Dorothy O'Grady: Dotty Dog Walker or Secretly Sandown's Sinister Seaside Super Spy? Content from the guide to life, the universe and everything

Dorothy O'Grady: Dotty Dog Walker or Secretly Sandown's Sinister Seaside Super Spy?

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Sandown Bay

On 9 August, 1940, Dorothy O'Grady was found walking her dog Rob, a cross-bred black retriever, on Yaverland's seafront on the Isle of Wight. On 18 December she became the first, and only, woman to be convicted under the 1940 Treachery Act1, and sentenced to death by hanging. Rob had been put down.

Though her sentence was commuted at the last minute, so she was not the only woman to be executed for spying in Britain in the 20th Century, the question has remained ever since. Was Dorothy O'Grady a spy?

Dorothy O'Grady

Londoner Dorothy's childhood was, by all accounts, unhappy. She was born in 1897, but never knew who her real parents were. She was adopted by George and Pamela Squires, but her adoptive mother died when she was ten. Although she initially attended a convent school, she was sent to be raised in the St John's Hostel Training School for Girls, a boarding establishment that trained girls to be domestic servants, and later attended the London Female Preventative & Reformatory Institution for the Friendless and Fallen charitable institution.

She married Vincent O'Grady, a London fireman almost 20 years her senior2 on 21 August, 1926. Both Overnors3, they had bought the Osborne Villa Bed and Breakfast on the Broadway in Sandown on the Isle of Wight in early 1939, when Vincent retired. On the outbreak of war Vincent had responded to a call for all retired London firemen to re-enlist, and had returned to the capital.

In August 1940 Dorothy was a 42-year-old lonely landlady, short, plump, with poor eye-sight and a squeaky voice. Quiet and reserved, she spent her time alone with her dog, and had no known friends; even her neighbour did not know her name. With no tourists visiting England's front-line for bed and breakfast, and without her husband, Dorothy doted on her dog, taking it for walkies on the beach every day.

The Isle of Wight at War

In August 1940 the Isle of Wight was on invasion alert. The British army had retreated from Dunkirk, France had fallen, the Channel Islands conquered and the Battle of Britain begun. On 9 June the 12th Infantry Brigade was stationed on the Island to defend it in case of invasion. Bombs had first fallen on the Island on 16 June4. Many expected the Isle of Wight to be the next logical target, including Adolf Hitler himself, in his Directive No 16 on 16 July, 1940. When ordering the drafting of what would become Operation Sea Lion, he ordered:

Each individual branch of the Wehrmacht will examine from its own viewpoint whether it appears practical to carry out subsidiary operations, for example to occupy the Isle of Wight... prior to the general crossing.

The German 9th Army under Field Marshal Gerd von Rundstedt was assigned the task of invading the Isle of Wight, crossing from Le Havre. Although the invasion plan later was amended with the Isle of Wight no longer the prime focus of invasion, at the time Dorothy O'Grady took her dog for a walk on the beach on Sandown Bay on 9 August, 1940, the Island was still a key target.

Sandown Bay

Since the reign of Henry VIII it was known that any seaborne invasion of the Isle of Wight could only succeed at Sandown Bay. During Queen Victoria's reign an array of forts5 had been built to defend the 5-mile stretch of golden sand that was now seen as a gateway to England. In July 1940 an experimental Chain Home Low army-manned radar station had been set up at Culver Cliff, next to the Royal Navy's shore signals and wireless station in Sandown Bay's northern side to detect enemy shipping movements and low-flying aircraft. Dorothy O'Grady's home overlooked Sandown Bay; she lived in exactly the right place at exactly the right time to be of assistance to any German invasion. Anti-invasion defences sprung up around the Island, the Sandown Bay piers, Sandown Pier and Shanklin Pier, as well as nearby Ventnor Pier, all were sectioned6. Travel to or from the Island needed a special permit.

On 12 August, 1940, the Isle of Wight was the Luftwaffe's prime target. The top-secret Radar Chain Home station at RAF Ventnor was targeted for attack by 20 Junkers Ju 88s, each armed with four high-explosive bombs, strafing the area with machine guns. The Ventnor radar station was the only radar station in the country in the entire war to be destroyed, remaining out of service until after a reserve station at Bembridge was completed on 23 August. The Isle of Wight had its own shipbuilding and aircraft factories in Cowes and East Cowes and was close to both the Royal Navy's headquarters at Portsmouth, and the key port of Southampton.

This was the environment the Isle of Wight was in when Dorothy O'Grady was found walking her dog on the beach. Walking on the beach was almost literally stepping on a minefield, at a time when Winston Churchill was making his speech about fighting on the beaches, not walking dogs there. Defended by searchlights, anti-aircraft guns, mines, barbed wire, 'dragons' teeth' anti-landing-craft devices, pillboxes, iron rails, old Great War naval guns and trenches, the beaches were strictly out of bounds for civilians.

However, any German invasion would need to know exactly where these defences were located. Where were the big guns positioned? Where were the men stationed? German Intelligence had Ordnance Survey maps of the Island and plenty of photographs, taken before the war and by reconnaissance aircraft, but with the defences camouflaged, only a spy actually living in Sandown Bay, who, say, owned a guest house placed on the cliff overlooking the bay and opposite the garrison stationed at Sandown Barracks, would be able to provide this information.

Spy Culture

Many of the most popular films in Britain during the late 1930s and early 1940s were spy thrillers. Films such as The Thirty-Nine Steps (1935) and The Lady Vanishes (1938), Foreign Correspondent (1940), Night Train to Munich (1940) and Saboteur (1942) were box-office hits in the cinema. Films released in 1939 included Spy for a Day, The Spy in Black, Spies of the Air and Traitor Spy. Beloved familiar characters of the time such as Inspector Hornleigh got in on the act by capturing spies on an express train in Inspector Hornleigh Goes To It (1940). Cottage to Let (1941) included fifth columnists and secret inventions. In low-budget comedies Arthur Askey and George Formby would foil the plots of swarms of German spies as well as unmask quislings and traitors and everything would turn out nice again. All these films reinforced the Government-endorsed message that not only did careless talk cost lives, anyone could be a spy and traitor. Even someone like Dorothy O'Grady.

What Dorothy Did

Throughout the summer of 1940, Dorothy seemed determined to walk her dog on the beach at Sandown, even though it was out of bounds to civilians under the new Defence Regulations. On 9 August she was caught by the Royal Northumberland Fusiliers walking her dog on Yaverland beach. This beach was beneath the cliff top location of Culver Fire Command, where the Victorian forts housed modern weapons to defend the Island from enemy ships and aircraft. To get to the beach, she had crossed the barbed wire and passed all the signs warning her that she was trespassing in an out-of-bounds area. She later claimed that her dog had run off down from the cliff path and she followed to rescue him, but according to the soldiers' reports, her method of rescuing her dog from the beach was to sit down and eat an apple while watching her dog paddle on the seashore.

She was soon discovered, and, as this was the third time she had claimed she was on the beach because she was 'looking for her dog', it was decided to report her to the police. On hearing this, Dorothy became alarmed and offered the soldiers 10 shillings to let her go and forget about seeing her, an act of bribery that only raised their suspicions and made them more determined to report her. She, and her dog, were then walked a further 3 miles to Bembridge. There her name and address was taken, and as it was decided that her actions were a nuisance and an arrest would deter others from trespassing, two summonses issued for offences under the Defence (General) Regulations Act of 1939 were issued, with a magistrates court date of 27 August. Her charges were for entering the foreshore, contrary to regulation 16a and acting in a manner likely to prevent or interfere with the performance of the duties of HM Forces. Minor offences which would warrant a stern ticking off and a fine, but nothing too serious.

On 27 August, however, she did not attend court. The police were sent to Osborne Villa to call for her, but she had fled, leaving only a note No more milk till I return pinned to the door...

What Dorothy Did Next

Dorothy had fled, but where had she, and her dog Rob, gone? Why would she run away from having her knuckles rapped if she had nothing to hide? Had she rendezvoused with a German submarine? Left to assume a different identity elsewhere? For two weeks southern England was searched for a sign of Dorothy, whose suspicious actions had convinced local police that she must be a fifth-columnist quisling. However, with permits needed to leave the Island and the high state of security in the crucial period of the war, Dorothy O'Grady was trapped on the Isle of Wight. Unable to get to the mainland, she settled for the next best thing; she fled 21 miles west to the opposite side of the Island, where she had booked herself into the Latton House guesthouse in the village of Totland under the name of Pamela Arland. Totland is a village in the middle of the Freshwater peninsula, the second most heavily defended part of the Isle of Wight during the Second World War, after Sandown Bay, with 10 forts in the area7 defending the Island and entry to the Solent.

There, too, she was seen hanging around the forbidden coastal areas, cutting the military telephone wires in the Alum Bay area. She was arrested on 10 September at the guest house, reportedly in the toilet, attempting to flush paper, and not of the toilet variety, away. In her room were detailed hand-drawn maps of Sandown Bay and the Isle of Wight, showing defensive positions in such detail it even included exactly where troops were billeted.

Go To Gaol, Do Not Pass Go

Dorothy O'Grady was now accused of nine charges, under the 1939 Defence Regulations Act, 1911 Official Secrets Act and 1940 Treachery Act. She was being investigated by MI5 and was tried in Winchester Castle's Great Hall on Monday 16 December, 1940. The first four charges she stood accused of were punishable by death:

  1. Conspiracy with intent to help the enemy
  2. Making a plan likely to assist the enemy's operations
  3. Intent to impede the British Armed Forces by cutting a military telephone wire
  4. Forcing a military safeguard8
  5. Approaching a prohibited place for purposes prejudicial to the state
  6. Making a plan of potential use to the enemy
  7. Acts which might prove prejudicial to the nation's defence
  8. Sabotage
  9. Possession of a document with information purporting to relate to the nation's defence measures

Dorothy O'Grady pleaded 'Not Guilty', and the trial lasted two days before the jury found her not guilty of two of the nine charges, including conspiracy, but guilty of seven, including three punishable by death. On 17 December the judge, Mr Justice Macnaghten, donned a black cap and sentenced her to hang. Although she displayed no emotion as this sentence was read, she later described her reaction with the words:

The excitement of being tried for my life was intense. The supreme moment came when an official stood behind the judge and put on his black cap for him before he pronounced the death sentence. The man didn't put it on straight. It went over one of the judge's eyes and looked so funny that I was giggling inside and had a job not to laugh. It was hard to keep a straight face and look serious and solemn as I knew a spy should. I found it disappointing that I was going to be hanged instead of shot. My next disappointment was to learn they would put a hood over my head and tie my hands behind my back before taking me to the scaffold. This upset me. I protested, 'What is the good of being hanged if I can't see what is happening?'

Her death sentence, the first Briton convicted for treachery under the 1940 Treachery Act and the only woman sentenced to be hanged for treachery in the 20th Century in Britain, quickly became national, and even international news, reported as far away as Australia and New Zealand. Especially as a Dutchman, Charles van den Kieboom, had been hanged for treachery in Britain the day before. Her story made it to the 18 December's front page of the Daily Mirror, pushing America's signing of the vital lend-lease arrangement which would enable Britain to continue to fight effectively against Nazi Germany onto page two. Her execution was scheduled for Tuesday 7 January, 1941.

An Appealing Reprieve

Dorothy O'Grady may have been resigned to die, but having been granted legal aid, she had a lawyer who refused to give up. While she spent Christmas Day in a cell waiting for her execution, with a little piece of Christmas pudding, a few sweets and some cake, her 45-year-old barrister, John Scott Henderson, put in an appeal against her sentence on Boxing Day. He claimed that judge Sir Malcolm Macnaghten had prejudiced the outcome of the trial. With an appeal under misdirection of the jury granted, a new hearing was scheduled for the Old Bailey for Monday 10 February, 1941.

Henderson worked hard in creating a case to try to save Dorothy O'Grady from the gallows, but on 22 January disaster struck; his chambers were destroyed by a German bomb, and the legal documents and defence destroyed. Fortunately the Crown Prosecution lawyer, John Trapnell, let Henderson move into his chambers and share the Crown's documents regarding the case, taking it in turns to use them. At the hearing the capital charges under the Treachery Act were quashed, though she was still found guilty of breaking the Official Secrets Act and Defence Regulations. Instead of death by hanging, Dorothy O'Grady was sentenced to 14 years penal servitude in Aylesbury prison. Although she had been saved from being executed, this was on a legal technicality, not because she was found innocent of wrongdoing. Her harsh sentence surely implied that she was clearly guilty of something?

I Spy?

Nine years into Dorothy's 14-year prison sentence, the longest term a woman had yet spent in Aylesbury prison, her husband, Victor, became seriously ill. Dorothy successfully appealed for early release to look after him, and she was freed on Friday 24 February, 1950. Her first act on her release was not to see her husband again, but to head straight for the Sunday Express newspaper office in London's Fleet Street, where she handed over a copy of her autobiography and gave the first of many often contradictory interviews about her actions. Her story was that she was never actually a spy, but was a bored, lonely housewife. One day she decided that the best form of entertainment was for her to pretend to be a spy, as that way she would be living a thrilling life. She said that she started wearing paper swastikas beneath her clothes, drew maps of the Island's strategic sites using guide maps she had collected to give to the Bed and Breakfast's visitors who never came, and challenged herself to get through barbed wire fences and into forbidden areas. One day, while in Ventnor where many soldiers were billeted, she was almost killed when the Luftwaffe destroyed the Royal Marine Hotel in the raid against Ventnor's Radar Station.

She insisted in every interview she gave after being freed until her death in 1985 that she had pretended to be a spy out of boredom. She stated:

All my life I had never been anything. I had always been insignificant. I never had a close friend, even at school. I felt tremendously bucked when I saw that they thought me clever enough to be a spy. It made me feel somebody instead of being an ordinary seaside landlady. Yet I was astonished when they believed it all. I never imagined they would.

Dorothy returned to the Isle of Wight on Saturday 4 March, 1950, with her interview making the front page on Sunday 5 March. However she was still considered a traitor on the Island, with many shops refusing to serve her. Vincent O'Grady died on 27 August, 1953, and once again Dorothy was alone on the Island, this time surrounded by a hostile neighbourhood who felt that she had betrayed them. She turned the guesthouse into a home for long-term boarders. Now and then she enjoyed the attentions of journalists after her story, whether for newspapers or local television – although when her story was published in the Reveille, she became infuriated. Not because it portrayed her as a spy, but because it described her retriever Rob as a spaniel. In her final interview in 1981 she said:

I have learned to accept that people are never going to forgive me for being convicted of spying. I never was a traitor. I had a fair trial but I got myself into trouble through being an exhibitionist. I wanted to be noticed. I wanted to shock people and be talked about. I was never a spy.

She also said how much she enjoyed the celebrity status she had in prison, and described her 9-year prison sentence with the words:

I was quite a personality there because they looked up to me, thinking I was a real spy... The only bad thing was when a member of staff's relative died in the war and she took it out on me, wrecking my room and taking my nice handkerchiefs. But I didn't hold it against her, it was understandable because she thought I was a spy... It wasn't an ordeal because I enjoyed it, and I think I would do the same again now if I were younger.

On 11 October, 1985, Dorothy O'Grady died at the Tower House nursing home in Lake Hill, within a mile of her home at Osborne Villa. She was 87.

The Dread of Something after Death?

Though dead, Dorothy O'Grady was not forgotten. In 1992 her story inspired James Friel's novel Careless Talk. In 1994 Maureen Lipman played her in the Radio 4 play The Spy Who Never Was. It was natural that the Isle of Wight's MP Barry Field would, in May 1995, decide to look into the Dorothy O'Grady story, following her file's release from the Crown Prosecution Service's confidential records office to the Public Records Office. He wished to find out what the facts were once and for all, and, he hoped, prove her innocence for good.

Shortly after looking into her file, Barry Field declared:

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's file contained evidence of how, before the war, she was convicted for theft, forgery, including of banknotes, and four times for prostitution, using the alias Pamela Arland. The file noted that she was found wearing swastikas and had repeatedly tried to bribe soldiers in order to gain access to military zones, not just on the occasion of her arrest. One of the highly detailed maps she had drawn included a detail of Culver Cliff's revolutionary experimental radar station. This she had labelled on a map as 'Wireless station on top of Culver Cliff - most important in the kingdom', and had cut the military telephone cables between searchlight sites and gun batteries six times. It also stated that, when MI5 interviewed her, she had said she had several Dutch9 friends who had recruited her before the war. During air raids while at Holloway prison awaiting trial, she had been caught trying to use her prison cell's light to send Morse code messages to the German bombers and, when arrested in Totland, had tried to swallow tablets in an apparent suicide attempt. At her trial, her counsel, John Scott Henderson, had offered no evidence for her defence and Dorothy was not asked to speak. Also on file was a highly unusual note from the Director of Public Prosecutions, Sir Edward Atkinson himself, which read:

I think that the sentence of death ought to go forward. If this woman is reprieved, the knowledge of her reprieve would go not only to the public, but also go to the German intelligence service.

Surely all of this could only mean that Dorothy O'Grady had indeed been a spy? And if not, then why was it that, despite the Freedom of Information Act allowing the release of files from the National Archives (provided the files were not of a personal nature that would contravene the Data Protection Act), shortly after this story was published, Dorothy O'Grady's file, number HO45/25408, disappeared, lost somewhere between the Home Office and the National Archives at Kew?

However, doubt again surfaced. Her 'suicide pills' that she tried to take were in fact tablets to help unblock stuffy noses. Much of this newly-unclassified evidence could be attributable to Dorothy O'Grady pretending to be a spy, and did not prove she actually was one. Although she drew maps and liked to wear swastikas, there is no evidence that she passed on any information she had gathered. She had no radio, no communications equipment, and though she tried to flash a light to signal German bombers, she didn't actually know either Morse code or German. It was also revealed that Guy Liddell, MI5's counter-espionage officer, had concluded during his investigation:

Personally I doubt whether she is guilty of anything more than collecting information. She probably pictured herself as a master spy, and cannot bring herself to say that there was really nothing behind it at all.

In 2012 Adrian Searle, author of The Isle of Wight at War, published The Spy Beside the Sea, the most thorough account to date of Dorothy O'Grady's life, containing many previously unreleased facts. These include more information about her early life, her prison record, possible connection with genuine German spy Vera Schalburg as well as reports on her mental state. She was summarised as being psycho-sexually disturbed, with strong masochistic tendencies, including the use of broken glass and sharp objects in masturbation, and an enjoyment of being punished. These tendencies would come to the fore during times of boredom, such as she felt when alone in her house in 1940, having little contact with other people. Seems that Sandown's sinister seaside super spy was merely dotty, depressed, deranged and disturbed after all.

Or was she...?

1A person would be convicted if they had 'intent to help the enemy, does, or attempts or conspires with any other person, to do, any act which is designed or likely to give assistance to the navy, military or air operations of the enemy, to impede such operations of His Majesty's forces, or to endanger life.'2Although her husband was old enough to be her father, the Great War had succeeded in wiping out many men of her generation.3Someone living on the Isle of Wight though not born there.4The first raid destroyed a telephone wire, some windows and is believed to have killed some rabbits. The Island had over 1,600 air raid alerts, with only Dover in England having more air raid alerts during the war. Many of these air raid alerts were caused by German aircraft attacking convoys near the Island or targets in the south of England such as Portsmouth and Southampton, the 8th and 9th most-bombed parts of Britain during the war. The Island became a convenient place for the enemy to drop bombs when returning from their main targets.5Culver Battery, Bembridge Fort, Redcliff Battery, Yaverland Battery, Sandown Granite Fort and Sandown Barracks Battery.6Had entire sections of the pier removed to prevent their use as landing platforms for enemy troops.7Freshwater Redoubt, Needles Old Battery, New Needles Battery, Hatherwood Battery, Warden Point Battery, Fort Albert, Cliff End Battery, Fort Victoria, Golden Hill Fort and Bouldnor Battery.8A safeguard is a detachment posted for the protection and defence of persons or places. 'Forcing a safeguard' means to violate or bypass the detachment, such as by deliberately trespassing in fenced off areas and avoiding the guards posted there.9Although the Dutch were Britain's allies during the war, two of the 16 spies executed in Britain during the Second World War had been Dutch.

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