7 Most Audacious Prisoners Escapes in History

Smalls Escaped Slavery

Robert Smalls was a slave, and a skilled sailor in May, 1862. The son of a slave mother and a white father, he was only 22 when he planned his daring escape. The Union Blockade had, for some months, been accepting runaway slaves, so Smalls knew he only had to reach the Union ships. He had already decided that he would not be retaken alive, planning to fight and sink the ship if his plan failed.

He served as part of a slave crew on a ship, the C.S.S. Planter, with only a white captain and two white mates. On May 13, 1862, the Captain and two mates were off the ship. Smalls and the other members of the crew sailed the heavily armed cotton steamer out of the Charleston dock, and stopped to pick up waiting family members at a pre-set rendezvous point. Smalls, wearing the Captain’s wide-brimmed hat, navigated the ship out of Charleston Harbor. Smalls’ resemblance to the Captain in build and features had been noted, and likely helped his disguise. The ship crossed Confederate waters, with Smalls giving the correct coded signals at various checkpoints, including Fort Sumter. It was only after the C.S.S. Planter was out of range of rebel guns that forces at Fort Sumter realized that all was not well.

In less than four hours, Smalls and his crew reached the Union Blockade. They raised a white flag of surrender, a bedsheet brought on board by Smalls’ wife. He had brought 17 others, including nine men, five women, and three children with him to freedom. Eight of those were members of the original slave crew. Smalls wife and children were among those he rescued.

As the first Union ship reached the C.S.S. Planter, Smalls stepped forward and said, according to eyewitnesses, “Good morning, sir! I’ve brought you some of the old United States guns, sir!”.

Following their escape, Smalls and his crew received half of the value of the Planter from the U.S. Congress. During the war, Smalls served the Union. Smalls went on, after the war, to purchase his owner’s old home, and to serve in the South Carolina Assembly and Senate, and then in the U.S. House of Representatives.

Frank Morris and the Anglin Brothers

There has, in the history of the Federal Penitentiary at Alcatraz, been only one successful escape, in June 1962. Even the success of that escape is questionable—even today, no one knows if the three men made it from the prison to land, or if they drowned on their journey. With that, here’s what is known about the escape of Frank Morris, Clarence Anglin, and John Anglin.

The Anglin brothers were bank robbers; however, they chose targets that were closed, and did not use weapons in their crimes. They did, on the other hand, try very hard to escape from prison. The two men were both skilled swimmers, and accustomed to swimming in very cold waters.

Frank Morris began a life of crime while still in his early teens. He was most notable for his intellect, being exceptionally gifted.

Morris and the Anglin brothers planned their escape with a fourth man, Allen West. West was unable to remove the ventilation grill in his cell to join the others, and cooperated with investigating authorities.

The four men, using a plan crafted by Morris, had adjoining cells. Each worked to increase the size of the ventilation opening in his cell. These ventilation openings led to an unused utility corridor. They carefully worked to conceal their work, and used a variety of found objects to widen the corridors. In addition, they crafted papier-mache heads to hide their efforts, using a mixture of soap and toilet paper, painted with paint from the workshops, and with hair from the barbershop floor.

On June 11, 1962, the three men climbed through the ventilation holes into the service corridor, then up a ventilation shaft to the roof of the prison. They slid down a kitchen vent pipe, and climbed two 12-foot barbed wire fences. They reached a hidden spot on the coastline and inflated a raft, setting out for Angel Island. A widespread search provided no definitive answers as to the fate of the three men, but various individuals have claimed to have seen them and had contact with them in the years following their escape from Alcatraz. The U.S. Marshals have kept the three escapees on their “Most Wanted” list.

Henry “Box” Brown

Henry “Box” Brown was born into slavery around 1815, and by the late 1840s was working, as a slave, in a tobacco factory. His wife, then pregnant with their fourth child, was sold away from him in 1848. He was helpless to save his family, and resolved, after some months of grief, to escape.

Brown had more freedom than many slaves, and was a member of the First African Baptist Church, bringing him into contact with a number of free blacks. With help from friends in his church, white sympathizers and abolitionists, Brown crafted a plan—he would ship himself to freedom in a box sent from Richmond, Virginia to Philadelphia, Pennsylvania.

A white sympathizer, Samuel Allen Smith, helped to pack Henry Brown into his box, labeled “dry goods” for shipping. The box measured only three feet long by two feet wide, and two feet, 8 inches deep. The box was lined with coarse wool cloth. Brown carried only a small bladder of water and a few biscuits for his journey. The box was nailed shut and secured with strapping, then marked with “This Side Up”.

After 27 hours, including several spent miserably upside-down, Brown reached Philadelphia and the box was delivered to the Philadelphia Anti-Slavery Society. Upon being freed, Brown greeted the men, and recited a Psalm. They dubbed him Henry “Box” Brown for his successful journey to freedom.

Samuel Allen Smith attempted to ship other slaves to freedom; however, these attempts failed and Smith was jailed. After the passage of the Fugitive Slave Act, Brown sailed to England, and worked as a magician, employing his box in his act.

Treblinka Death Camp Revolt

Treblinka II was a Nazi death camp, in operation from July 1942 to October 1943. As part of the Final Solution, the camp, built during Operation Reinhard, was responsible for the deaths of some 700,000 to 900,000 Jews in the 14 months it was in operation. Unlike some camps, Treblinka II was not a labor camp—it maintained only a small group of forced laborers to handle body disposal, called the Sonderkommandos.

By 1943, the Germans were suffering increasing losses, and Jewish workers at Treblinka began to organize, forming the Organizing Committee. While they suffered some significant losses, including the capture and suicide of one of their leader, by August they had a copy of the key to the weapons room at Treblinka, and had learned of the revolt in the Warsaw ghetto. They believed the camp was likely to be liquidated in the near future, so the brave revolt offered a sole chance for survival.

The revolt at Treblinka took place on August 2, 1943. In total, some 300 men were involved in the revolt at Treblinka. With the key to the weapons room, the prisoners had access to weapons. They were able to kill some members of the SS in private workshops at the camp, before seizing machine guns and beginning a massive assault on the German and Ukranian camp guards. Some buildings were set on fire, and they continued the fight to allow as many prisoners as possible to escape. Three hundred men got away from the camp in the revolt.

The SS immediately began hunting the escaped prisoners. Of the 300 that escaped, around 100 men survived Treblinka. These are the only survivors of the Treblinka death camp. The recaptured prisoners were forced to aid in the dismantling of the camp, then shot. The survivors of Treblinka provided key evidence about the camp, particularly Jankiel Wiernik, who took shelter with a Pole and later published his account of the revolt.

Stalag Luft III: the Pommel Horse, and the Great Escape

Stalag Luft III was a Nazi prison camp for Allied prisoners-of-war. Unlike Colditz, Stalag Luft III had a lower proportion of guards to prisoners; however, it had a clear drawback for those hoping to escape. The dirt at Stalag Luft was quite unusual, with a gray dusty surface and yellow subsoil. Tunneling of any sort would soon become obvious to the guards, making escape more difficult.

A small group of British POWs, Lieutenant Michael Codner, Flight Lieutenant Eric Williams, and Flight Lieutenant Oliver Philpot, found a creative solution, and dug their tunnel to freedom. The prisoners constructed a large pommel horse, a piece of gymnastics equipment, from the plywood used for Red Cross packages. The pommel horse was large enough to hold both dirt and men. Each day the men carried the pommel horse to a spot near the fence. There, they practiced gymnastics, while men worked under the pommel horse, digging an escape tunnel. The sound of the gymnastics practice provided coverage for the noise of digging. Over time, the three men completed their tunnel, and all were successfully able to escape in October 1943 and be repatriated to Britain.

In another daring escape, Squadron Leader Roger Bushell made a plan to get 200 inmates out of Stalag Luft III. Bushell didn’t plan to dig one tunnel for a few men, but three tunnels, called Tom, Dick and Harry, to provide a route to freedom for a large number of POWs. He also believed that if one tunnel was found, the remaining two tunnels would remain, as it was unlikely the Germans would imagine the creation of multiple tunnels. More than 600 prisoners were involved in the creation of these three tunnels. These were not just simple tunnels, but even had ventilation systems, lights and small rail cars to remove soil. The men created a number of ways to release the excavated sand onto the ground without attracting notice. Eventually, “Dick” was filled in and used for storage, as a change to the structure of the camp made it otherwise unusable. “Tom” was discovered late in 1943 by the Germans.

“Harry” was complete in March of 1944. Originally, the escape had been planned for summer, but the deadline was moved up due to increased SS activity. On March 24, 1944, 76 men escaped through Harry; all were prior escapees, spoke German, had worked extensively on the tunnels, or were otherwise deemed especially important. It took the Germans some time to find the entrance to Harry, and when they did, they soon discovered the size of the escape operation. Seventy-three of the 76 escapees were recaptured.

Escape from Sobibor

The extermination camps in Eastern Poland, including Sobibor, Treblinka II, and Belzec were part of the first phase of the Final Solution, or plan to eliminate the Jews of Europe. In all of these camps, the vast majority of those who arrived were dead within minutes, or a few hours, at most. At Sobibor, a group of 600 Jews were kept alive at the camp to do the work the Nazis required. As at Treblinka, the Sonderkommandos had, by 1943, realized that their lives were likely to end, and action was the only option. They planned a mass outbreak, but had little hope of survival. Instead, they hoped to take the camp down with them.

On October 14, 1943, at 4:00 PM in the afternoon, a small, organized group killed nine SS guards and several Ukrainian guards before afternoon roll call. The majority of the prisoners had no knowledge of what was happening. When the first dead SS guard was found, the leader of the outbreak, a Jewish Red Army officer, Alexander Pechersky, jumped onto a table and yelled, “Those of you who survive, bear witness, let the world know what has happened here.”

There was an open span of 140 meters between the camp and the forest, which offered the possibility of survival. Of the 550 men in camp, 400 ran. Around 80 of those were killed before reaching the forest, and another 170 killed in the forest. In total, 58 of the escapees from Sobibor survived the war, and they did bear witness, with one, Thomas Blatt, providing testimony at the war crimes trial of Jan Demanjuk in 2009.