[citation needed] At the time of the English settlement at Jamestown, which was established in May 1607, Opechancanough was a much-feared warrior and a charismatic leader of the Powhatans.

As Chief Powhatan's younger brother (or possibly half-brother), he was sachem[7] of a tribe situated along the Pamunkey River near the present-day town of West Point.

[citation needed] The natives and the colonists came into increasingly irreconcilable conflict as tobacco (which had been first developed by Rolfe) became the colony's cash crop.

The relationship became even more strained as ever-increasing numbers of Europeans arrived and began establishing "hundreds" and plantations along the navigable rivers.

But the colony eventually rebounded, and colonists later killed hundreds of natives in retaliation, including many warriors poisoned by Dr. John Pott at Jamestown.

[9] Before dying, Opechancanough reportedly said, "If it had been my fortune to take Sir William Berkeley prisoner, I would not have meanly exposed him as a show to my people.

Historians, including Carl Bridenbaugh,[11] have speculated that Opechancanough was the same Native American youth who was a chief's son and is known to have been transported voluntarily from the village of Kiskiack, Virginia, to Spain in the 16th century at the age of 17 and educated.