No one has ever really studied Michael Oakeshott’s relationship to the left. After all, since Oakeshott is generally classified as a conservative political thinker, there is presumably little to study. Yet on a second glance there is more to the matter. His contemporaries certainly found Oakeshott hard to pigeonhole. It was not obvious to them that he was a “conservative.” In the 1950s and 1960s he was called “a melancholy Hegelian, a speculative moderate in the tradition of Hume, a Burkean, an Epicurean, a Bohemian aesthete, the Proust of Political Science, a Hobbesian, a High Tory, a patriot, a lonely nihilist, a conservative skeptic, a libertarian Whig, a potential fascist, and even a logical positivist.”
While Oakeshott is not commonly regarded as having been on the left himself, posthumous readers who do identify themselves in this way have sometimes taken an interest in his thought. Chantal Mouffe, for example, has argued that his ideas are “productive for the formulation of radical democracy.” Furthermore, if we examine Oakeshott’s writings, we find that he actually had quite a lot to say about the left, particularly through his work as a reviewer, where he was prolific. Moreover, as it now turns out, the conventional view of Oakeshott’s place in the history of ideas has been arrived at in ignorance of his own early political views. There is incontrovertible evidence that in his youth Michael Oakeshott was a socialist. Although this initial attachment to socialism was soon abandoned, and in public he never referred to it later, he continued to express positive opinions towards certain elements of left-wing thought throughout his career.
Oakeshott’s early socialism was grounded on moral rather than economic considerations. In his youth, he was never interested in questions having to do with the redistribution of wealth, because he was convinced that a spiritual transformation of values was more important. Long after he had left socialism behind, however, he continued to be convinced that the major political problems of the age were not primarily economic in nature. He was not, for example, committed to the idea that capitalism was integral to freedom, and he even appears to have accepted much of the socialist critique of capitalism, though not its proposed solutions. Perhaps more importantly, Oakeshott was initially attracted to a form of socialism that treated the individual and society as interdependent. This suited his romantic tendency, which made him insist strongly on individual autonomy, but which was also compatible with the influence of idealism. His Idealism tempered his individualism with the recognition that the existence of the self required others for its full realization. In one form or another, he always retained these views.
A lasting attachment to personal freedom allowed Oakeshott to find common ground with anarchists like Herbert Read and Pierre Proudhon, but also, surprisingly, with Herbert Marcuse’s reading of Hegel. This enduring sympathy for anarchism, however, was counterbalanced by an increasingly hostile attitude to other elements of left-wing thought. We can separate out the different positions Oakeshott took to three major strands of left-wing thought: Marxism and communism; Fabianism and democratic socialism; and anarchism and the Frankfurt School.
With respect to Fabianism and democratic socialism, for example, in the 1940s and 1950s Oakeshott was prepared to concede that these ideas represented a middle way that was not to be rejected out of hand. By the 1960s, however, he could be found declaring that Fabian socialism, generally regarded as a moderate doctrine, was a delusive form of rationalism that had fostered dreadful political judgment amongst its leading exponents. A similar development is visible with respect to Marxism and communism. Oakeshott began by being moderately critical of the potential of Marxism for dogmatism and of Soviet communism for repression in the 1930s. But World War II hardened his views, and by the 1960s he was contemptuous towards Marx and saw the Soviet regime as legitimated by nothing more than rhetorical sleight of hand.
Yet Oakeshott actually shared a vocabulary with Harold Laski, now remembered chiefly for his Marxism, for much of the interwar era. This has generally gone unremarked, because the most substantial of Oakeshott’s early writings on politics have only emerged posthumously. But in fact he continued to use the discourse of the General Will, in which the definitive feature of the ideal state was thought to be its possession of a common purpose, well into the 1930s, even after he had left socialism behind. Oakeshott’s mature political philosophy, as presented in On Human Conduct (1975), appears from this point of view as the final outcome of an effort to emancipate himself from this vocabulary, a process in which the essays of Rationalism in Politics (1962) represent an interim stage. Readers have not generally appreciated the extent to which these essays were in fact a work of self-criticism, because Oakeshott’s own youthful rationalism has also only recently come to light. His mature thought was the product of a search for a new set of terms in which he could express his enduring philosophical attachment to the political individualism that had attracted him to socialism in the first place.
Telling this story requires looking beyond Oakeshott’s major published works. The essays in Rationalism in Politics discussed socialism and communism only in passing. Their allusive and elliptical quality stemmed partly from a deliberate effort to avoid such conventional ideological labels. As for On Human Conduct, it employs a terminology all its own. We cannot ignore these works entirely, but we need to rely heavily on the numerous reviews he produced, because they used a more conventional political vocabulary. Oakeshott was a prolific reviewer, and he did not fight shy of argument. His aim was not simply to summarize the text, but to deliver a critical verdict, so the fact that many of his reviews often show sympathy for certain left-wing ideas, even though he had long abandoned socialism himself, is all the more significant. Piecing this material together, we can uncover what looks like a concerted effort to engage with some of the most notable socialist writers of the day, as well as with some major critics of socialist thought, such as James Burnham and Raymond Aron.
It seems, then, that the place of left-wing ideas in Oakeshott’s thought is worth examining after all. A review of the subject helps to explain why contemporaries found him so hard to classify, and what it is that readers on the left have found congenial about his thinking. It also supplies a fresh perspective on the development of his own political theorizing.