The Mistakes of World War II Quiz


By: Zoe Samuel

7 Min Quiz

Image: JasonDoiy/E+/Getty Images

About This Quiz

World War II remains the largest military conflict the planet has ever known. This horrifying event kicked off in 1939 with Hitler's invasion of Poland - though arguably it was in the works much earlier, with the Anschluss with Austria and the invasion of the Sudetenland in Europe starting in 1938, plus Japan's aggression into China commencing in 1937. By the fall of 1939, the Allies - the UK, France, and friends - were at war with the Axis - Nazi Germany and Mussolini's Italy, plus their friends. The USA and Japan stayed out of it at first, but when Japan decided to get involved by striking Pearl Harbor as well as a number of British and French assets in Asia, the U.S. declared war in 1941, and the Asian conflict ramped up.

The single biggest error in the war is generally held to be Hitler's ill-timed invasion of the USSR, which turned neutral Russia into an enemy who then brought to bear its almost limitlessly enormous army against him on the Eastern front. This cost Hitler dearly in blood and treasure and crippled his ability to fight on the Western front. As far as the Asian theater is concerned, the largest mistake Japan made is not just attacking the USA but failing to do so thoroughly, thus waking the "sleeping dragon" without first chopping off its head. The largest mistake from an intelligence point of view was Germany's failure to realize that the British had broken the German's Enigma codes and knew what they were up to.

Still, knowing these mistakes doesn't mean you know all the major mistakes of the war or the details of the above... or do you? Let's find out!

Who was the "war magician" whose fake tanks convinced Rommel that the Allies had plenty of forces in the area around Alexandria?

The Maskelynes was a family of magicians going back more than 100 years. Jasper was the latest in line, and his "Magic Gang" unit worked miracles in the African theater of war. He made troops appear where they were not and used a mirror trick to make the Suez Canal "disappear" so that German bombers ended up wasting their loads on the desert miles away. This enabled Allied troops and oil supplies to keep moving, thus assisting in the ​victory over the "Desert Fox" himself, the fearsome Nazi leader, General Erwin Rommel.


What stupid thing did Neville Chamberlain say before the war began?

Chamberlain's policy of appeasing the Nazi threat meant throwing Czechoslovakia, Austria, and all the Jews in Germany under the bus to avoid what Churchill already knew was an inevitable war. Once Germany attacked Poland, Chamberlain finally declared war. Historians say the Nazis could likely have been stopped much quicker had the Allies put their foot down sooner.


What offensive did the Germans launch that prompted the greatest loss of military life in world history - for them?

Barbarossa is the most significant military event of the war, in terms of both blood shed, treasure expended, and importance to the ultimate outcome. Attacking Russia was a monstrously stupid mistake on Hitler's part, as it meant fighting on two fronts instead of one and tackling some of the most hostile terrains​ against an enormous army that knew the area and was adapted to the climate. While the Nazis succeeded at first, Barbarossa came to a screeching halt with their defeat at Stalingrad, which historians mostly rate as the turning point of the war in Europe (and certainly Eastern Europe).


Which branch of British intelligence was almost completely ineffective in the Burma campaign?

The SOE or Special Operations Executive was founded to help local resistance "set Europe ablaze," later expanding into other theaters of the war. They had some great successes at rallying local opposition in Europe and sabotaging the Nazis. However, in Burma, where they were seen as the agents of an unwelcome imperialist power, they lacked local support and couldn't really get much done. However, it is worth reading about the things they did in Europe, as it was frankly incredibly cool stuff!


What was the name of a figure who deceived the Germans about where the Allies would land on D-Day?

The Man Who Never Was is the name by which a brilliant British scheme is now known, thanks to a movie by this name. The Germans knew the Allies were ready to invade Europe, and they had to decide where to put their best forces to defend the coast. Ewen Montagu, a British agent, cleverly loaded up the body of a homeless man with ID and paperwork that "proved" the Allies were planning to land at Calais, the nearest point in France to the British coast. The Germans found the body and thought it was an officer whose small plane had gone down. They moved their strongest forces to Calais. When the invasion came in Normandy, they had to scramble to get there - at which point the Allies had a beachhead and were too entrenched to dislodge.


During what event on the German-Dutch border did an awful lot of British spies end up dead?

Venlo is a town on the border of Germany and Holland. It was the site of an Allied intelligence failure whereby the Germans successfully lured members of the Secret Intelligence Services into a trap. They then dragged them over the border into Germany and tortured them for information. They used the presence of these men to paint the Netherlands as involved in a plot to kill Hitler, and this formed their pretext to invade the previously neutral Netherlands (which they probably would have done anyway, but the excuse surely helped them).


Who did Hitler mistakenly believe would be his ally, not his enemy?

Hitler thought the USA had some good ideas, like segregation and slavery. He also enjoyed the way that it was a more openly patriotic society and appreciated the role of violence more than the soft western Europeans. There were also fascists in the USA who were outright supporters of Hitler (we'll hear more about them later in this quiz). He also liked some British elements who supported him, like Oswald Mosley and the Brownshirts. While he did not like anything about the USSR's beliefs, he did at least imagine that Stalin could be worked with. Thus, at some point, he deluded himself into thinking that all the key Allies would be his friends, and just let him conquer Europe without a fuss.


What target did the Japanese utterly fail to attack at Pearl Harbor, thus missing an amazing chance to cripple the U.S. military?

Pearl Harbor resulted in terrible losses of personnel, aircraft, and ships for the United States. However, the Japanese missed a real prize during the raid: a massive fuel depot that was essential to the USA's speedy mobilization in the wake of the attack. As a result, the U.S. Navy was in the water and chugging its way to war pretty darn quickly. Without that fuel, they might have been delayed enough to let the Japanese establish superiority in the western Pacific that would have made them even harder to dislodge.


What Norwegian location did the Special Operations Executive successfully destroy, that the Nazis should really have defended harder?

The heavy water plant at Telemark was where the Germans were trying to create the material necessary for a nuclear weapon. The Special Operations Executive, who we mentioned earlier, launched an unbelievably heroic raid to destroy it. This, plus German alienation of the best rocket scientists in the world, meant that the Allies got the bomb first.


Where was the "Bridge Too Far"?

As immortalized in a 1974 book and 1977 movie, the bridge at Arnhem was the last place from which the Germans could escape the Netherlands back to Berlin, when retreating from the Allied advance after D-Day. The Allies chased them and got cocky, going outside the range of their reserves and supply lines. At the bridge in Arnhem, the Germans rallied and inflicted losses on the Allies, punishing their hubris. It was a literal "bridge too far," and the origin of that saying.


What mistake did Stalin make early in the war?

Stalin was indisputably an absolutely terrible man who murdered millions of people. However, because Stalin's ideology was mostly about crushing dissent - with genocide being a "by-product" of this - Hitler's was about intentionally murdering and enslaving millions of people. Thus, Churchill made the decision that Stalin could be worked with, while Hitler simply had to be stopped. It was great news for the Allies that the peace pact between Hitler and Stalin thus fell apart, enabling Britain and later the USA to team up with the USSR to preserve democracy and freedom... at least for some countries.


What was the name of the Japanese military code broken by the American intelligence services?

While the British cracking of Enigma was the singular intelligence achievement of the war, the codebreakers of America's intelligence services also did a great service to their nation. They cracked Purple, the leading Japanese naval code, and the Japanese didn't know about it for years. This meant the Americans had the jump on an awful lot of Japanese activity for the second half of the war.


What was the name of the place where British codebreakers hacked the German Enigma code?

Bletchley Park is a manor house in Milton Keynes, Buckinghamshire, about 90 minutes from London. It was located there for secrecy, and to make sure it wasn't bombed. Mathematicians and armies of support staff worked out of the house itself plus a number of "huts" full of brilliant and brave minds - a third of whom were women. Codenamed Ultra, this team decrypted the German messages and so gave the Allies actionable intelligence about where and when German forces would be. Their information was so good that one British general, who did not know it had come from codes, thought that they must have astonishingly brave armies of spies who walked right into German units.


What caused the Bletchley codebreakers to be temporarily shut out of decrypting Enigma​ until they broke it again?

The Enigma machine had letters that were on three wheels, and you had to know how to align them each day to make them generate the right codes. Then you could decrypt this and read it in German, which wasn't always easy. Once a fourth letter was added to the "Shark" code version of Enigma used by German U-boat submarines, the Bletchley team were locked out and it took another nine months to hack back in. They did eventually do it, thankfully.


What notable achievement by the Abwehr (German intelligence) postponed their defeat by six months?

One of the fortunate advatages the Allies enjoyed was that the Germans were really, really bad at intelligence gathering. This was partly cultural and partly that they didn't see the value in it. Even though British people were on the lookout for German spies throughout the war, we later learned that absolutely none of significance ever managed to infiltrate British military or political institutions. It was a very lucky mistake for the Allies.


What did America totally forget to actually have before the war started?

The Americans actually didn't have a network of intelligence-gathering tools abroad before World War II, impossible as it is to imagine such an oversight now. Britain sent trainers to help "Little Bill" Donovan create the OSS or Office of Strategic Services, a forerunner of the CIA. Hoover, head of the FBI, regarded it as a rival and was absolutely furious about it, but the OSS performed a number of key functions in ensuring Allied victory!


Which of these is NOT a major reason that the Allies won?

​The Nazis lost due to being out-manufactured, to be sure; if they were going to win it would probably have required a swifter victory to make this difference unimportant. They also suffered enormously from junior people not telling the truth to senior people, or it being ignored, because it didn't fit with how they thought the world ought to be; a characteristic of fascist regimes that often contributes to their collapse. After all, a group that believes themselves superior will struggle to admit that they need to change tack because their enemy is being really smart. That, plus the resources they wasted murdering people and policing populations who hated them, added up to defeat.


What appalling mistake condemned thousands of Japanese to a grisly death?

Before the atom bomb was dropped, a demand for surrender was issued, and the Japanese Emperor did, in fact, send a response: "Mokusatsu." History records this as being entirely defiant, as if he said, "No comment," taken to mean, "We shall ignore your petty bomb." However, there is another translation of his words that could mean, essentially, "We're thinking about it and then we'll respond." The Allies thought he'd told them to shove their offer to end the war peacefully, and made good on the threat that this response would lead to "utter destruction."​ The two atomic bombs claimed 250,000 lives, possibly because of a bad translation.


How did the British trick German bombers during the Blitz, so they didn't hit key civilian and military areas?

The blackout would not work against modern smart bombs, but during WWII, it was actually a smart move. German bombers had to navigate by the stars and by what they could see on the ground. This meant that during the Blitz, a good thick set of curtains and keeping the lights off in the streets and on the houses made it genuinely hard for them to see what on earth they were bombing. This spared many lives and valuable military installations.


Who did Hitler stupidly alienate from helping him, thus guaranteeing that the Nazis would not develop an atom bomb first?

The Nazis' nonsensical racial beliefs weren't just evil; they were also stupid. Talented Jewish figures, like Einstein, fled their regime, while others, like Oppenheimer, simply never wanted to work there in the first place. Indeed, many of the intelligence services of the USA and Britain were populated by Jews and Jewish refugees from Poland, Hungary, Romania, etc, who had personal reasons to see the Nazis fail. This meant not only did they not get the atom bomb first, but​ they also missed out on a lot of the best codebreakers. It was quite literally self-defeating.


What mistake did France make in fortifying its "Maginot Line" of defenses?

After World War I, France decided that Germany would never invade them again as they had before! So they built an incredibly well-reinforced border, the Maginot Line, to keep them out. However, they only covered the border with Germany, instead of the border with Belgium and Holland. This made it very easy for Germany to just roll through the Low Countries and go around the French defense.


What mistake did the Poles initially make when the Red Army invaded them right after the Nazis did?

Parts of Poland briefly forgot that Russia historically quite likes conquering their land, meaning that they were quite pleased to hear of the Red Army's arrival. However, Stalin was very wary of war with Germany and was officially neutral. He was there to conquer Poland and establish a border with Germany that he could defend if he had to. This resulted in poor Poland being carved up and popping out of existence for several years.


What did Romania do that they later regretted?

Romania made an error in siding with Germany, though given the information they had at the time, it was reasonable to imagine the alternative was invasion by the Nazis. They joined the Tripartite Pact and fought against the Allies. After the Romanian government was overthrown in 1944, Romania got with the winning team and became one of the Allies. This means the history of the war there is really confusing!


At what battle did Admiral Nimitz successfully trick the Japanese into thinking his carriers were elsewhere, thus enticing them to attack when he would surely win?

Midway was a military turning point at which the Japanese fleet was essentially crushed. Nimitz's bluff worked beautifully and his choice to commit all his carriers to Midway gave him the opportunity to eradicate the Japanese as a serious threat to the U.S. mainland. From this point onward, it was clear the Japanese would never beat America; they could only hope to fight a sufficiently costly war that ​would force a peace that was acceptable to them. This goal was ultimately not achieved.


What silly principle did British and American intelligence work on at first, that certainly cost lives?

At first, the British did not trust the Americans as they had not joined the war in a timely manner, and, as we have learned, Hitler saw the USA as a possible ally. The Americans did not trust the British as they were imperialists. The two got over it and started cooperating fully in 1942, which is the genesis of the "special relationship" that underpins American influence in Europe.


Which group of spies secretly made themselves useful to the democratic Allies during the war, but betrayed them after the war in favor of the Russians?

The Cambridge spies were British born men who bought into the idea that communism was a great system and they should totally support it. They were mostly very naive, though they didn't repent when they learned how bloody Stalin's "communist" regime actually was. Figures like Kim Philnby and Donald Maclean rose high in the inteligence services and sold their homeland out to the USSR for years. They were, however, dedicated to the Allies' cause during the war itself.


Which American Jewish figure helped to persuade FDR that America must join the war?

Secretary of the Treasury Henry Morgenthau was a prominent American Jew, and thus had both the ear of the president and connections to what was happening in Europe. His backing helped get America to sign the Lend-Lease agreement to provide arms to the Allies before it became one of them, and also motivated the USA to join the war, which was not a foregone conclusion.


What ship of German Jewish refugees was tragically turned back from U.S. borders, prompting the deaths of many?

This was one of many such tragedies; a number of nations simply refused to take refugees even when it wa obvious that genocide was underway. Congress failed to pass a bill to save 20,000 children, which was nixed primarily by segregationists. Fortunately, not everyone was so heartless. for example the British Kindertransport effort helped get plenty of Jewish children out before they were murdered, at the expense of several wealthy British figures - most of them Jewish themselves - who sponsored the effort to ensure that the state would not have to lay out one penny for the children (without which promise, they could not have saved their lives).


Where did Britain fail to have enough resources to act on reliable intelligence?

As a major imperial power, Britain hubristically forgot to fortify its possessions in Asia against the Japanese. This resulted in Malaysia and a number of other places being simply overrun right after Pearl Harbor.


What military strike did Hitler postpone that, had he done it when originally planned, might well have crippled Britain and changed the course of the war?

Sea Lion was the incredibly detailed plan the Nazis put together to invade Britain. If they had won the Battle of Britain and gained air supremacy, it is likely they would have invaded and Britain would have been hard-pressed to stop them. The plan for conquest was - in classic Nazi style - planned down to the last detail, including concentration camps for all men of military age and a list of 2,​500 specific Brits they intended to murder first. The list included military, political, industrial, and media leaders, with a number of prominent British Jews.


What really stupid military decision did Hitler make about how to run his war effort?

Even while the tide of the war had turned and Hitler's ideas were clearly stupid, he refused to listen to his generals. Stalin had suffered from this problem early in the war but figured out how to get over himself and accept that he wasn't a general. The fact that Hitler insisted on making so many decisions himself meant that his troops reacted very slowly and often did the wrong thing, which historically speaking, is a great thing!


What ghastly mistake did members of the IRA, the Irish Separatist Movement, nearly make?

While it is not commonly discussed, it's sadly true that the IRA did send emissaries to organize a way to team up with the Nazis, since they both hated the British and Churchill in particular (and the latter in particular, not without cause). However​, the Germans only sent low-level people who were unable to make anything major happen, which is very good news for the people of Ireland. It didn't turn out very well for the IRA either, as it justified a huge crackdown on them.


What error did purity-minded MPs try to get Churchill to make, that he thankfully refused to do?

A contingent was very angry with Churchill when he got into bed with Stalin, largely because Stalin had previously declared neutrality. As Churchill put it, though, if Hitler invaded hell, he would have worked with Satan to stop him!


How many people did Hoover's FBI believe Russia had sent to spy on them during the war, and how many were there really?

Hoover was a very paranoid man, but when it came to remembering that allies actually do spy on each other, he seems to have missed the boat on this one. The FBI said they spotted five Russian spies, but later confessions and research show there were at least 80 Russians spying on the USA during the war.


What naive assessment was common in good society in Britain, the USA, and France before the war?

All these idiotic positions were accepted by large portions of society, some as late as 1938. Indeed, in that year, more than 20,000 American Nazis rallied at Madison Square Garden! Video of this horrific event can be found and is deeply disturbing. Similarly, many people thought communism was all rainbows and flowers, and had no idea about gulags and disappearing dissidents. Both groups were soundly disabused of these delusions.


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