Gibraltar of the East: The Fall of Singapore

The Second World War has several famous battles and engagements. In the early years of the war, the Axis was beating back the Allies and gaining ground at a rapid pace. One by one, Allied countries fell to the Germans and the Japanese. China. Hong Kong. Poland. France. Denmark. Greece and The Netherlands. The Axis seemed unstoppable. Between 1939 and 1942, Europe and Asia were choked by the oppression of German and Japanese military might which was determined to strangle them to death.

The British were confident, however, that they could fight off their aggressors and keep them at bay. The might of the British Empire would keep the Nazis and the Japanese at bay and would hold them off alone until reinforcements eventually arrived from America. That was what they would do and that was what they were sure they could do! But for all their planning and scheming and thoughts of colonial and imperial strength and power, the British armed forces suffered blow after blow at the hands of the Japanese, who conquered Hong Kong and the Malay Peninsula. The biggest blow to British morale and to the ego of British military leaders, however, was the loss of what they saw as their greatest and most powerful, their impregnable and indestructable fortress…The island of Singapore.

The fall of Singapore is something that, when you think about it, should never have happened. It’s something that you think would never have happened. But the British army, airforce and navy, unprepared for the Japanese plan of attack, did not provide contigency plans for what might happen if their first lines of defence were breeched, or indeed, if they were bypassed altogether. With the fall of Singapore came the biggest British military disaster since the Battle of the Somme in 1916.

Singapore in the 1930s

Singapore is a tiny island nation off the southern coast of the Malay peninsula, seperated from it by the Strait of Johor. Modern Singapore was established in 1819 by Sir Stamford Raffles, a British statesman who saw Singapore as a wonderful place to establish a British colony and trading-port. Over the next one hundred years, Singapore grew and prospered. Its position in the middle of the Southeast Pacific made it a convenient port for ships to stop at during long voyages between Europe and Asia. The island flourished thanks to international trade and by the early 20th century, boasted a large population of immigrant Chinese and a significant number of British expatriates. Due to its status as a free trading port where almost anything was loaded, offloaded, traded, bought and sold, Singapore became known as the ‘Crossroads of the Orient’; the port city where ships from all over the world could dock.

Singapore’s Chinatown as it appeared in the 1930s

In the 1930s, Japan was on the march. Starting in 1937, the Second Sino-Japanese War between the Chinese and the Japanese threatened to sweep across Asia and crush everything. The Chinese were already weakened from political in-fighting between the Communists and the Capitalists and in its weakened state, China was steamrollered by the Japanese. The British, who had built up Singapore as a prosperous trading-post and naval base, were fearful of a Japanese invasion. Singapore had to be protected. In the years leading up to the Second World War and during the opening years of that conflict, Singapore and the Malay Peninsula were bolstered with more troops and better defences. The British thought that it would be easy to defend Malaya and Singapore because the British would outsmart their enemy. And if the Japanese came by sea, the batteries of coastal-defence cannons would blast their ships out of the sea.

British Defences

The British Empire would defend its prized colony of Singapore down to the last man. To do this, it would build up Singapore as an impregnable fortress, which gave the island the nickname the ‘Gibraltar of the East’. To defend Singapore, the Royal Navy sent two warships: The Prince of Wales and the Repulse, to guard the island and to be the Royal Navy’s first-response team to any enemy naval activity in the area. The Prince of Wales was up-to-date and modern: Built in 1939, it was brand-new, the perfect naval-response weapon to fight off the Japanese. The Repulse on the other hand, left something to be desired. A relic of the Great War of 1914, it was already over twenty years old by the time it was sent to Singapore. If the Prince of Wales was put out of action, the Repulse would become an easy target. Apart from naval preparations, Singapore and the Malay Peninsula would also be defended by the British Army and Empire troops from Australia, New Zealand and India. By 1941-1942, the British and Empire forces numbered 85,000 strong, facing off against just 35,000 Japanese, more than enough to stop the slow-moving land-based Japanese. And if they came by sea, the might of the British Navy would blast the stinking Nips right out of the water!…Or at least, that was the plan.

British Malaya; 1941

“…Yesterday, the Japanese government also launched an attack against Malaya. Last night, Japanese forces attacked Hong Kong. Last night, Japanese forces attacked Guam, Last night, Japanese forces attacked the Phillipine Islands. Last night, the Japanese attacked Wake Island and this morning, the Japanese attacked Midway Island. Japan has therefore undertaken a surprise offensive extending throughout the Pacific area…”

– Pres. Franklin Delano Roosevelt; radio address, December 8th, 1941

1941; a year which will live in infamy. Between December 7th and December 8th of that year, the Japanese Empire launched a surprise offensive against many countries in the South Pacific region. It wasn’t just the American naval base at Pearl Harbor that was hit, but many other places in the same region, including British holdings in Hong Kong and the Malay Peninsula. Hong Kong’s defensive forces, severely outnumbered by the Japanese, surrendered in a little over three and a half weeks after the Japanese launched their assault, surrendering to them on the 25th of December…Christmas Day, 1941. Some Christmas.

In Malaya, the fighting lasted much longer. The Japanese were very interested in Malaya; it had a lot of natural resources that they wanted, like tin mines and rubber-plantations. At the time, a significant portion of the world’s rubber came from Malaya, and the Japanese wanted in. The fighting was fierce, with British, Indian and Australian troops on one side, and the forces of the Imperial Japanese Army on the other. Despite everything, the Japanese were steamrolling the Empire forces further and further back, further and further south. It seemed like every week, a town or city on the Peninsula would fall to the Japanese.

On the 8th of December, the Japanese landed on the west coast of Malaya. On the 11th of December, the city of Jitra fell. Then the garrison at Penang, which fell on the 17th of December. A few weeks later, the Malayan capital of Kuala Lumpur also fell, on the 11th of January, 1942. The Japanese were surging south and the British could do nothing to stop them.

The Japanese Sweep

How was it that the Japanese, supposedly backward, slanty-eyed, yellow, cowardly, second-class people, which the British certainly saw them as, could defeat the might, power and imperial strength and know-how of the invincible British Empire? Even in Singapore, when British forces were more than double the strength of the Japanese?

The key to the British defeat in Malaya and Singapore lay in close-mindedness, a lack of foresight and I suppose to a small extent, a belief in racial intellectual superiority. The British believed that the Japanese would invade Singapore by sea. They were so convinced of this that they even set up coastal defences and cannons to blast the Japanese Navy out of the water. The idea of the Japanese invading by land from the north was absolutely preposterous. To begin with, they’d have to get through all those jungles and dirt tracks and the rain and the flooding…impossible with trucks and heavily-loaded tanks. Although the British did concede that defence of the Peninsula should be taken into account, the defences set up were inadequate to deal with the rapid movements of the Japanese…who invaded on bicycles.

That’s right.


Like the one you ride around the park.

The Japanese mobilised their troops on bicycles. Light, fast and easy to carry, bicycles could move quickly through the jungles and over flooded roads and could go places that larger, motorised vehicles could not. They exchanged their heavier tanks for lighter and more mobile tanks that could move faster and not get bogged down in the mud. The speed at which the Japanese could move meant that the British couldn’t hold their defences and despite dynamiting every bridge, road and crossing-point across every river, gorge and valley that they could find, they were unable to slow down the Japanese advance significantly enough to set up a proper defence and hold off their attackers.

The Invasion of Singapore; 1942

By early 1942, Singapore was in deep trouble. Hong Kong had fallen just a few days before and the British lines were breaking over and over again as the Japanese came charging southwards. The city of Singapore was being bombed extensively by the Japanese Air Force and the island did not have enough airplanes or anti-aircraft guns to fight off or even engage in an air-battle. Terrified civilians were being evacuated from the Port of Singapore by merchant-ships and military vessels which had been ordered to pull out. British and Empire forces set up defensive positions on the northwest side of the island where the Strait of Johor was narrowest – the likeliest spot for the Japanese amphibious landing on the island. Military engineers had destroyed the causeway bridge between Singapore and Malaya, which would delay the Japanese, but only for a little over a week. Once the Japanese got a toehold on Singaporean soil, they were unstoppable. The Japanese found weak spots in British defences and exploited them. At the same time, British offensives failed time and time again. The Japanese invaded Singapore on the 8th of February, 1942. In six days, they had pushed the British back until they controlled less than half the island.

On the 14th of February, Japanese forces committed one of their worst attacks against civilians, since the Rape of Nanjing, in which hundreds of thousands of Chinese men, women and children were murdered and raped by Japanese soldiers invading the Chinese city of Nanjing in December of 1937. It was on this day, the 14th of February, that the Japanese reached one of Singapore’s main medical institutions: Alexandra Hospital. Built in 1938, the hospital was one of the most advanced medical institutions in Southeast Asia at the time.

British Military Hospital, Alexandra Hospital, Singapore; 1938

The Japanese soldiers stormed the hospital that afternoon, bayonetting doctors, nurses, patients and orderlies. Anyone not bayonetted was rounded up and locked up. They were then taken out into the hospital grounds and bayonetted or decapitated. Anyone left was sent to Changi Prison. The commanding officer of Japanese forces in Singapore, General Yamashita, was appalled and infuriated by the attack on non-combatant, unarmed and surrendering medical staff and civilian and military patients at the hospital. He had as many of the soldiers responsible as could be found executed for the crime and personally apologised to surviving staff and patients.

While Hong Kong held out for nearly one month, Singapore fell in a week. Japanese forces landed in Singapore on the 8th of February and forced Australian and British troops further and further back until on the 15th of February, the Allies were defending a tiny area in the southern part of Singapore where the Civic District is today. Just a few miles behind the Allied lines was the mouth of the Singapore River and the Pacific Ocean.

The Fullerton Building at the mouth of the Singapore River. The British signed their surrender here to the Japanese in 1942 and the structure remained the Japanese HQ in Singapore throughout their occupation. Today, the same building is the Fullerton Hotel

Singapore was now being shelled relentlessly by Japanese artillery and bombed by the Japanese Air Force. Water and fuel supplies were almost non-existent; ammunition, weapons and other military hardware was either destroyed or in short supply. On the evening of the 15th of February, 1942, the British forces surrendered to the Japanese. It was, and remains, the largest surrender of British military forces in history.

The Occupation of Singapore; 1942-1945

Japanese soldiers marching through Fullerton Square in southern Singapore

For the next three and a half years, Singapore was under Japanese occupation. Basic foodstuffs and daily necessities such as rice, vegetables, meat, water and clothing became extremely rare and people struggled to make ends meet. The shelling of Singapore had damaged and destroyed buildings, knocked out powerlines and ruptured water-mains. The chronic shortages of food led many people to grow their own vegetables and fruits to survive. The Japanese continued to attack Singapore’s Chinese population, rounding men up and shooting them in the jungles.

During the occupation, the British, knowing that they could not yet hope to retake Singapore, did carry out espionage and sabotage missions against the Japanese in Singapore. Operations carried out against the Japanese included Operation Jaywick, in which a small group of Australian soldiers infiltrated the Port of Singapore. They successfully destroyed seven Japanese ships without losing any of their own men. In August 1945, the British launched another attack against the Japanese, sneaking into Singapore Harbour with midget submarines. They mined a Japanese warship, hoping to sink it. Although the mines detonated successfully and the midget submarines made successful escapes from Singapore, the target ship, the cruiser Takao, was not damaged enough for it to sink (it was eventually destroyed in 1946 as a target-ship during naval exercises).

The Allies continued to attack Singapore throughout the occupation, sometimes in more open ways than others. While the British and Empire armed forces limited their activities to sabotage and spying, the Americans attacked Singapore from the air. Between November 1944 and May 1945, the RAF and the USAAF carried out eleven air-raids on Singapore, attacking fuel-dumps, naval facilities and docks around Singapore that were essential to the Japanese war effort. Mines were also laid around Singapore to disrupt Japanese naval movements in the area.

The Liberation of Singapore; September, 1945

After the defeat of Nazi Germany in May of 1945, the Allies turned their attention fully towards Japan. The Soviet Union declared war on Japan and the Americans were planning to invade the Japanese mainland (this plan was later scrapped in favour of the atomic bombs on Hiroshima and Nagasaki). After the dropping of the bombs in August, 1945, the British made plans to recapture Singapore. They sailed for Malaya and successfully captured Penang. With their presence in Malaya established, they made for the island nation of Singapore on the 2nd of September. Although reluctant and wanting to fight to the death, the Japanese eventually surrendered peacefully when the British landed in Singapore on the 4th of September. The commanding officer of the Japanese forces in Singapore, General Seishiro Itagaki signed the terms for British reoccupation of Singapore when the cruiser HMS Sussex docked off the coast of Singapore. Eight days later, the Instrument of Surrender was signed at the Municipal Building (today Singapore’s City Hall) on the 12th of September.

City Hall, Singapore

Unable to cope with the humiliation of defeat, when General Itagaki told his officers of their surrender to the British, up to three hundred of them committed suicide using grenades, in their rooms at Singapore’s famous Raffles Hotel (which had been used as a base by the Japanese during the occupation).

Raffles Hotel, Singapore, in the 1930s. Japanese army officers committed mass suicide here in 1945 after their surrender to the British

With the successful ousting of the Japanese, even if it was three and a half years too late, the returning British forces were given a hero’s welcome by Singaporean civilians. In February, 1942, the Japanese had ordered the British to march through Singapore carrying a Union Jack flag and a white flag of surrender as a final humiliation after having lost their colonial stronghold to a superior military force. The Japanese had been told that no Union Jack flags existed on the whole of Singapore, as they had all been burned prior to the Japanese invasion, a statement that was probably a lie. A British officer held captive in Singapore’s Changi Prison retained his personal Union Jack flag and kept it hidden from the Japanese. The flag was used in the prison during the funerals of British and Empire soldiers who died as a result of Japanese brutality. When Singapore was liberated, this flag was handed to Lord Louis Mountbatten, who signed the British acceptance of the Japanese surrender, and who raised this flag over the island to signal the return of peace and stability to Singapore. A newsreel of the liberation of Singapore and the raising of the Union Jack may be viewed here.

September, 1945. Singaporeans hold a parade to celebrate the end of the Japanese occupation and the return of British forces