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The importance of Julius Cæsar in Churchill’s mind can be demonstrated by his devotion to Shakespeare’s Julius Cæsar, his references to Cæsar as a politician and general, and his account of Cæsar’s invasion of Britain in A History of the English-Speaking Peoples. That Churchill should refer to Cæsar is no surprise; perhaps more surprising are the number and nature of comparisons of Churchill to Cæsar. This paper will explore the long and varied association of these two statesmen.