The question of whether or not the occupants of Bayleaf were literate takes on more significance when we consider the evidence for whether or not they were bailiffs. The link between the occupants of Bayleaf and the office of the bailiff derives in the first instance from the belief that ‘Bayleaf’ is a corruption of the word ‘bailiff’. However, as we have seen, it is more likely that Bayleaf took its name from the original occupant, who was probably Henry Bailey. Whilst the surname ‘Bailey’ derives from the office of bailiff, by the 15th century the link between the occupation and the surname had become historic. Weight has been added to the Bayleaf/bailiff association by the reference in Lady Bridget Willoughby’s will of 1556 to ‘William Wells my bailiff’. Who William Wells was and his relation to the tenants of Bayleaf is unclear. His name does not appear in contemporary tax records for Chiddingstone or the adjacent communities, which may indicate that he fell below the tax threshold or that his status as a dependent servant exempted him. Whilst it is reasonable to assume he was related to Edward or Thomas Wells, he may have been part of their wider kin network, resident either in Chiddingstone or its environs. We do know that between 1513 and 1518 the Bore Place bailiff was a man called William Walker, who had no connection with Bayleaf. In his will of 1519 Sir Robert Rede left Walker a tenement called ‘Mayes’ in the neighbouring village of Sundridge, and it is likely that this is where Walker lived during Rede’s lifetime.