In the pre-dawn hours of August 19, 1942, 6,000 troops, including almost 5,000 Canadians, 1,000+ British forces and 50 US Army Rangers, crossed the English Channel in a raid on the French coastal town of Dieppe.

The raid, codenamed “Operation Jubilee”, relied on precision timing and surprise, both of which were almost immediately lost when the eastern flank of the landing force met a German convoy. The resulting firefight alerted the rest of the German forces, and the Allied soldiers that came ashore at Berneval and Puys incurred heavy loss of life.

Running behind schedule, the main landing force landed at Dieppe as day was breaking, losing the advantage of darkness. Hundreds were gunned down as they waded to shore. The 14^th Tank Regiment struggled to move their vehicles through the stones that covered the beach: of the 29 tanks that attempted to land, only 15 made it off the rocky beach.

Despite being a combined operation involving the British army, navy and air force, there was insufficient firepower assigned to effectively counter the German forces who had commanding views of the beaches from clifftop gun nests and whose strength was at its deadly peak at that point in the war.

Within six hours, the raid was called off and evacuations began. By then more than 900 Canadians lay dead and nearly 2,000 more were captured. Less than half the force made it back to English soil to regroup and recover from their injuries. Dieppe became a byword for Canada’s tragic losses, underscored by the seeming futility of the entire raid.

But in 1995, historian David O’Keefe discovered a single sentence in a British declassified secret document. That led to nearly 20 years of combing through newly released documents that pointed to a rationale for the Dieppe raid: a top secret “pinch operation” to steal German Enigma machines and codebooks for the cryptographers at Bletchley Park. The operation, incredibly, was masterminded by British naval Commander Ian Fleming, the future creator of James Bond.

O’Keefe’s unprecedented findings are outlined in his book One Day in August which reveals the desperation, the daring and the hubris that led to the tragedy of Dieppe, and helps shed light on an agonizing chapter in Canada’s history.

What was the Enigma machine, and why were missions to “pinch” them seen as crucial?

The Enigma machine is an electromechanical machine that Germans used to encrypt their messages. It wasn’t a radio – it didn’t transmit – but it sat beside a radio. It substituted each letter of your message with a scrambled letter. Everybody in the German forces had to set up their Enigma machine the same way so there were codebooks and tables and setting sheets sent on a monthly basis. The odds of breaking into a three-rotor machine without any kind of captured material or codebook was a 150 million, million, million to one. Those are the same odds as winning the lottery every week for 150 years, so you can see why Germans had a lot of faith in it, and why a lot of blood and treasure was used by the Allies to try to get it.

Codebreaking was done at Bletchley Park, famously with Alan Turing. A lot of the combined operations raids were being put on specifically to capture the material to cut down the odds for codebreakers at Bletchley Park. Once they can get their first break to see how the Germans conceptualize setting up their cryptography, then they can start working on it themselves.

But as they were breaking into the three-rotor in spring of 1941, they realized that the Germans had developed a four-rotor machine which took the odds to 92 septillion to one. British intelligence were terrified about the four-rotor because if it came in full force that would black out Bletchley Park completely.

This is the sentence that started it all for you: “As regards captures, the party concerned at Dieppe did not reach their objective.” When, where and how did you come across this note?

Even though the British government admitted that Ultra existed in the 1970s they got cold feet and only released 5,000 pages of material and none of it was how they did it. [Note: Originally a term denoting the highest level of secrecy given to intelligence gleaned from enemy communications, “Ultra” became a catch-all term for the operations of Bletchley Park.]

As a result, they starved out the historical community by not giving them anything and the Ultra files were seen as a white elephant. But 1995 was the big watershed moment. In 1995, the Clinton administration, with the stroke of a pen, declassified most World War 2 documents. The Americans were involved in Ultra once they got in the war, and their declassification kind of forced the hand of the British.

That’s when I found the one document that showed there was a special commando unit referred as the Intelligence Assault Unit, later called the 30^th Assault Unit, raised by Naval Intelligence, to go after specifically anything to do with the new four-rotor machine. In the document, it says “The party concerned at Dieppe did not reach their target.” That was the first time you saw Ultra directly linked to the worst day in Canadian military history.

You can’t just simply ignore that but the problem was, it’s one puzzle piece and you don’t know what the rest of the puzzle is. Eventually I reached out to GCHQ [Government Communications Headquarters in the UK], which is current incarnation of Bletchley Park, and told them what I was working on, and asked for them to deny, refute, or support my findings. Within two days they sent me the appendices to the Ultra secret history that was in the process of being declassified. Now there was a template for what a pinch raid looks like, and you can go back and see how the other raids fit the template perfectly. These operations were not ad hoc.

The second paragraph in the document said, “No raid should be laid on for Signals Intelligence purposes only. The scope of the raid should be wide enough to presuppose normal operational objects.” You have to be able to dress it up, make it big and slip your operation in the middle of it. That’s what they were doing because that’s what the pinch “doctrine” called for.

Why Dieppe?

People have said, “It was practice for D-Day” but that’s akin to putting a Lada in a Formula One race. In March 1942 when they suddenly planned Dieppe with a week’s notice, they had discovered that German ships in the Channel were being outfitted with the four-rotor. Dieppe was at the midpoint in the Channel and it’s a supply base, so the code books and machines would be stockpiled in Dieppe. They saw it as one-stop shopping: “If we don’t get into this now, we will never get into it and the four-rotor will spread.”

The biggest challenge is properly gauging the ability of your opponent. The Allied intelligence was good at figuring out the numbers they really flailed when it came to understanding the quality. The belief about German forces at Dieppe was that they were static defenders who had been sitting around for two years. But the Germans were at their peak at that time – their B-team could win gold.

Your book lays out details that make the losses of Dieppe seem inevitable, like the reliance on surprise, planning only 30 minutes for the infantry units to reach their targets and achieve their objectives, topped off with over-confidence engendered by the success at St. Nazaire. How accurate is that assessment?

Previous pinch operations were not necessarily successful in getting the Enigma machines but they are low in casualties, until Dieppe. By the time we get to the planning of Dieppe, Mountbatten’s Combined Operations team is starting to cut corners: “Nothing bad has happened so far, why would it happen now?”

If the target is deemed to be A1 – which anything to do with Enigma was seen to be – it would justify the mounting of special operations to obtain it. They were not shy about incurring casualties – it’s a gambler mentality, though they were not anticipating Dieppe. Unfortunately for the Allies, they paid a heavy, heavy price in the process.

When they’re planning the raid on Dieppe, in their minds everything works. But what if you don’t get both headlands? We’ll throw a little smoke here. We won’t have the kind of firepower we need because this is all based on surprise. There were fundamental errors right from the start just compounded by wishful thinking. Every time there was a roadblock, they had a response for why they were going, whether that answer was legitimate or not. You can see the disaster of Dieppe coming almost from its inception in March 1942.

One of the surprises in the book is the role of Ian Fleming, the future creator of James Bond, in the planning of Dieppe and the pinch operation. How much responsibility can accurately be put on Fleming for the day’s terrible losses?

Fleming was a very Machiavellian character and not very compassionate but he would not have been alone. That attitude was shared and supported by others. Fleming is just the messenger that delivers the imperative.

The historical Ian Fleming has become a minefield: people think he was either James Bond himself or the unimportant guy with “the in-tray, the out-tray and the ashtray.” He was in between. He was never really in the field, except for the Dieppe operation when he was offshore as the relay man to get any pinched material back to England.

Fleming’s portfolio within Naval Intelligence was vast and that’s what made him important and perhaps also dangerous. He was liaising with Bletchley Park all the time to assess what their needs were because he was the one responsible for suggesting pinch operations. He was also on the Joint Intelligence Committee which advises the chiefs of staff. Even though his boss Rear Admiral John Godfrey is sacked after Dieppe Fleming remains an incredibly influential figure in the intelligence setup.

Arguably I think responsibility sits with Mountbatten and his planners because Fleming is saying “I will get the commando unit but you will be responsible for getting them there and getting them out.” The criticism of Mountbatten’s organization is very fair, that they were enthusiastic amateurs.

Dieppe was, and is, one of the talismanic moments in the Canadian psyche: our soldiers were valiant and got slaughtered, and the terribleness of that loss has become the narrative. Did that view have an impact on how your research was received?

All the criticisms are still valid. There was a legitimate purpose to the operation and why they were going which they couldn’t talk about for security reasons. But the price and futility are still in play.

When we broke the story, a lot of news agencies ran with the angle of “Fully vindicated!” and we were like, let’s temper this a bit; we still have 907 Canadians who died in six hours. It’s important to know there was an altruistic objective but it doesn’t change the fact that the original accusations that it was a slaughter and poorly planned, they all still apply. And that’s the key: it’s trying to get the facts properly centred as opposed to slanting to either side.

In a Global News interview in 2012, you made the statement that, for many years, many veterans of Dieppe had no clue why they were there. Describe what kind of impact that would have had (and did have) on veterans.

The experience of Dieppe Veterans was heartbreaking. They trained for two years and their battle was over in six hours. Many of those who were lucky enough to get off the beach alive ended up in the horror that was German prisoner of war camps for years. In January 1945 POWs were marched across Europe, used as human shields for the Germans.

When they arrived back at their regiment, no one knew who they were. The regiments had rebuilt and had gone into action in Normandy and Holland; they had developed a band of brothers legacy after fighting for 10 months.

There was a Dieppe Veterans’ association that was formed because most of the Dieppe Veterans didn’t feel like part of their regiment when they got back. Ron Beal, who took part in the documentary Dieppe Uncovered, was one of their presidents.

The concept of regiment is not just recruitment or the name you yell when you’re running up the hill in battle. It’s supposed to be a family and you take care of family members. The ball wasn’t intentionally dropped but the Dieppe Veterans didn’t get the respect that they deserved, largely because no one knew what they were there to do.

You close your book with Dieppe Veteran Private Ron Beal saying to you, “Now I can die in peace. I know what my friends died for.”  How did it feel to hear that?

I went home that night terrified would be the way I’d put it because I thought, my research had better be top-notch. It was a humbling lesson to understand that what we do as historians has such power and such impact. We have to make sure we do our jobs right.