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From Finest Hour 98, Riddles, Mysteries, Enigmas

Q: I was mortified today when unable authoritatively to rebut a coworker's repetition of the "Churchill was a dunce at school" canard (with the usual emphasis on Latin and Greek). --Andrew Isaac

A: See Jim Golland's Not Winston, Just William? (Harrow: Herga Press 1988), a revisionist account of Churchill's Harrow Schooldays -- revisionist in that it proved that he was not the dunce he and others said he was. Golland noted that anyone who could recite 400 lines of Macaulay's Lays of Ancient Rome, and write a future history of an attack on Russia which presaged what actually happened in later years, could not be stupid.

Golland also said it unlikely that Churchill entered Harrow without knowing Latin (as WSC writes in My Early Life) -- it was a prerequisite, even for Lord Randolph's son. The bottom line is that Churchill was mediocre at what bored him, and very good at what interested him: English and History for example. At Sandhurst, which emphasized these subjects along with military tactics and strategy, etc., he finished near the top of his class.
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