• Military
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• Ukraine

September 10, 2025, 12:52 PM View Comments ()

In December 1941, as Japanese bombers and landing ships converged on Singapore, British Prime Minister Winston Churchill still clung to the belief that the British territory and naval base remained impregnable—”our boasted fortress,” as the British commander responsible for its defense called it. Its surrender was, in Churchill’s devastating assessment, the “worst disaster and largest capitulation in British history,” the defeat leaving a “scar on his mind,” his physician later said.

In reality, Singapore was no impregnable fortress. As the Japanese launched their final assault, Churchill sent desperate orders: “There must at this stage be no thought of saving the troops or sparing the population. … Commanders and senior officers should die with their troops. The honour of the British Empire and of the British Army is at stake.” Yet no amount of exhortation could compensate for the strategic failures that had made defeat inevitable long before the first shots of World War II were fired.

Today, as European leaders craft their response to Russian aggression in Ukraine—and as NATO holds emergency Article 4 talks after Russia’s overnight drone attack on Poland—they risk repeating the same fundamental error that doomed Singapore: substituting tactical gestures for strategic clarity and allowing political convenience to drive what should be comprehensive strategic imperatives. The parallels are sobering, revealing how self-deception creates a predictable cascade toward military disaster.

Singapore’s destruction emerged from Britain’s grand strategic delusion in the Far East—the fantasy that naval supremacy could substitute for territorial defense, rooted in the imperial strategy of the 1920s that treated Singapore Naval Base as the cornerstone of Far Eastern defense. British planners envisioned a war with Japan unfolding in three neat phases: Singapore’s garrison would hold the supposed fortress while the British Main Fleet sailed from Europe to defeat the Japanese in a decisive naval battle and subsequently blockade Japan’s home islands. By 1937, according to naval historian Stephen Roskill, “the concept of the ‘Main Fleet to Singapore’ had, perhaps through constant repetition, assumed something of the inviolability of Holy Writ.” This strategic framework completely disregarded the changing character of naval warfare, the rise of air power, and the impossibility of defending a land-based fortress solely through sea-based operations.

Europe’s current approach to Ukraine follows a similar self-delusion. The continent’s leaders have embraced what amounts to a strategy of limited steps—providing enough support to prevent Ukraine’s collapse while avoiding commitments that might require genuine strategic sacrifice and risks. Yet there exists no coherent theory of success defining what Europe actually wants to achieve in Ukraine, other than avoiding direct military engagement with Russia and ending the conflict through some kind of negotiated settlement. This is risk management rather than grand strategy—the Europeans only define what they want to avoid rather than what they seek to accomplish. This approach offers no path toward a sustainable outcome and no metrics for measuring success beyond termination of the current conflict.

This absence of strategic clarity reflects a deeper problem: Europe has not reached a consensus on whether keeping Ukraine independent is worth the risk of a direct military confrontation with Russia. De facto, Ukraine already constitutes part of European security—Russian missiles striking Ukrainian infrastructure directly threatens European energy networks, Ukrainian grain exports affect European food security, and Ukrainian territorial integrity determines the credibility of European deterrence. Were Ukraine to fall, Europe could face consequences that extend far beyond humanitarian concerns: NATO confronting strengthened Russian forces at the Polish and Romanian borders, millions of additional refugees fleeing a collapsed Ukrainian state, and an ongoing insurgency inside Ukraine.

But it doesn’t require a Russian victory to create a dangerous situation: Western fatigue and Ukrainian disillusionment could drive Kyiv toward accommodation with Moscow. Either way, Ukraine in the Russian orbit would provide the Kremlin with battle-hardened Ukrainian soldiers for future conflicts and control over Ukraine’s ramped-up defense industry, massively altering the balance of power in Europe. But this reality has not been communicated to European voters, creating a dangerous gap between political decision-makers and their constituents.

European leaders’ strategic avoidance becomes particularly perilous with a French presidential election scheduled for 2027, Italy’s support for Ukraine steadily waning amid domestic economic pressures, Germany’s governing coalition proving brittle ahead of federal elections, and far-right and far-left parties ascending across the continent. Without a clear conversation with voters about Europe’s strategic objectives in Ukraine—and absent a compelling strategic narrative explaining why Ukrainian success serves European interests—any coalition of the willing risks political fragmentation.

By my analysis, a European coalition-of-the-willing deterrence force might deploy three to five brigades—about 15,000 to 34,000 troops—to Ukraine in order to help deter renewed Russian aggression following a future cease-fire. While European leaders appear to be tilting toward a more modest mission primarily focused on training Ukrainian soldiers, with the principal deterrent remaining Ukraine’s armed forces, a more ambitious coalition could provide a deterrence force integrated with Ukrainian forces specifically to prevent another Russian invasion, which should be Europe’s most critical strategic objective in Ukraine.

Actually deploying these European forces would be an uphill battle and requires, among other things, a significant reshuffling of NATO’s defense plans for its eastern frontier. There are also national caveats to consider: Germany has made its participation—essential for the entire mission’s logistical sustainability—contingent on a U.S. security guarantee for Ukraine that remains largely undefined. Senior U.S. officials have indicated to their European counterparts that Washington would be prepared to contribute “strategic enablers”—including intelligence, surveillance, and reconnaissance; command and control; and air defense assets—to any European-led deployment. But these commitments remain conditional on European nations taking the lead on any postwar Western force, creating a catch-22 similar to the one that plagued British imperial planning: Europe needs U.S. capabilities to make its deterrent credible, but the Americans demand European commitment before providing those capabilities.

Air power remains a challenge, too. For a robust ground mission to Ukraine, the Europeans would need to be able to conduct missions to suppress and destroy Russian air defenses—capabilities that European air forces have let atrophy in recent decades, instead relying heavily on U.S. assets during NATO interventions in the Balkans, Libya, and elsewhere. For a three-brigade minimum deterrence force requiring about 70 combat aircraft, European coalition-of-the-willing members can realistically deploy only around 60, creating at least a 10-aircraft gap that could only be filled by the participation of Turkey. A more robust five-brigade force would require more than 100 aircraft, stretching the shortfall to 40 or more aircraft and demanding capabilities that simply do not exist in European militaries. This precisely mirrors the resource constraints that characterized British planning for Singapore: assuming capabilities that political decisions make unavailable and then building operational concepts around those faulty assumptions. Three to five brigades would stretch European capacity to the absolute limit, and it remains unclear how long such a force could sustain itself.

What could a European deterrence force even achieve against Russia, given the latter’s much higher risk tolerance and continued designs on Ukraine? A three-brigade force cannot deny terrain against a determined Russian offensive, but it could provide sufficient resistance to make a Russian breakthrough militarily costly and politically questionable. This scenario might theoretically compel Russia to commit a larger force to ensure breakthrough, dramatically escalating Russia’s military costs and political risks by potentially triggering wider NATO involvement. Such escalation dynamics could theoretically preserve a cease-fire agreement by making its violation prohibitively expensive for Russia.

Singapore fell because British strategy treated military planning as an extension of political preferences rather than an analysis of actual requirements, but the deeper cause lay in imperial overstretch and resource inadequacy that British leaders refused to acknowledge. Japan’s blitzkrieg through British Malaya that covered more than 400 miles in less than two months, the shocking air attacks that sank the HMS Prince of Wales and Repulse battleships, and the surrender of more than 130,000 British and Commonwealth troops revealed the bankruptcy of a grand strategy that had attempted to maintain global commitments without commensurate resources. Yet even this catastrophic demonstration of strategic failure did not trigger a fundamental rethinking of Britain’s role in the world for another decade or more, with Churchill and his colleagues treating Singapore as an aberration rather than confronting the structural impossibility of defending a global empire with inadequate forces. European leaders today exhibit a remarkably similar denial about the gap between their ambitions to secure the continent and their countries’ actual military capacity, preferring incremental policy adjustments to an honest and fundamental assessment of what it would require to defend the continent.

Today’s European leaders are in a Singapore trap, crafting a training mission designed to signal resolve rather than achieve an actual military objective. They are systematically avoiding not only the resource questions—including strategic trade-offs such as revising NATO regional defense plans—but also the question of what Europe would be willing to risk that would make deterrence more likely to succeed. History proves unforgiving: As Churchill saw in Singapore, no tactical competence can compensate for strategic confusion when facing enemies willing to pay the full price of their ambitions.

Without an honest conversation with European voters about what deterring Russia in Ukraine and along NATO’s eastern frontier requires—accepting the possibility of European casualties, sustaining permanently expanded forward deployments, and restructuring NATO’s regional defense plans—a European coalition of the willing risks becoming another “boasted fortress” that might look impressive on paper but turns out to be strategically hollow when tested by reality.