Improbable as this sounds, Oakeshott was the subject of MI5 surveillance. The source of this nugget is the book Philby: The Spy who Betrayed a Generation by Bruce Page, David Leitch and Phillip Knightley (Introduction by John le Carré), Penguin, 1969. Here is the excerpt:
It may be that the failure on the part of the MI5 “trace” system to produce any left-wing evidence against Philby would not have been very relevant. Firstly, it was not certain that a senior SIS man in 1941 would have turned away a much-desired recruit merely because the much-distrusted MI5 reported adversely on him. And indeed, the “trace” system at the time made some ludicrous errors: we have been told of a case in which the conservative academic, Michael Oakeshott, was “traced” as a left-winger due to an absurd misreading of the title of a Cambridge undergraduate society of just the kind described in the previous chapter (p. 167 – emphasis added).
But then again, given his penchant for women with left-wing sensibilities, notably Jennifer Hart (husband of H.L.A. Hart), one can see how a low-grade operative sitting outside a known sypathizers’ residence only to see Oakeshott arrive and leave, would make such an inference.
