Henry's father was a schoolmaster and his father, Henry's paternal grandfather, although he began life as a shepherd, taught himself mathematics and astronomy and left his life on the hills to become a schoolmaster in Lewes. Henry learnt to play chess at a young age and soon became interested in chess problems.
Henry's ama ay isang guro at ang kanyang ama, Henry's ama lolo, kahit na siya ay nagsimulang buhay bilang isang pastol ng mga tupa, tinuturuan ang sarili sa matematika at astronomy, at pakaliwa ang kanyang buhay sa Hills upang maging isang guro sa Lewes. Henry learnt to play chess sa isang bata na edad at sa lalong madaling panahon ay naging interesado sa chess problema.