The fact that life is a gamble was not something Michael Oakeshott regretted. He liked the uncertainty of the human world and admired people who embraced it wholeheartedly. In one of the last conversations I enjoyed with him before he died in 1990, he talked of a novel he had been reading that related the adventures of Canadian gold-miners. ‘Think of it!’ he enthused. ‘Staking their lives on a single throw!’
Oakeshott seems not to have done anything of the kind himself, but he had a lifelong interest in betting on horses. A Guide to the Classics, first published in 1936 and co-authored by Guy Griffith, a friend of Oakeshott and, like him, a fellow of Gonville and Caius in Cambridge, is one of the results of this engagement. The authors come up with a number of practical maxims, chief among which is that a horse can be expected to win the Derby only if it is the offspring of one that has already won or been placed in the Derby or the St Leger. Whether such precepts would have enabled anyone to make money consistently seems doubtful. An obituary records that in 1929 Griffith collapsed in a railway station in Vienna on reading in an English newspaper that a horse on which he had bet had lost by a short head. When asked what was wrong, he said that half his studentship money had gone. Later Griffith seems to have been more successful, financing a wine cellar and a majestic Rolls-Royce from his winnings. Oakeshott’s score of wins and losses seems not to have had a material impact on his fortunes. For both authors, the point of betting on the horses was not so much profiting from the wager as the satisfaction that came from picking the winner.