The Bailey or Bailiff was a man of great importance and was paid accordingly by his master. Where a shepherd earned 4 shillings per annum and a ploughman 8 shillings, the Bailey would receive six pounds. He lived in the Manor House at the Lord's expense and was responsible for the administration and supervision of the general agricultural policy. Then term Bailey, now obsolete in England, is still common in Scotland wher it is used as Chief magistrate or Sheriff. In the 14th Century Dionisy-eri-la-Baillye owned shops and houses at the Old Bailey. The name BAILEY may be derived from more than one source. One of these is the old French "Bailli" originally meaning "carrier" but later "administrator".

This most interesting surname has three distinct origins. Firstly it can be an occupational name for a steward or official from the Old French "baillis" or "bailif", and middle English "bail(l)". The word survives in Scotland as "bailie", the title of a municipal magistrate, but in England has developed into "bailiff", an officer of the court. The second source is topographical, denoting one who lived by the outermost wall of a castle or fortified town from the middle English "bail(l)y" as can be seen in the case of the Old Bailey in London which was part of the early medieval walls. Thirdly, the surname can be locational, from "Bailey", in Lancashire which means "berry wood". One Roger le Baylly appeared in the Suffolk Pipe Rolls in 1230, while the Assize Court Rolls of Lancashire recorded a Ralph de Baylegh in 1246. Walter Bayley (1529-1593) educated at Winchester and fellow of Oxford, was Queen Elizabeth's physician. One William Butterworth Bayley (1782-1860) an Anglo-Indian, was educated at Eton and rose to the rank of Governor-general of India (1828-1830), he later became a director of the East India Company. The first recorded spelling of the family name is shown to be that of Roger le Baylly, which was dated 1230, in the Suffolk Pipe Rolls, during the reign of King Henry 111, known as "the Frenchman", 1216 - 1272.