english history · history · Scottish History

Best Escapes from the Tower of London!

So I see you’re a prisoner, thrown into the Tower by order of the King/Queen. What are you in for? Were you a traitor to the crown? Did you fall out of royal favor? Or were you just in the wrong place at the wrong time?

Whether you are truly innocent or guilty or whether you are rich or poor; your fate will remain the same. You need to take matters into your own hands and plan an escape! The Tower of London may seem daunting. It may be a heavily guarded fortress surrounded by a moat, but over 40 prisoners have escaped over the centuries. Maybe you can learn a thing or two from them…

Here are some tips and tricks from the stories of four of the greatest escapes from the Tower of London:

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1. The first escape ever definitely needs to be a part of this list. His name was Ranulf Flambard who was known for being King William Rufus’s royal clerk. Flambard is believed to have referred to his fiery personality and was known as a strong speaker, clever, and lively. He could also be very dominant and forceful. Ranulf entered the church and even helped William the Conqueror compile the Doomsday Book. After William I’s death, Ranulf went on to serve his son, William Rufus.

Ranulf became connected with the corruption of William Rufus’s reign as he proved to be a ruthless lawmaker, treasurer and chaplain. He helped to run the country when needed and found interesting ways to make cash for the crown by exploiting the poorer citizens. He was known as greedy, but also he helped to build the first stone bridge across the Thames river and expand the young Tower of London.

After William Rufus died in 1100, the new king (Henry I) moved against Ranulf. Ranulf was disliked and this arrest gain Henry favor with his new subjects. Ranulf was officially charged with embezzlement and was imprisoned in the Tower. He was the first state prisoner recorded and would become the first to escape.

Typically, wealthy prisoners were granted more privileges than ordinary people. He was able to keep servants and have meals served to him. This allowed him to connect and speak to people on the outside. Early February, Ranulf held a banquet for the jailors (using his own personal funds) and got them drunk. Once they men had become inebriated enough to pass out, Ranulf proceeded to grab a rope which had been hidden previously and climb out through a tight window. He met up with a prearranged horse that took him to the waiting ship which would take him to Normandy.

What did we learn from Ranulf’s escape in 1101?

  • It’s good to be rich.

Money had a large part to play in his escape as it allowed him to have extra privileges, afford the wine to get the guards drunk and to arranged his getaway ride. There are theories that King Henry may have turned a blind eye to his escape. The two men quickly made peace after Henry defeated his brother in Normandy which caused the slimey Ranulf to change loyalties again. Ranulf Flambard eventually settled peacefully in Durham and would live until 1128.

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Arrest of Roger Mortimer

2.  The famous Roger Mortimer also escaped the clutches of the Tower in 1323. Mortimer is famous for bringing the end to Edward II’s reign and for being Queen Isabella’s lover. He would go on to become a virtual dictator after Edward II’s forced abdication. Edward II was a weak king (nothing like his strong father Edward I) and gave too much power to his vain and greedy favorites such as Piers Gaveston and Hugh Despenser. Edward’s wife, Isabella of France, would have easily found Mortimer more appealing as he was handsome and confident while her husband treated her terribly (and was most likely more interested in the opposite sex).

In 1322, Roger Mortimer was locked in the tower after a failed revolt against the King. Mortimer found a way to convince his jailors to do what he asked and to smuggle messages to his followers outside. Isabella herself sent a warning to Mortimer once she found out that Edward was planning on executing him soon.

On August 1st, Mortimer began his escape plan. It was the feast day of St. Peter ad Vincula and the jailers would be having a banquet in honor of the day. Gerard d’ Alspaye was the second in command at the Tower and had been allied with Mortimer. it was D’Alspaye who had secretly been adding sleeping draughts to the wine of the banqueting men. Once everyone was asleep Mortimer and D’ Alspaye dug their way out using a crowbar against the great stone walls. The work was extremely difficult, but the men knew that they had a time limit to accomplish this. The men climbed through the rough hole which emptied into the royal kitchens. The cook, who was an ally, showed them the best way to escape. This was by going up the chimney…

Together the men climbed up the sooty chamber and found themselves on the roof. They proceeded to use a rope ladder and escape to a prearranged boat on the Thames. They proceeded to escape to France.

Edward II was naturally furious and took most of that out on his wife by locking up her household staff and stripped her of her allowance/personal living expenses. He even took away her children and gave them to the care of his hated lover, Despenser. It wasn’t until 1325 when Isabella would reunite with Roger Mortimer. Edward II foolishly sent Isabella to negotiate peace with France and agreed to allow their son/heir to go with her. With her son at her side and her military lover, Isabella began to defy her husband and called for his removal and the removal of the Despenser family. Together they invaded England in 1326 with a large army and overthrew Edward II while they executed the hated Despenser. Meanwhile, after Edward’s abdication he died under mysterious circumstances.

Mortimer would go on to rule as a new tyrant through the guardianship of young Edward III. Edward III was not keen on Mortimer and in the end locked up his guardian where this time he was executed.

Mortimer’s strategy?

  • Know what holiday is coming up and if the guards will be partaking in festivities
  • become friends with those within the jail (and it doesn’t hurt to be the Queen’s lover either!)
  • make use of sleeping medicine

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3. John Gerard had the unfortunate experience of being Jesuit priest during the era of Queen Elizabeth. It was a risky move moving to England know the fierce Protestant government and Gerard spent eight years living life on the edge. Many families housed secret Catholic priests who were constantly hunted down. Catholics were considered traitors during this period in English history, just as Protestants not too many years before. Gerard probably hid in the common “priest holes” which concealed a room to hold Catholic ceremonies and hide priests during searches. But in 1594, Gerard was captured by the government after being betrayed.

While in prison Gerard was tortured using manacles. He was suspended by his wrists and left to dangle with no support. According to Nigel Jones’ book, this questioning and torture lasted for hours. After multiple questioning sessions, Gerard’s wrists became extremely swollen and bruised. He was in agony, yet still remained stubborn. He suffered waterboarding sessions as well. Gerard was left unable to dress or feed himself due to his injuries.

Gerard would also befriend his jailor (like others before him), a Warden named Bonner. Bonner was sympathetic to Gerard’s troubles and helped him during the times he could not do many basic tasks for himself. Gerard began to see that influence over this man could work to his advantage. First, he had Bonner obtain cash from his friends on the outside which Gerard would use as money to continue bribing the Warden. He also used the money to buy oranges. It may seem strange how oranges connect to this story, but Gerard actually used them as a type of invisible ink. Gerard would write with the orange juice and this would become briefly visible when heated. Bonner would deliver these messages to Gerard’s Catholic contacts on the outside.

Gerard was able to contact another Catholic prisoner (John Arden) who was also imprisoned in the Tower and they began to create their escape plans. Using his new minion, Gerard sent messages to Arden and, eventually, got to hold private meetings in Arden’s cell. Soon Arden’s wife smuggled in rope during one of her regular visits, which would be valuable in their escape.

On October 3, 1597 the escape plan was put into action and a getaway boat was prepared outside the walls. Bonner (accepting bribe money but still clueless to the escape plot) brought Gerard to Arden’s cell and locked him in. Arden and Gerard broke the cell door which led to the roof and were about to climb down to the boat, but the tide changed causing the boat to drift away and almost get destroyed against the London bridge. There would be no escape that night.

The next evening the two men were again on the roof and watched the new getaway boat row up to the original spot. They set up the smuggled rope and the men at the boat secured it to the ground. Arden slid down first, but Gerard had a little more difficulty due to the injuries sustained from the manacle torture. He could barely hold on and began to fall, desperately clinging for dear life. The rope was loosening and one of the men from the boats had to retrieve Gerard himself. The men managed to row away silently.

But what happened to Bonner? The greedy (but clueless) Warden had allowed all of this to happen right under his nose. John Gerard never forgot about him and sent a letter warning Bonner of what happened. He told him to escape and promised him a lifetime annuity. Bonner took this advice and even ended up converting to Catholicism later in life.

John Gerard continued his Catholic mission in England as long as he could, but after the failure of the Gunpowder plot he left. He died in Rome in 1637.

Gerard’s Strategies?

  • Obtain a loyal minion with the promise of gold (or other valuables)
  • get creative with everyday objects

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4. William Maxwell, 5th Earl of Nithsdale, was Scottish and a loyal Jacobite (those who wanted to bring the Stuarts back to power). He had pledged allegiance to the exiled James II as a young man and married a woman whose loyalty to the Jacobite cause and her husband would be key to his eventual escape. After the failed Jacobite rebellion of 1715, Lord Nithsdale was captured and condemned as a traitor. When Lady Nithsdale heard of this arrest she immediately stepped into action. She took her maid on a journey to London in the dead of winter. She would not allow her husband to be condemned and executed.

Once she arrived in London she learned that all the Jacobite prisoners had already been sentenced to death. They only had three weeks to live. Lady Nithsdale was desperate and went so far as to dress as a palace maidservant to sneak into the palace. She threw herself at the King’s feet begging for mercy for her husband. Naturally, she was thrown out by security.

She was given permission to visit her husband in his Tower cell and during these visits she took note of the layout of the prison. During these visits she came up with another plan of action. She decided she would take the theatrical approach and dress her husband as a woman in order to smuggle him out. She recruited her landlady and her husband to help with his plan. Mr. Mills would be their coach driver and Mrs. Mills (along with two other ladies named Miss Hilton and Mrs Morgan) would accompany Lady Nithsdale in the prison.

It was the day before Lord Nithsdale was to be executed as a traitor. This plan needed to work that day or all would be lost. Now this plot is going to sound very complicated and I have tried to make the most sense of it through my research: Lady Nithsdale came to the Tower with Mrs. Mills, Ms. Hilton and Mrs. Morgan (along with their coach driver Mr. Mills). They were under the pretense they were visiting Lord Nithsdale for the final time before his execution. It was imperative they played the emotional and weeping woman throughout this whole visit. Mrs. Morgan wore two identical dresses at once into the tower and Lady Nithsdale made sure to bring a bag of makeup as well. Lady Nithsdale could only bring one companion with her at a time per Tower rules to visit her husbands cell, but this was all to their favor as you shall soon see. First Lady Nithsdale brought Mrs. Morgan to her husband’s cell. Once the cell door was closed, Mrs. Morgan quickly removed a layer of her dresses and had Lord Nithsdale dress in the spare outfit. Lady Nithsdale then proceeded to use her cosmetic supplies to make her husband look like more of a convincing female. He would also wear a scarf around his face, a maid’s cap and a red wig. The idea of this disguise was to make Lord Nithsdale look more like Mrs. Mills.

Mrs. Morgan left the room making a convincing show of sadness and crying. Miss Hilton came in next and added a female cloak to Lord Nithsdale’s costume. While all of this was happening, the women would continue to have loud conversations about petitioning the King for Lord Nithsdale’s release in order to dissuade any guard suspicions. At this point Miss Hilton left and Mrs. Mills came up to the cell. The women continued their weeping performance to play up the role of “an emotional woman” which the guards would have expected. After adding her contribution, Mrs. Mills secretly left. Lord and Lady Nithsdale were alone and now it was time to truly find out if this plot would work. Together Lady Nithsdale and the new “Mrs. Mills” left the room carefully, both making it seem like they were weeping women. The guards did not even notice. At this point Lady Nithsdale turned back alone to her husband’s now empty cell as if she was going back up to give a solitary goodbye to her husband. Meanwhile, the real Lord Nithsdale made his way into the coach and Mr. Mills drove them away to their prearranged hiding place.

In the old cell, Lady Nithsdale held loud conversations and she played the part of both her husband and herself! She would adjust her voice to imitate her husband. I believe Lady Nithsdale missed her calling as an actress since she completely fooled the guards with this performance. After about half and hour of this show, she  finally left the cell and called out to the emptiness “keep your head up and hopes high!” She returned to the entrance and let the guards know that they should not disturb her husband as he was spending his last night on earth in prayer.

The theatrics had actually worked. To the surprise of everyone the next day, Lord Nithsdale did not arrive at this execution. Together the husband and wife would eventually find safety in Rome where they would live quietly until their deaths in the 1740s.

Lord Nithsdale was lucky he had found himself a clever and loyal spouse who orchestrated everything for him. Lady Nithsdale is a great example of a strong woman who just wouldn’t take no for an answer. She would continue to fight for what she thought was right until the very end. Without Lady Nithsdale and her theatrical schemes, Lord Nithsdale would have been executed the following day.

To escape the Nithsdale way you need:

  • acting ability (make sure you know different types of voices)
  • many loyal friends
  • convincing costumes

There are many other exciting tales of escapes that could help you plot your own, but just don’t take any inspiration from Prince Gruffydd ap Llywelyn. Gruffydd was a noble of Wales and was imprisoned by Henry III in 1241 as a hostage to ensure good behavior from the rebellious Welsh. He hated imprisonment and decided he wanted to escape. He began well by creating a rope of knotted sheets, yet he did not take his own weight into account. Gruffydd was a bit plump and as he started descending the side of the Tower wall his homemade rope broke due to the weight. Gruffydd, sadly, fell to his death.

Don’t be like Gruffydd.

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Food for Thought:

Which prisoner’s techniques were your favorite?

Are there any other famous escapes that you know about? How did they achieve their goals?


Further Reading:

Tower: An Epic History of the Tower of London by Nigel Jones


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