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An Errand in the Wilderness

America [is] the only country in which the starting point of a great people has been clearly observable.

—Alexis de Tocqueville

Most of the first British settlers on the North Atlantic seaboard came to the New World because they were impoverished, persecuted, fleeing from the law, or alienated from family, society, or politics. Although they were subjects of the Crown, they welcomed its distance.

In 1607 three ships owned by the Virginia Company dropped anchor off the banks of the James River, near the mouth of the Chesapeake Bay. About a hundred passengers, most of whom would never see England again, founded Jamestown, named after the Stuart monarch of the day. They were male and mostly adventurers. Not until the following year did women arrive: a Mistress Forrest and her maid, Anne Burras, followed by a few more a year later, including Temperance Flowerdew, the wife of Captain George Yeardley, who later became governor of the colony. They were a pitiful but vital addition to what would be the first permanent British colony in the Americas. In 1619 the company recruited about 150 Englishwomen to travel to the colony and wed the males. These brave, poor, and desperate volunteers, while compensated for their journey, were unprepared for the hardships at sea and those at their destination. Within a few years, many died from starvation or disease, or in raids by indigenous people.1

The charge from James I was threefold: Create a settlement on the southern Atlantic coast as a buffer against Spanish conquistadors encroaching on what would be British America; reap the bounty of the land—gold and silver was the hope, but tobacco was the bonanza; and convert to Christianity the descendants of clans who had lived in that hemisphere tens of thousands of years before Europeans sailed into their world.

The first two goals were, after many setbacks, successful, but the third was a grotesque charade and failure. Few natives joined the Church of England, and many resisted the white man’s incursions. They were experienced warriors whose arrows, spears, and tomahawks might have outmatched the invaders, especially when the tribes captured and bought guns. But they were not armed with European immunities against European diseases. They succumbed quickly up and down the Atlantic seaboard. By some estimates, 90 percent of the coastal indigenous population died from alien microbes.

Twelve years after the founding of Jamestown, a British privateer, the White Lion, attacked the São João Bautista, a Portuguese slave ship, off the coast of New Spain (now Mexico). The British seized the human cargo, consisting of twenty captives from the Kingdom of Ndongo, a region in what is today Angola. They were sold into bondage to work in the tobacco fields in the Virginia Colony.2

Two infamies inflicted on people of different color stained the American soul and soil for centuries to come.


More than a decade later, in 1620, a new wave of settlers set forth for New England. They called themselves Pilgrims, a radical offshoot of Puritanism, which rose out of the Protestant Reformation in Europe. The Pilgrims were passionately and inflexibly pious or, as they said, godly. In their eyes, mainstream Anglicanism had relapsed into worldliness and, worse, into corrupt Catholic practices. Their mission was to establish a place where their “true” religion could flourish, unimpeded by magistrates who served the king and the Church of England, now an ocean away.

The Pilgrims who sailed on the Mayflower to establish the Plymouth Colony had made a permanent break from England and had rejected the church that bore its name. After another ten years, mainstream Puritans came to Massachusetts, bent on reforming—that is, purifying—Anglicanism. Both sects were followers of John Calvin, the charismatic, fiercely unbending French reformer whose theology, an offshoot of Martin Luther’s, emphasized God’s sovereignty, teaching his followers that only those elected by Him would find salvation in eternity.3

The Puritans had maintained an uneasy truce with King James I, but his successor, Charles I, was a threat to their community and religion. As royal intolerance intensified to oppression and persecution, they looked for guidance in the Bible. For many, the Book of Exodus provided an answer. They would put an ocean between themselves and an earthly sovereign. That would allow them to be the masters of their own land and servants of their Lord.

Unlike the Jewish people in their Egyptian captivity, the Puritans did not think of themselves as turning their backs on an alien land. Rather, they set off to New England to keep the flame of their faith burning until they could return to Old England after it had become purified under a Puritan government. Their sojourn came to be called an “errand into the wilderness.” Their errand was not intended to be forever; when finished, they expected, they would go home.4

Even though they were increasingly out of favor with King James, the Puritans were well established in English business circles. Under their influence, a commercial venture in Massachusetts Bay was reorganized as a colony. The company’s directors hoodwinked His Britannic Majesty by presenting him a prolix charter that was larded with scrapes and bows to the throne. The numbing verbiage seems to have camouflaged a deliberate omission: there was no mention of where the annual stockholders’ meeting would be held in the future. That sleight of pen permitted the directors to move the seat of governance from London to the colony itself, thereby weakening the control of the Crown.5


The principal agent of that step toward quasi-independence was John Winthrop, the first leader of the Massachusetts Bay Colony. In that capacity, he was both a holdout of a vanishing system of governance—religious patriarchy—and an experimenter of proto-republicanism.

He arrived in an eleven-vessel fleet in 1630, leading a flock of more than seven hundred to their new home. The Great Puritan Migration was underway.

Winthrop’s fame today comes largely from a sermon titled “A Model of Christian Charity” that he reputedly wrote aboard the Arbella, the flagship of the flotilla. Yet there are no known contemporaneous sources that would fix a date and a place where he might have delivered it, or how it was received, or whether he delivered it at all. For all we know, Winthrop’s message bypassed his seagoing parish and went right into a time capsule, widely unknown for three centuries, until his prophecy became a paean to a strong, righteous example of the world during the Cold War and after. In 1989 Andrew Delbanco, a professor of American studies at Columbia, consecrated it as “a kind of Ur-text” of the national narrative.6

Of the some six thousand words Winthrop composed, a single sentence was elevated to a place in U.S. presidential rhetoric in the twentieth and twenty-first centuries: “We must consider that we shall be as a city upon a hill. The eyes of all people are upon us.”7 John Kennedy made it a bipartisan trope for his successors to invoke America’s moral strength, magnanimity, optimism, championship of liberty, and leadership in the world. Ronald Reagan picked it up, as did Barack Obama.


Winthrop’s immediate, practical, and somber purpose was to fortify his fellow passengers’ faith that the Lord would protect them in the face of certain and unknown perils. His message was one of pride, responsibility, and liberation. As the Puritans waited for the purification of the Church of England and England itself, Winthrop loosened the rule of the colony from London by moving its seat from Salem to Charlestown without royal permission. This ploy gave the Puritans a latent, subtle advance in the direction of self-governance.8

While future generations came to revere Winthrop as an inspiring orator, in his own time he earned respect for his leadership in his alternating terms as governor and lieutenant governor of Massachusetts over twenty years. He exercised a firm but moderate and fair hand in an era of authoritarianism, initiating several features of governance that would serve the United States a century later. He reined in zealotry among the clergy and respected the laity’s consent for the laws of the community by encouraging petitioning and participation in civil debates.9

As governor, Winthrop was no democrat by today’s definition, nor was he a despot. The minutes of the first meeting in Charlestown suggest that he invited male members of the community to attend the sessions and voice their reactions to the decisions. The outcome of the meeting “was fully assented unto by the general vote of the people.”10

Winthrop rejected “mere”—that is, direct—democracy, but he had laid the ground for the representative, or indirect, variant that the founders would favor.11


John Winthrop was one of the most judicious and esteemed conservatives in the New England hierarchy, and Roger Williams—a courageous, passionate radical—was one of the most controversial.

Before joining the Great Migration, Williams believed that Puritanism needed to be cleansed of corruption and made more inclusive. He had no patience with the idea that Puritans were the vanguard of the Church of England. Much as the Pilgrim separatists, he wanted a clean split from Anglicanism.

Williams was the ultimate freethinker who scandalized much of the community by openly expressing his personal convictions with ferocious eloquence, particularly when he was railing against efforts to impose how people should pray: “Forced worship stinks in God’s nostrils.”12 He had his God, others had theirs. He joined the Baptist branch of Protestantism, which shared his toleration of other sects.

Williams was unswerving in his own faith, and he was certain that those of other denominations were destined to hell. But that ultimate judgment was for God to make. He was also convinced that mortals were unable to interpret God’s law wisely; when they tried, they distorted its meaning, stumbling into earthly injustice. From that premise, he opposed—loudly and often—theocracy in general, and any government involvement in religious affairs. He denounced the concept of Christendom, since it was a political domain of the church, and scoffed at the British Crown’s claim to jurisdiction over the settlements in North America.

He had left England several months after the Arbella flotilla, arriving in Massachusetts in early 1631. He spent five years in the Bay Colony, quickly earning a reputation as a gadfly on many issues, especially the settlers’ cruel treatment of the Native Americans. He chided his fellow Englishmen for bigotry and rejected a law that permitted the eviction of natives from their villages and hunting grounds. He was put on trial for “diverse, new, and dangerous opinions,” charges that amounted to sedition and heresy.13

Winthrop disagreed with almost all of Williams’s unorthodox ideas and concurred with the General Court’s decision to expel him from the Bay Colony. Nevertheless, Winthrop suggested that Williams turn ignominy into opportunity: he should move to Narragansett Bay, neighboring the Massachusetts Bay Colony, for “high and heavenly and public ends.”14 Williams took the advice and founded the colony of Rhode Island as a haven for those “distressed for conscience.” He stood his ground on expansive religious tolerance:

There goes many a ship to sea, with many hundred souls in one ship, whose weal and woe is common, and is a true picture of a commonwealth or a human combination or society. It hath fallen out sometimes that Papists, Protestants, Jews, and Turks may be embarked in one ship; upon which supposal I affirm that all the liberty of conscience that ever I pleaded for turns upon these two hinges: that none of the Papists, Protestants, Jews, or Turks be forced to come to the ships’ prayers or worship, nor be compelled [restrained] from their own particular prayers or worship, if they practice any.15

Williams’s notoriety reached John Locke, who was impressed by this fearless promoter of religious toleration. Locke was a thinker, while Williams was a doer, pushing for colonial laws that embodied liberal values—much to the horror and disgust of his fellow governors.16

Williams’s own errand in the wilderness carried a stunning portent of America’s destiny. He leaped ahead of the abstract thinkers back in the land of his birth, transforming their ideas into a whole new way of governing. He guided Rhode Island wisely and compassionately, under the authority of a charter to establish religious freedom, the first in the New World.17

He was an early convert to the cause of abolition of slavery and taught himself several tribal languages to enable him to cooperate fairly with Native Americans. Celebrated and detested, in life and after his death at seventy-nine, he was one of America’s first liberals, long before that hardy skein was woven into the American political tapestry.

Despite the religious, ethical, and political gulf between Williams and Winthrop, the radical considered the conservative a friend who offered him a new opportunity to pursue his mission. For years after their parting, Williams kept up a correspondence with Winthrop, effusive with gratitude and respect.18

That Williams could move to another jurisdiction more receptive to his views was an option unlikely to be found in England. This demonstrated yet another advantage of the dangerous, hardscrabble, and vast New World: it was far more accommodating to individualists.


Anne Hutchinson was among those intrepid, strong-minded figures. Like Williams, she was a deeply religious maverick and crusader for those who shared her ideas about worship and salvation. And, like Williams, she came under fire for challenging the authority of the Puritan church. But unlike Williams, she became a fierce and lasting enemy of Winthrop.19

Despite the disapproval of the authorities, she ministered to women in Boston, first as a nurse and midwife, providing care for those who were sick or in labor. She held meetings at her home so women of the community could discuss the week’s sermon, pray together, and enjoy a rare opportunity to socialize.20 Hutchinson’s gatherings soon attracted people from surrounding villages, who came to hear her divergent religious views and critiques of the local ministers’ sermons. To Winthrop’s fury, prominent townsmen became curious and began to attend, disrupting what Locke called the “received doctrines.” Hutchinson preached that salvation was received “not by conduct, not by obeying the commandments, by giving alms, praying, fasting or wearing a long face.” Instead, she urged accepting “God’s spirit within,” much along the lines of Williams’s freethinking.21

Hutchinson was bound to get into trouble, and Winthrop was the chief prosecutor for her trial on charges of speaking “in derogation of the ministers” of the colony and “[troubling] the peace of the commonwealth and churches.” She handled her own defense vigorously, matching her all-male interrogators in her knowledge of scripture and church doctrine. But when Hutchinson referred to her “immediate revelation”—a personal communication from God, who vowed to curse the Puritans and their descendants if they harmed her—the judges pounced, charging that she was a danger to civil order and “a woman not fit for our society.”22 The verdict echoes down the centuries of misogyny in America. Today she might be shunned as a “nasty woman.”

When she was exiled from Massachusetts, Roger Williams invited Hutchinson and her husband William, a former member of the General Court, her younger children (she had fifteen, with the older ones back in England), and a group of followers to settle in Rhode Island. There she found more than refuge: she became the first—and last—female cofounder of an American colony.23

Even after Hutchinson left the Massachusetts Bay Colony, Winthrop kept track of her so he could vilify her from afar. When he learned that she had suffered a molar pregnancy, he declared, “See how the wisdom of God fitted this judgement to her sin every way, for look as she had vented mishapen opinions, so she must bring forth deformed monsters.”24

When Hutchinson’s enemies in Boston threatened a takeover of Rhode Island, she moved her family down the coast, near New Amsterdam, a town on the southern tip of Manhattan Island where Dutch settlers congregated. The Dutch colony was in a simmering conflict with a local tribe. In 1643 it boiled over. Hutchinson and all but one of the younger members of her family who were living with her perished in a massacre aimed at terrorizing the white settlers. When word reached the Bay Colony, its leaders saw it as the “just vengeance of God.”25 Winthrop concurred.

Three hundred years later, Eleanor Roosevelt extolled Hutchinson as the first of America’s foremothers—and literally so, since she was an ancestor of Franklin D. Roosevelt and George H. W. and George W. Bush.26


John Winthrop’s health declined on the threshold of his seventh decade. When he died peacefully, still in office, he was widely mourned. The same could not be said of the Puritans’ royal nemesis. Two months before Winthrop’s death, King Charles I had been beheaded for treason. His marriage to a French Catholic princess had stirred protests among Anglicans and other Protestants, and his claim of absolute power under the divine right of kings clashed with the English and Scottish Parliaments, who were jealous of their own prerogatives.

Civil war erupted in 1642, ending with Charles’s defeat and capture. He refused demands for a constitutional monarchy, and he spent most of his last days imprisoned on the Isle of Wight, where the Arbella and its fleet had set sail nineteen years earlier. He was executed on January 30, 1649.

The principal signatory of the warrant for the king’s execution was Oliver Cromwell. As Lord Protector of the Commonwealth of England, Scotland, and Ireland, he was the most powerful Puritan of all time and virtual dictator of the country that Winthrop and others had left for a new life in a new land.

Crossings of the Atlantic were slower and more dangerous in winter, so when the news of the regicide arrived, many of the members of the Great Migration rejoiced. Winthrop’s son Stephen returned to England to serve in Cromwell’s government. John Endecott and Richard Bellingham, then governor and deputy governor, respectively, of the Bay Colony, wrote to Cromwell, thanking him for his “continued series of favours” to “us poor exiles, in these utmost ends of the earth.”27


The Cromwell Protectorate had lasted only six years before it collapsed, soon after Cromwell’s death in 1658. His son and successor, Richard, was ousted by the military, and the royalists returned to power. Now it was Cromwell’s turn to be convicted of treason, albeit posthumously. His body was disinterred from Westminster Abbey and hanged, by tradition, on the Tyburn gallows for the public to gawk and cheer, “Long live the King!”

Our Founders' Warning

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