The senior line of the Hawtrey family had been seated at Chequers, Buckinghamshire since the thirteenth century. William Hawtrey of Chequers sat for Buckinghamshire in 1563 and his brother, Michael, for Bedford in 1572. A cadet branch was established early in the sixteenth century when a younger son, Ralph Hawtrey, married Winifred Wollaston of Ruislip, a village 20 miles away across the county border. Their second son, Edward, married Elizabeth Dormer of Lee, Buckinghamshire, who bore him four children.
Nothing is known of Hawtrey’s education. His economic prospects depended on the lease his family had held since 1532 of the lands of the rectory of Ruislip,
Hawtrey had connections with the Dormer and Pye families in Buckinghamshire and played a part in the settlement of the 3rd earl of Bedford’s estate.
It was probably his family connections rather than his record as a magistrate or subsidy commissioner that recommended Hawtrey to Wendover in 1628. The borough, which was unincorporated, was owned by the Hawtreys of Chequers by the late sixteenth century. In 1628 the owner was Mary, daughter of Sir William Hawtrey and widow of Sir Francis Wolley†, and it was probably she who was responsible for the election of her kinsman.
Hawtrey continued to prosper in the 1630s. He had £1,300 out on loan to the 4th earl of Bedford (Sir Francis Russell*), among others, in May 1635,
