The family from which the Constables of Flamborough were descended held the high office of Constable of Chester for many years after the Conquest, and this was the origin of the name. They were related by marriage to many other powerful families, including the de Lacys and the de Veres, and were often in office as High Sheriffs of the County, Constables of important castles, and Commanders in the army.
By the beginning of the 16th century the Constables were the Lords of more than thirty manors in Yorkshire and fourteen in Lincolnshire. But the tragic conclusion to the Pilgrimage of Grace ended the career of Sir Robert Constable and resulted in the confiscation of all the family estates.
Sir Robert's grandson, another Robert, successfully petitioned Queen Elizabeth for their restoration, and the family seems to have resumed residence at Flamborough, although some property had to be sold to settle old debts. Robert's son, William, was knighted in 1599 for his services under Essex in Ireland, but being involved with the Earl in the conspiracy of 1601, he was arraigned for High Treason. Released without trial on a special letter from the Queen (who said he had been unwarily drawn in), he was made a baronet by James I in 1611.
He was, however, very extravagant, and although he sold Holme in 1633 and Flamborough in 1636, he became a bankrupt. Imprisoned for non-payment of Ship Money, he turned against the King, becoming a colonel in the Parliamentary army, and his name is amongst the signatories to the warrant for the execution of Charles 1. He died in 1655 without surviving issue, and with him the Flamborough branch of the family came to an end.