Leslie was the son of T. W. Eastwood of Hoylake, Cheshire. He was a boy at King William’s College, Isle of Man, and Worcester College, Oxford. He came to the Dragon School as Master in 1907. He took Form IV, and was always most enthusiastic and keen on coaching the boys in their games. He attended all the Old Dragon dinners, and was stage manager of The Pirates of Penzance, 1914. He played football regularly for the Oxfordshire Nomads and he took his M.A. in 1913. He cruised with the Skipper on Blue Dragon II to the Orkney Islands in April 1910. In Easter 1912, he sailed with the Skipper, Tom Higginson, Hugh White, and Ivor Day in Blue Dragon II, from Trondhjem to Sandnaesjoen; and again in the summer of the same year 1912, from Hammerfest to the North Cape, and back to Skjaero. In 1914 he sailed his last voyage in the Blue Dragon, from Marstrand in Sweden to Christiania, whence he hastened, at the news of the war, to return to England via Bergen and Newcastle, and immediately joined up. He got his commission as 2nd Lieutenant in the King’s Own Royal Lancaster Regiment.
One of his colleagues writes: ‘Much of the success of the boys in the upper part of the school was due to the grounding they received in his form, and he has been and will be as much missed by his colleagues as by the boys whose affection he won spontaneously. He leaves a gap which we shall find it very hard to fill, as he knew what was wanted and what to expect from a boy. He was no respecter of persons, and consequently his advice was generally sought by those who knew, and was respected by a still wider circle.’
He was wounded in the Dardanelles, and died in hospital at Alexandria on the 19th September 1915, having suffered from dysentery as well as from his wounds. He is buried at the Alexandria Military and War Memorial Cemetery.
The Skipper writes: ‘Leslie Eastwood had been with us since 1907, and had become a first-rate schoolmaster. His form was noted for its “thoroughness”. Strict without being severe, he won the respect and love of his boys, and they would at any time do anything for him: it was very seldom indeed that he had to “send in” a boy to me, and yet he had his form always under control. At games he was most keen and successful in his coaching, and showed a manly and loyal spirit that was most stimulating. He came as a young graduate fresh from College, and very soon cured himself of those mistakes which every young schoolmaster must make. As a comrade to me on the Blue Dragon he was splendid, and it was greatly owing to his determination that we succeeded in reaching the North Cape.’