Bennett was one of the sons of Thomas Bennett, a member of a large family of English merchants who dealt extensively in international trade during the seventeenth century. His mother’s name is unknown. Bennett was probably born in or near Wivelscombe, Somersetshire, England, where he was baptized on August 6, 1609. He could scarcely have avoided being involved in the young Virginia colony. His uncle Edward Bennett, one of the great London and Amsterdam merchants, was auditor of theand in 1621 patented a large property called Bennett’s Welcome near the former Indian village of Warraskoyack in what became Isle of Wight County.
In about 1628 Richard Bennett traveled to Virginia to take over management of Bennett’s Welcome. Two of his uncles and a younger brother had perished in the colony, but Richard Bennett thrived and used the transatlantic influence and affluence of his family to achieve almost immediate prominence as a prosperous planter and political leader in Virginia. He lived on another of Edward Bennett’s properties, Bennett’s Choice, on the Nansemond River, and during the 1630s patented more than 2,000 acres of land at Bennett Point and Parraketo Point. Eventually he amassed more than 7,000 acres in Virginia and Maryland, with much of it obtained through the headright system, which awarded him a right to 50 acres for each colonist he transported to Virginia. Overall his family sponsored the immigration of approximately 600 settlers, many of them Puritans, who were to provide him a base of political influence after 1640.
Bennett’s political career began with his election to the House of Burgesses as a representative from Warrosquyoake in 1629, and he became a commissioner for that district two years later. He was appointed to the governor’s Council in 1642, the same year that he patented 2,000 acres along the south bank of the Rappahannock River. During the turbulent years of the English Civil Wars and Protectorate, Bennett was the highest-ranking and most active Puritan leader in the Chesapeake. With his brother Philip Bennett he recruited three Puritan ministers from the Massachusetts Bay Colony in 1642 to serve the Calvinists of Upper Norfolk County.and other Anglicans were hostile toward the Puritans, however, and made them unwelcome.
In 1646 Bennett organized a mercenary Puritan army to assist the exiled governor of Maryland, Leonard Calvert, in ousting a gang of brigands from his capital at Saint Marys City. Many of the mercenaries remained in Maryland and became the vanguard of a vast Puritan migration to that colony during the years between 1648 and 1650. Bennett’s commercial and political connections by then included, of Virginia, and Maurice Thompson, the most influential of all the Puritan merchants of London. Throughout the period Bennett engaged in profitable commerce with England and the Netherlands.
On September 26, 1651, the English Council of State appointed Bennett and Claiborne to a four-man commission to force or negotiate the submission of the Chesapeake Bay colonies to the Commonwealth of England. Supported by a Parliamentary fleet, Bennett, Claiborne, and Edmund Curtis, who succeeded to the commission after the other two original members drowned during the transatlantic voyage, accepted Virginia’s bloodless capitulation aton March 12, 1652, and obtained the surrender of Maryland’s leaders two weeks later.
The General Assembly then elected Bennett to the vacant office of governor of Virginia. He served from April 30, 1652, to March 31, 1655, with Claiborne as secretary of the colony. Their administration represented a spectacular temporary triumph for Maurice Thompson’s London-based group of mercantile imperialists, which had significantly influenced the Chesapeake’s commercial and political evolution since the 1620s. Hoping to achieve the elusive goal of a united, centrally administered Chesapeake, Bennett and Claiborne sought to abrogate Maryland’s charter rights to the land north of the Potomac River. By appointing Protestants friendly to Virginia to offices in Maryland and placing like-minded militia colonels on the Council in Jamestown they brought a measure of stability to the Chesapeake. On July 5, 1652. Bennett and a select group of Virginia Puritan émigrés ended a decade of Indian warfare in Maryland by negotiating a comprehensive peace treaty with the powerful Susquehannocks, Claiborne’s longtime business partners in the upper Chesapeake beaver trade.
Bennett’s ambitious attempts to expand Virginia’s political control throughout the Chesapeake region, with unprecedented authority accorded to the House of Burgesses, was a significant milestone, but such profound and rapid change was destined to be short-lived. Given the prevalent revolutionary turmoil in England, Bennett’s government lacked the support it needed to withstand either the growing resentment of Virginia’s planters toward the new Navigation Acts, designed as they were to terminate the profitable commerce between the colonies and the Netherlands that had helped make men like Bennett wealthy, or the resistance of Catholics and Anglicans to the ideological rigidity of the Puritan leadership in Maryland. The bloody Battle of the Severn on March 25, 1655, fought between the Catholic pro-Calvert forces and Puritans near Bennetts’s own lands at Greenbury Point, Maryland, produced such gruesome atrocities that it probably precipitated Bennett’s retirement from the governor’s office six days later.
It is to Bennett’s credit that no such turmoil occurred in Virginia and that even political rivals with religious differences respected the peaceful succession of power at Jamestown. In December 1656 the General Assembly appointed Bennett one of its lobbyists in London, but instead of acting to increase Virginia’s power, at Cromwell’s instigation he helped negotiate a treaty of November 30, 1657, with Cecil Calvert, second baron Baltimore, that restored Maryland’s charter rights and original boundaries. Bennett served again on the governor’s Council from 1658 until his death, much of the time during the second administration of his old adversary, Sir William Berkeley. From 1662 to 1672 he also served as the second major general ever appointed in the Virginia militia and helped defend the colony against invasion during the Second Anglo-Dutch War.
Bennett’s political designs for a greater Virginia were thwarted, but in his personal life he achieved linkages across the many divisions that separated the two Chesapeake colonies. Late in the 1630s he married Maryann Utie, widow of Councillor John Utie. Their only son, Richard Bennett, attended Harvard College, married into a prominent Catholic family in Maryland, resided there for most of his life, and had a namesake son who became one of the wealthiest planters in Maryland. Bennett’s daughters chose influential husbands from both colonies. Elizabeth Bennett married Charles Scarburgh, a Puritan from the Virginia Eastern Shore, and Anna Bennett first wed, of Virginia, and then married St. Leger Codd, of Northumberland County, Virginia, and Cecil County, Maryland.
Bennett bequeathed 5,300 acres of land on Maryland’s Eastern Shore to three of his grandchildren and donated 300 acres to his local parish to be applied “towards the relief of four poor, aged, or impotent persons.” Bennett died, probably at Bennett’s Choice, between March 15, 1675, when he dated his will, and April 12, 1675, when it was proved in court.