William Edward Chesterman was born in Hungerford in 1859. Aged twelve, and weighing 4 stone, he became apprenticed to Henry Woolcot at Beckhampton.
He first rode in public in 1874, in the white and blue colours of Mr Fisher. Riding Alexandra at Windsor in the Eton Handicap, he finished unplaced.
He rode Sir George Chetwynd's Cat's-Eye in the 1875 Stewards' Cup but the colt was unplaced behind the Fred Archer-ridden Trappist. The following Thursday at Goodwood he gained recompense when making every yard on Cat’s-Eye in the Chichester Stakes, winning by eight lengths.
William was not strong enough to keep The Grey Palmer – an awkward ride – straight in Warwick’s Leamington Stakes and was beaten a neck by A. Cook riding Simon. However, the horse was turned out later that week for the County Handicap and this time William made no mistake.
Still just 15 years of age, William had just two more mounts that year: Wigwam in the Portland Plate and Chypre in the Alexandra Plate. Neither was placed. That year, 1875, he rode two winners.
William went on to become a professional jockey and won the 1877 Manchester November Handicap on Hopbloom for the Duke of Montrose.
With his career failing to take off in Britain, he moved to France and rode there for as few years until he was refused a licence to ride in February 1894.
He died in Chantilly in April 1913.
His brother, George Chesterman, was also a jockey. They were not twins as most reports said at the time. George died in poor circumstances in Lambeth on July 25, 1902.
