Michael Oakeshott was the son of Francs Maude (Hellicar) and Joseph Francis Oakeshott, a civil servant and a major member of the Fabian Society. George Bernard Shaw was a friend. Michael Oakeshott attended St. George’s School, Harpenden from 1912 to 1920. He enjoyed his schooldays, and the Headmaster Cecil Grant later became a friend. During 1920, Oakeshott went to Gonville and Caius College, Cambridge to read History, where he obtained an MA and subsequently became a Fellow. While at Cambridge, he admired the British idealist philosophers J. M. E. McTaggart and John Grote, and the medieval historian Zachary Nugent Brooke. The historian Herbert Butterfield was a contemporary and fellow member of the Junior Historians society. Michael Oakeshott was dismayed by the political extremism that occurred in Europe during the 1930s, and his surviving lectures from this period reveal a dislike of National Socialism and Marxism. Although his 1939 essay ‘The Claim of Politics’ defended the right of individuals not to become directly involved, during 1941, Oakeshott joined the British Army. He reportedly wished to join the Special Operations Executive (SOE), but the military decided his appearance was “too unmistakably English” for him to conduct covert operations on the Continent. He was on active service in Europe with the intelligence unit Phantom, which had Special Air Service (SAS) connections, but he was never in the front line.

During 1945, Michael Oakeshott was demobilized and returned to Cambridge for two years. During 1947, he quit Cambridge for Nuffield College, Oxford. After only a year, he secured an appointment as Professor of Political Science at the London School of Economics (LSE), succeeding the leftist Harold Laski. He was deeply unsympathetic to the student action at LSE that occurred during the late 1960s, on the grounds that it disrupted the goals of the university. Oakeshott retired from the LSE in 1969. In his retirement he retreated to live quietly in a country cottage in Langton Matravers in Dorset. He lived long enough to experience increasing recognition, although he has become much more widely written about since his death. Michael Oakeshott refused an offer of being made a Companion of Honour, for which he was proposed by Margaret Thatcher.