Fruitcake Prison Break 

Éamon De Valera Addresses Crowd
Posted in: Fruitcake, Community

How Éamon de Valera Ate His Way to Freedom

History is riddled with stories of creative escape attempts. In 1934, American gangster John Dillinger escaped from prison with the help of a wooden gun. It was crudely carved, painted black, and poorly polished but extremely effective. It was realistic enough to frighten his guards into opening his cell door. Pascal Payet, a Frenchman with a penchant for Hollywood-style escape tactics, fled prison in a hijacked helicopter on three separate occasions. In 2017, eleven Alabama inmates confused a guard into accidentally opening an exit door by smearing peanut butter over the illuminated ‘exit’ sign; in doing so, they were able to disguise the door’s destination.

Despite the determination of these escape artists’ breakout attempts, all escapees were later recaptured. Their tactics, however, highlight the creativity and ingenuity of individuals wanting to break free. But perhaps the most creative prison escape of all time belongs to a man named Eamon de Valera. He escaped with the help of…. a fruitcake!

Irish Republican Party (Sinn Féin) photographed on Monday, 10 July 1922. Éamon de Valera, center-most. - NLI Ref.: HOG235

Who was Éamon de Valera?

De Valera was an Irish politician and statesman, who served as Ireland’s Prime Minister and President for a large portion of the mid-twentieth century. However, it had never been de Valera’s intention to have a political career.

Classically trained as a teacher, de Valera took his first steps into the political realm in 1913 when he joined a group known as the Irish Volunteers. Essentially a militia, the Volunteers were comprised of Irish Nationalists who believed in ‘Home Rule’ - the idea Irish citizens should be ruled by an Irish government. You see, during this time, British rule of Ireland had been in effect for over 300 years. This group was a collection of members of the Gaelic League, the Ancient Order of Hibernians, and the Sinn Fèin Party, which de Valera would later lead.

Not all Irish citizens supported the idea of Home Rule. An equally large number of Irish citizens believed in British rule; this group was known as the Unionists. Tensions between these two groups mounted for over two decades as the country teetered on the brink of civil war.

As a member of the Volunteers, de Valera’s responsibility grew in 1916 when he was tasked with leading a secret battalion of men to rebel in an event known as the Easter Rising. The Rising was intended to take place all across Ireland with Irishmen and -women rebelling against their local pockets of British rule; however, due to various circumstances, the rebellion did not go as intended. De Valera was captured and imprisoned. Because of de Valera’s massive popularity within the growing anti-British Irish population, British officials imprisoned de Valera and seventy-two other republican comrades at Lincoln Prison: a forty-seven-year-old, notoriously secure prison from which no one had yet escaped.

Well, that’s until de Valera was mailed a fruitcake. A special, Irish fruitcake.

Fruitcake Bake & Break

While in jail, de Valera, a devout Catholic, became an altar boy for the prison church. One day, de Valera discreetly pilfered the chaplain’s master key and upon returning to his cell, began making a replica. Using the heat from his hands, he warmed lumps of old candle wax until it was soft enough to shape into a copy of the key.

With his wax copy safely in hand, de Valera had to find a way of sending word to his fellow revolutionaries for assistance. However, since all forms of communication between prisoners and freemen were heavily monitored, this would require more stealth and cunning. De Valera enlisted the help of fellow prisoner Sean Milroy whose artistic skills were bound to fool the guards. Milroy drew a postcard depicting a small man attempting to fit a comically large key into a door. Turns out, this comically large key was an outline of the wax replica de Valera had made. They addressed the postcard to his co-conspirators, Collins and Murphy, and waited.

A Suspicious Number of Fruitcakes Later

A little while later, Murphy delivered a cake to the prison in which they had concealed a replica key. Suspicious of the cake’s potential contents, the warden used a thin knife to poke holes all around the cake’s surface. When the warden did not feel the tip of the blade pierce any concealed items, he deemed it suitable to deliver to de Valera. Unfortunately, the whittled key was too small. De Valera realized the original wax key had most likely shrunk over time as the wax dried out.

Once again Milroy’s artistry was utilized to conceal a second key impression in the center of an ornate Celtic pattern. And once again, Murphy delivered his second cake to the prison. After anxiously watching as the cake underwent the warden’s same invasive inspection process the cake was deemed acceptable and delivered to de Valera. But alas, the second attempt also did not work.

Fearful the continuous stream of cake deliveries was causing suspicion, Murphy decided for one more escape attempt. He decided to conceal a blank key and a complete set of files inside a third and final cake. However, a regular cake would not successfully conceal such hardware. So instead, Murphy baked an oblong fruitcake whose dense texture might help hide the tools and fool the warden. Turns out, Murphy was right! After being poked and prodded, the third cake was delivered to de Valera. Excising the key and files, de Valera enlisted fellow inmate Peter DeLoughry, who fashioned a key capable of unlocking the jail cell. Finally on February 3, 1919, after weeks of hard work, de Valera used his newly fashioned key to make his escape.

Fruitcake Freedom

During his incarceration, de Valera’s political party, the Sinn Féin party, had won the majority of seats in the 1918 general election signifying British rule of Ireland was abolished. In January of 1919, members of the Sinn Féin party assembled to form an Irish parliament known as the Dáil Éireann. Upon de Valera’s escape from prison a month later, the newly established parliament decided to elect him President of Ireland. Had he not escaped using a fruitcake as his key to freedom, de Valera would not have had this opportunity. 

If You Liked This Story, Then You'll Love This...

Think Éamon de Valera was creative for using a fruitcake to help him successfully escape prison? Sounds like you're a person who enjoys ingenuity and out-of-the-box thinking. You should definitely read our blog, 10 Ways to Reuse Your Fruitcake Tin. Here you’ll find some of the best tips, tricks, and life hacks for how to use your leftover DeLuxe® Fruitcake tins, courtesy of some of our most loyal Collin Street Bakery customers.


February 12, 2021
Jackie Placidi
February 26, 2021 at 11:52 AM
I recently told a friend - "When I die, my family will find a huge stash of Collin Street Bakery fruitcake tins neatly stacked in my basement". :)
Collin Street Bakery
March 3, 2021 at 1:12 PM
We LOVE this!
Esperanza Angeles
February 26, 2021 at 11:56 AM
Beautiful story of a great man. I admire him for his courage and his accomplishments and what he did for Ireland. I grew up in the Philippines with the Irish priests Order of St. Columban who baptized my family,married my parents and my oldest brother and when I visited Ireland 6 yrs ago, I met one of the priest who has retired there and had lunch with him.Unfortunately, they were replaced by Filipino priests in the 1990’s? And I believe they have all left the country. We love Collins fruitcake and my brother who lives in Forthworth ,Texas always make sure we get his Christmas gift of your fruitcake.
Collin Street Bakery
March 3, 2021 at 1:18 PM
Thank you so much for sharing your story with us! We are glad you enjoy our products.
Robert Hodge
February 26, 2021 at 12:55 PM
Cakes are good
Collin Street Bakery
March 3, 2021 at 1:18 PM
Thank you!
Trevathan Roseann
February 26, 2021 at 1:37 PM
I love everything you have but I especially love fruitcake!
Collin Street Bakery
March 3, 2021 at 1:18 PM
Thank you so much!
Trevathan Roseann
February 26, 2021 at 1:38 PM
I love your fruitcake!
Collin Street Bakery
March 3, 2021 at 1:19 PM
Thank you!
Derek Greatrex
February 26, 2021 at 2:30 PM
As an Englishman I obviously don't admire de Valera much. Sinn Fein, or their terrorist wing the IRA, waited until Britain was bogged down in the horrors of trench warfare in WW1 (joined in 1917 by the US) before they launched their violent attack. And ever since they have been killing innocent British citizens in an attempt to control Northern Ireland, which remains part of the UK. Not really a subject for a light-hearted fruitcake advert!
Julia Stevener
February 26, 2021 at 4:02 PM
Great story!
BJ Whiteman
March 1, 2021 at 12:23 PM
Great to learn about Ireland’s history and the fruitcake. Love your fruitcake!
Collin Street Bakery
March 3, 2021 at 2:10 PM
Thank you! It is an interesting topic.
Collin Street Bakery
March 3, 2021 at 1:23 PM
Thank you!
Phoebe Anderson
February 27, 2021 at 1:01 AM
Hands down, this is absolutely the best fruitcake that I have ever eaten! To me, it is not Christmas without a Collin Street Bakery fruitcake; and now l have decided that it is a perfect birthday cake and Valentine's Day gift as well. I think that l want one for Easter as well. I could think of a whole year of occasions for a fruitcake. I love them that much.
Collin Street Bakery
March 3, 2021 at 1:42 PM
Thank you so much! We also think our fruitcake fits all special events year-round.
Jeanette Hammons
February 27, 2021 at 9:03 AM
I hated fruit cakes all my life until I tasted Collin Street's fruitcake. I have never found another brand that taste this good.
Collin Street Bakery
March 3, 2021 at 1:42 PM
We are so glad to have changed your mind about fruitcakes.
Sherrill Porterfield
February 27, 2021 at 2:09 PM
Keep these historical stories coming! I'm so sorry to read one of the comments re: continued physical abuse in that part of the world, and it's a terrible tragedy if the person who posted their criticism of your story has apparently suffered as a result of political strife. I understand their criticism, but man's inhumanity to man will never change. Only in Heaven will there be no sorrow or pain. May those who suffer find peace in that. But hopefully, there will be FRUITCAKE in Heaven !!! BRAVO to all y'all at Collin for marketing a product that is all about JOY. We can't change history, but we CAN be the change we want to see in the world. And I want to see more people eat fruitcake (-:
Collin Street Bakery
March 3, 2021 at 1:47 PM
Thank you for sharing your kind words with us. We also would LOVE to see more people eating fruitcakes!
February 28, 2021 at 12:23 PM
My mom always bought us collin street fruitcake for Christmas and gave them as gifts. Love the Eamon de Valera story. We named our son after him
Collin Street Bakery
March 3, 2021 at 1:49 PM
How wonderful!
February 28, 2021 at 12:52 PM
De Valera would have been executed along with other Easter Uprising conspirators, except for one fact: Given that he had been born in New York, he was a United States citizen, and thus what he had done was not "treason" against the British Crown.
R M Conway
February 28, 2021 at 4:07 PM
I don’t like violence myself; however, surely you realize the Irish people were forbidden their religion, language, etc, and they were starved and beaten. That treatment tend to make people angry, you know. The violence was most certainly not all on one side.
March 2, 2021 at 12:34 PM
Hands down the best fruitcake I have ever eaten. We saw your product on "The Best Thing I Ever Ate" T.V. show and the rest is history
Collin Street Bakery
March 2, 2021 at 2:53 PM
Thank you so much! We appreciate your kind words.
Leave your comment
© Collin Street Bakery Accepted Payment Methods
American Express
Diners Club