By 1600, England was lagging far behind in the European race for empire. Spain had followed Christopher Columbus's epic voyage of 1492 with a massive campaign of colonization and exploitation in the New World. Within a century, Spain had built a complex empire stretching from the tip of South America into the southern regions of the present-day United States. The gold and silver pouring in from Spanish territories drove Spain's entire economy and financed its massive navy.
The political and religious turmoil that erupted from the tumultuous rein of Henry VIII was a large reason England lagged behind. But with the ascendance of the cagy Elizabeth I to the throne in 1558, England began to put its political house in order—and began to dream of empire.
England's imperial visionaries looked enviously at Spain while concocting their plans. Most prominent among these was Richard Hakluyt the younger. A clergyman, geographer, and advocate of English expansion, he assumed that enormous wealth still awaited discovery in the New World. Hakluyt suggested that America offered a cornucopia of natural resources that could be turned into valuable goods by English skilled craftsmen and Indian laborers, working side by side. Other visionaries, like Sir Francis Drake, figured that until England developed its own sources of colonial wealth, it might as well steal a little of Spain's. For Drake and John Oxenham, looting Spanish ships became a national obligation; haunting the sea lanes used to deliver Spain's New World fortunes, plundering Spanish gold and silver, they became legendary as national heroes in England and villainous pirates in Spain.
Development and piracy came together in Walter Raleigh's plans for an American colony during the 1580s. A soldier and adventurer, and a favorite in the Queen's court, he used his influence with Elizabeth I to secure royal support for a New World adventure. Influenced by Hakluyt's vision, Raleigh drafted a colonial plan built on expectations of valuable local resources that could be turned into wealth for England through the skilled work of his colonists. But he had also followed Drake's career, and he also expected to use his North American colony as a naval base from which he would launch raids on the Spanish gold fleet.
But the colony Raleigh planted at Roanoke, an island off the coast of modern-day North Carolina, never really got off the ground. Raleigh arranged for 75 settlers to be deposited there in 1585, but they had to be removed after conflicts with the local Indians and inadequate supplies put the colony at risk. Undeterred, Raleigh sent a second batch of 121 settlers in 1587. But political disturbances in England prevented Roanoke's supporters from re-supplying the colony until 1590—and when supplies finally arrived that year, the ship carrying them found the colony completely empty, and only one mysterious word—"Croatoan"—scratched on a post offered a clue as to the colonists' fate. But what did it mean? Were the lost colonists of Roanoke Island attacked and killed by the Croatoan Indians of the Chesapeake? Or had they gone off to live with the Indians, assimilating into the Croatoan tribe? We still don't know the answer.
Raleigh tried one more time, in 1602, to find his lost colonists, but he turned up nothing. Raleigh's dreams of organizing a successful American colony would never be realized. But even as Raleigh's colony vanished into thin air, other New World ventures were being prepared. In 1606, a group of London investors organized the Virginia Company, planning to undertake a commercial colonization scheme in the same region as Roanoke. Still drawing from Hakluyt, this privately-funded joint stock company mapped out a complex colonial venture that aimed to exploit America's valuable resources to replicate Spain's New World success.
In other words, Spanish achievements continued to inspire English efforts—but in one very important way, Spain's colonies disgusted rather than inspired the English. Descriptions of Spain's brutal enslavement of Indians and Africans circulated widely in England; appalled English expansionists insisted that this sort of harsh and un-Christian exploitation of human beings would not be part of their colonies.
Obviously, Jamestown did not work out quite as they planned. Slavery did emerge within half a century of the colony's founding. Nor did the complex economy envisioned by theorists like Hakluyt and the leaders of the Virginia Company soon develop. Instead, a one-dimensional agricultural economy based entirely on cultivation and export of tobacco emerged by the 1620s. This economy relied less on skilled workers and complex commercial transactions than on the backbreaking labor of increasingly unfree people.
Jamestown, however, did ultimately prove successful; by the end of the seventeenth century, Virginia was England's most valuable colony. But between the vision and reality of this New World colony lay a brutal and unanticipated history that included both staggering exploitation and unprecedented opportunity for English settlers willing to brave the harsh conditions of the Chesapeake.