Early Cayleys


Osbern de Cailly (11th century). Probably descended from Richard the Fearless, 3rd Duke of Normandy.

  • Guillaume de Cailly m. Maude de Beaumont. Came to England with the Norman Conquest, probably fighting at Hastings.
    • William de Cailly. Held lands in East Anglia and Sussex, including at Trumpington near Cambridge, where the mill features in Chaucer’s Miller’s Tale.
    •  Humphrey de Cailly (see below)
    • Osbern de Preaux (born Osbern de Cailly, but took his wife’s name on marriage). Inherited some of his father’s lands in Normandy but renounced his claim to most of the Cailly land in Normandy when he acquired other lands through his wife.
    • Roger de Cailly m. Petronella de Vere. Took over most of the Cailly lands in Normandy when his father went to England.


Osbern de Preaux had 4 sons and 1 daughter. The oldest son, Osbert de Preaux had six sons, among whom were:

  • Jean des Preaux (d. 1218), who in the 1180’s headed a commission set up to resolve differences between Philippe-Auguste, King of France, and the English crown. He had lands in both England and Normandy, and founded the priory of Beaulieu in Hampshire, where he and some of his descendants were buried. When Philippe-Auguste invaded Normandy (then ruled by King John of England), he sided with the French. His English lands were confiscated. After conquering Normandy, Philippe-Auguste probably sent him as an envoy to England. One of his sons, Guillaume de Preaux, accompanied Richard I of England on the Third Crusade: he saved Richard’s life in one battle, but was taken prisoner. Richard I exchanged 6 captured emirs to secure his release. Another of his sons became Archdeacon of Rouen.
  • Peter des Preaux (d. between 1207 and 1212) who was one of King John’s chief commanders in his wars with Philippe-Auguste of France, and was warden of the Channel Islands. In 1204 he defended Rouen against the French. He negotiated an armistice under which Rouen would be surrendered if no relief came within 30 days – and none did. After the surrender, there were rumours that he had been bribed, but he seems to have retained King John’s favour. He was a signatory to the treaty finally ceding Normandy to the French, and joined King John in England.
  • Guillaume or Raoul des Preaux, who held lands in Touraine. He lent King John money and was granted the income of the Viscounty of Lieuvin until the debt was paid, with tenants forced to pay double the normal rent to him. Following John’s loss of Normandy, he initially stayed there but came to England late in John’s reign.


Humphrey de Cailly, son of the Guillaume who came to England with the Norman Conquest, had a son, Simon de Cailly (d. 1218), who owned extensive lands in Norfolk.

Among Simon de Cailly’s children was Roger de Cailly, who probably held the main Cailly lands in Norfolk, and was rich enough to make large loans to King Henry II. Roger de Cailly had at least two sons:

  • Osbern de Cailly (d. before 1200), who was one of the more important Norman barons, acquiring some of his lands by marriage. One of his daughters, Matilda, married Henry de Vere, and, after Henry’s death, Regnald de Bosco. Another, Alice, married Stephen de Longchamp who fought under King John of England against Philippe-Auguste, was imprisoned after he lost a fortress, and in the end stayed in Normandy, giving allegiance to the French King. Stephen de Longchamp died in 1214 in the Battle of Bouvines, fighting for the French. A third daughter, Petronella, married Geffrey de Bosco.
  • John de Caly, who inherited the main family lands in Norfolk.

John had at least one son, another John de Caly, whose widow Margery married Michael de Poynings, whose name – derived from the Sussex manor of Poynings – suggests that by then the Cailly family had started to acquire lands in Sussex. This John had four sons:

  • Hugo de Caly
  • Elias de Caly and Ralph de Caly, who entrusted lands to the Priory of Lewes when they went on crusade and seem never to have recovered them
  • Adam de Caly, who inherited the main lands in Norfolk, and joined in baronial rebellions in the last years of the reign of King John.

Elias and Adam married into the powerful Giffard family. Elias’s great-grandson, another John de Caly, inherited the Giffard lands in 1327.

Adam de Caly’s main heir, Osbert de Caly, fought for Edward I in Wales in 1287.

Osbert de Caly‘s younger son, Hugh de Caly, is probably the first member of the family recorded to have held lands in Yorkshire, and from him the Yorkshire Cayleys descend. The older son, Adam de Caly, married Emma de Tateshall, whose family owned extensive lands in Sussex and elsewhere. Adam had at least three children:

  • Thomas de Cailly, Adam’s main heir, who married Margaret de Norwich. She was the daughter of Sir Walter de Norwich, Justice of Norfolk, who was appointed Treasurer to King Edward II in 1314. In 1307 Thomas inherited a third of the Tateshall lands in Sussex, Hampshire and elsewhere. He fought against the Scots, and attended several parliaments as a baron. Following his death in 1316 without an heir, his lands passed to his nephew Adam de Clifton.
  • Margery de Caly, who married Roger de Clifton: as a result of this marriage the Clifton family inherited the main Caly/Cailly lands in East Anglia and elsewhere when the senior branch of the family had no male heirs.
  • Adam de Cailly, who fought against the Scots and was the Adam de Cailly ransomed from them in about 1328. See the blog post Ransomed from the Scots.
  • Edmund de Caly, subject of the blog post More Medieval Mayhem, was probably another son.