Early Life
Leonard Cheshire was the son of Geoffrey Chevalier Cheshire, DCL, LLD, FBA, a barrister, academic and influential writer on English law. He had one brother, Christopher Cheshire, also a wartime pilot. Cheshire was born in Chester, but was brought up at his parents' home near Oxford. Cheshire was educated at the Dragon School, Oxford, Stowe School and Merton College, Oxford. While at Oxford he became friends with John Niel Randle. On one occasion at Oxford he was bet half a pint of beer that he could not walk to Paris. With no more than a few pennies and a pocket handkerchief he won his bet. Cheshire graduated in Jurisprudence in 1939. He went to stay in Germany in 1936 with a family in Potsdam.
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“... business training in early life should not be regarded solely as insurance against destitution in the case of an emergency. For from business experience women can gain, too, knowledge of the world and of human beings, which should be of immeasurable value to their marriage careers. Self-discipline, co-operation, adaptability, efficiency, economic management,—if she learns these in her business life she is liable for many less heartbreaks and disappointments in her married life.”
—Hortense Odlum (1892–?)