The Craziest Escapes From The Tower Of London

Celina Pham
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1 Video View·Apr 28, 2026
Hello, I'm Matt Lewis and I'm an author and historian and I'm here today with History Hit
at the Tower of London, one of the world's most famous prisons. There's been executions galore,
heads rolling across Tower Green, but one thing you might be surprised by is the sheer number
of people who've managed to escape from these walls. The White Tower at the centre of this
magnificent complex was begun in 1066 by William the Conqueror in the wake of his victory at the
The layout we see today was largely competed by Henry III and has remained essentially unchanged
since the late 13th century. In its time the tower has been a lavish royal residence, a mint,
an armoury and even a royal zoo, but it has a darker reputation too. During the Tudor period
it became a place where people went to wait to die, never to emerge from again. But that wasn't
always true. Plenty of people have tried to escape from the Tower of London and a few have even
succeeded, using bravery and creativity to find ways to break out of one of history's most famous
prisons. This is one of the rooms in the Salt Tower at the Tower of London, often used to house
prisoners. Their graffiti litters the walls to remind us of those that were kept here as prisoners.
But one man would escape from the Salt Tower. His name was John Gerrard. He was a Jesuit priest,
a Catholic in Elizabethan England and unfortunately for Gerrard that made him an enemy of the state.
John Gerrard first arrived in England in 1584 but he was arrested for failing to have the proper
paperwork. His bond was paid a year later by Antony Babington, the man who would eventually
be executed for trying to secure the escape of Mary Queen of Scots. Gerrard went back to Rome
where he was given another mission, to return to England again and to keep the flame of the
Catholic faith alive. He came back to England in 1588 and this time he posed as a well-to-do
gentleman, a gambler, a man who liked fashionable clothes. But in reality his mission was dangerous.
Gerrard spent time hiding in cramped priest holes while those who hunted Catholics sought him out.
Gerrard managed to evade the authorities for six years until he was finally captured in 1594 and
brought here to the Salt Tower at the Tower of London to be a prisoner. When he refused to give
up names of fellow Catholics in England under questioning, Gerrard was tortured, hung in chains
by his hands. He was repeatedly asked for names but he refused to answer any questions or to give
up any name except that of Jesus. Eventually he was taken to the rack but when Gerrard threw himself
on his knees and pleaded with God to give him the strength to be pulled apart before he gave
up a single name, his tormentors decided it simply wasn't worth it. He was returned here to his cell
in the Salt Tower where he would plot his escape. For some reason John Gerrard was allowed to visit
a fellow Catholic, John Arden, who was imprisoned in the Cradle Tower nearby. During their visits
John Gerrard realized that Arden's tower overlooked the water below and he thought this offered an
ideal chance to escape. Arden wrote to friends on the outside and with their help he arranged a
scheme to spring them from the tower. The plan went into action on the 3rd of October 1597. Gerrard
made the short journey to visit Arden in the Cradle Tower as he usually did. When the two men
were locked in their room together they set to work removing the stone around the bolt on the
door to the roof. By midnight they'd made it to the top of the tower and were ready to make their escape.
When the boat appeared as arranged they were about to signal when a man in a nearby house
came out and began talking to the boat crew mistaking them for fishermen. They held a long
conversation during which Gerrard and Arden hid on the roof of the Cradle Tower. By the time the
man had gone back into his house the tide meant that they'd missed their chance. They made their
way back down to their cell and gave up for the night. Gerrard was surprised to find out that the
next day, the 4th of October, they were all set to make another attempt and this time they saw the boat
with no problems. They lowered down a weighted thread to which the men in the boat tied a rope.
Pulling this back up they secured it to a hook at the top of the rope and John Arden lowered himself
down to the boat that was waiting. John Gerrard began the journey too but his hands were so mangled
by his torches that he found the going impossible. He would write later that he got stuck halfway,
his hands giving up on him and his breath giving way, but he managed to force his body to struggle
on. Eventually he made it to the side of the boat but had to be pulled in by Arden and the others.
Gerrard made his escape from the Tower of London and sheltered by the Catholic network for a
further eight years, continued his mission in secrecy in England. He would then make his way
back to Rome where he was encouraged to write an autobiography to tell his story. It's a visceral
tale of the depredations of hiding in priest holes and constantly being under threat of capture,
never mind the torture that he endured here at the Tower of London. Gerrard lived in Rome teaching
other Jesuits for their missions to England until the age of 73 and he would die in peace 40 years
after his brave escape from the Tower of London. Ranulph Flomberd was a Norman who was born around
1060. He first entered the service of Bishop Odo of Bayeux and then later transferred into the
service of his half-brother William the Conqueror. Ranulph's administrative skills found a great
home in royal service. He was involved in the compilation of Doomsday Book and soon made a
really strong name for himself. When the Conqueror died in 1087, Ranulph transferred his service to
William Rufus, the Conqueror's son. He rose even further in royal favour. He was royal chaplain,
he became the treasurer, he was even described as the justicia, the highest office in the kingdom.
But when Rufus died in 1100 and was succeeded by his youngest brother as King Henry I,
Flomberd was made a fall guy for all of the unpopular policies of the previous reigns. It
was him who'd been screwing money out of the nobility and the church and he was brought here
to the Tower as its first recorded state prisoner to pay the price. Now while he was a prisoner here,
Flomberd developed a reputation for throwing lavish parties and in February 1101 he threw one
very lavish party, ordering in extra barrels of wine. As his guards became more and more drunk
and collapsed in heaps in the corners of the room, Flomberd turned over one of the barrels
and pulled out the rope that his friends had put in the bottom of it for him.
Tying it securely, he lowered himself down from one of the Tower's windows and made his escape
by river in a boat that was waiting for him. He escaped across the channel to Normandy where he
made it to the court of Henry's older brother, Robert, Duke of Normandy and he entered the
service of the Duke, encouraging him to invade Henry's England and try to take his throne.
The invasion ultimately failed and Robert was captured in battle in 1106.
Rannell Flomberd managed to make his peace with King Henry and he would live out his days
working as Bishop of Durham. He's responsible for the building of the cathedral up in Durham.
So Rannell Flomberd is the first recorded state prisoner ever to be housed at the Tower of London
and he's also its first escapee. It was hardly an auspicious start. Roger Mortimer was one of those
Welsh marcher lords, a hard breed of men who operated on the very edge of royal authority
on the Welsh borders. They were a tough, independent breed. Roger was a royal ward from
a young age and he eventually served Edward I before continuing to serve his son Edward II.
But by 1321, Roger had fallen into opposition to Edward. He supported the Earl of Lancaster
and was captured at the Battle of Boroughbridge, brought here to the Tower of London as a prisoner.
Initially sentenced to death, this was commuted to life imprisonment here at the Tower.
But Roger wasn't settling for that. In 1323, during some celebrations for the feast of Saint
Peter Advincula, Roger took advantage of the fact that all of the guards were drunk
and managed to escape from his cell, helped by one of the Tower's guards.
They climbed up one of the kitchen's chimneys, scaled down the wall on the other side,
and managed to make it over the outside walls with a rope ladder,
rowed away in a waiting boat. Roger made it all the way to France, where he met up with Edward
II's estranged wife, Isabella of France, who was already plotting against her husband.
There's always been some suspicion that Roger and Isabella became lovers, but what's certain
is that they became political bedfellows. They would return to England at the head of an army
and they drove Edward II from the throne of England, replacing him with his 15-year-old son,
the new King Edward III. When Edward III was crowned, Roger became the effective head of
government, ruling the kingdom on behalf of the minor king. He made himself Earl of March
to reinforce his dominance in that Welsh border region. But he was unpopular. When Edward III was
nearly 18, he decided to take government into his own hands. He broke into Nottingham Castle,
where Roger and his mother Isabella were staying, and he arrested Roger and had him dragged back
here again to the Tower of London. But this time, there was to be no escape. He was hung
like a common criminal at Tyburn, just beyond these walls. His family was stripped of lands
and titles, although his grandson would eventually win them back through good service and a strong
relationship with Edward III. Roger Mortimer escaped from the Tower of London and went on
to effectively rule a kingdom, but he would end up back here, hung as a common criminal.
Only one woman has ever escaped from the Tower of London. Her name was Alice Tankerville,
and she escaped from these walls in 1534. The year before that, Alice and her husband, John Wolfe,
had plotted the murder of two merchants. Alice had befriended the two men and they'd convinced her
to allow them to take her for a boat ride on the river. When they reached a pre-arranged spot,
the two merchants got a surprise, but probably not the one they were expecting.
John Wolfe leaped out from behind a tree onto the boat and stabbed the two merchants to death.
John and Alice tied the bodies together and threw them into the Thames. They rode back
to the city, broke into the merchants' rooms and stole all of their money. Six months later,
the two bodies washed up on the shore of the Thames. There must have been some evidence that
pointed to John Wolfe in the murder, because he was arrested quickly and imprisoned here at the
Tower of London. Alice came to visit him almost every day. She managed to befriend one of the
jailers, John Board, and Wolfe was eventually released, probably for lack of evidence.
But he fled to France, leaving Alice behind. John Board, who was probably smitten by Alice at this
point, agreed to take care of her in Wolfe's absence. The following year, in 1534, Wolfe
returned, but he was almost immediately rearrested. And there must have been some new evidence,
because Alice was also thrown into a cell and hung in chains. The smitten John Board agreed
to help Alice escape her fate when she was condemned to execution. He smuggled some keys
into Alice, and one night at 10 o'clock, she freed herself from her chains,
made it out through the cell door and up to the roof where she met John Board.
But Board had got his timings wrong. They were met by the night's watch. When they recognised
Board and asked him what he was doing back at the Tower at this time of night, they found his
explanation unconvincing. And when they turned their attention to the woman at his side,
they recognised the prisoner, Alice Tankerville. Alice and John Wolfe were convicted,
found guilty of piracy because their crimes had taken place on the water.
And so they were condemned to a pirate's death. Taken to the pirate gallows at Wapping,
they were chained to the bank at low tide and allowed to drown as the rising tide overtook them.
William Maxwell, the 5th Earl of Nisdale, was a Jacobite. He favoured the old pretender. This
brought him into conflict with royal forces, and when he was defeated at the Battle of Preston,
he was brought to the Tower of London as a prisoner. And here, in 1716, he awaited his
execution. But one person refused to give up on William, and that was his wife, Lady Winifred.
She set out from their home near Dumfries in Scotland to travel to London to try to save
her husband. She bustled her way into the presence of King George I to beg for a pardon for William,
but she was unsuccessful. She came up with a brilliant but complicated plan to save her
husband. The day before William was due to be executed, Lady Winifred arrived here at the Tower
of London with some of her ladies. They were all dressed in the same dark cloaks, and they were
surprisingly tall. They were allowed in to see William to say some final farewells, and his
guards were obviously distracted by the weeping and the wailing of the women, because at one point,
one of the women who left the cell and walked straight past the guards wasn't a woman at all.
Inside the cell, each of these women had been wearing an extra layer of clothing, and from it,
they created an outfit for William. Winifred remained in the cell when her husband left,
carrying on a long conversation with him, doing a passable impression of William that fooled the
guards until she believed he'd had enough time to get away. She then left and joined her husband,
and they managed to escape to Rome, living out their life in peaceful happiness there.
When they died, William and Winifred's bodies were returned to England, buried in her family's
crypt near Arundel. It was an act of bravery and creativity by Lady Winifred that saved William
Maxwell's life.
