The Age of Stupid Strategy: How the West Mastered the Art of Losing

MICHAEL RAINSBOROUGH

Writing in the Telegraph, former Defence Secretary Ben Wallace declared President Trump and Vice President J.D. Vance “clueless” on Ukraine. A verdict echoed, in more measured tones, across British and European commentary – especially after Zelensky’s Oval Office showdown with Trump over how (or whether) to end the war. Much Western media took Ukraine’s side, casting Zelensky yet again as the plucky Churchillian underdog battling Putin’s dictatorship – now allegedly aided by White House appeasers. If only it were all that simple.

Trump and Vance have never made a secret of their intention to extricate the US from the Ukrainian morass. Whatever the rights and wrongs of their approach, should they take strategic advice from those like Ben Wallace? The same Ben Wallace who, in the Telegraph in October 2023, triumphantly proclaimed:

Whisper it if you need. Dare to think it. But champion it you must. Ukraine’s counteroffensive is succeeding. Slowly but surely, the Ukrainian armed forces are breaking through the Russian lines. Sometimes yard by yard, sometimes village by village, Ukraine has the momentum and is pressing forward.

Reality, of course, had other plans. Ukraine’s much-hyped counteroffensive – on which so many Western hopes rested – failed, particularly in the Zaporizhzhia region, where efforts to reclaim lost coastline barely dented Russia’s first defensive line. The foray into Kursk also proved ineffective in altering the military balance on the ground. Now, with 20% of its territory lost and outmatched in manpower and resources, Ukraine is stuck in a war that isn’t going anywhere.

Yet European leaders keep talking tough – floating ideas like putting troops on the ground or enforcing a no-fly zone. But with West European militaries too feeble to operate without the US, such gestures are optimistic at best, delusional at worst. And in the absence of a ceasefire, those troops would make fine targets for the Russians – escalating a war that already lacks any obvious end goal.

Groundhog Day Warfare – the Habit of Repeating Failure

Setting aside the conflict’s origins, battlefield realities and the merits of Trump and Vance’s diplomacy (all topics worth scrutiny), the loudest voices in media and politics seem allergic to a basic question: Why does this keep happening? Western backing of Ukraine appears poised to join the long list of strategic debacles – Afghanistan, Iraq, Libya, Syria, Yemen – each a masterclass in self-inflicted disaster. This is the elephant in the room expertly ignored by those who claim to be elephant watchers.

These interventions have toppled imperfect but functional governments, destabilised entire regions, bled Western coffers dry, managed the rare feat of weakening both soft power and deterrence, and unleashed blowback – most notably, waves of uncontrolled migration that have rattled Western societies. And yet, no one stops to ask the obvious: Why do we keep stepping on the same rake? Repeating failure while expecting success isn’t just folly. Calling it insanity might actually be too kind.

What follows is an attempt to dissect this pattern of failure – to trace the roots of Western strategic cluelessness and explain why it keeps coming back. Why, in other words, does good strategy seem to be so difficult for Western policymakers?

First, let’s be clear about the terms. ‘Good strategy’ means achieving meaningful goals, maximising interests and getting things done as efficiently as possible. It’s about weighing costs and benefits, balancing risk and reward, understanding both your strengths and your adversary’s, and – crucially – knowing when to quit while you’re ahead.

At its core, good strategy follows the principle of proportionality. Simply put, that is the art of knowing what is worth fighting for, what it will likely cost, and if necessary, when to cut your losses. It is the ability to tweak, pivot or abandon a course of action when reality fails to cooperate. It’s about being prudent.

Prudence isn’t about timidity – it’s about smart risk-taking. Prudence doesn’t mean paralysis; it means asking the right questions before charging in. Why are we doing this? What’s the endgame? And, most importantly, is this really worth the trouble?

Bad strategy, on the other hand, is the craft of barrelling ahead with a plan that was either doomed from the start, poorly conceived or stubbornly clung to even as its goals slip further out of reach.

The Extinction of Common Sense – Why Good Judgement is Rarer than a Unicorn

Prudence in decision-making – questioning what one aims to achieve at a proportional cost – is no guarantee of success, but it is a hallmark of sound judgement. This elusive quality fuses reasoning, contextual awareness and an instinct for pragmatic adaptation to shifting circumstances. Capturing it remains an inexact art, but it is the defining trait of those who master strategy and statecraft rather than merely dabble in it. It is the practice of Metternich and Castlereagh in orchestrating stability in post-Napoleonic Europe, Bismarck and his deft power politics to unite Germany, and of Field Marshal Alan Brooke, navigating existential peril with a clear sighted understanding of how Allied strategy in Europe should map out to defeat the Nazis in the West.

Of course, the practice of good judgement – good strategy – is always easier said than done. Choices often unfold amidst uncertainty, often with a determined adversary actively seeking to thwart one’s interests. A host of factors conspire against clear-eyed decision-making: time constraints, resource scarcity, gaps in knowledge, and the ever-present pressure to act. These are the very elements that Carl von Clausewitz, the Prussian soldier-scholar, termed “fog and friction” – the mundane yet formidable forces that turn even the simplest strategic tasks into arduous ordeals.

Why, though, is good judgement – defined here as the willingness to weigh costs and consequences with due care – so conspicuously absent in contemporary Western politics?

The Paradox of Expertise – More Think Tanks, Worse Thinking

The systemic dysfunctions of foreign and military policy present a striking paradox. Nowhere is the cultivation of strategic thought more explicit than in the West – particularly in the Anglophone world, where institutes, think tanks, armed forces academies, university courses, books and journals devote considerable energy to refining strategic reasoning. The focus is clear: defining national security priorities, drawing lessons from history and identifying the conditions for effective policy making. In short, the very precepts of sound strategy. And yet, from within this self-proclaimed ecosystem of expertise, we have witnessed a remarkable proliferation of strategic missteps.

Richard Rumelt, a specialist in corporate strategy, offers a useful taxonomy of strategic malpractice. Good strategy, he argues, is about concentrating resources to tackle the “crux” of a problem. Bad strategy, by contrast, is a miasma of high-minded aspirations devoid of actionable objectives. While his framework is invaluable for businesses and bureaucracies, it is less directly applicable to national strategy, where the symptoms of dysfunction tend to be more subtle. After all, the chronic failures of contemporary Western strategy are not due to a lack of action. If anything, the problem is an excess of it – disproportionate, miscalculated and often disastrously expensive.

The Proportionality Problem – Bringing a Sledgehammer to a Knife Fight

So why do Western nations struggle with proportionate action? Historically, prudence played a more central role in strategic decision-making. Consider Britain’s empire: a small maritime nation that managed, for nearly 150 years, to rule a third of the world’s land surface with fewer administrators than a modern city council. That requires more than just audacity. It demands a rigorous balancing of resources against objectives. Even when decolonisation became inevitable, Britain’s exit strategy for the most part prioritised minimising costs and maintaining favourable post-imperial relations.

None of this is to suggest that policymakers of the past were infallible or that post-Cold War strategy has been uniformly hopeless. The 1990-91 Gulf War remains a textbook example of limited war for defined ends. Western interventions in the Balkans – though endlessly debatable – ultimately nudged some of those conflicts towards resolution. And Britain’s 2000 intervention in Sierra Leone, unlike so many others, is generally considered a success. The lesson here is not that the past was a golden age of strategy but that, once upon a time, Western powers understood the virtues of restraint and proportionality. These days, they often seem to have forgotten both.

It is difficult to deny that Anglo-American strategic planning – both in concept and execution – has gone spectacularly off the rails since 2001. The core problem is a chronic inability to approach problems proportionately. Instead, there’s a tendency to either wade into interminable wars or engage in half-baked regime-change escapades, or in the case of Ukraine, sponsor an ill-thought-out proxy war against a major geopolitical power, as if strategy were a series of impulsive dares rather than a discipline requiring foresight.

When Winning is an Afterthought: the Rise of Anti-Strategy

For those inclined to think this an exaggeration, let us consider the seminal architects of these recent follies.

Take, for instance, the ‘Letter to President Clinton on Iraq’ dated January 26th 1998, penned by the eminences of the Project for a New American Century. Among its signatories were Francis Fukuyama, William Kristol and Robert Kagan, along with a veritable who’s who of the US foreign policy establishment. Armed with Ivy League degrees, ensconced in prominent Washington think tanks or comfortably tenured at prestigious universities, they urged Clinton to “enunciate a new strategy” to “secure the interests of the US and our friends and allies around the world”.

And what was this grand strategy? It was the “removal of Saddam Hussein’s regime from power”. They assured the President that “diplomacy is clearly failing” and that military action was the only acceptable course. Lest anyone think them naïve, they solemnly acknowledged “the dangers and difficulties” – before proceeding to dismiss them in favour of decisive action, which, they assured, would serve “the most fundamental national security interests of the country”.

If that weren’t enough, the explicit contempt for prudence and proportionality was laid out with even greater brazenness in a January 2002 paper for the Carnegie Endowment for International Peace. Its authors, Robert Kagan and William Kristol, ridiculed those who had the temerity to advocate “limiting American involvement overseas, for avoiding the use of ground troops, for using force in a limited way and only as a last resort, for steering clear of nation-building, for exit strategies and burden-sharing – those who prided themselves on their prudence and realism”. “If we fail to address the grave threat we know exists”, they thundered, “what will we tell the families of future victims? That they were ‘prudent’?”

The strategic illiteracy of these quotations is self-evident. They exemplify how a fundamentally anti-strategic mindset permeates influential segments of the Western foreign policy establishment. Various explanations could account for this persistent failure, but as a provocation, one hypothesis is worth considering: the flawed strategic thinking of the past two decades can be traced to the enduring influence of a total war mentality.

Total War Brainrot – How World War II Still Haunts Western Thinking

Total war – the idea that an entire society must be mobilised for an existential struggle – looms large in the Western imagination as the formula for victory in both world wars. The winner, as the story goes, is the side that can best harness its national energies, endure the hardships and grind the enemy down to exhaustion. This mentality slid seamlessly into the Cold War, which was framed as yet another titanic ideological contest, culminating in the Soviet Union’s collapse in 1990-91. But while the Cold War ended, the reflexive impulse to apply totalising solutions to every problem did not. This is the root of much Western strategic folly.

The logic of total war fosters a Manichean worldview in which prudence gives way to grandiose, all-encompassing objectives, cast in stark moral terms: good versus evil, light versus dark, us versus them. This moral absolutism carried over into the post-Cold War era, shaping the US administration’s ‘war on terror’ and ‘Axis of Evil’ rhetoric after 9/11, which provided a sweeping justification for military interventions. But the persistence of total war thinking extends beyond actual wars. It can be seen in the way Western political discourse has been drenched in warlike language ever since 1945. We’ve fought the ‘war on drugs’, the ‘war on poverty’, the ‘war on cancer’ and even the ‘war on alcoholism’ – an especially tenacious and well-entrenched enemy.

This tendency reared its head in the ‘war on Covid’. The British Medical Journal observed that the pandemic response was awash with bio-military metaphors: where physicians became “warriors on the front lines” and entire nations were conscripted into the “fight” against the virus. Governments, adopting the total war playbook, assumed extraordinary powers to “defeat” Covid – shutting schools and businesses, restricting human contact, enforcing social distancing, mandating masks and vaccines, and treating even mild scepticism about these measures as a near-treasonable offence.

That total war thinking that influenced the Covid era wasn’t a vague undercurrent; it was explicitly proclaimed. In late 2020, one US analyst sombrely assured us that “Clausewitz would almost certainly endorse a national COVID-19 strategy and war effort in which the Government executes its powers to compel the entire nation-state into a uniform response”. This, of course, bears an unsettling resemblance to Erich Ludendorff’s 1935 treatise Der Totale Krieg – a work so militantly statist that even Clausewitz, had he been available for comment, might have asked to be left out of it.

Leaving aside the question of whether Clausewitz’s opinion on epidemiology can be reliably summoned from beyond the grave, or whether applying militarised rhetoric to non-violent medical and social challenges makes any conceptual sense, the key problem with the total war mentality is that it treats proportionality and prudence as expendable. It demands that every problem, no matter how specific or containable, be met with an overwhelming response.

The Totalitarian Instinct – Why We Keep Trying to Control the Uncontrollable

A totalising mind is one often consumed by ideology and is therefore rarely flexible. Sure, it can pinpoint a single objective with precision, but that precision often comes at the cost of adaptability – or any ability to admit it might be wrong.

The price for acknowledging its blunders? Usually astronomical. It’s a mindset that requires over 50,000 combat deaths and $141 billion to realise that trying to prevent the collapse of a corrupt South Vietnam to the communists wasn’t worth the effort. It’s the same conviction that had to endure years of insurgency and a catastrophic sectarian civil war before it grudgingly acknowledged that invading Iraq – especially after the non-discovery of weapons of mass destruction and the underwhelming enthusiasm of the populace to be ‘liberated’ – was a colossally bad idea. It’s a mindset that only learns the folly of nation-building in Afghanistan after a two-decade, multi-trillion-dollar charade.

And let’s not forget the mind that still believes the expenditure of trillions of dollars, countless social harms and lives lost in the name of halting a virus was worthwhile, even when studies suggest all that effort may have reduced mortality by a pitiful 0.2%. Meanwhile, the strategic clairvoyants who invoked Clausewitz to justify a single-minded, nationally directed COVID-19 response – because apparently that’s how you “concentrate force” and “promote shared objectives” – might want to note that researchers from Johns Hopkins University found lockdowns to be “ill-founded” and “should be rejected out of hand”.

What’s the common thread? These poor strategic choices aren’t the result of a few bad decisions; they’re a chronic pattern of repeat offences. So why does this keep recurring? What drives this enduring strategic relapse? The answer might just lie in the obsessive grip of total war thinking. But is that enough to explain it all?

People as Pawns – the Fantasy of a Conquerable Public

Totalising responses can be justified in moments of supreme emergency – when national survival truly hangs in the balance. In such circumstances, as with Britain in World War II, the public is likely to see – or be convinced of – the necessity of large-scale sacrifices. They may also accept the logic of unrestricted objectives, such as unconditional surrender, which required not just the defeat but the invasion, occupation, and – in Germany’s case – dismemberment of the enemy as the price of victory.

In other words, people recognise extreme responses as proportionate when the threat itself is existential. The real problem, however, is the post-war habit of applying the total war blueprint to threats that by any reasonable measure do not imperil the physical survival of nations. This tendency represents one of the more pernicious quirks of modern Western strategic thought – or what passes for it. So how did we arrive at this state of affairs?

One clue lies in the nature of 20th Century world wars, which were, at their core, wars of the people – conflicts requiring the full mobilisation of society against an enemy. Such wars demanded mass participation and, crucially, mass consent. A shared fate, a common enemy and the imperative to defend a particular national way of life were prerequisites for sustaining total war as a viable concept. Without public buy-in, total war simply could not function.

The question, then, is what happens when the grand, existential struggles fade away? In 1998, following the Cold War’s conclusion – the last of the great totalising conflicts – the philosopher Anthony Giddens declared that the West was now “without enemies” and that large-scale inter-state war was increasingly unlikely.

One might assume this would herald an era of international relaxation, in which states could afford to mind their own business. Not so. Thinkers like Giddens instead envisioned a new grand project, one in which the West would embark on an ambitious mission to “connect issues of national and global governance”. In place of superpower struggle, a “liberal imperialist posture” emerged – dedicated to enforcing a democratic “rules-based order” across the world, whether the world wanted it or not.

Unlimited Goals, Limited Competence – How to Demand Everything and Achieve Nothing

After the Cold War, this totalising outlook evolved into a relentless pursuit of a ‘New World Order’, an idealistic vision to spread liberal values globally. This was especially appealing to Western elites at the so-called “end of history” when everything supposedly aligned in a utopian narrative. A single, overarching strategic framework replaced more sceptical, pragmatic assessments of national interests, favouring military interventions shrouded in the lofty promise of cosmopolitan virtue.

The problem with such totalising ideologies is that they cannot maintain coherence without total support from the population. The sacrifices required to uphold this liberal international order – whether it’s ousting ‘rogue’ regimes in the Middle East or supporting Ukraine against Russia – are hard to sell to a public that isn’t facing an existential threat. Why should people support endless interventions, especially when the objectives are vague and the rewards uncertain?

Framing problems in simple moral binaries – democracy vs autocracy, freedom vs tyranny – along with the recurring invocation of World War II imagery (always confronting the ‘new Hitler’, be it Slobodan Milosevic, Saddam Hussein or Vladimir Putin) resonates with many in the West, particularly governments and media. Such rhetoric may sound stirring in speeches, but it loses its appeal as the costs rise and the goals remain vague. Eventually, people question whether the response is proportional, and the national consensus begins to fracture, leaving scholars of realpolitik and much of the public alike wondering what happened to the art of achieving clear, measurable objectives.

Welcome to the Ineptocracy

An uncompromising liberal idealism, rooted in an age of non-total threats, offers one compelling explanation for the strategic blunders of recent years. When people don’t feel their survival is at stake, they become reluctant to bankroll the ambitious schemes of those still fixated on a neo-total war doctrine. The real question, then, is why policymaking has drifted so far from popular consent – and why policymakers cling, with near-religious fervour, to an outdated way of thinking: replacing an understanding of public sentiment with the policy obsessions of an increasingly cloistered ‘expertocracy’.

There are many layers to this mystery, not least the social forces nudging Western societies toward a post-democratic era, where new elites view the public as an inconvenient problem to be managed. One glaring consequence is the sequestration of strategic decision-making within a closed circle of technocrats – a priesthood that often dismisses popular sentiment as crude, uninformed and hopelessly out of sync with cosmopolitan orthodoxy. These self-anointed experts, credentialed in the sacred art of grand strategic theorising, have crowned themselves the arbiters of what constitutes sound policy.

And here we return to the paradox. Judging by the past three decades, the effectiveness of strategy appears to be inversely proportional to the number of universities and think tanks devoted to studying it. The more intellectual horsepower thrown at strategy, the more spectacular the failures.

Which leaves us with an uncomfortable question: are we part of the problem? Have we, the self-styled curators of strategic wisdom, unwittingly cultivated the belief that strategy is some esoteric knowledge, accessible only to a select few – while the unwashed masses, predictably, should be kept at a safe distance?

Are we, the supposed custodians of good strategy, in fact, just another part of the machinery that keeps producing bad strategy?

Michael Rainsborough was Professor of Strategic Theory at King’s College London and between 2016 and 2019 was Head of the Department of War Studies. He is now a Professor of Strategic Theory in Australia. His latest book is A Front Row at the End of History: The Untimely Essays of David Martin Jones and M.L.R. Smith, 1999-2024.

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This article (The Age of Stupid Strategy: How the West Mastered the Art of Losing) was created and published by Daily Sceptic and is republished here under “Fair Use” with attribution to the author Michael Rainsborough