Opechancanough
Opechancanough (1554 - 1646) was the chief of the Native American Powhatan tribe from 1618 until 1646. He was a feared warrior and famously captured John Smith of Jamestown, who was almost executed until Chief Powhatan's daughter Pocahontas intervened. After becoming chief, Opechancanough attempted to convince the settlers to leave Jamestown, which had previously belonged to the Powhatan.
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In 1622, he abandoned diplomacy and tried to drive the settlers out altogether, launching a series of coordinated attacks from the James River to the Falling Creek in which a third of the settlers were killed. This prompted the settlers, notably Dr. John Potts, to kill hundreds of warriors in retaliation.
In 1644, Opechancanough launched a final major attempt to drive the colonists away (the third Anglo-Powhatan war), killing around 400 people. Two years later, he was captured by Sir William Berkeley's forces, paraded through the streets and subsequently murdered by a British soldier.