Osbert was born before 1225. He was the son of Adam Cailly. In the reign of Edward I, he claimed assize of bread and beer, view of frankpledge, etc in towns of Bradenham, Oxburgh, Cranwick and Hilburgh, Norfolk, as having been possessed by his father from the Conquest.
Osbert de Kailli or Cayley in the reign of Hen. 3d, by his deed sans date, gave to Sir John le Briton all his water or fishery which he had in Cressingham Magna, anciently called Claphamdam, with the appurtenances which begin at the head of a ditch which is between the meadow of the Prior of Norwich and the meadow of William at the Cross of Cressingham, and goes on through the said meadows to a place called Hutsotespool. The witnesses were Sir John de Dunham, Sir William Fransham, Knts. and others.
In 1270 he was one of the collectors of the Twentieth in Lincolnshire.
In 1287 he was with the army in Wales, so he must have died after that.
Some sources, including Burke's Dormant Peerages, name Osbert de Cailly as the husband of Emma de Tateshall; others, his son Adam. Dates mean that is unlikely that Emma's husband was Osbert: Thomas de Cailly, Lord of Buckenham, Norfolk, and son of Emma and her husband was not born until about 1282.
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