Singapore Unlikely Power Chapter 5 Part 2 - The Fall of Singapore and Japanese Occupation

Churchill called December 10, 1941, “the worst day of the war.” Not because of some abstract strategic loss. Because on that day, the Royal Navy lost two of its biggest ships to Japanese aircraft. And with them, any illusion that Britain could defend Singapore.

This is the part of the book that reads like a disaster movie. Everything that could go wrong did go wrong. And Perry doesn’t hold back in showing exactly how badly the British failed.

Force Z and the End of Battleship Thinking

Britain sent the battleship Prince of Wales and the battle cruiser Repulse to Singapore. That was the “fleet” everyone had been promised for years. Two ships. The crew of the Repulse jokingly called her HMS Anonymous because the press only cared about her shiny younger companion.

Here’s the thing. These two ships had no aircraft carrier with them. Their commander, Admiral Tom Phillips (nicknamed “Tom Thumb” by his own crew), believed big guns could handle airplanes just fine. He was wrong. Fatally wrong.

The Japanese had some of the best naval aircraft and torpedoes in the world. Admiral Yamamoto liked to quote the saying “the fiercest serpent can be overcome by a swarm of ants.” On December 10, the ants proved him right. Both ships went down. Hundreds of experienced sailors died.

Perry frames this as a perfect metaphor. Britain sent a fleet “too important to lose but too weak to survive.” That sentence basically sums up the whole British position in Southeast Asia by this point.

The Bluff That Broke an Empire

The Japanese reached Singapore on February 8, 1942. The city was chaos. Uncontrolled fires, smoke, the stench of burning oil and rubber mixed with rotting corpses. The great naval base that cost so much money sat relatively untouched. As Lee Kuan Yew would later say with magnificent understatement, it proved “not much help in World War II.”

And here’s the detail that just floors me every time. General Yamashita, the “Tiger of Malaya,” later admitted the whole thing was a bluff. He had 30,000 troops against over 90,000 British defenders. He was terrified they would figure out how outnumbered the Japanese actually were.

They never did. The British army was a mess. Frequent command changes, personality clashes, inept officers, raw recruits. The RAF had too few planes. The fleet was at the bottom of the sea. The monsoon rain came down and the British soldiers sheltered under rubber trees while the Japanese rode bicycles down the peninsula.

On February 15, the British surrendered at the Ford Motor Company building. Today Singapore marks it as “Total Defense Day,” a reminder to never depend on someone else for your security. The largest British military defeat in history. Thousands of prisoners marched through the streets while Singaporeans stared at their bedraggled former colonial masters.

Even Hitler noticed. “It means the loss of a whole continent,” he said. An Australian sergeant put it more simply: “After Singapore, Asia changed. For the British it would never be the same again.”

Life Under the Rising Sun

Perry spends a lot of time on the occupation, and for good reason. Three and a half years of Japanese rule left marks on Singapore that shaped everything after.

The Japanese renamed Singapore “Syonan” (Light of the South), pushed the clocks ahead to Tokyo time, changed the calendar to 2602, removed the statue of Raffles, and replaced British holidays with Japanese ones. They wanted to erase the British past completely.

But here’s the problem. The occupation was brutal. The Kempeitai (military police) used torture routinely. Prisoners lived on weevily rice and damp sugar. Growing your own food became a matter of survival. Sweet potatoes and tapioca were lifelines. Prisoners composted soil and watered plants with diluted urine. That’s how desperate things were.

The Chinese population had it worst. In “Operation Cleanup” (sook ching), the Japanese rounded up Chinese men between eighteen and fifty. Anyone wearing glasses or with soft hands was suspect since they might be intellectuals. People were taken away on trucks, never seen again. Perry notes that perhaps as many as ninety thousand were killed.

The future prime minister Lee Kuan Yew was forced to work for the Japanese during this period. He was beaten and humiliated. Decades later, he told a US diplomat that the occupation taught him “people will obey authorities who can deny them food, clothing and medicine.” That lesson would inform everything he later built.

The Strange Voyage of Netaji

Perry includes this fascinating detour about Subhas Chandra Bose, called “Netaji” (Revered Leader) by his followers. Bose was an Indian independence fighter who went to Germany looking for Nazi help against the British. When the Nazis proved useless, he wanted to get to Japan.

So they put him on a U-boat. The descriptions of submarine life are vivid. Diesel stench soaking into the bread. Black underwear because nobody ever changed it. One toilet for fifty people. Bose sat in a six-square-foot corner of the officer’s mess, editing a book while the boat crossed half the world.

Off Madagascar, they transferred him to a Japanese submarine. The Japanese cook had thoughtfully stocked up on curries before departure. Bose eventually made it to Singapore, where he organized an Indian National Army and a Provisional Government of Free India that declared war on Britain and America. Indian women at his rallies threw their gold jewelry at his feet.

It’s a wild story. And Perry uses it to show how Singapore kept serving as a launchpad for Asian liberation movements. First Sun Yat-sen and China. Then Bose and India. The city’s connections to the wider world kept making it matter, even under occupation.

The Rising Sun Sets

By the war’s final months, the Japanese empire was collapsing from within. They couldn’t protect their sea lanes. American submarines sank merchant ships faster than Japan could replace them. Singapore’s entrepot trade dried up. Food shortages hit everyone, occupiers included.

The Japanese naval command had been waiting for one great decisive surface battle that never came. While they waited, their supply lines fell apart. Back in Japan, the government was publishing recipes for fried tea cakes made from rice bran without sugar or eggs. One person’s review: “Looks just like good custard, but it tastes bitter, smells like horse dung, and makes you cry when you eat it.”

When the British returned in September 1945, they forced the Japanese soldiers to take the same long walk to Changi prison that Allied prisoners had taken in 1942. Poetic justice, maybe. But the Singaporeans watching felt complicated things. Happy to see the Japanese go. Not exactly thrilled to see the British back.

A Malay woman put it perfectly: “We were certainly glad that the British had returned to liberate us from the Japanese, but we placed very little weight on their promise to protect us in the future. Our gods had feet of clay.”

Perry’s verdict is sharp. The Japanese had “a colossal opportunity to win friends” but came as conquerors, not liberators. “Asia for the Asians” really meant “Asia for the Japanese.” Still, the occupation did one thing the Japanese didn’t intend. It proved to Singaporeans that they could get along without the British.

And that realization would change everything.

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