At the start of World War II, Singapore had symbolized the British Empire’s presence in Southeast Asia for nearly a century. When its garrison surrendered to the Japanese on February 15, 1942, Prime Minister Winston Churchill called it the worst disaster in his country’s military history. Everything that could go wrong had gone wrong. The British had pre-positioned a grossly inadequate number of aircraft and warships. Japanese bombers had sunk the only two capital ships defending Singapore—the battleship Prince of Wales and battle cruiser Repulse—when those vessels tried to contest the Japanese landings along the Thailand-Malaya frontier. The British defense of Malaya was a marvel of incompetence. Lieutenant General Tomoyuki Yamashita completely outgeneraled Lieutenant General Arthur Percival. With a force of only 70,000 he managed to kill or capture over 138,000 British, Indian, Australian, and Malayan troops.

Such details imply that with better generalship Singapore could have escaped capture. In fact, most students of the campaign believe that even in the best circumstances, a successful defense was improbable. The naval base that gave Singapore its strategic significance was located on the northern end of Singapore Island, well protected against attack by enemy warships but nearly bereft of protection against a land assault. While it is a myth that the island’s coastal batteries could fire only out to sea, they were supplied mostly with armor-piercing shells of limited use against ground forces.

As early as 1937, the British general staff had concluded that a Japanese land attack was feasible and could capture Singapore in two months’ time. Little was done about this, however. Many of the British, Indian, and Australian forces eventually deployed to block a Japanese advance were inadequately trained. Furthermore, the Royal Air Force constructed air fields in the northernmost part of the colony for the 178 war planes assigned to defend Malaya, which forced the British army to defend them and left it with a long, vulnerable seaward flank.

Nor did the British revisit their naval strategy for Singapore. The naval base held few warships. Instead it was intended to receive and supply a British battle fleet that would be dispatched to Singapore if an emergency arose. With the outbreak of war in Europe, however, the Royal Navy had its hands full in the Atlantic. And with the fall of France, it had to defend the Mediterranean as well. Sending a substantial battle fleet was therefore out of the question. Sending only the Prince of Wales and Repulse was a pathetic bluff.

Logically, the British might have cut their losses by stationing only a token force at Singapore, similar to the 10,000 troops sacrificed at Hong Kong. But Singapore’s status as a jewel of the British Empire, and its mythic characterization as the “Gibraltar of the East,” practically forced Churchill to make a major bid to hold it—not enough, as matters turned out, to do so successfully, but enough to swell the number of forces lost and make the disaster even worse than it would otherwise have been.

It is impossible to imagine a single twist of fate that could have saved Singapore. But what if a combination of events had turned in Britain’s favor? Suppose the British defense had been better conducted. Suppose the carrier Indomitable, which had been assigned to join the Prince of Wales and Repulse, had not run aground. Suppose instead that it had arrived on station and that its aircraft had fended off the swarms of enemy bombers and allowed the two capital ships to contest the Japanese landings.

Suppose that Yamashita, whose audacity earned him the sobriquet the “Tiger of Malaya,” had shown greater caution. Suppose that, when the Japanese finally landed on Singapore Island, Percival had counterattacked (as he planned to do until dissuaded by subordinates)—an attack, we now know, that would likely have defeated Yamashita’s troops, which had badly outstripped their supply lines. And suppose that the Japanese high command then did not reinforce Yamashita enough to make another try.

This is a mighty string of suppositions. But if, by whatever wizardry, Singapore managed to elude capture, what then? Would that have substantially altered the war in the Pacific?

In fact, the principal positive result would have been humanitarian. The Japanese could not have sent most of Singapore’s defenders to labor on the infamous Burma-Thailand Railroad, where 16,000 of them died. Nor could the Japanese have terrorized the population of Singapore and murdered as many as 50,000 of its Chinese residents.

From a strategic standpoint, however, it is unlikely that Britain’s retention of Singapore would have redounded to the Allies’ advantage. The denial of Singapore to the enemy would not have been a serious problem for the Japanese. Although historically the Japanese navy did use Singapore as a port, the need to combat the United States meant that its major bases were the Home Islands, Rabaul, and Truk.

As a naval asset, Singapore was of dubious value. British First Sea Lord Dudley Pound had declared in August 1940, “There is no object in sending a fleet to Singapore unless it is strong enough to fight the Japanese fleet.” Days before the outbreak of the Pacific War, British Admiral Tom Phillips and his American counterpart, Admiral Thomas C. Hart, concurred that Singapore held no potential for offensive operations. Pound considered Trincomalee, Ceylon, superior to Singapore as a base from which to protect the Indian Ocean—and historically Trincomalee proved effective for that mission.

From an army standpoint, Singapore was no better as a springboard for offensive operations. The Japanese could easily block any attempt to move north along the Malayan peninsula. True, heavy bombers based on Singapore could have struck targets across a wide swath of Japanese-occupied territory in Southeast Asia. But, and here is the key problem, any resources dispatched to Singapore, whether aerial, naval, or army, would have come at the expense of theaters where they were more urgently needed.

And yet, even if Great Britain had staved off the 1941–42 invasion attempt, for reasons of imperial prestige it could never have abandoned Singapore. Instead, it would have been condemned to an endless effort to keep the island resupplied and reinforced. The vital Atlantic and Mediterranean theaters would have suffered. Offensives elsewhere might have been delayed or might have failed outright. Even if it remained in British hands, Singapore, the renowned “Jewel of the East,” would have proven only an overpriced bauble.