In the summer of 1561, Spanish explorers abducted a Powhatan Indian youth from the Chesapeake Bay tidewater region and brought him to the royal court of Spain. The kidnapping set off a chain of events that would alter the course of American colonial history.

The abduction itself wasn’t unusual, since the Spanish in America often trained Native youth to serve as interpreters, or pressed them for information about local peoples and perhaps the whereabouts of gold or silver. But “Paquiquineo,” as Spanish officials rendered the young man’s name later that year, would in time re-emerge as Opechancanough, the most formidable warrior chief encountered by Europeans in 16th and early 17th century Virginia.

After returning to his homeland, he helped build the greatest chiefdom along the mid-Atlantic and spent the rest of his life defending his people from European invaders, whose mindset and strategies he had studied at close range. A brilliant tactician and charismatic leader, he successfully thwarted Spanish efforts to establish a Chesapeake settlement. And 50 years later, with his coordinated 1622 attack on the Jamestown colony, he came close to ending English colonial ambitions in the region. But while he stands as one of the greatest military leaders in early America, his achievements remain almost completely unknown.

Following his abduction, Paquiquineo—reputed to be the brother of Powhatan, principal chief of a confederacy of Algonquian-speaking tribes—was transported across the Atlantic to the court of King Philip II in Madrid. A deeply religious man, Philip oversaw an immense empire of recently conquered territory in the West Indies and Central and South America, whose Indigenous peoples he considered heathens. He saw it as his sacred duty to convert them to Catholicism.

The king believed Paquiquineo, intelligent and high-born, could help achieve that goal. Specifically, he might play a vital part in establishing a holy mission that would convert Indian peoples and facilitate Spanish settlement beyond Florida, the first major European territory claimed in North America. The Spaniards baptized and educated Paquiquineo, honoring him with the princely Spanish name of Don Luís de Velasco, after the viceroy of New Spain.

In 1570, nine frustrating years after his abduction, Paquiquineo/Don Luís was returned to his homeland as part of a small Jesuit mission to the Chesapeake, intended as the prelude to Spanish colonization. With unshakeable faith in Don Luís’s piety and commitment to convert his people to Christianity, the missionaries allowed themselves to be led deep inland without armed support. But they’d been deceived. Within six months of landing, Don Luís led an Indian war party that killed all eight Jesuits, sparing only a young servant boy. He completely destroyed the mission—and with it, the Spanish hoped to create future settlements in the Chesapeake Bay.

Don Luís’s motives for the betrayal aren’t difficult to fathom. While living in Mexico City and Florida in the years before returning to his own land, he’d seen firsthand how Spanish conquest and conversion to Catholicism had destroyed Indian ways of life and beliefs. He knew if he let Jesuits establish a beachhead in the Chesapeake, more soldiers and settlers would follow, eventually taking the land and destroying his people.

As one of a very select few Native Americans who had traveled across the Atlantic—and returned—Don Luís understood better than his peers the grave, looming threat Europeans posed, whether from Spain or elsewhere. His awareness likely played a major role in encouraging his brother, Chief Powhatan, to begin building a massive chiefdom encompassing more than 30 different tribal groups, which would be able to mount an effective defense against Europe’s powerful invaders. From the mid-1570s to the early 17th century, the chiefdom, called by the Powhatan Indians Tsenacommacah, expanded rapidly across coastal Virginia. By the time English colonizers arrived, it reached from south of the James River to the shores of the Potomac River.

In May 1607, 104 Englishmen set up camp on the banks of the James River on land they called Jamestown, but which actually belonged to the Paspahegh people. At first, relations with people along the river were cordial, if sometimes uncertain. But as more settlers arrived, including women and children, relations deteriorated, eventually leading to full-scale hostilities. The first English-Powhatan war played out along the James River Valley between the winter of 1609 and the spring of 1614, at which point the English had established settlements all along the river. Effectively beaten, Powhatan was quickly replaced by his war chief, who the English called Opechancanough (pronounced: O-pee-can-can-no), but who the Indians knew as Paquiquineo and the Spanish as Don Luís.

Opechancanough, applying lessons learned in his encounters with the Spanish, adopted a very different strategy than his brother’s, one that avoided pitched battles with well-armed English soldiers. Instead, he reassured the English of his good intentions and held out the likelihood his people would convert to Protestantism. Taking this approach, he successfully duped the colony’s leadership as well as most settlers, allowing him to forge alliances and gather men to launch one of the most devastating Indian attacks on Europeans in American history.

In the early dawn light of a chilly March morning in 1622, groups of Powhatans gathered in the fields and woods near English settlements and waited patiently for a signal. When it came, they began walking towards the settlers’ houses, seemingly in no great hurry. Since many had been trading with English families for years, dropping by when they had something to barter or share or borrow, nothing appeared out of the ordinary. Once inside the settlements, however, at about 8 a.m., Opechancanough’s warriors fell violently upon the English, “not sparing either age or sex, man, woman or child,” Edward Waterhouse, a contemporary, wrote. Following initial attacks, more warriors, anywhere from 50 to a few hundred, joined the fighting to finish off survivors, burn settlements and slaughter livestock.

A bird’s eye view would have revealed destruction and mayhem all along the James River: sheets of flames consuming houses, farm buildings, wharves and boats; dense columns of smoke billowing up from burning plantations and slaughtered livestock. Coming into sharper focus, men would have been seen grappling one another in desperate hand-to-hand combat, Indians hurling themselves upon the English, killing them in their homes, yards and fields. The screams of the dying and injured would have been clearly audible all along the river, together with the yells of warriors, shouts of alarm from settlers, the crack of musket fire and clash of steel. So sudden and unexpected was the attack, few settlers glimpsed the weapon that brought them to their end. On that “fatal day,” approximately 350 English men, women and children—a quarter to a third of the entire colony—died, clubbed, stabbed or shot to death with their own tools and weapons.

Opechancanough did not expect a single day’s attack, even such a well-executed one, would succeed in expelling the English from his lands immediately. Over the next few months, while the English reeled from the disaster, warriors continued to raid and plunder settlements. Amid a scene of utter desolation, the sense of dread was palpable. “God forgive me,” William Capps, an established tobacco planter, observed, “I think the last massacre killed all our Country,” and “besides them they killed, they burst the heart of all the rest.”

Settlers began abandoning their homesteads, seeking refuge at better-protected plantations nearby, foreshadowing Governor Sir Francis Wyatt’s general order of late April to evacuate all outlying settlements and move to eight well-fortified locations along the James River. Local leaders even considered transporting the English to the Eastern Shore, where Indians remained on good terms with the settlers, to reduce further losses.

Meanwhile, Opechancanough continued planning. In the summer of 1622, he sent messengers with gifts to the chief of the Patawomecks, a powerful people living on the Potomac River, urging him to join his war against the settlers, boasting that “before the end of two Moons there should not be an Englishman in all their Countries.” By destroying plantations and industrial sites and cutting off food supplies, he believed they could render the English so weakened and demoralized they would either eventually fall victim to his warriors or be forced to flee the colony.

Ultimately, the great chief’s strategy failed. The English kept coming, despite their terrible losses from war, famine and disease. Opechancanough simply didn’t have sufficient warriors to counter wave after wave of new arrivals from across the Atlantic. Within a few years, the English had recovered from what they called the “barbarous massacre” and began establishing settlements across the region, beating back Indian peoples as they moved inexorably north and west. Driven by bitterness and despair, Opechancanough managed to inspire another generation of warriors to rise up against the English in the mid-1640s, killing approximately 500 settlers before he was captured and taken to Jamestown. There, nearly 100 years old, he was shot in the back by one of his guards and died.

Compared to the warrior chiefs of the 18th and 19th centuries—Pontiac, Tecumseh and Sitting Bull—little scholarly attention has been given to the Powhatan wars of the early 17th century and Opechancanough’s leading role in them. Yet it was he, in the guise of the pious convert Don Luís, who limited the expansion of Spanish settlement along the eastern seaboard of North America—and he who resisted English settlement in Virginia for nearly half a century. His extraordinary life, battling two of Europe’s greatest powers, confirms him as one of the greatest military leaders in American history.

James Horn, historian and president of the Jamestown Rediscovery Foundation, is the author of A Brave and Cunning Prince: The Great Chief Opechancanough and the War for America, among other books.