Everything in war is risky, but depending on who leads an army, some bets are better than others. Mistakes are always made, but when the biggest risks on the battlefield pay off, they pay off big. When they fail, they often fail just as hard.

In wartime, however, a failed bet can result in the loss of thousands of lives, loss of initiative, or total loss of war. During World War II, the stakes were high enough that the commanding generals risked all three every time they planned an operation. Some of these risks were worth it, others were not.

These are the risks that were not.

1. Germany: not to seize Moscow when she had the chance

In its early days, Operation Barbarossa was a resounding success. The Nazi Wehrmacht made incredible territorial gains from the early days of the fighting. They captured hundreds of thousands of Red Army soldiers with each advance. Hitler’s belief that he could knock on the door of the Soviet Union and break down the whole rotten structure was coming true. Then he inexplicably stopped listening to his staff.

Hitler ordered his army groups to capture Soviet forces on the flanks of the main advance rather than move towards Moscow. If he had asserted his advantage for the Soviet capital instead of diverting his panzer forces, he would have avoided a two-month delay and could have negotiated a separate peace with the USSR, perhaps even convincing the Japanese to attack the Soviets in the east instead. of Pearl Harbor.

2. Japan: halfway

While there was no way for the Japanese to know that the United States knew when and where the next Japanese invasion would come, they still engaged four aircraft carriers in the Battle of Midway and lost them all. Worse yet, Midway was not even necessary for the Japanese Navy’s planned defense of the original islands. They only targeted the island because the United States believed it was vital to his interests.

To top it off, Japanese Admiral Isoroku Yamamoto devised an overly complex invasion plan for such a small atoll, based on intelligence at best optimistic and at worst completely false. Since the first casualty of war is the plan, too complex a plan was a bad idea for such a bet. The battle resulted in an unbalanced, game-changing victory for the United States.

3. Italy: the invasion of Greece

In 1940, Italy was still the lesser power of the Axis Pact. Yet Italian dictator Benito Mussolini was overcoming Fascist Italy’s victories over Ethiopia and Albania, as well as his contribution to Fascist victory in the Spanish Civil War. So, despite being at war with the British in North Africa, he decided to launch an invasion of Greece to help realize his vision of a new Roman Empire.

This, however, never materialized. About two weeks after the initial invasion, the Greeks (literally) stopped the Italians in their tracks. With the help of the British Royal Air Force, the Greeks not only drove the Italians back from Greece, but also pushed towards Italian-held Albania. It was only after the intervention of Germany that the Greeks were subdued and Mussolini’s hope of obtaining great power status was dashed.

4. United States: Monte Cassino

The fight for Monte Cassino was a battle the Allies technically won, but a handful of victories like Monte Cassino would have been devastating for the United States. Monte Cassino was an ancient stone-built abbey, perched on a high hill, an excellent defensive position, and the US 5th Army was very labor-intensive.

The Allies launched four assaults on Monte Cassino, a fortification which many contemporaries believed could have been bypassed. They must have attacked the abbey first through a minefield and once through a flood. When the Allies took it, they found only wounded soldiers. The rest had simply retreated to the Hitler line.

5. Great Britain: Operation Market Garden

For some reason, Western armies are obsessed with “being home before Christmas” and Operation Market Garden was one more in a series of failed attempts to achieve this baffling achievement. It was an ambitious operation, too complex which could have been avoided given the various alternatives.

The Allies allowed a substantial German force to escape after capturing the port of Antwerp, there was another way to cross the Rhine at Driel, and help from the Dutch resistance was ignored. They are all potential game changers for the operation. Instead, the result was an Allied advance that stretched far too long with a command structure that was described as “loose”.

6. The Soviet Union: not preparing for a German invasion

Soviet intelligence at this time was one of the best among what would become the Allies in wartime. Almost all the agents of the Soviet NKGB (ancestor of the KGB, the Soviet intelligence service) were shouting at Stalin from all corners of the globe that the Germans would attack the USSR in 1941. But Stalin did not want it.

According to the Mitrokhin Archives, a mine of secret KGB documents released by a Soviet defector in the early 1990s, Stalin preferred to analyze intelligence reports himself, rather than having them provided by an analyst. NKGB agents reported the planned invasion of the Soviet Union a year before Operation Barbarossa, but Stalin refused to believe it and threatened with execution any agent reporting such information.