Regarding Silver s timber leg Silver specifically says that he learned his craft as a sailor while in the navy In fact he specifically mentions that he was a master mariner which indicates he was an officer on a warship yes the pirate could have been lying regarding his former rank and that he lost his leg in battle which would doubtlessly lead to his retirement from active naval service However with the skills of a former naval officer incidentally who would have been trained in navigation he would have had an easy time joining up with a pirate crew He was likely lying about serving under Captain England given the dates Also Silver was Flint s quartermaster which in the Royal Navy is the helmsman s position Given that his one legged status does not seem to make him any less lethal a pirate he takes down a man by nailing him in the spine with his crutch there is no reason to suppose that he retired from the life of a gentleman of fortune because he had one leg He retired because Flint died