Henry Fleete (or Fleet) was an early English trader in the Colony of Virginia and Province of Maryland. He was a Burgess representative for the Virginia Colony, and interacted with William Claiborne during the time of conflict between Protestant Virginians and Catholic Maryland leadership. During a trading expedition with Henry Spelman of Jamestown, he was abducted and held captive by the Anacostan people for almost five years.

Family and early life Fleete was the son of William Fleete of Chartham, Kent, and Debora Scott Fleete.Virginia Gleanings in England (Continued). The Virginia Magazine of History and Biography, vol. 28, no. 4, 1920, pp. 340–45. JSTOR, http://www.jstor.org/stable/4243787. Accessed 6 Dec. 2024. He was a great-grandson of Thomas Wyatt the Younger. Henry had brothers named Edward, John, and Reynold. His father, William Fleete, was of the Virginia Company of London.Morrison, A. J. "The Virginia Indian Trade to 1673." The William and Mary College Quarterly Historical Magazine, vol. 1, no. 4, 1921, pp. 217–36. JSTOR, https://doi.org/10.2307/1915333. Accessed 9 Dec. 2024.

In Virginia colony Henry Fleete emigrated to Jamestown, Virginia in 1621 with incoming John Harvey (Virginia governor).

During a trading expedition with Henry Spelman of Jamestown, Fleete was abducted and held captive by the Anacostan people for almost five years. He was 24-25 years old at the time of his capture.Pendergast, James F. The Massawomeck: Raiders and Traders Into the Chesapeake Bay in the Seventeenth Century. United States, American Philosophical Society, 1991. Henry was ransomed to the government of Virginia in .

Fleete returned to England to tell others of his abduction, and persuaded William Cloberry and his organization associates to finance fur trade with natives in Virginia, specifically North American beaver fur. Fleet was master of the bark Paramour for Cloberry & Company.

Fleete settled at "St. George's Hundred" on land granted to him near the St. Georges Creek. Fleete's house, West St. Mary's Manor was built around 1627 and used for meetings.

In September, 1631, the Warwick sailed from England to Virginia with Fleete acting as factor and Captain John Dunton as the shipmaster. Fleete traded around the Potomac River, but was arrested for tax evasion by rival traders Charles Harman and John Utie.Neill, Edward D. “Virginia Carolorum: The Colony during the Days of Charles the First and Second (Continued).” The Pennsylvania Magazine of History and Biography, vol. 9, no. 4, 1886, pp. 407–23. JSTOR, http://www.jstor.org/stable/20084726. Accessed 9 Dec. 2024. Henry Fleete was put on trial for tax evasion, but let free.

Maryland affairs In 1634, "Captain Henry Fleete, gentleman" sailed with Leonard Calvert's colonists to act as a guide for the natives in Virginia and Maryland.Hall, Clayton Colman. Narratives of Early Maryland, 1633-1684. United States, Charles Scribner's Sons, 1910. While most of the settlers were Roman Catholic, Fleete was listed as a Protestant. With Governor L. Calvert, Fleete negotiated with the Piscataway people and Yaocomico to settle the colony in St. Mary's City, Maryland in exchange for armed protection for the natives' enemies.

In April, 1635, Fleete became involved with William Claiborne when he and Captain William Humber seized the pinnace Longtail (commanded by a Thomas Smith) practicing without a license.Claiborne, J. Herbert. "William Claiborne of Kent Island." The William and Mary College Quarterly Historical Magazine, vol. 1, no. 2, 1921, pp. 74–99. JSTOR, https://doi.org/10.2307/1923023. Accessed 9 Dec. 2024. Claiborne's business partners, Cloberry & Company, had become unsatisfied with the fur shipment amounts, and considered Claiborne's right to Kent Island invalid. This led to a few more skirmishes and eventually, a time of riot in Maryland.

In 1635, "Fleete's Hill" trading post was established near Petersburg, Virginia. Fleet Street in Petersburg is named after him. In , Fleete was sailing cargo for Maryland in the ship Deborah.

Henry Fleete is also credited for capturing infamous Opechancanough with Virginian forces in 1646.

Fleete died in Lancaster County on a plantation property. Fleete's and both like north of the mouth of the Rappahannock River. His descendants go by the surname "Fleet".

Notes

Further reading Fleet, Betsy. Henry Fleete: Pioneer, Explorer, Trader, Planter, Legislator, Justice & Peacemaker. United States, Whittet & Shepperson, Printers, 1989. Fleet, Henry. A Brief Journal of a Voyage Made in the Bark Warwick to Virginia and Other Parts of the Continent of America. 1631.