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A Nazi Spy in Sandown!

REF NR: 2283

This is the very strange and sad story of Mrs Dorothy O’Grady who lived at Osborne Villa in Sandown at the beginning of the Second World War.


Dorothy was the first (and indeed only) woman of any nationality to be sentenced to death for spying in Britain during WWII. Had the sentence been enforced, she would have been the only British woman executed for espionage activity carried out in the UK during the entire 20th Century.


The actual sentence was eventually reduced to a 14 year period and she served only 9 years of those; but was she actually a Nazi spy in the first place? The story is one that has a great deal to do with the mind of Mrs. O’Grady and has been meticulously researched by the island historian, Adrian Searle in his book, The Spy Beside the Sea.

Mrs. O’Grady and her elderly husband opened a small guesthouse, just before the start of WWII which was unfortunately not a good time for bountiful tourism here on the island. During the phoney war, she used to walk her dog Rob up and down the various footpaths, often straying into forbidden areas and then being told off by the various military and police authorities for being a dithery old lady who must keep to the correct walking paths.

One of her jottings that the Ministry felt could be useful if it fell into enemy hands


Things took a turn for the worse on one of her walks when she was again arrested. This time the authorities had grown tired of her excuses and decided to make an example of her, so that others would not do the same.  She was booked for a minor offense of wartime trespass and expected to attend court to be formally told off and fined. However, when she did not turn up, the police were dispatched to Osborne Villa to arrest her. On arrival, they discovered the house was locked and Mr O’Grady was nowhere to be seen.

After three weeks a member of the public recognised her and she was arrested under the name of Pamela Arland, staying in a Totland Bay boarding house.  The name she was using was another sad part of the story as, prior to coming to the island, this was a pseudonym used by her for the purposes of prostitution in London. While in Totland, she apparently still made sketches of military garrisons and was fond of asking local children of the whereabouts of the troops and gun emplacements in return for sweets.

She was immediately taken to the mainland, where she was interrogated by MI5 and various security departments - subsequently admitting to all charges. At her trial the verdict was reached swiftly and she was sentenced to death. However, after a successful appeal based on the original trial having been misdirected by the judge, her death sentence was reduced to 14 years imprisonment.

The story did not end there. When she was released after serving nine years as a model prisoner, she immediately went to Fleet Street where she declared that she was never a spy and had only pretended to be "as a bit of a lark to bring a bit of excitement into her life”. 

There seems to be a mixed opinion as to whether or not she actually was delivering any information to the Germans. Adrain Searle in his new book has trawled the official papers in the UK and in Germany and there appears to be no British or German confirmation.  Her early childhood and teenage years can be read in Searle's book, which is filled with chaos and sadness. It’s most likely this avant-garde approach to life unsettled her mind, detaching her greatly from conventional past-times.

Further Reading
'The Spy Beside the Sea' by Adrian Searle the Kindle version is still available via Amazon and other online sites, the printed version can be purchased from most bookshops in the UK (including several on the Island) and via many online book ordering sites. rrp £12.99.

Images shown are by kind permission of The National Archives and Adrian Searle