5 More Daring Escapes From The Tower of London

John Paul Davis

7 mins

20 May 2020

In my previous article, The 5 Most Daring Escapes From the Tower, I covered the stories of Ranulf Flambard, Alice Tankerville, Edmund Neville, William Maxwell, and the mysterious World War One officer known only as Subaltern.

In its 1,000-year history, there have, of course, been other stories of escape from the famous walls. Here are five more daring decampments.

1. Roger Mortimer, 1st Earl of March, escaped 1322

Born at Wigmore Castle in 1287, Mortimer is one of the Tower’s more controversial figures.

As a young man he caught Edward I’s eye for his prowess in battle and became a firm friend of the future Edward II.

After the latter ascended the throne, however, Mortimer developed frustrations at the young king’s military ineptitude and tendency to promote undeserving favourites, such as Hugh le Despenser.

This set him on the path to rebellion.

roger mortimer

15th-century manuscript illustration showing Roger Mortimer with Isabella of France, Edward II’s queen (Credit: Public Domain)

Though initially successful, Mortimer surrendered, outnumbered, to the king at Shrewsbury in 1322. He was stripped of his lands and brought to the Tower.

When his initial death sentence was commuted to life imprisonment, Mortimer continued to plan insurrections using his influence with his gaolers and those outside. His letters eventually fell into royal hands and his original death sentence was reissued for August 1323.

Informed of his sentence by Queen Isabella – with whom he had engaged in an affair – Mortimer used the feast day of St Peter ad Vincula on 1 August to his advantage with the continued aid of his gaolers.

The constable’s deputy added sleeping drugs to the refreshments as the constable and the gaolers joined the celebrations in the great hall.

An inside man brought a concealed crowbar to Mortimer’s cell, along with a pair of rope ladders.

After creating a gap, Mortimer and his cellmate crept into the adjoining kitchens and, aided by the cook, made their way up an unused chimney to a ladder placed over the side of the inner ward.

Using a second ladder, they escaped the outer wall, reached a boat waiting to take them to Greenwich, and sped away into the night.

Sadly for Mortimer, his time in the Tower was far from over.

After successfully ensuring the abdication of Edward II in 1327, Mortimer acted as regent to the teenage Edward III.

After three years, however, the young king rose up against the man implicated in the suspicious death of his father and sent him back to the Tower.

The Tyburn Tree, at the present day location of Marble Arch (Credit: Public Domain)

Mortimer was an early victim of the ‘Tyburn Tree’. Dubbed the ‘greatest traitor’, he had, in the words of his son, Geoffrey, turned from honourable knight to ‘king of folly’.

2. Robert Hauley and John Shakell, escaped 1378

Within a year of Richard II’s coronation, Hundred-Year-War veterans John Shakell and Robert Hauley spent time in the Tower.

Hauley had captured the Aragonese noble, the Count of Denia, during the Battle of Nájera in 1367. Denia’s request to return home to raise his ransom was accepted in return for a hostage.

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Denia died en route home, but Hauley and Shakel refused John of Gaunt’s furious order to release the hostage, the captivity of whom was regarded as a political and diplomatic embarrassment, being the Count’s son and thus of the Royal Blood of Aragon.

All that is known of how the pair escape the Tower is that it was through violent means.

With the alarm raised, the constable, assisted by some fifty men of the garrison, chased the absconding pair up Tower Hill to where they sought sanctuary, in Westminster Abbey.

The escapees interrupted a mass in honour of the festival of St Taurinus and the ensuing mob followed them inside, recapturing Shakell and hacking to death Hauley as he circled the choir.

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The constable and his confederates – excluding the boy king Richard II, his mother and his uncle John of Gaunt – were later excommunicated for desecrating the holy site.

In memory of his apparent martyrdom, Hauley was interred in the south transept with a long brass effigy marking his place of rest. Shakell reached a compromise with Denia’s son, and was eventually buried close to Hauley.

3. Father John Gerard and John Arden, escaped 1597

Grandson of an early Lutheran purged at Smithfield in 1540, and son of a Lancashire Catholic knight kept in the Tower for his own conspiring, John Gerard had experienced many London gaols before joining the Jesuit mission in 1588.

After several narrow escapes, the betrayal of a servant in 1594 saw him moved to the Westminster home of the notorious catholic pursuivant Richard Topcliffe and later the Salt Tower at the Tower of London.

John Gerard wrote an autobiography including his experiences of torture in the tower (Credit: Public Domain).

Tortured incessantly, his wrists becoming so swollen he was unable to feed or dress himself, Gerard struck up a friendship with his gaoler, Bonner.

Once feeling in his hands returned, he convinced Bonner to make contact with his friends at the nearby Clink Prison, in addition to receiving a large collection of oranges, the juice of which he kept in a special container.

After obtaining some paper to wrap a present of a rosary for his friends, Gerard wrote a short invisible note using the orange juice and a toothpick.

While his friends outside the Tower put plans in place for an escape, Gerard used mime to make contact with fellow prisoner, the Northamptonshire recusant John Arden, who was being held in the Cradle Tower on the riverside wall of the outer ward.

After Gerard was granted permission to pay regular visits to Arden’s cell, Arden’s wife smuggled a length of cord to them.

2012 map of the Tower of London, showing the Salt Tower where Gerard was held at number 22. The Cradle Tower, where Arden was held and where the two men escaped from, is number 33. (Credit: Thomas Römer/CC).

On 3 October 1597, the pair tried for the first time.

Bonner – unaware of their intentions – escorted Gerard to the Cradle Tower and locked them in to celebrate mass, following which they made their way on to the roof around midnight.

The escapees met with boat problems on their first attempt but the following night they had better luck.

The boat moored, Gerard tossed the smuggled cord over the moat with the aid of a small iron ball, which his friend tied to a heavy rope. In turn, Gerard pulled the rope over the moat and attached it to a cannon on the roof.

The rope threatened to give way under the extra weight when Gerard followed Arden down. However, by sheer determination, they struggled their way to freedom.

In a touching epilogue to the story, Gerard wrote to the new lieutenant clearing Bonner of blame, as well as the Privy Council concerning the lieutenant.

A final letter he sent to Bonner himself, warning him not to show for work that day. He accepted Gerard’s offer of 200 florins annuity and became a Catholic.

4. John, 1st Earl Middleton, escaped 1651

Former Scottish Parliamentarian and now royalist lieutenant general John Middleton carried out what must surely be regarded as the strangest escape ever made from the Tower.

Portrait of John Middleton, 1st Earl of Middleton (Credit: Public Domain).

Middleton was brought to the Tower in the aftermath of the future Charles II’s defeat at Worcester in 1651, and kept under the security of ‘three lockes’.

Middleton later revealed that he was awoken one night by the ghost of his late friend, Laird Boccani, who predicted that he would escape within three days.

Inspired, perhaps, by the antics of the Irish royalist Daniel O’Neill a decade earlier, Middleton took the prediction to heart.

He successfully walked out of the Tower precisely three days later after fooling the guards by dressing up in women’s clothing.

5. George Kelly, escaped 1736

Educated at Trinity before becoming a deacon and fleeing to Paris, the intelligent young future Jacobite George Kelly became secretary to Francis Atterbury, the Bishop of Rochester, and later party to the Atterbury Plot against George I in 1722.

When Atterbury and Kelly secretly returned to London in 1720, word of their arrival leaked. On being detained, Kelly drew a sword on the officer and, with his free hand, burnt any incriminating documents.

Released on bail, his continuous plotting saw him relocated to the Beauchamp Tower. After two years in the Tower, he protested that the harsh conditions were harming his health and was moved to Number 8 Tower Green.

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In 1730 he requested escorted trips to Hampstead for better air. Aided by a medical report, in 1736 he penned a further letter about his asthma and was granted five hours a day to wander the city, where he purchased a horseman’s coat from one of the capital’s retail outlets.

At around 2 p.m. on 24 October, Kelly left for a regular jaunt carrying the recently collected coat over his arm.

Returning after dark he informed his warder that he planned to visit the son of another warder.

The unsuspecting guard wished him good night, oblivious as the red-coated Kelly turned and departed the Tower unchallenged.

In an act reminiscent of Gerard, after boarding a ship to Calais, he penned a series of letters apologising for his escape, as well as requesting his books become the property of his friend.

In 1745 he joined the Jacobite rebellion and later fled to France to become Bonnie Prince Charlie’s secretary.

John Paul Davis is the international bestselling author of 10 thriller novels and three historical biographies. A Hidden History of the Tower of London is his first book for Pen & Sword.