On Oakeshott on the Art of the Deal

Back before he won his first presidency, I tried to write on the rise of Trump neither by underestimating him as a political phenomenon nor by writing as a political partisan on him. Since his initial electoral victory, I have felt little need to add to the voluminous punditry on the subject. Today, I deviate from that self-imposed silence because in re-reading Oakeshott I had a sense that, perhaps, on some level I fundamentally misunderstood the disease of which Trump is a symptom.

In his classic essay (1947), “Rationalism in Politics,” Michael Oakeshott (1901 – 1990) identified political rationalism with books that purport to teach political technique to new men. Such books can be recognized with ‘art of’ in the title (e.g., “A stream of books flowed from the presses on the 'art of poetry', the 'art of living', the 'art of thinking.'” (p. 17 in the (1962) Basic Book edition.) It is, then, no surprise that Donald Trump rose to fame with a (1987) book titled, Trump: The Art of the Deal. As Wikipedia reports, this book “contains an 11-step formula for business success, inspired by Norman Vincent Peale's The Power of Positive Thinking.”

At first sight it may seem wholly perverse to associate Trump with the category of ‘rationalism’ that Oakeshott develops in that essay. It is universally agreed by those with a modern education — Oakeshott’s children of rationalism — that Trump is a grifter and a demagogue (a political category also recognized by Oakeshott in “Rationalism in Politics.”) If anything, the self-described modern rationalist sees in Trump, who has a tenuous relationship with truth, the avatar of the politics of irrationality (e.g., fascism).

But before you protest, for Oakeshott rationalism is paradigmatically “over-impressed with its own accomplishment.” (p. 18) Rationalism attracts “men in a hurry to appear educated but incapable of appreciating the concrete detail of their total inheritance.” (p. 19) In fact, the rise of rationalism in politics is, according to Oakeshott, itself a symptom of a politics by and of new men (and women). This is an inevitable byproduct of liberal democracy with its distrust of inherited aristocracy.

And when in that context purported political expertise turns out to be, as it must (according to Oakeshott), hollow then arises the Trumpista: “Indeed, so impractical is a purely rationalist politics, that the new man, lately risen to power, will often be found throwing away his book and relying upon his general experience of the world as, for example, a business man.” (p. 30) But whatever this knowledge is, “it is not knowledge of the political traditions of his society.” (p. 3) In fact, crucially, rationalism is the politics “of felt need” ((p. 5) even “sovereignty of felt need”), which produce “crises” that cry out for solutions (a border wall, a tariff, expulsion, etc.).

Oakeshott identifies rationalism, which can come in degrees, in a classical and modern kind. (He rejects both.) The classical kind is paradigmatically Plato, but also, and in some sense, stricter, the long reign of scholasticism. The modern kind is articulated most prominently since humanism by Machiavelli, and later Bacon and Descartes, and coincides with the decline in the belief in providence.

Oakeshott identifies modern rationalism with a number of characteristics, three of which pre-eminently: first, “the blank sheet of infinite possibility.” Existing laws must be burned, and we must “start afresh.” Second, the politics of perfection. Third, the politics of uniformity. (p. 5) There is “no place in his scheme for a ‘best in circumstances,’ only a place for ‘the best.’” (p. 5)

As an aside, unlike most twentieth century self-described Anglosaxon ‘conservatives,’ Oakeshott does not pretend to revere the US Constitution. He thinks it’s a document that could only have been promulgated by new men, who refuse to acknowledge their own ‘violence’ and the ‘accidental circumstances,’ that shaped their ‘self-evident’ and ‘eternal’ truths. (p. 28) More subtly, for him the American experiment is a regime that entrenches the power of ignoramuses in politics.

Be that as it may, it’s quite clear that for Oakeshott, it’s men like Bentham, Owen, and Godwin that are the paradigmatic modern rationalists (not to mention Marx and Engels). And (he is explicit about this) that in Road to Serfdom even Hayek — who attacks rationalism in politics with equal vigor — offers, in fact, a species or style of rationalism: “the fact that it is a doctrine. A plan to resist all planning may be better than its opposite, but it belongs to the same style of politics.” (p. 21)

And it is in this sense that by Oakeshott’s lights even Trump is rationalist: Trump rejects tradition for a fresh start. For, “the Rationalist is not always a perfectionist in general, his mind governed in each occasion by a comprehensive Utopia;” — nobody would ascribe that to Trump — “but invariably he is a perfectionist in detail.” (p. 5) and this is one of Trump’s vices. He falls in love with his own schemes. That is, no rationalist is capable of moderation.

Despite my moniker (‘nescio’) and my skeptical sensibility, I am myself not an Oakeshottian conservative. But I find thinking with Oakeshott useful because he helps me understand how Trump is, in a certain sense, not the opposite of the technocratic ideal of the expert in government, but rather its distorted grotesque mirror image.

I use ‘grotesque’ because for Oakeshott apprenticeship is central to true education. In such an education (to simplify) explicit knowledge-that and know-how is acquired over much extended time. Trump, of course, was the star in a show, which offers lip-service to the ideal, The Apprentice, which was characterized by a kind of neo-Darwinian contest of survival, but no actual apprenticeship in the true sense, which involves, by participation, observation, and emulation, “learning the nuances which compose the tradition and standard of behaviour which belong to a great profession.” (p. 34, emphasis in original).

We need not agree with Oakeshott’s preference for a politics dominated by great families who can teach their sons and grandsons how to rule empire, nor to wish for a Trump victory, to recognize that Trump himself is less of an aberration than his critics would like to imagine. By this I do not mean some original sin narrative or the idea that his rise is punishment for our crimes (or that he is a necessary evil by which providence works its way out).

Rather, it is inherent to mass liberal democracy that it is the rule of new men (and women) who have a transactional relationship to the demos. This is most unseemly presented when our oligarchs become jumping cheerleaders or, like Jeff Bezos who takes a knee to hedge his bets. But it is the bread and butter of all interest groups. And part of this transactional nature is the (s)election of leaders who promise new norms and decisive action on solving our social problems.

That is to say, there is a fundamental dangerousness to mass democracies which produces quite partial to their ‘own’ governments. It’s only the sanitized histories of our past and our anti-politics-as-it-is-practiced political theories that obscure this from us, time and again. To speak in my own voice, if liberalism is to compete with the great variety of rising, democratic non-liberalisms we must re-learn to recognize this danger and to understand our hidden kinship with those who wish to destroy us.