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.

[7] During a trading expedition with Henry Spelman of Jamestown, Fleete was abducted and held captive by the Anacostan people for almost five years.

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.

[7] In 1634, "Captain Henry Fleete, gentleman" sailed with Leonard Calvert's colonists to act as a guide for the natives in Virginia and Maryland.

[citation needed] 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.