The Puritan Dilemma: The Story of John Winthrop

Puritans believed that—although they could never fully overcome the evil that infected the world and their very selves—they had a solemn duty to try to battle it. Good government punished breaches of God’s commandments and God in turn would reward such a government. The rulers of England failed to enforce the Puritan understanding of God’s commands, at least with vigor, but their active opposition to Catholicism (with the exception of Mary Tudor) made them tolerable in Puritan eyes. When disasters struck England, however, Puritans worried that their monarch’s lack of Puritan zeal had finally incurred God’s wrath. They placed some hope for improvement in Parliament, in which they (though still a minority) could make their voices heard.

A 1620s depression in the textile industry hit Winthrop’s home county hard. To compensate, he obtained a government income by serving on the Court of Wards. This state institution auctioned off the royal right to control minors who inherited land held from the king. The winner of the auction became guardian to these fatherless children and could exploit their lands for their own benefit. This position forced Winthrop to leave his home and wife four times a year to travel to London, where he saw firsthand the problem of government corruption. 

From the Puritan perspective, the political situation worsened with the ascension of King Charles I in 1625. Charles decided to rule without Parliament and embraced a High Church vision of the Church of England that Puritans considered to be only a step away from returning to Catholicism. They also feared that Charles’s favorite bishop, Laud, would spread his Arminianism (a theology that said a person’s free will played a role in accepting faith, which Puritans believed to be a heresy undermining complete dependence on God’s grace and predestination).

Meanwhile, Catholic states on the European mainland were beginning to turn back the Protestant tide. Puritans saw these series of setbacks to Protestant Christianity as a punishment sent by God for the evils tolerated in their societies. With the English government turning away from their ideals, they believed worse must be in store. Some Puritans were tempted to give up on their church and government. These separatists withdrew to form their own churches. One group went first to Holland, and then America, where they founded the “Pilgrim” colony of Plymouth. 

Winthrop, however, believed he was called to work within the world, however imperfect it might be. He and Puritans like him hoped to save their neighbors by improving the sinful societies in which they were trapped. Leaving would not save them or even let Winthrop escape sin, since sin was part of the human condition. To withdraw would be a failure of charity.

When Charles dissolved Parliament in 1629, England had been establishing colonies in the Americas for 20 years. Most had struggled to turn a profit or even survive, but companies continued to speculate and seek royal charters. Some Puritans had participated in founding these colonies, albeit more to create a safe haven for their faith than in hope of quick riches: Creating “a shelter and a hiding place” (37) in Winthrop’s words. 

Winthrop began to grow interested, especially in the newly reorganized Massachusetts Bay Company, as the political situation deteriorated and after two of his sons had contact with some of these groups. Henry, one of those sons, had embraced a life of sin (in Puritan eyes), which Winthrop saw as the fruits of living in a society where Puritan influence had failed. Perhaps, he thought, immersion in a new and more godly society would save Henry and young men like him.

Winthrop approached the decision to emigrate cautiously and analyzed it with legal precision. The arguments he made circulated in written form among the Puritan community and had considerable influence. He argued first that America presented better economic opportunities than an overcrowded England beset by depression and corruption in most trades. A sober Puritan sought God above riches, but work ought to earn its just fruits and could be a sign of God’s favorable predestination. English society had an unhealthy expectation that people indulge in luxuries, thus cutting into their profits and corrupting the youth. Furthermore, he argued, God must have a judgment of wrath in store for the sinful Church of England. A Puritan colony overseas might find shelter from that wrath. 

The only compelling counterargument was that by going overseas, Winthrop and his fellow Puritans would deprive the home country of godly men and leaders at precisely the time of crisis when they were most needed. Winthrop suggested they could do good by converting the Indigenous Americans, and were too few to matter much in England anyway. Still, he struggled with the fear of deserting his duty to his countrymen.

The leaders of the Massachusetts Bay Company urged Winthrop to join them. They argued that England had enough men of proven leadership ability, whereas few of them would consider leaving for a harsh life in the colonies. Winthrop could do more good there, likely in a position of more importance than he could achieve in England under Charles’s anti-Puritan policies. Perhaps a “pure” community in the wilderness could, in the future, serve as a source of revitalization for the broader Church of England. Of course, those hopes assumed that the settlers of Massachusetts could stick to their godly purpose, and no one knew what sort of men would eventually live or rule there.

Most companies that obtained a royal charter to found a commercial colony had a board that met in England (usually London) and sent a governor overseas to enforce their orders on the colonists. The presence of the charter-holders in England allowed the state to easily control them. Several leading members of the Massachusetts Bay Company, however, hatched a bold plan to hold their board meetings in America, so the board members and governor of the company would be colonists themselves. In effect, the colonists would rule themselves and be distant enough from England to escape outside interference—an enticing prospect for Winthrop’s idealistic vision. 

Winthrop learned also that several leading Puritans would go only if he went too. So, in August 1629, he and 11 other leading Puritans officially committed to be part of the new colony. To save what was good in England, he decided he had to withdraw from the world that he knew to nurture that good overseas, where it might flourish. He, and the other leading Puritans, vehemently denied that doing so made them separatists.

Over the hectic six months that followed, Winthrop sold his familial lands and put his affairs in order. Margaret, being pregnant, was to stay behind for a little while, along with some other family members. John Jr., one of Winthrop’s adult sons from his first marriage, stayed behind as well to care for her, to finish settling the estate, and to ensure supplies reached the new colony.

The company held a meeting before leaving and elected Winthrop governor, thrusting even more work on him. Winthrop circulated his own deliberations in written form to the Puritan community as he tried to attract godly settlers, weed out those applicants who sought only economic gain, and still try to make sure the colony had skilled artisans in every necessary craft. Winthrop brought along four families as skilled servants at his own expense, and other rich Puritans did likewise. He also had to negotiate a compromise on sharing profits with investors who had put money in before the company became a Puritan experiment and wished to stay in England. Through hard work and diplomacy, he largely accomplished these goals.