Churchill’s darkest hour: the Fall of Singapore and the military disasters of 1942

The bleakest moment for Britain's wartime prime minister came not in 1940 – when his popularity soared and he was convinced a German invasion was impossible – but in 1942, as Taylor Downing explains.


On the morning of Friday 13 February 1942, with Japanese forces just a few miles from the city of Singapore, the commander- in-chief of imperial forces, Lieutenant-General Arthur Percival, called a conference of senior officers. He announced he had received orders to fight to the finish and the defence of the city must continue.

His principal corps commander, General Sir Lewis Heath, said his troops were exhausted, totally dispirited, and there was no point in further fighting. The commander of the Australian troops defending the island, General Gordon Bennett, argued that the only option was surrender. When Percival said he had to consider his honour, Heath replied, ‘You need not think about your honour. You lost that a long time ago up in the North [of Malaya].’

Japanese photographers were on hand to capture one of the most humiliating disasters in British imperial history. General Percival (far right), accompanied by officers bearing the Union Jack and a white flag, en route to surrender negotiations.

The Japanese had timed their invasion of Malaya to coincide with their attack on the US Pacific Fleet at Pearl Harbor on the morning of 7 December 1941. Malaya had become a wealthy British colony exporting tin and rubber. The Japanese wanted to assault their two principal adversaries, the US and Britain, by air and land at the same time. They landed ground troops about 500 miles north of Singapore in Thailand and at Kota Bharu in northern Malaya.

Once ashore, even though their troops were relatively few in number, they advanced rapidly. Their ultimate objective was Singapore, the naval fortress, but one where the guns faced out to sea and there was no defence from a land assault.

The Japanese were led by a ferocious, determined, and quick-thinking commander, General Tomoyuki Yamashita. The British and imperial troops that faced them were poorly equipped and had suffered from being a low priority while Britain prioritised home defence against invasion and the war in North Africa. Moreover, the troops in Malaya had had little or no training in jungle warfare.

Map showing the Japanese blitzkrieg down the Malay Peninsula. Unlike the Germans, they came on bicycles.

The first disaster came at Jitra (near Changum) in the first couple of days. Totally overwhelmed by the Japanese advance, two Indian brigades were forced to retreat, leaving behind more than 300 trucks and armoured cars, along with enough food and ammunition to supply a division for three months. Some 3,000 troops were captured.

Japanese advance

The well-trained but lightly equipped Japanese forces then pressed south. To speed their advance, they deployed light tanks, thought to be inoperable in jungle warfare. And the infantry often used bicycles for transport.

Imperial troops were trained only to operate on roads. They would adopt a position along a main road and prepare a defensive barrier. Japanese troops would approach, head into the jungle or mangroves, and outflank the defenders, who, to avoid being cut off, would be forced to retreat in disarray.

This was repeated night after night. Morale hit rock-bottom. The locals would look on and chant ‘Orang puteh hari’ (‘The white men are running’). As the imperial power, Britain owed a duty of protection to its colonial citizens. Sometimes, European settlers were evacuated. The Asian populations were instead left to years of brutal occupation by the Japanese.

Map of Singapore on 8 February 1942, showing the deployment of imperial troops.

One by one, major British static defence lines collapsed: along the Perak river at the end of December; the Slim river in early January; the city of Kuala Lumpur in mid-January. As the imperial forces withdrew, communications collapsed and supplies of petrol and huge depots of food, equipment, and vehicles were abandoned. Retreating units leapfrogged each other in hasty withdrawals. Entire units were wiped out, either killed, wounded, or left behind to surrender.

When the defenders had withdrawn to their final defensive line north of Johore, Australian troops were thrown into the action. They fared no better and could not prevent the seemingly unstoppable Japanese advance. It was a rout of disastrous proportions.

With the Japanese advancing rapidly down through Malaya, Churchill had told the Australian Prime Minister, John Curtin, that Malaya might well fall. ‘I do not see how anyone could expect Malaya to be defended, once the Japanese obtained command of the sea and while we are fighting for our lives against Germany and Italy,’ he told Curtin.

An Australian anti-tank regiment firing on the Japanese during the Malaya campaign, January 1942.

In an openly racist remark, he said that the Japanese had advanced so rapidly because up to that point they had faced only tiny numbers of ‘white’ troops, ‘the rest being Indian soldiers’. In reality, the Indian units had all been ‘milked’: that is, the best officers and NCOs had been sent off to fight in the Middle East. But Churchill still expressed confidence that Singapore could be defended and that a ‘counter-stroke will be possible in the latter part of February’.

Reinforcing Singapore

Meanwhile, reinforcements continued to arrive in Singapore. On 13 January, a British and American convoy brought a brigade from the 18th British Division that had originally been sent from Britain to North Africa but had been diverted to the Far East. After three months at sea, the men disembarked, but there was no time for acclimatisation or training, and they were deployed within days.

On 24 January, 1,800 replacement Australian troops arrived. They had been rushed from Australia, and some had only just completed their basic training. Many had never even fired a rifle.

Percival now had about 100,000 men to defend the small island of Singapore, where, with the influx of refugees, the civilian population had roughly doubled in size to about one million.

On 31 January, Indian and Australian forces withdrew and blew up the Causeway that linked the island to the mainland. Reinforced and with substantial provisions, they prepared for what many imagined would be a long siege, lasting several months until new forces arrived to relieve them.

Oil tanks on fire, Singapore, 1942. The island fortress was virtually defenceless against Japanese artillery and aerial bombardment.

But officers were amazed at how little had been done to prepare defences on the island. According to one report, Percival had refused to sanction their preparation, claiming, ‘Defences are bad for the morale of troops and civilians.’ Engineers were rapidly deployed, and barbed wire, mines, and booby traps were laid, but all in haste at the last minute.

Percival tried to reorganise his command and repeated the order that all units were to fight to the death. But at senior levels a sense of hopelessness prevailed. However, the Japanese still faced a major challenge to get enough men on to the island to defeat a far larger force.

After barely a week’s pause, Yamashita launched his attack on the island at 10.00pm on 8 February. He launched his principal thrust against the north-west of the island where the Australian 22nd Brigade held the line. The Japanese crossed the Straits in small canvas boats shielded by a heavy barrage from their artillery. At this point they were most vulnerable. But, unaware of what was happening, the defenders did not open fire. Phone lines had been destroyed, leaving commanders in the dark. Three waves of Japanese infantry from two divisions, supported by engineers and mortar units, landed on the island before dawn. Some Australian defenders fought fiercely. Others pulled back. The Japanese rapidly established a beachhead on the north-west of the island. These first few hours had proved decisive.

During the following day, a half-hearted counter-attack was launched. It failed. The rear lines began to fill with retreating soldiers. Yamashita, realising the lack of coordination among his enemy, ordered his men forward at speed. When they entered Tengah airfield, they were surprised to find aircraft in good working order, and fresh bread and soup still on the tables of the officers’ mess. The next major objective was the one piece of high ground on the island, Bukit Timah, overlooking the city and harbour of Singapore. Yamashita anticipated a major battle for this vital piece of ground but the defending forces were so disorganised that only a single battalion of Argyll and Sutherland Highlanders stood between the advancing troops and their objective. They could not hold them up for long, and the Japanese seized Bukit Timah and its vast supply dumps of food and ammunition with barely a fight.

General Tomoyuki Yamashita (1885-1946) [ABOVE] thumps the table and demands unconditional surrender. General Arthur Percival (1887-1966) [BELOW] sits directly opposite.

After the Supreme Commander, General Archibald Wavell, had paid a visit to Singapore, he received an urgent telegram from Churchill in London on 10 February. The Prime Minister wrote ‘There must at this stage be no thought of saving the troops or sparing the population. The battle must be fought to the bitter end at all costs.’ Churchill went on, ‘The honour of the British Empire and of the British Army is at stake… the whole reputation of our country and our race is involved.’ Wavell passed this on to Percival, adding that ‘It will be disgraceful if we yield our boasted fortress of Singapore to inferior enemy forces.’ Percival included this in his Order of the Day on 11 February. Such words evoking racial pride and imperial honour could not have brought much cheer to men who everywhere saw their army disintegrating.

One by one, the final outposts across the island fell to the relentless Japanese advance. The first of the reservoirs containing the city’s water supply was seized on 11 February. By Saturday 14 February, the defenders had retreated to a small enclave around the city of Singapore. There was a major water shortage. The artillery had run out of shells, as had the anti-aircraft units, meaning that Japanese bombers could roam as they pleased.

The large multinational, imperial army that had been retreating almost continuously for more than two months knew it was trapped in the city of Singapore without escape. Many British and Indian troops blamed the Australians for hopelessly failing to stop the Japanese landings. Some Indian units began to desert. Other stragglers from a variety of outfits were found wandering around the city or in abandoned cellars. Japanese bombs and shells continued to rain down, and the many refugees packed into the city had nowhere to hide. Reports spoke of ‘pandemonium’ in the city streets. Some battalions fought fiercely as the Japanese advanced into the wealthy, smart suburbs, only to find that the unit on their flank had simply disappeared.

On the other side, the Japanese troops were exhausted and now at the end of long supply lines. Occasionally they resorted to terrible atrocities. As the staff at the Alexandra Hospital tried to surrender, about 50 of them were massacred, with one patient bayoneted on the operating table.

General Neil Ritchie (at the centre, with a pipe) studies the map with other desert generals. It did not help. The Battle of Gazala was a disaster and led directly to the fall of Tobruk.

Percival feared that an angry and desperate enemy would commit the sort of appalling massacre that the Japanese had carried out in Nanking, China a few years before, raping and murdering tens of thousands of civilians while beheading soldiers who had surrendered. One of his officers urged him to admit defeat ‘while Japanese soldiery could be controlled by their commander’.

On 14 February, Percival messaged Wavell ‘Both petrol and food supplies are short…Morale of Asiatic civil population is low under bombing and shelling from which they have no protection.’ During the day, Churchill – who was at Chequers – rang his army chief, General Alan Brooke. They agreed that further defence was futile and might only provoke a terrible massacre. Churchill and Brooke finally accepted that the game was up.

At 4.30pm on Sunday 15 February, a small delegation led by General Percival with a British Colonel as translator walked up the Bukit Timah Road towards the Ford factory that had become the Japanese headquarters. As they walked up the hill carrying a union flag and a white flag of surrender, Japanese photographers and cameramen filmed them. When they reached the factory, they sat around a table and were filmed again. Yamashita knew how to stage-manage the event. He sat at one side of the table looking fierce and very much in charge; Percival sat on the other side looking gaunt and weak. After 40 minutes of haggling, Yamashita lost his temper and declared emphatically that if Percival did not sign the surrender he would launch an assault into the city within the hour. Percival gave way. The surrender was signed. A ceasefire came into effect at 8.30pm. The photographs of the surrender rapidly went around the world, and to many symbolised British imperial humiliation. It was the nail in the coffin of British colonial rule in Asia.

The Japanese blitzkrieg advance through Malaya had been every bit as impressive as the German advance though Belgium and France nearly two years before. But this time there was no Dunkirk, no miraculous deliverance that enabled hundreds of thousands of men to get away to fight another day. Instead, this blitzkrieg ended in a city packed with refugees under continuous aerial and artillery bombardment, where facilities were failing and the military defence had disintegrated.

The surrender was of the largest number of British-led troops in history – British, Australian, New Zealand, Indian, and Malayan. About 85,000 men had capitulated to a Japanese force of about 23,000.

Churchill saw the collapse of the fortress at the heart of Britain’s defence of the Far East as a terrible blow. In a speech at Caxton Hall to the Conservative Party Central Council in March, he did not hold back. In the last 12 months, he told the party members, British forces had been driven out of Cyrenaica, Greece, Crete, and Malaya. Hong Kong had fallen, and he claimed ‘Singapore has been the scene of the greatest disaster to British arms which our history records’. He couldn’t make it any worse than that.

But things did get worse. Three German capital ships, battlecruisers Scharnhorst and Gneisenau, and heavy cruiser Prinz Eugen, sailed right up the Channel. Despite intense efforts to sink them by the Navy and the RAF, they sailed through the Straits of Dover in broad daylight. That the Navy could not even protect the White Cliffs provoked howls of outrage in the press. The usually loyal Daily Mail even blamed Churchill himself, and contrasted the humiliation of the Channel Dash with the heroic defeat of the Armada three and a half centuries before.

Defeat in Malaya was followed by retreat in Burma. Another colonial capital, Rangoon, fell to the Japanese. British and imperial troops retreated across the mountains of the north and the Japanese reached the gates of India. It was the longest retreat in British military history.

Anthony Eden (1897-1977), serving as Foreign Secretary, was canvassed as a replacement for Churchill as Prime Minister in the dark days of 1942.

There was further humiliation in North Africa in June 1942. The Eighth Army under General Neil Ritchie was resoundingly defeated by Rommel’s Afrika Korps at Gazala, and began a speedy withdrawal into Egypt. This was followed by the surrender of the garrison at Tobruk. Around 35,000 men surrendered to an Axis force of roughly half that size. Half a million gallons of petrol and three million ration packs were also captured. In 1941, Tobruk had held out for eight months; in 1942, the city fell to Rommel in a weekend. Churchill was in a meeting with President Roosevelt at the White House when the news came through. He later wrote ‘It was a bitter moment. Defeat is one thing. Disgrace is another.’

The humiliating run of military disasters greatly added to popular criticism of the Prime Minister and his government. The press was convinced that Churchill was carrying too much responsibility as both Minister of Defence, controlling wartime military strategy, and Prime Minister. Mass Observation recorded a range of comments supporting this view. ‘I reckon Churchill’s got too much on his hands to conduct this war properly,’ said one 50-year-old man. A younger man said, ‘Make Anthony Eden Minister of Defence and give him a free hand.’ A 25-year-old woman commented, ‘I think Churchill’s taking too much on himself.’

This popular criticism created a political crisis for the PM. He faced a vote of no-confidence in the House of Commons in January and a vote of censure in June. Not surprisingly, he defeated both. But a credible alternative leader emerged in Sir Stafford Cripps, the austere left-winger who seemed better able to capture the mood of the nation in 1942. Again, Mass Observation picked up on his growing support, and recorded Cripps as ‘the first alternative leader-figure since the fall of Chamberlain’.

That he should be Prime Minister at such a dreadful moment in the country’s military history really galled Churchill. ‘Poor old PM in a sour mood and a bad way,’ Sir Alexander Cadogan noted after a Cabinet meeting. When his daughter Mary visited Downing Street for a lunch with her parents, she found her father seriously depressed. ‘Papa is at a very low ebb,’ she wrote. ‘He is worn down by the continuous crushing pressure of events.’

Many people imagine Churchill’s worst moment was in 1940 with the fall of France, the Battle of Britain, and the Blitz. But, ironically, this turned out to be his ‘finest hour’. The run of humiliating defeats in 1942 proved a far greater threat to his political survival. He desperately needed a military victory. With the Eighth Army under the new command of General Bernard Montgomery, Churchill waited anxiously for a new offensive in North Africa. Brendan Bracken, a friend and enthusiastic supporter of the PM, said to a colleague, ‘If we are beaten in this battle, it’s the end of Winston.’

But, of course, when that battle did come at El Alamein at the end of October, it brought victory. The PM’s political fortunes revived. Churchill had survived and would go on to lead the country to the end of war. But the military disasters of 1942 had taken him to the brink of political defeat. It had without doubt been Churchill’s darkest hour. •

Taylor Downing’s new book, 1942: Britain at the Brink, was published by Little, Brown in January 2022.
All images: WikiCommons, unless otherwise stated.