Abstract

This essay takes up Noel Annan’s claim that “The key to Oakeshott” is in the relatively neglected book on horse racing, A Guide to the Classics. The analysis develops Oakeshott’s anti-rationalist, skeptical perspective by examining how he approached the topic of handicapping horse racing. Like politics, and practical life more generally, horse racing requires experience in the face of contingency and suggests a conservative and playful response is the appropriate one.