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Even though there is no evidence Tom Winter liked his martini cocktails “shaken, not stirred”, the dashing Special Forces hero was a key real-life inspiration for Ian Fleming’s famous fictitious character. Winter was tall, dark, handsome and courageous – and he took part in some of the Allies’ most daring hit-and-run raids on enemy targets during the Second World War. Like James Bond, he had the knack of always emerging alive from the most dangerous of situations.
Furthermore, Fleming, who was a naval intelligence officer during the war, met Winter, a high-explosives expert, when they were both on secret operations in West Africa in 1942. It is very likely they met again after the war too.
Some years later Fleming, who by then had quit banking for a career as a writer, created his Bond character, a Secret Intelligence Service (MI6) agent codenamed 007 and with a licence to kill.
Since 1953, Fleming’s 14 Bond books have sold more than 100 million copies worldwide. The latest, Bond film, No Time To Die, starring Daniel Craig, is released in the UK this week having been postponed three times over 18 months due to the pandemic.
It is not an overstatement to say that the country’s cinemas are relying on Bond to bring fans flocking back to big screens.
007 author Ian Fleming based his famous spy in part on real life Special Forces hero Tom Winter
Fleming, who died in 1964 aged 56, once described his fictitious spy as “a compound of all the secret agents and commando types I met during the war”.
However, Winter was undoubtedly a major inspiration for the Bond character, described by Fleming as having “dark, rather cruel, good looks”.
But who was Tom Winter and what did he achieve during his career that made him a key model for James Bond?
My interest in the decorated war hero stems from my passion for bravery and the fact that nearly three years ago I purchased Winter’s gallantry and service medals to add to my Special Forces collection.
Thomas William Winter was born on New Year’s Day 1905. Little is known about his early life but, while working as an engineer, he enlisted into the Army on November 4, 1939, shortly after the outbreak of the Second World War. By then, he was 34 and older than most of his fellow soldiers.
After seven months as a mechanics instructor with the Royal Army Service Corps, Winter volunteered for the Parachute Wing, No2 Commando, in 1940.
This later became No11 Special Air Service and he was posted for duties with the Special Operations Executive (SOE), which specialised in secret actions behind enemy lines.
After completing his training, Winter worked with the Small Scale Raiding Force (SSRF). During 1942, while the rank of warrant officer, he took part in three key missions – codenamed Operations Postmaster, Dryad and Aquatint.
Sgt Major Tom Winter’s gallantry and service medals
The first two operations led to him being awarded the Military Medal. The third resulted in abject failure and dire consequences for all involved.
Britain’s Special Forces units, including the famous SAS and lesser-known (and long-defunct) SSRF, have their origins in the early 1940s when military leaders realised the value of using small, mobile and highly-trained units to launch hit-and-run raids on a far larger enemy force.
Operation Postmaster was a highly secret joint raid in West Africa by 11 men of the SSRF and four from the SOE.
It was particularly sensitive because the main target for the raid – the harbour of Santa Isabel on the island of Fernando Po was Spanish territory. Spain was neutral during the war and so the British Foreign Office and Admiralty were keen to distance themselves from the attack for fear of diplomatic repercussions.
Skyfall: Winter, with his parachute in 1940, cheated death several times
The targets were a large enemy liner carrying valuable cargo and two smaller enemy craft that would be of great use to the Navy. It was proposed to board them at anchor, capture them and bring them to British waters in Lagos.
After months of preparation in Freetown, Sierra Leone, the order to go ahead was given on January 6, 1942. Five days later, the 15 raiders boarded two tugs — Vulcan and Nuneaton — manned by 17 local volunteers and headed for their objective.
The raid, under the command of Major Gus March-Phillipps, founder of the SSRF, was carried out on January 14. Of the three enemy ships, Burundi and Likomba were moored together and were approached by the Nuneaton raiders, including Winter.
He and Captain Graham Hayes were assigned as first to board, to take care of any resistance and to set the explosives on the anchor chain. Strict orders were given that no shots should be fired.
Winter and Hayes left the tug to take to the water in collapsible canoes — known as folbots – and paddled to the first target. Confronted by two men with knives in their teeth and coshes in their hands, the single night watchman promptly dived overboard and swam for the shore.
Finding no further opposition, the two men quickly laid their charges on the anchor chain and stern cables while one of the tugs attached a towing cable to the target. The tug then went slowly ahead and took the strain on the cable.
Winter and Hayes then set off the charges. Similar actions took place on the second smaller craft and the larger liner, boarded by a small party led by Major March-Phillipps.
The attack could not have gone more smoothly. All three enemy ships were captured and 29 prisoners were taken. Some were used to sail the three ships to British waters at gunpoint.
Less than nine months later, on the night of September 2, Winter was part of a 12-strong raiding party, including March-Phillipps, for Operation Dryad.
This involved an attack on the Casquets lighthouse on a small island six miles west of the Alderney in the Channel Islands.
Here a small German observation post had been set up, with a radio station.
At 9pm, the raiders set off from Portland, Dorset, aboard Motor Torpedo Boat 344 (MTB). Moving swiftly across the water, she arrived at Casquets Island at 10.45pm and was anchored before the force rowed ashore, landing on the small beach at midnight.
Daniel Craig as James Bond in No Time To Die
Next, the raiders scaled the steep rocky ascent to the lighthouse, making their way through barbed wire defences. On reaching the lighthouse courtyard unobserved, they split into smaller groups, each with its own objective. Winter and a comrade were tasked with securing the lighthouse tower, only to find
The German garrison of seven men were taken by surprise and captured. Their weapons, including a 20mm cannon, were thrown into the sea; their radio smashed; and any useful paperwork such as codebooks, diaries, and letters were seized.
Returning to the MTB, the raiders and their prisoners, arrived back at Portland at 4am, just seven hours after leaving.
Yet again it was “mission accomplished”.
Just nine days later, the raiders, once again led by March-Phillipps and including Winter, were on the offensive again in Operation Aquatint.
The objective for the raid in occupied Normandy was to test enemy defences, collect information, and take prisoners.
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Unlike the two earlier raids, it was a disaster.
Twelve raiders left Portsmouth, again in MTB 344, shortly after 8pm, arriving off the coast at 10pm. Moving slowly towards the shore, the MTB appeared to arrive at its objective of Sainte-Honorine at midnight.
Most of the raiders boarded their collapsible boat leaving one man on the MTB, and landed 20 minutes later. Only then did they realise they were in the wrong location – Saint-Laurent-sur-Mer, about a mile from their objective.
The force dragged the boat onto the beach and moved towards the village itself, only to see a small German patrol of eight or nine men. A firefight ensued, and the raiders made a fighting retreat to their boat.
They managed to get about 100 yards off the coast, until their boat was located by other machine-gun posts along the shore, and by a heavy calibre gun emplacement.
Taking heavy fire, the boat began to sink and the raiders attempted to swim to the MTB, which had been discovered, hit and forced to temporarily withdraw.
Unable to reach the MTB, the surviving raiders swam back to shore, where Winter was fired on again and finally captured.
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Three of the nine men who had arrived on French soil were killed, while six others were captured, two of whom were executed under Hitler’s infamous “Kommando Order”.
Taken prisoner, Winter was brutally interrogated by the German SS, before spending the next two years held at PoW Camp 344 in Ober Silesia from September 30, 1942, until December 14, 1944.
While a PoW, he sent coded letters to his wife, Lily, that provided the War Office with valuable information, gleaned while on working parties, about factories in the area producing equipment for the German war effort.
Eventually, Winter escaped, later recalling: “I used French uniforms to escape, was fired on but was not hit.”
Typically, he made no attempt to get back to Britain, instead linking up with resistance fighters and eventually British forces as Germany was forced to retreat throughout 1945.
These daring exploits too captured Fleming’s attention when he learnt of them after the war.
Winter’s Military Medal was announced on June 20, 1946 when his citation concluded: “On all occasions when in action he has acted with courage and resourcefulness, coupled with a real desire to engage the enemy. He has at all times shown himself to be a very capable NCO [Non Commissioned Officer] and a fine example to his men.”
Winter died on April 12, 1995, aged 90.
My respect and admiration for him are immense. Time and again he displayed what I call “cold courage” in that he embarked on a highly dangerous mission knowing there was a strong chance he would be killed, wounded or captured by the enemy.
Like millions of others, I will watch the next Bond film in the cinema over the coming days and, as the credits roll, I will certainly spare a thought for Thomas William Winter who was, in so many ways, the real-life James Bond.
● Lord Ashcroft KCMG PC is an international businessman, philanthropist, author and pollster. Find information about his work, including his six books on bravery, here. Follow him on Twitter and Facebook