Other famous “escapes” turn out to be fiction. Some may wonder why we have ignored the 4,000-mile Gulag-escapee trek across Siberia, the Gobi Desert and the Himalayas immortalized in the book The Long Walk (1955) and the recent film The Way Back (2010). Why did we? Because contemporary research suggests it never happened.

As ex-Army Ranger and helicopter pilot Kris Kristofferson famously wrote and sang, “Freedom’s just another word for nothin’ left to lose.” Though he certainly didn’t have POWs in mind, that timeless line could be the escapee’s anthem: If all you have to look forward to is beatings, hunger, loneliness and possible execution, what’s to lose by trying to escape?

1. Libby Prison

During the Civil War, Confederate forces sent Union officers and enlisted men to separate jails, feeling that officers might incite the ranks to all manner of malfeasance. But this practice meant that Libby Prison, a large officers’ pen in Richmond, Va., at any one time found itself with 1,200 very smart guys as inmates, ranging from lieutenants to colonels (and one general), most of whom had recently been civilian doctors, lawyers, professors, engineers and others with a wide range of smarts. Ideal escape artists.

By early 1864 a well-developed protocol for prisoner exchanges had broken down, and the Libby inmates were suddenly looking at incarceration for the duration rather than repatriation. Now they seriously wanted out.

Built in the 1840s as warehouse space, Libby took its name from ship chandler Luther Libby, who leased the building in 1861. The Confederates seized the warehouse, barred its windows, whitewashed the lower exterior walls to make easy targets of potential escapees and stationed a few guards. Over a period of 57 days rotating teams of Union officers dug four tunnels, three of which had to be abandoned when they hit obstacles. The fourth led into a tobacco shed across the street from the prison, and on the night of Feb. 9–10, 1864, 109 Union officers scrambled through it, brushed the dirt off their blue greatcoats and in groups of two and three strolled out onto the street. (A Southern soldier wearing a Union overcoat was a common sight, as the garment was greatly preferred to its Confederate equivalent.) Fifty-nine of the officers made it back to Union lines in one of the largest prison breaks ever staged.

The escapees’ success is attributable in part to their guards’ ineptitude. Sentries outside the prison paced in one direction, then wheeled and paced the other way, making it easy to determine when their backs would be turned. And at daily roll call leading up to the escape, Union officers had surreptitiously switched positions, ensuring the call would tally with the correct prisoner count, even though four or five of them were always down in the cellar digging.

2. Winnie the POW

It’s hard to imagine him as a gun-toting guerrilla fighter—the chubby, brandy-loving, stogie-smoking Winston Churchill the public admired during World War II and the 1950s— but that role is exactly what got him into a pickle during the Boer War. Churchill went to South Africa as a war correspondent, stringing for two British newspapers. That didn’t prevent him from packing heat—a broomhandle Mauser pistol. In November 1899 Churchill was aboard an armored train carrying 120 British soldiers when the locomotive struck a barricade of stones, and a force of several hundred Boers ambushed the train. Leaving his Mauser on the locomotive, Churchill directed the clearing of the tracks under fire and helped tend to the wounded.

The Boers soon subdued and captured the Brits, including Churchill. But on his second night in a Pretoria prison he scaled a latrine wall and dropped into a darkened garden—and was out. Freedom lay nearly 300 miles away in neutral Portuguese East Africa. Churchill hopped a freight train that first night, bailing out when daylight came. The alarm had been raised, and every Afrikaner in the area was looking for an “Englishman [who] speaks through his nose and cannot pronounce the letter S.”

Churchill fled on foot for two days, sheltered in a friendly Englishman’s coal mine for three more and finally boarded a freight train headed into Portuguese territory. Hidden under bales of wool, he escaped detection by a Boer search party. Once Churchill reached safety in Portuguese East Africa, he immediately issued the 19th-century equivalent of a press release about his adventure and thus set aflow the tide of history that would, in another 40 years, make him the most famous Englishman in the world.

3. The Tunnelers of Holzminden

On the night of July 24–25, 1918, 29 British and Australian officers in the reviled German Holzminden POW camp slipped down a substantial tunnel—180 feet long, six feet high in places—beneath the wire and back up into a bean field, making good their escape. The Germans eventually recaptured 19 of the escapees, but 10 made it back to England.

Thirteen men had excavated the tunnel over a period of nine months, working in rotating teams of three: one man to dig, another to ferry out the dirt and the third to work the bellows of an artfully crafted air pump to keep the digger alive. These men kept the tunnel a secret from other prisoners till the night of the escape. Only then, after the 13 had crawled out and been given an hour of getaway time, was the tunnel opened to others willing to try their luck. Seventy-five of the 550 officers in the prison lined up in order of rank and importance, but by the time another 16 men had clawed their way out, rubble blocked the tunnel.

Two things had distinguished Holzminden: The Germans had assumed it to be escape-proof, and overseeing the camp was an especially arrogant, vicious and vindictive commandant, Hauptmann Karl Niemeyer. The Allies considered Holzminden the worst POW facility in Germany, and the officers dug the tunnel probably as much to humiliate Niemeyer as to attain freedom.

4. Catch Me If You Can

During World War II Luftwaffe Hauptmann Franz von Werra was a cocky Messerschmitt Bf 109 pilot who played Berlin’s PR network like a tin drum: While other pilots had dogs as mascots, von Werra had a lion cub, and the newspapers loved it. But by far his finest stunt was evading British and Canadian pursuers to become the only German prisoner of the empire to successfully make it back to his unit.

Shot down in September 1940 during the Battle of Britain, von Werra slipped away from a group of detainees during an exercise walk a month later and managed to evade British soldiers, police and the Home Guard for six days before being caught (two Home Guardsmen had collared him on the fourth day, but von Werra had overpowered them and run off). Then he got serious. Von Werra and four other Luftwaffe pilots spent a month digging a tunnel and fled from another prison camp one December night.

Von Werra split off on his own and by morning had found his way to an RAF base, where he claimed to be a Dutch pilot attached to Coastal Command. He had crash-landed his Wellington bomber the night before, he explained, and needed to get back to his station. He was sitting in the cockpit of a Hurricane fighter, within seconds of lighting off its Merlin engine, when caught a second time.

Apparently having had enough of the troublesome young German, the British sent him to Canada, figuring an ocean would keep him at bay. Fat chance. Von Werra dove from a window of the train transferring prisoners from Montreal to an Ontario POW camp, fled into the frigid dark and crossed the iced-over St. Lawrence River to Ogdensburg, N.Y., where he turned himself in to police.

In early 1941 the United States remained neutral, so the German embassy was able to contest von Werra’s extradition back to Canada. After spending several weeks sampling Manhattan nightlife as hero fighter pilot “Baron von Werra,” he crossed on foot into Mexico with phony documents and made his way via Panama, Peru, Bolivia, Brazil, Spain and Italy back to Germany, where his insights into sophisticated British prisoner-interrogation techniques proved valuable.

5. Sledge Patrol

Ib Poulsen, a young Dane, was the highest-ranking officer in the world’s smallest armed force. He was the only captain in the Northeast Greenland Sledge Patrol, a cadre of 15 Scandinavians and their Inuit guides tasked with patrolling 500 miles of coastal Greenland aboard dogsleds. They were to look for Germans intent on setting up weather stations to broadcast observations crucial to U-boats and long-range Luftwaffe aircraft tracking Russia-bound convoys.

On March 23, 1943, they found such intruders—or rather, the Germans found them. After a brief nighttime firefight between 19 Wehrmacht troopers armed with submachine guns and grenades and three Sledge Patrolmen with single-shot hunting rifles, Poulsen became separated from the others. It was 50 below, and having lost his dogs, sledge, rifle, boots, winter gear and food, the Dane had a choice: Surrender or walk 230 miles to the nearest Allied station, from which he could put out an alert the Germans had landed.

Poulsen chose to walk. He scrounged in abandoned huts along his route, finding blanket scraps, clothing odds and ends, frozen beans, an old rifle and a pair of battered skis useful only as a drag-sled. With these crude supplies he risked a journey no native Greenlander had ever attempted, much less survived. The trek ultimately took 11 days, and when he reached the station, he learned that one of his mates had already transmitted an emergency radio broadcast about the Germans.

By October 1944 a rapidly recovered Poulsen and his Northeast Greenland Sledge Patrol had so thoroughly harried the Germans, even managing to capture of one of their commanders, that the intruders left the icy subcontinent, most of them as U.S. prisoners. And the Allies ultimately used observations from Greenland to launch the Normandy Invasion in what turned out to be a tiny window of acceptable weather.

Author David Howarth recounted Poulsen’s feat in his 1957 book The Sledge Patrol: A WWII Epic of Escape, Survival and Victory.

6. No Picnic

Felice Benuzzi was an Italian consul stationed in Ethiopia when World War II began. In 1941 the British sent him and hundreds of other expats to a prison camp within sight of 17,057-foot Mount Kenya. There was no way to escape Africa—it was too big, trackless and alien—but escaping the loosely guarded camp was possible, even if only temporarily. Benuzzi, who had grown up mountaineering in the Italian Alps, became obsessed with the idea of climbing the mountain that every day lurked as a backdrop to his daily tedium.

He found two accomplices, and over six months they slowly collected coldweather gear and food and fashioned ice axes and crampons from camp scrap. “We are leaving the camp and reckon to be back within 14 days,” read the polite letter they left for the liaison officer of the Italian compound on Jan. 24, 1942. They had underestimated their sabbatical by just four days.

Reaching the mountain meant first evading all the Kenyans who’d have happily turned them in for a 10-shilling reward, then making it through a forest filled with big game that presented a very real risk to three unarmed men. The hike up the mountain took the three into bitter cold, and the summit attempt was an exercise in technical climbing, using a questionable belaying rope made from prison bedframe springing.

Beaten back by a sudden blizzard, the trio failed to make it up the highest of the three peaks atop Mt. Kenya, but two of them managed to summit the third-highest and there erected an Italian flag. Then Benuzzi and his climbing cohorts did indeed return to the prison camp, where they were sentenced to 28 days of solitary confinement—a sentence commuted to seven days by the British camp commandant, who admired their “sporting effort.” Benuzzi’s memoir about the experience, No Picnic on Mount Kenya (1953), remains in print and is considered required reading for any serious climber.

7. Pacific Odyssey

Neither Army Air Forces Lieutenant Damon Gause nor Army Captain William Osborne had any nautical skills, yet they fled from the Philippines in 1942 by sailing some 3,200 miles over 59 days to Australia, an interisland voyage through the Sulu, Celebes and Java seas that would have taxed a master mariner. Their vessel was a leaky, 20-foot castoff fishing skiff with a small diesel engine they often had to fuel with coconut oil. Navigation gear? A small hand compass and an old National Geographic map of the Far East. Food and water? Whatever they could find or scrounge from islanders en route.

Gause was a pilot, but since there wasn’t a flyable U.S. airplane in the Philippines after Dec. 7, 1941, he became an instant infantryman. Captured when Bataan fell, he joined the infamous Death March but escaped by killing a Japanese guard with the soldier’s own knife and then swimming the 3 miles to Corregidor. When that fortress fell, he pushed off for the mainland in an outrigger canoe. Washed up on a beach after the canoe sank, Gause again escaped death when a Japanese patrol kicked his semiconscious form and decided he was dead. The charmed airman eventually made his way to the island of Mindoro, where he met Osborne, another Bataan escapee.

Though Osborne outranked Gause, he recognized the lieutenant’s abilities and put him in charge of their escape. Having found the fishing skiff, they erected a crude tree-trunk mast, fashioned a sail from flour sacks and shoved off. Gause guided the skiff through a typhoon, encounters with Japanese ships and a submarine, and a strafing attack that wounded Osborne. Challenged one night by a Japanese patrol boat that blinkered an incomprehensible Morse message, the cunning Gause flashed back “Banzai Nihon!” (“Long Live Japan!”), the only Japanese words he knew, and got away with it.

Gause ultimately got to fly again but was killed in March 1944 during dive-testing of a P-47 over England. Gause wrote of his experiences in the short but evocative book The War Journal of Major Damon “Rocky” Gause.

8. Longest Walk

In May 1940 German airborne Oberleutnant Cornelius Rost had jumped onto Belgium’s famed Fort Eben-Emael in one of Germany’s most stunning early victories. But in 1944 he was captured deep inside Russia, sentenced to 25 years hard labor and imprisoned in a Siberian lead mine with thousands of other German prisoners. In October 1949, with the help of a fellow German serving as camp doctor, he escaped and trekked nearly 7,000 miles to Iran by walking, hitchhiking, hopping trains and riding everything from dogsleds to river rafts. It remains history’s longest recorded escape-and-evasion mission. (Some accounts record the distance as 8,800 miles, but that includes the final leg by air from Tehran to Munich, done in freedom.)

Although the basic story is indisputably true—Rost did escape to freedom through some of the harshest terrain and weather in the Northern Hemisphere—the specifics will never be known. In the early 1950s German writer Josef Bauer extensively interviewed Rost and turned his story into As Far As My Feet Will Carry Me, a quasi-novel taken to heart by a country desperate for stories of stubborn victory amid defeat. The book also became a popular German TV miniseries and, in 2001, a big-budget feature film. But the tale of “Clemens Forell” (Rost reportedly so feared Soviet KGB retribution, even in the West, that he insisted on cloaking his identity) today bears little relation to reality.

Rost died in 1983, a broken man crippled by the lead poisoning he’d endured in the Siberian mine, and the details of his real story died with him.

9. Escape From Laos

Dieter Dengler first honed his survival skills in 1944, at age 6, when his tiny Black Forest village became a target of U.S. fighter-bombers. His mother told him he needed to learn to live in the woods on his own, if it came to that. So he did.

A penniless Dengler came to America in 1957. Surviving by his wits and charm, he became a citizen, attended college and was accepted into a Navy flight-training program. When he earned his wings, Dengler chose not jets but the enormous old Douglas A-1 Skyraider, as it reminded him of the P-47s that had stirred his interest in aviation 20 years earlier. Dengler was already famous in the naval-aviator clique for having aced all three of the weeklong escape-and-evasion exercises thrown at him during training; nobody but Dengler ever consistently beat the Marine instructors.

He would need all his survival skills after being shot down during his first combat mission in 1966. Dengler survived his crash landing in Laos uninjured, was briefly captured by the Pathet Lao, but escaped again. Recaptured, he was tortured before being turned over to the North Vietnamese and imprisoned in a remote POW camp in South Vietnam with Army helicopter pilot Duane Martin and five Air America crewmen.

All seven escaped after seizing the guards’ weapons and killing several of them. Dengler and Martin struck out together through as hostile a jungle as existed anywhere. A machete-wielding villager killed Martin, but Dengler endured 23 days of eating insects and potentially poisonous vegetation before finally managing to signal a passing fellow Skyraider pilot. The ensuing rescue almost never happened: Those in charge of approving such a multiplane mission said they had no record of a downed U.S. airman in the area. Dengler is often reported as the only American ever to escape the North Vietnamese. In fact 33 did, all from camps south of the DMZ (as was Dengler’s) or in Laos.

Dengler’s story, somewhat fictionalized and embellished, is the subject of the 2007 Werner Herzog film Rescue Dawn. Dengler himself committed suicide in February 2001 rather than give in to the ravages of ALS (aka Lou Gehrig’s disease) that had wasted his body far more thoroughly than a Vietnamese jungle ever did.

10. The Maze Prison Escape

On Sept. 25, 1983, 38 members of the Irish Republican Army escaped from Northern Ireland’s Maze Prison in a caper that could well have furnished the plot for an Ocean’s 11 film. The Maze was a group of separate walled cellblocks within a walled prison, all contained within a British army base. The prisoners pulled off the escape largely with military precision, utilizing good intelligence, psychology and tight timing, and took advantage of the fact that one of the most escapeproof, technologically advanced prisons in all of Europe was staffed by complacent guards.

The IRA plotters began their breakout by befriending their guards through unfailing politeness, even delivering their tea and biscuits. Accustomed to having obsequious wards wandering around their central guardroom in H-Block 7, the guards left the door wide open, as the room had no air conditioning. When the time came for the prisoners to overpower the guards, using six pistols smuggled in by the IRA, they had practiced the theatrics of the takeover for maximum effect; none of the guards was left with the slightest doubt he’d be killed if he dared not cooperate. Wearing uniforms stripped from the guards, the prisoners rounded up more “screws” and soon controlled the entire cellblock—without raising an alarm.

The next component of the break was a box truck that made a daily round of the prison, delivering food and supplies. It had become such a routine sight that security was nonexistent. The escapees quickly hijacked it, tied the driver’s foot to the clutch and had one plotter lie on the floor of the cab, pistol cocked and pointed at the driver. They then loaded the truck with the other 37 prisoners.

Despite resistance from several guards, who delayed the escapees while other guards blocked the main gate with their cars, the response to the breakout was so inept that all 38 escapees were able to flee on foot. British officials recaptured 19 escapees within two days, but an equal number reached IRA safe houses. The Thatcher government was mortified, and ultimately the PR benefit of the breakout was vastly greater for the IRA than had the prisoners been pardoned and released.

Irish republicans still call it “the Great Escape.”