Wingfield was born in 1550 at Stoneley Priory, near Kimbolton, Cambridgeshire, England, the son of Thomas Maria Wingfield and his wife Margaret Kay. Thomas Wingfield, a member of Parliament who belonged to a well-established political and military family, died in 1557, and in 1562 Margaret Wingfield married James Creuse (also spelled Cruwys and Crewes), who became the adolescent Edward’s guardian. Wingfield was raised as a Protestant; the “Maria” in Edward’s and Thomas’s names honored their godmother, King Henry VIII’s sister Mary Tudor.
As he came to manhood, Wingfield was the protégé of his father’s brother Jaques Wingfield (d. 1587), who was heavily involved in the Elizabethan conquest of Ireland, serving as Master of Ordnance in Ireland, as Constable of Dublin Castle, and as a member of the Irish Privy Council. In 1569 Wingfield accompanied his uncle to Ireland in order to assist him in the plantation of the province of Munster. In this capacity, he likely encountered Sir Humphrey Gilbert and Sir John Popham, who would later become major figures in the early English attempts at colonization in North America.
Wingfield appears to have remained in Ireland until 1576, when he went to London and was admitted to the legal training program at Lincoln’s Inn. He left the Inn, however, before completing his studies there, and, in company with his brother Thomas Wingfield, served as a captain of foot in the Low Countries, fighting in support of the Protestant Dutch Republic against Spanish Catholic forces. In 1588 he, along with Sir Ferdinando Gorges, a future settler of New England, was taken prisoner by the Spanish at Bergen-op-Zoom, and was held first at Ghent and then at Lille until he and Gorges gained their release through a prisoner-of-war exchange in June 1589.
Wingfield briefly returned to England in 1593, when his friend and neighbor Anthony Mildmay secured him a seat in Parliament, representing Chippenham, Wiltshire, but he played little role in the House of Commons. In the 1590s Wingfield also returned to military service in Ireland, although scholars disagree about which years he was there. He spent several years in the English garrison at Drogheda, where the muster-master was Sir Ralph Lane, who a few years earlier had played an important role in the Roanoke colonies sponsored by Sir Walter Raleigh. He also served at the garrison at Dundalk. In 1600 he took up an appointment as a feoffee, or governor, of Kimbolton School, near Stoneley Priory.
The Virginia Company of London
By this time, Wingfield was well into middle age, but healthy and energetic. As a man with many years of military experience, accustomed to life outside England, he was an attractive recruit when his second cousin Bartholomew Gosnold sought investment in the newly organized Virginia Company of London. Wingfield, then retired from active military service, threw himself wholeheartedly into raising funds for an expedition to North America, and, because of his extensive network of wealthy friends and family members, achieved considerable success. In partnership with Gosnold, he recruited about forty of the men and boys who would make up the voyage’s personnel, drawing them largely from the ranks of younger sons of the gentry. On April 10, 1606, Wingfield, along with Richard Hakluyt (the younger), Sir Thomas Gates, and Sir George Somers, became a patentee of the Virginia Company of London. Of these men, Wingfield was the only one to immediately make the voyage to Virginia himself, making him both an “adventurer” who raised funds and a “venturer” who went to sea. On December 20, 1606, Wingfield joined the convoy of three small ships, the Susan Constant, the Discovery, and the Godspeed, under the overall command of Captain Christopher Newport, and set sail from London’s Blackwall Dock.
Gaining and Losing Power
Although Newport was in command of the voyage, the Virginia Company had decreed in an order dated November 20, 1606, that once the ships reached Virginia Newport was to open a small box, which contained a list of settlers to be members of the settlement’s governing council. This was accomplished on April 26, 1607, following landfall, and Wingfield, Newport, Gosnold, John Smith, John Martin, John Ratcliffe, and George Kendall were all appointed to the Council. The Virginia Company had further stipulated that the councillors forebear selecting a president until they had decided on a site of settlement. On May 12, Wingfield designated a site approximately fifty miles upriver as the locus of settlement, and named it Jamestown in honor of King James I. The following day, the councillors elected Wingfield as their president, in what has been referred to as the first democratic election held in British America. Although Wingfield had clashed with Smith in the course of the voyage, and at the age of fifty-seven was significantly older than his fellow councillors, he was in many ways the obvious choice for this position, because of his important role in the establishment of the Virginia Company and his extensive experience not only in military matters, but also in plantation ventures in Ireland.
Although Wingfield had initially been a popular, even an obvious, choice for the leadership of the settlement, he soon aroused controversy among his fellow settlers. He and Smith (who had been denied his seat on the Council, largely because of Newport’s and Wingfield’s mistrust of him) continued to clash, both in terms of personality and on issues of military strategy against the Virginia Indians of Tsenacomoco. Wingfield’s fellow colonizers were impressed when his leadership was instrumental in repelling a fierce Indian attack against the newly erected Jamestown Fort on May 26, but as the summer went on the settlers, many of whom were unaccustomed to hard labor, became increasingly unhappy with the diminishing food supplies, ongoing Indian attacks, oppressively hot weather, and Wingfield’s harsh disciplinary regimen.
On September 10, the surviving settlers deposed Wingfield from the presidency of the Council, charging him with a number of offenses, including hoarding food, having secret sympathies with Spain’s imperial ambitions in North America, and being an atheist. The former president was imprisoned in the Discovery, where he remained until January 1608, when Newport returned to Jamestown from a voyage to England. Newport ordered that Wingfield then be moved inside the fort, in company with Smith, who had been sentenced to hang after losing two settlers to the Indians. Newport released both men, but he did not move to reinstate Wingfield as president, as the charge of atheism was sufficiently serious that it was necessary that Wingfield return to England to face trial. On April 10, 1608, Wingfield returned to England with Newport, and never returned to the Virginia colony.
After his return to England, Wingfield wrote a long response to the various charges against him and, in particular, convinced the Crown that the charge of atheism was a groundless one concocted by disaffected Jamestown settlers; he was set free. Despite the traumatic nature of his departure from Virginia, Wingfield spent much of the rest of his life involved in the colony’s affairs, including raising funds and sending supplies for the Jamestown venture. He died at Kimbolton in 1631, and on April 13 was buried there at Saint Andrew’s parish church. In the nineteenth century scholars rediscovered his manuscript detailing his experiences in Virginia, which was first published in 1859 as A Discourse of Virginia.
For many years, Wingfield was viewed quite unfavorably in terms of his conduct as Jamestown, not only because of his removal from the presidency, but also because John Smith described him in such negative terms in his extensive and widely circulated commentaries on the early years of the Virginia colony. In retrospect, Wingfield was probably too old to provide effective leadership to a group of boys and men who were mostly in their teens and twenties, and while his severity as a disciplinarian may have been effective among soldiers, it aroused significant hostility among the settlers.
Many of the problems that Jamestown endured in its first months, however, such as Indian hostility, exceptionally hot and dry weather, and a scarcity of food, were neither Wingfield’s fault nor within his control. Moreover, his choice of an easily defensible site for the first settlement and his knowledge of effective processes of fort-building contributed to the colony’s ability to survive its difficult early years. Wingfield’s Discourse of Virginia, although insistent in its justifications of his actions, provides a crucial eyewitness account of the first year of the Jamestown settlement, supplementing John Smith’s better-known narrative.