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How a fruit cake helped Eamon de Valera escape Lincoln Prison


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Eamon de Valera was a leading figure in Ireland’s fight for independence

Eamon de Valera went on to become one of Ireland’s most influential statesmen. But his politics were not the only thing that earned him a place in the history books – exactly 100 years ago, he was also the mastermind of an audacious prison break involving, cake, candles and a cartoon on a postcard.

The future president of Ireland was exercising in the yard at Lincoln Prison when he spotted his path to freedom – a door, which led to the outside.

In that moment he hatched the simplest of plans: get a key and get out.

Eamon de Valera had already served time for his involvement in the 1916 Easter Rising in Dublin – a series of violent clashes between Irish rebels and British forces over independence, which resulted in the deaths of 450 people, 250 of them civilians.

The passionate republican had been spared the death sentence, unlike 15 of his fellow rebellion leaders, and on his release the following year, he became the leader of Sinn Féin and MP for East Clare.

But in May 1918, as the British sought to discredit de Valera’s party and its military arm, the Irish Republican Army (IRA), the politician and 72 other leading Irish nationalists were arrested on allegations of conspiring with Germany.

Some were sent to jail in Usk in Monmouthshire, while others, including de Valera, were packed off to Lincoln.

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Eamon de Valera was born in New York in 1882 to an Irish mother and Spanish father, but moved to Ireland aged two

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Erik Grigg

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Since it opened in 1872 only de Valera and his associates Sean McGarry and Sean Milroy have ever escaped

Lincoln Prison, an imposing building to the east of the city centre, opened in 1872 and in its 46-year history, there had not been a single escape.

Fearing a delegation to the US was about to tell the Americans that Ireland would be satisfied to remain partly under British control, de Valera was desperate to break out.

What followed was a plot so bold de Valera’s grandson Eamon O’Cuiv described it as akin to Andy Dufresne’s escape in the 1994 film the Shawshank Redemption – “only it really happened”.

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Castle Rock Entertainment/Getty Images

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In the film adaptation of Steven King’s novella, Andy Dufresne, played by Tim Robbins, spent 19 years tunnelling through his cell wall

Having spotted the door in the exercise yard, de Valera’s next step was to find a key.

His Catholic background had led him to act as server in the prison chapel, where he spotted the chaplain’s set of keys. Waiting until his back was turned, the prisoner made an impression of this crucial piece of equipment using a wedge of wax he had collected from the chapel candles.

The next problem de Valera and his fellow revolutionaries faced was how to get it to the IRA. With their letters scrutinised by prison guards, they came up with a ploy to send the dimensions on a postcard.

Fellow prisoner Sean Milroy was put to the task and drew a cartoon of a drunk man trying to fit a large key into a tiny keyhole on what appeared to be a harmless Christmas card. The proofreaders were duped: the image sent to their associates was, in fact, a copy of the impression taken by de Valera.

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UCD Archives De Valera Papers, reproduced by kind

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A replica of the key was disguised in a Christmas card sent from the jail

On the outside, a key was cut to the dimensions on the card and smuggled into the prison inside a cake. According to a statement given 30 years later by conspirator Liam McMahon, it was taken to the jail by a man called Fintan Murphy.

McMahon said in the statement: “He said he was a commercial traveller, and somebody in Manchester had asked him to bring this cake. He was taken inside [and] the head warder was called, who brought a very thin knife, and started prodding the cake.

“Fintan was in agony over the thing, as to what would happen in the event of the knife touching the key. Anyway, he never contacted the key, and the cake was put in.”

The plot failed, however, as the key did not fit the lock.

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Harry Boland and Michael Collins, left and centre, were sent to help free de Valera, right

De Valera, who realised the wax must have shrunk before the drawing was made, later wrote: “As I examined the joy at having got [the key], it was qualified by a feeling that it was too small.”.

A second cartoon was despatched – this time with the key impression disguised at the centre of an ornate Celtic pattern – and a second key was smuggled into the prison inside another cake.

When that failed, yet another was baked – “an oblong fruit cake”, McMahon recalled – this time containing a blank key and a set of files so it could be shaped to fit the lock.

The blank was given to fellow prisoner Peter DeLoughry who had been able to examine a prison lock after managing to take it apart using a contraband screwdriver. With that extra knowledge, it was he who was able to fashion a master key capable of unlocking any door in the jail – and of winning de Valera his freedom.

At about 7.40pm on 3 February 1919, de Valera, Milroy and a third man, Sean McGarry, used the key cut by DeLoughry to open their cell doors and lock them behind them. Slipping out into the dark and misty exercise yard, they made their way to the gate.

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On the other side, top-ranking republicans Michael Collins and Harry Boland were among those waiting for them.

Collins had also had a key cut, but when he tried to open the gate from the outside it snapped in the lock. Fearing their luck might have run out, de Valera slotted his key in from the other side, poked out Collins’ broken key, turned the lock and the three men slipped through.

As the group made their way away from the prison, they encountered some convalescing soldiers loitering with their girlfriends outside a nearby hospital but managed to stroll past without arousing suspicion.

After a short walk, they arrived at the Adam and Eve pub, where a taxi was waiting to whisk the men on to Worksop in Nottinghamshire. By the time their escape was discovered, at about 9.30pm, the men had taken another taxi from Worksop to Sheffield where a car was waiting to take them to a safe house in Manchester.

Recounting the escape later, de Valera said he had been poised to lock the door to the exercise yard gate when he was urged by his comrades to hurry away from the prison. “Had I locked that door, nobody would ever have known how we had escaped,” he said.

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BMH.WS0274, Military Archives, Ireland

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Liam McMahon’s statement revealed the details of the cake

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Erik Grigg

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The escaped prisoners were taken by taxi from outside the Adam & Eve pub to Worksop

Mr O’Cuiv first heard the tale of his grandfather’s escape when he was a young boy. He said his mother’s birth certificate – she was born in August 1918 – lists her father’s address as Lincoln Prison.

“This was as successful and as neat an escape as you could imagine,” he said. “It was based on a bit of cunning and cleverness.

“As I grow older the more I look at it and think what a neat escape it was: no violence, no nothing – just out of the door and gone.”

Mr O’Cuiv said the story was one “people in Ireland love” and according to Lincolnshire County Council historian, Dr Erik Griff, “lots of Irish people” visit the prison to see where de Valera enacted his great escape.

However, the former inmate’s grandson admits the plan was not without its flaws, and that putting Collins, Boland and de Valera in the same place was a big risk.

“It would have been a bit of a disaster [if they had been caught] – you would have lost three of the big players,” he said.

“It’s like saying what if the Germans had managed to bomb Buckingham Palace and kill the king, or kill Churchill?

“It was maybe a bit foolhardy but the idea was to send their best men, their most reliable organisers.”

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Eamon de Valera was an avid supporter of the Irish language movement and in 1913 joined the Irish Volunteers, a military organisation set up in opposition to the unionist militia the Ulster Volunteers

During his incarceration de Valera’s Sinn Féin party had swept the boards at the 1918 general election, winning 73 of the 105 Irish seats – with de Valera, despite being behind bars, winning both in Clare East and Mayo East.

But party members refused to take their seats in Westminster, and, on 21 January 1919, assembled at the Mansion House in Dublin to form an Irish parliament, known as the Dáil Éireann.

Following his escape, de Valera returned to Ireland where, at the April meeting of the Dáil, he was named president. By the time of his death in August 1975, aged 92, he had been elected taoiseach (prime minister) three times and served as president of Ireland from 1959 until 1973.

More than 200,000 people lined the streets of Dublin for his funeral, taking the opportunity to honour the man who helped free them from British rule.



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