Its Hard to keep a Good Man in Jail

As long as there have been prisons, there have been prisoners willing to attempt daring escapes. Today’s prisoners have resorted to helicopters and escapes that seem more suited to a James Bond movie.

Here are some of the most daring that have taken place over the last 800 years. Many of these escapes have fascinated the public enough to have been made into movies.

Sir Roger Mortimer

When most people remember Roger Mortimer, it is for his later exploits as the lover of Queen Isabella. However, long before he was her lover, he was one of the few prisoners who ever escaped from the Tower of London. It is believed that he drugged his guards before going over the wall and from there to France to join the Queen. He did have some help in his escape, but it was daring none the less. This was in 1323. In 1330 he was again sent to the Tower, this time by King Edward III and his fate was not so happy. He was taken to Tyburn to be hung, thus end all traitors.


While Napoleon was not really confined in a prison while he was on the Island of Elba, he certainly was a prisoner. One has to wonder what the powers that be were thinking. Napoleon had shown himself to be very resourceful in the past and leaving Napoleon pretty much to his own devices was a big mistake. The fact that he was daring enough to escape is not all that surprising, but it certainly was in character. After his defeat at the Battle of Waterloo, Napoleon was sent in exile to the Island of St. Helena from which escape was impossible.

The Great Escape

The Great Escape, took place in Germany during World War II. It was not a very successful escape but the sheer magnitude of the attempt has made it one of the most celebrated. 76 prisoners escaped out of a prisoner of war camp and most were recaptured, only 3 ultimately reached freedom. 50 of those who escaped were executed by the Gestapo. A 1963 movie starring Steve McQueen has kept their story alive and gave the world a true picture of what life in a prisoner of war camp was like.

Libby Prison

Libby Prison was located in Richmond, Virginia. It was where Union prisoners were held and since the war wasn’t going well for the south, it was going even worse for prisoners. It was the job of able-bodied men to try to escape and the prisoners here were quite successful. On February 9, 1864 109 men escaped, with 48 being recaptured, two drowning in a nearby river, and 59 successfully making it back to Union territory.


Alcatraz has the reputation of being an inescapable prison; it isn’t called “The Rock” without reason. Its location in San Francisco Bay means that escape must be by water. While that has discouraged most prisoners, it was seen as a challenge by others. Three prisoners who attempted to sail off of the island prison were Frank Lee Morris, Clarence and John Anglin in June of 1962. No one knows for sure what happened to them once they left the island. Bodies have never been found nor have the men ever turned up anywhere else. They could have gotten away but it is unlikely. The water was ice cold and the currents are strong. They were experts at escape which is why they were assigned to Alcatraz in the first place.

Current prisoners are resorting to much more high tech escape methods. It seems however that the percentage that are successful is not a great deal higher than it ever was. Hopefully officials are also adding some high tech to their arsenal.