In one of his most famous passages, Michael Oakeshott used a metaphor of a ship to make the point that politics cannot bring salvation. Instead, he argued in “Political Education,” the task is the ongoing effort to navigate the perilous sea, keeping the vessel of political life afloat:

In political activity, then, men sail a boundless and bottomless sea; there is neither harbour for shelter nor floor for anchorage, neither starting-place nor appointed destination. The enterprise is to keep afloat on an even keel; the sea is both friend and enemy; and the seamanship consists in using the resources of a traditional manner of behaviour in order to make a friend of every hostile occasion.

Examining modern Western politics, with its rationalist and ideological ethos, one might ask—by Oakeshott’s metaphor—whether to don life jackets and rush to the rescue boats. The task of keeping the ship afloat without a fixed destination has been taken up by new navigators, who often ignore the practical knowledge of seamanship in their quest to escape the boundless sea. Their imagined harbours vary, yet all share a desire for salvation from life’s adventure, with its successes and failures. The difficulty is that these journeys are fraught with danger and the realisation that the harbour is unreachable. Political activity has thus become the politics of shipwreck: drifting endlessly toward an unattainable goal and often failing to secure the imagined salvation.

Oakeshott and other thinkers have traced modern politics’ journey from a boundless ocean to a shipwreck. Yet none has more precisely accounted for this shipwrecked politics in the Anglophone world than Shirley Letwin. An American-born intellectual who made Britain her home, Letwin became a central figure in the LSE Right—a circle of London School of Economics academics in the Oakeshottian tradition—and a key contributor to the broader New Right that helped propel Margaret Thatcher to power. So prominent was she that Milton Friedman, writing in the National Review on her death, called it “a severe loss to the cause of human freedom.”

Letwin’s contributions are many, especially on the idea of law. One of lasting significance is The Pursuit of Certainty—an Oakeshottian work tracing how our answer to the central question of Anglophone political thought—“what sort of activity politics is”—has shifted. Anglophone politics moved from a moderate, sceptical, realistic, and limited activity—like sailing the boundless ocean—to the conviction of new navigators that “politics was no longer one of several human activities and at that not a very noble one; it encompassed all of human life.”

Originally published in 1965 and later republished by Liberty Fund, The Pursuit of Certainty remains one of the most penetrating studies of how modern politics forsook moderation in favour of the rationalist quest for certainty. The book stands as a major work of intellectual history, examining David Hume, Jeremy Bentham, John Stuart Mill, and Beatrice Webb through a sequence of interconnected essays. It develops Letwin’s doctoral thesis, written under the influence of Friedrich Hayek and the University of Chicago’s Committee on Social Thought, which explored the transformation of British liberalism from its classical form into a modern variant increasingly aligned with socialism. Whereas the thesis possessed a clear structure and defined purpose, the book might leave readers unsure why these particular thinkers were chosen or what unifies the work, were it not for Letwin’s own clarification in the introduction.

Letwin explains that these thinkers reveal “how the conception of politics changed in England,” since “each represents a distinctive way of looking at politics, which has become intertwined with others and obscured in political practice, and yet remains a vital part of the political tradition in England.” This interpretive choice gives the book its coherence, even though the transitions between thinkers sometimes feel more thematic than narrative. While her interpretations—especially her moderate reading of Hume—possess clear intellectual-historical value, the key concern here is what the work reveals about the evolution of modern politics. All four thinkers contributed to this transformation, yet its nature and consequences are most clearly discerned when contrasted with the moderate politics exemplified by David Hume, to whom we now turn.

Moderate Politics

For Letwin, Hume exemplifies the moderate man: a figure shaped by admiration for balance, civility, and irony, and a rejection of puritan zeal. He embodied scepticism, convinced that human life cannot bear grand systems or theological certainties. This temperament led Hume to repudiate the classical rationalist tradition—which sought to base politics on reason—and to reject any political or moral system claiming certainty over human affairs. As Letwin notes, Hume “was critical of moralists who tried to reduce [politics] to a single principle” and of “man’s ability to make all his notions coherent and consistent, or to perceive a permanent truth.”

Hume’s moderate disposition and scepticism yield not a political doctrine but a disposition—one “that considers visions of another, better world, or indeed any desire to impose some ideal pattern of life or government on all men, irrelevant to politics.” For Hume, politics is a matter of prudential judgement, shaped by circumstance and guided by moderation, scepticism, and recognition of limits. It is not a politics of zeal, enthusiasm, or heroism, nor one treating “political disputes as a struggle between good and evil,” which he linked to civil war and fanaticism. Instead, a political disposition “looked for a moderation of disagreement, not for its disappearance. A balance between evils was the best one could hope for.” Humean politics trusted in government as an office, with the rule of law and decency safeguarding against arbitrary power, rather than in crusades for perfection.

Letwin aptly summarises Hume’s politics as

an art not a science. It is the art of choosing the least evil. It is guided by a sense for what civilization at its best can produce, and depends on a capacity for making fine discriminations, for seeing differences of degree where the vulgar only roughly distinguish kinds, for recognizing the connotations of things without losing sight of their true proportions. It requires sureness about rules and great delicacy in applying them. It is above all an activity of judging.

Reading Hume as an exemplar of moderate politics is not novel, though it remains contested. Letwin’s treatment, however, is one of the book’s most accomplished achievements: she rescues Hume from caricature as a detached philosopher and restores him as a thinker engaged with political conduct within the conservative tradition. Her contribution is especially notable in identifying Hume—not Edmund Burke, often called the father of modern conservatism—as the foremost representative of British moderation, scepticism, and prudential politics. This reflects the development of her own thought. In an earlier essay, “Rationalism, Principles, and Politics,” she criticised Oakeshott on Burkean grounds for privileging only prudential principles. In The Pursuit of Certainty, she adopts a more Oakeshottian stance, applying it even in critique of Burke. She may have been influenced by Oakeshott’s review of Russell Kirk’s The Conservative Mind, where he noted that “it would perhaps have been more fortunate if the modern conservative had paid more attention to Hume and less to Burke.”

Letwin sees John Stuart Mill as the intellectual successor who abandoned Bentham’s modesty.

Letwin acknowledges affinities between Hume and Burke and credits the latter with greater influence on modern conservative politics, yet she maintains that their approaches diverge in key ways. The first difference, she argues, lies in style. As she notes, “Burke … spoke not to the House of Commons at all, but to humanity, to eternity, to God. His orations … came close to furnishing politics with a sacred text.” This casts Burke as a grand romantic rather than a moderate. Yet this reading is debatable. Burke’s rhetorical elevation can be seen less as metaphysical than strategic—a way of mobilising political imagination against abstract theorising rather than sacralising politics. While intellectually stimulating, Letwin’s critique risks underestimating the practical dimension of Burke’s statesmanship and the rhetorical demands of his context.

The second difference that Letwin identifies rests on firmer ground, namely the substance underpinning Burke’s and Hume’s respective views of political activity. As she argues:

Hume’s politics is built on convenience, Burke’s on truth. It is only natural then that whereas the emotions Hume considered appropriate to political institutions were loyalty, obedience, respect, or scepticism, Burke saw in political institutions objects of love and veneration.

For Letwin, Hume saw politics not as a sacred mission but as a secular, limited activity—an art of managing passions, habits, and institutions to secure stability and decency. By contrast, Burke viewed politics in quasi-religious terms: “Society becomes the Temple of God, and the state, along with the Church, is its guardian,” thereby, as Letwin notes, infusing “a cosmic spirit into politics.” By sacralising politics, Burke transformed “political questions into moral crusades … what Hume called fanaticism and feared above all in politics.”

The spirit of Burke’s sacred politics can be explained not only as a matter of rhetorical expression but also as a reflection of his belief in a higher, divine moral law. Indeed, Burke grounded his political thought in the virtue of prudence, which he famously described as “the god of this lower world.” For this reason, Letwin observes that Burke “contributed very little to the development of a new view of political activity.” Yet, she also acknowledges that Burke’s sacred politics enabled him to grasp more effectively the revolutionary rationalism that animated the French Revolution and to appreciate the moral and patriotic resources necessary for confronting it. In this sense, Letwin recognises that Burke’s outlook, was ultimately more attuned to the temper of his age than Hume’s sceptical restraint might have been.

Letwin’s analysis arguably reflects her own preference for the sceptical tradition of British conservatism over the religious or metaphysically grounded one. She highlights the question of war as the clearest point of contrast between Hume’s and Burke’s political outlooks. Whereas Hume regarded war as “always the greatest evil, and to be avoided by every workable negotiation and compromise,” Burke viewed it as the ultimate means of securing justice in the world. For Letwin, this contrast illustrates that Hume’s politics might have accommodated the existence of a revolutionary France through diplomacy, while Burke’s sacred politics could not. In retrospect, had Hume lived to witness the French Revolution, he might well have supported a war against revolutionary France—though not on Burke’s moral or providential grounds, but rather for reasons of security and balance of power.

Nevertheless, in drawing this distinction between Hume and Burke, Letwin issues a warning about the dangers of transforming politics into a sacred activity. In this respect, she may be echoing Eric Voegelin’s New Science of Politics, which cautions against political theologies that seek to recreate the City of God on earth through political means. It may well be that, to avoid such pitfalls, Letwin’s Oakeshottian conclusion gains force—namely, that modern conservatives would do better to emulate Hume’s moderation rather than Burke’s sacralised politics. Particularly in a highly secularised world, a conservatism grounded in scepticism and prudence is likely to prove more coherent and appealing than one premised on metaphysical or sacred commitments.

Scientific Politics

Letwin’s critique of Burke was not that he lacked anti-utopianism or moderation, but that he turned political activity into a sacred sphere. By contrast, for Jeremy Bentham, politics was scientific rather than sacred. This science aimed for certainty in law, which Bentham saw as the antidote to the chaotic and irrational accumulation of common law precedents. His scientific politics rested on the principle of utility—the greatest happiness of the greatest number—providing a universal, impersonal standard for legislation. Bentham’s solutions, Letwin notes, “were not those of a moralist or a philosopher, but of an engineer or inventor,” seeking a perfectly codified legal system in which law is predictable and unambiguous. Only then, he believed, could liberty be secured.

Bentham departed from Hume by treating politics not as prudence or custom, but as a realm where “reason alone, in the narrowest sense of logical analysis, was relevant.” His aim, Letwin notes, was “to eliminate altogether the need to depend on judgement; he wished to replace practical wisdom with a technique.” Despite the ambition of his vision, Bentham rejected revolutionary upheaval, remaining a modest utopian who believed human affairs could be fully regulated through law and calculation. Yet this modest utopianism—reducing politics to logic and system—paved the way for his intellectual successors to abandon such restraint.

Letwin sees John Stuart Mill as the intellectual successor who abandoned Bentham’s modesty. She examines Mill’s upbringing and early adherence to Benthamite ideas of certainty, systematic reasoning, law, and reform—up to the point that this creed triggered a mental crisis. This, Letwin argues, is crucial: Mill rejects Benthamite certainty, recognising that rational calculation alone cannot yield a complete moral vision. A new creed was needed, one not merely logical but capable of offering “a complete view of man and the universe, not a partial, hesitant sketch of a corner.”

Mill’s new creed was a faith in the certainty of progress, viewing human history as gradual improvement guided by reason, liberty, and culture. This belief led him to a form of elitist radical politics, where only educated guidance could realise such progress. The certainty of progress required a new approach to politics, found in the emerging science of society—sociology. Unlike Bentham’s project, sociology offered a scientific foundation for politics, providing a practical tool for reform that united scientific reasoning with political action. Mill argued that those who should govern were “scientists who understood the laws governing human character and how to apply them under various circumstances. Their counsel would not be merely superior opinion; it would carry more than the weight of experience and wisdom.”

Much of today’s Right has likewise forsaken moderate and sceptical politics for a mode Hume would have called “a form of revolutionary enthusiasm.”

For Letwin, Mill was not a friend of liberty, despite On Liberty and Representative Government, even though he valued individuality for human flourishing—a point she agreed with. Mill’s liberty was not merely absence of restraint, but the condition for developing an “ideal individual.” This could be achieved only by those capable of self-government, who were also tasked with guiding society toward that ideal. Where society could not govern itself, a superior class of scientists could direct it, even despotically. Letwin notes that for Mill, “despotism is therefore a mode of government as legitimate as any other.”

Strikingly, Letwin’s critique in The Pursuit of Certainty echoes Maurice Cowling’s Mill and Liberalism (1963), which portrays Mill not as a liberal saint but a moral absolutist. The parallels emerge when Letwin writes of Mill’s argument in On Liberty:

enables the liberal to feel assured of his tolerance, and at the same time to feel it is right, even obligatory, to impose his own views on the less fortunate mass of people in want of uplifting. He provided a justification for withholding personal liberty from any claimant unable to demonstrate that he was pursuing the “right” ideal and was possessed of sufficient will power to pursue it steadily and energetically.

With Mill, Letwin identifies a new liberal intellectual committed to liberty, progress, and reason—yet whose politics often undermined the very values it claimed to uphold. Mill’s confidence in a science of politics was part of a wider movement seeking certainty in science rather than philosophy or religion. For Letwin, Mill is significant as a transitional figure: moving from Benthamite rationalism to a more ambitious scientific politics, ultimately aiming at the abolition of politics itself.

The End of Politics

The final thinker Letwin examines is the socialist Beatrice Webb. Given the least sustained treatment, Webb is shown as the embodiment of the pursuit of certainty in politics—the belief that social problems could be solved through methodical, scientific investigation. At the core of Webb’s vision was the conviction that expert knowledge, rather than tradition or sentiment, should govern society. Her approach was, above all, “a plan for replacing politics with science, politicians with scientific experts. It designed a government in which the uninformed public, and its haphazardly trained representatives, were made to recognize and submit to the knowledge of social scientists.” Webb’s politics thus constituted a managerial utopia, guided by experts, informed by sociology and economics, and directed toward the collective good of future generations—representing the culmination of the pursuit of certainty: politics as the earthly analogue of salvation.

Yet the pursuit of certainty as a route to salvation leads to the logical culmination of this evolution in the understanding of politics: the end of politics itself. In a managerial utopia that seeks to encompass all human conduct, the political enterprise becomes a ship bound for perfection, and any disagreement about the journey is construed as a threat—an obstruction to reaching the fixed, ideal destination.

Letwin observes the implications of Webb’s vision for the end of politics:

For once society is regarded as an organism, it is understood to have a unitary good and all the old political controversies become obsolete. The problem of reconciling conflicting desires of individuals, or of compromising between conflicting views of national ends, disappears. There remains only one end, the health of the social organism, and what every man should have can easily be determined by his function in the social machine … since politics would comprehend everything. Anyone who attempted to exclude government from some activities, or in any way to separate politics from the rest of life, would be advocating a return to anarchy and preventing human beings from realizing their highest potentialities.

Shipwrecked Politics

The book concludes with Beatrice Webb, yet without a closing chapter or postscript to encapsulate the consequences of the evolution Letwin traces through the four thinkers. This omission recalls the work’s central weakness—its lack of a clear structure or sustained narrative—only partially remedied by the introduction. To assist both the reader and Letwin in bringing the argument to closure, one might suggest that the British political tradition, as she presents it, has moved from Hume’s moderate politics to one animated by faith in reason, expertise, and social control, epitomised by Beatrice Webb. The book thus stands not merely as a diagnosis but as a warning of our current predicament: that the loss of sceptical restraint in steering the ship of politics, and the attempt to direct it towards a predetermined ideal, has led—or will lead—to shipwreck, when the pursuit of perfection founders upon the illusion that politics can be governed by infallible design.

Its dual status as both diagnosis and warning about the abandonment of Humean moderation amply justifies The Pursuit of Certainty’s place as a classic of liberty. Yet its value reaches further, offering a lesson for the modern Right facing a similar predicament. The difficulty, Letwin’s book suggests, is that much of today’s Right has likewise forsaken moderate and sceptical politics for a mode Hume would have called “a form of revolutionary enthusiasm.” Instead of navigating the ship of state upon the boundless ocean with prudence and restraint, the modern Right seeks to steer it into the harbour of salvation—an effort destined for shipwreck. The enduring challenge, then, is that modern conservatism has yet to heed Oakeshott’s warning: one cannot defeat rationalism by imagining a more acceptable form of it.

The book’s greatest limitation is that it provides no practical guide for addressing our current predicament. Humean conservatism, to which Letwin adheres, offers “no political principle or doctrine,” but rather “a disposition” shaping conservative politics. It is concerned with steering the ship steadily by preserving what is familiar, not directing it toward an imagined conservative salvation. In an age of fervent and overzealous right-wing politics, such modesty is unlikely to appeal widely. Yet The Pursuit of Certainty offers an implicit reminder to conservatives and friends of liberty alike: in times of ideological excess, a less enthusiastic politics may be exactly what is needed.