Henry Fleet was one of the expedition of twenty-six men aboard the Tiger who under Captain Spelman in March, 1623, went to trade for beaver skins and corn with the Anacostan and other Indian tribes near the head of the Potomac.
Fleet was with Spelman when he went ashore. After Spelman was killed and his head tossed over the river bank, Fleet was taken prisoner and carried to the village of the Anacostans. This is believed to have been located not far from the present monument of Washington, in Washington, D. C.
Fleet was about twenty-five years old and had but recently arrived in Virginia. His father was William Fleet of the London Virginia Company, which may have been the reason that Henry came to the New World. Henry was adventurous, quick-witted and intelligent. He made good use of his stay in the wilderness of the Northern Neck by studying his new environment. Later he wrote down some of these observations:
"It aboundeth in all manner of fish. The Indians in one night will commonly catch thirty sturgeons in a place where the river is not above three fathom broad. And as for deer, buffaloes, bears, turkeys, the woods do swarm with them, and the soil is exceedingly fertile." He also wrote that he had seen "plenty of black fox, which of all others is the richest fur." This animal was a large marten, so fierce that it was the match for any forest animal up to the size of a deer.
Henry was kept in captivity for four years, when his friends managed to ransom him. Small vessels were then trading with the Indians of the Potomac and news of him was probably carried to Jamestown in this way.
During the year 1627 the London Merchants were surprised by the arrival of Henry Fleet from Virginia. Startling tales of his adventures spread abroad. It was said that he had lived with the Indians so long that he had forgotten his own language, that he had often seen the South Sea; that he had seen Indians "besprinkle their paintings with powder of gold."
These stories impressed William Cloberry, a merchant adventurer, and chief man in the Guinea trade. Cloberry believed that Fleet could be useful to him as a trader among the Indians.
On September 6, 1627, the ship Paramour of London, one hundred tons burden, was licensed to clear with Henry Fleet as master. William Cloberry and Company were the owners.
Captain Fleet was well suited by nature and experience to be an Indian trader. For years he traded with the Indians along the Potomac—bartering "beads, bells, hatchets, knives, coats, shirts, Scottish stockings and broadcloth" and other "trucke," for beaver fur, tobacco and corn. Some of the Indian tribes traveled "seven, 8 and 10 days journey" to trade with him. He was the most regular and dependable trader the Indians knew.
By 1632 Captain Fleet was operating several boats in the Indian trade, and in that year he built a shallop and a "Barque" of sixteen tons for his own use. He also opened a trade between the Massachusetts settlement and the Potomac River. Sometimes he carried as much as eight hundred bushels of corn at one time from the Potomac to New England.