Fall of Singapore-1942
Winston Churchill had called the fall of Singapore one of the "worst disasters" ever. Along with Dunkirk it would be one of the darkest moments for the Allies during World War II.
From my perspective some of the factors which I feel were crucial in the Fall of Singapore are:
Thailand was looking for an opportunity to avenge its humiliation by France in 1893,1904, when the boundaries were redrawn by a series of treaties. After France fell to the Nazis, the Thai government sought the assistance of the Japanese in its war with now Vichy France. Also, Thailand was convinced that Japan would be the ultimate victor in the War, following its early success, and chose to go for a military alliance. This helped the Japanese to get a foothold in Thailand, and use it as a military base for launching operations into the Malayan Peninsula.
Britain greatly under-estimated the Japanese air force ability to attack Singapore from long distance air fields. In fact, when Singapore was bombed for the first time in December 1941, it was a rude shock for the British Far East Command.
Britain did not really focus much on the Far East and South Eastern Asia during the War, as they did on Europe. The Japanese were more prepared for the war and had better training, The best of the Royal Air Force was in Europe battling the Luftwaffe, while the untrained pilots were exposed to the well-equipped, better trained Imperial Japanese Air Force. The Mitsubishi Zero especially was a key factor in the Japanese supremacy in the skies.
The Allies had a numerically strong force - 85,000 under Lt.Gen Arthur Percival, and the British 18th under General Merton Beckwith-Smith was at full strength. However, most of the soldiers had no experience, nor any training, nor any knowledge of that area. The Japanese on the other hand knew the entire Malay peninsula inside out. They could move faster and, the most important factor, they were well versed in jungle fighting. The mangrove forests, swamps and jungles were familiar to the Japanese who had been running a campaign there for more than a year.
The Japanese had a fantastic intelligence network by which they gained first-hand knowledge of the Allied positions. Many Japanese spies slipped into Singapore as civilians, from where they reported back on all the Allied fortifications. General Tomoyuki Yamashita stationed himself at the Sultan Ibrahim Palace, from where he planned the entire invasion. Yamashita did it in the secure knowledge that the British would never attack the palace, and he turned out to be right.
But, in my opinion, the major factor was what Yamashita later claimed - that the Japanese Army was heavily outnumbered compared to the Allies with just around 30,000 men. He deliberately made a bluff to the Allies to end their "meaningless" resistance. Yamashita made it appear that the Allies were overcome on all sides by the Japanese when, in reality, they had the larger number. Had it been a Stalingrad-like situation, Japan would have lost badly in Singapore. They did not have the resources or men to sustain a long campaign. The British fell for Yamashita's bluff, and Percival was advised to surrender to avoid massive civilian casualties. By this time the Japanese had taken over large parts of Singapore, cut off the water supplies, and the Allied units were already beaten.