In the second in our series of Isle of Wight villains, Island Echo looks at the curious case of Dorothy O’Grady, who ran a boarding house in Sandown and was the only woman ever to have been sentenced to death for treason.
Dorothy O’Grady would appear to have been a bad lot. She was born in London in 1897. At the age of 20, she was convicted of forging bank notes. Then, in 1920, she received a further conviction for theft and was given a 2-year term of imprisonment. On her release, she racked up a series of convictions for prostitution.
Her life took on a more respectable turn when – in 1926 – she married London fireman Vincent O’Grady, 19 years her senior. On his retirement, the pair moved to Sandown, where they ran a boarding house on The Broadway opposite what is The Heights Leisure Centre today.
However, at the outbreak of the Second World War, her husband was recalled for duty with the London Fire Service, leaving Dorothy alone in Sandown with her black retriever, Bob. This is when Mrs O’Grady’s misadventures – which led to her being arrested and sentenced for espionage – began.
At the start of hostilities, the Isle of Wight was on full alert, in expectation of a German invasion. The beaches were heavily fortified to prevent an enemy force from landing and civilians were strictly forbidden from walking on the sands. Dorothy and her dog Bob, however, paid little heed. Dorothy’s walks would take her to Culver Cliff – below Bembridge Fort – which was a command post for anti-aircraft defences. She was observed flashing a light out to sea. She was then found to have a swastika on the inside lapel of her coat and was known to have expressed her admiration for Adolf Hitler.
At first, the authorities believed Dorothy to be insane. She was caught in the act of cutting telephone wires. When she was arrested, various maps of military installations around the Island were found in her possession.
Strangely, although this was in the middle of a wartime emergency, Dorothy was not held in custody and was summoned to appear before Magistrates in Ryde. However, she failed to show up, and when police arrived at Osborne Villa in Sandown, they found it locked and Dorothy gone.
Mrs O’Grady went on the run for 3 weeks, holed up in a boarding house in Totland Bay under the name of Pamela Arland, an alias she’d used as a London prostitute. She kept herself busy making more maps, cutting phone wires and offering small bribes for information about army gun emplacements.
Dorothy was arrested in Yarmouth. She was then taken to the mainland, grilled by Military Intelligence and charged with treason. She was tried at a secret session held at Hampshire Assizes, found guilty of 7 of the 9 charges brought against her, and sentenced to death.
Her lawyers launched an appeal and 2 of the most serious charges were dropped. Her sentence was reduced to 14 years imprisonment and she was dispatched to Holloway Prison.
Mrs O’Grady was released for good behaviour in 1950. She then gave an interview to the Daily Express, claiming that all her spy escapades had been little more than a foolish joke to brighten up her otherwise uneventful life. She was apparently a masochist who was thrilled to have been sentenced to death but disappointed not to have faced a firing squad.
Papers relating to Dorothy’s trial were released in 1995. However, they were subsequently mislaid and have not been returned to the public domain. At the time of her trial, her defence papers were destroyed in a German air raid.
Journalists reviewing the papers claimed they revealed clear proof of her guilt. The Times stated “she was not innocent but a dangerous Nazi agent”. According to the Express, she was the supreme mistress of the double bluff”. The Times claimed: “Not only was she indeed a Nazi spy, she was one of the most dangerous and cunning they had ever recruited.”
The-then Isle of Wight MP Barry Field had championed her cause – believing her to have been a harmless fantasist – but was shocked when the papers were released. He said:
“I set out to clear her name, but I am staggered by the treachery she sunk to. She could have altered the direction of the war.”
Dorothy O’Grady was further investigated by local historian Adrian Searle, who wrote a whole book on the subject entitled: The Spy Beside the Sea. According to Searle, O’Grady was a highly disturbed woman who sought the limelight.
Prison reports made clear she regularly self-harmed and heard voices which encouraged her to do so. There was also a sexual dimension to her behaviour, with the Prison Medical Officer Dr Violet Minster reporting that O’Grady had inserted an alarming collection of objects into her vagina, including a light bulb, more than 50 pieces of broken glass, a small pot and 100 pins.
Dorothy O’Grady moved to a warden-assisted flat – Porter Court in Lake – in 1971, where she died in 1985. Her carers were said to have described her as nice, polite and appreciative of all that was done for her. Apparently, she never talked about her wartime adventures.
So, was Mrs O’Grady a dangerous Nazi Spy or a foolish old lady with bizarre masochistic tendencies? Unless the government documents turn up again, we’ll probably never know…
She was crazy, pure and simple.
Unlike Boris Johnson and Nigel Farage who deliberately damaged this great country for their own personal gain.
True traitors, both of them.
You appear to be insane also.
No, he’s completely correct about the actions of Johnson. I’m not so sure about Farage, but Johnson was pro EU (he was even keen for Turkey to join) until he saw an opportunity to further his career through Brexit.
He then told an utter pack of lies and made false promise after false promise to “Get Brexit Done” and sucker the British people into giving him the top job (a job he was utterly unsuited to).
As we all know, now, Brexit has been the failure it was predicted to be, with not a single promised benefit coming to pass, while almost every single thing passed of as “project fear” has come true.
There can be little doubt that Johnson is responsible for doing more harm to this country than any other single person since WW2.
Obviously not as wise as your pen name would claim.
I think he may be beaten by present incumbent of No 10 listening to her plans last night.
No, I think Mike Timms has identified traitors correctly.
Intentionally harming the country, it’s prospects, and it’s reputation by coercing voters to go with an approach that will cause harm.
an approach which still, after years, produces no benefit – only disadvantage.
You would call that patriotism.
Plenty of downvoting.
But not one willing to post in defence of the pure idiocy they voted for. Not really surprising as there are no benefits of Brexit.
You were had. Suckered. Taken by fools and used by billionaire elites to make themselves even richer at your expense.
It is they who have “taken back control” and they took it back from you as much as the EU.
Downvote as much as you like, it doesn’t make you any less of an idiot.
At least we got back control of our borders.
There is one benefit of Brexit. The lack of EU workers means that striking is again an effective means of securing a pay rise because businesses now have nobody else to fill the roles.
Ha ha nice one Tony…lmao….that shut him up lol
Well said Mike Timms.
Oi nigel farage is God, your just deluded !!!!!
My just deluded what?
Oh, you mean “you’re deluded”?
Typical thick Brexiter.
Bird bird bird is the word
I’m proud to say my Grandmother had a hand in catching out at least one German spy during ww2.
Grass grass grass
Correct me if I am wrong, but wasn’t the queens uncle a German spy?
Now we pay traitors to live, and breed amongst us all.
The only outcry being of ‘this must never happen again’ is heard every time our special services are unable to prevent every bomb, stabbing or other terror attacks.
Those brave men and women who died for us fighting to keep out those wishing to do us harm would be heartbroken at what MP’s from all parties have allowed this country to become.
Lets put this into perspective.
Deaths due to terrorist action since Jan 2020: 4
Excess deaths due to Boris Johnson’s mismanagement of Covid: 139,000
You are looking at the wrong “traitors”. If anything Johnson and his cronies are worse traitors than the terrorists. They commit their atrocities for a cause. Johnson did it for his own personal gain.
Dare i say it ?
But IMO.
Some may say, that the wrong country lost the war…….shhhhh.
Fascinating story, I hope someone from ‘Netflix’ gets wind of this intriguing tale and turns it into a six part drama (cast Julie Walters to play Dorothy). Not sure there’s a ‘sexual’ element to her dangerous insertions, however I will reserve judgement until I’ve read Andrew Searle’s book. Thanks for publishing this, more of the same please.
I agree, a tv series would be good, just not Netflix- I’d like to be able to watch it for free!
Interesting article definitely lived in a fantasy world unfortunately at the time a dangerous fantasy world.
mmmmm…..i would’nt say no ?
She would fit in fine down Sandown sea front.