The Puritan Dilemma: The Story of John Winthrop

John Winthrop was a product of the minor English gentry and the Protestant Reformation. His grandfather gained the family estate in Suffolk from a seized Catholic monastery, and John Winthrop carried on the work of the Reformation with a Puritan fervor that surpassed that of his family. 

As a country gentleman and considerable landowner, he was expected to govern his neighbors, and he did. When he became convinced that going abroad would best serve the Puritan vision of a better society, he did. His fellow settlers recognized his merits as a leader, his legal education, and his social standing, and so they elected him their first governor in Massachusetts. He remained one of the most influential men in the new colony until his death in 1649. He frequently served as governor. His prudent decisions, such as moving to Boston Bay, helped the colony survive, then thrive, and overcome internal divisions.

Morgan narrates Winthrop’s biography mainly chronologically rather than thematically. Although the unfolding of events serves to characterize Winthrop, Morgan pauses at several points in the narrative to offer a direct characterization of the man. Chapter 1 is an exception to the rule. There, he describes at length Winthrop’s internal struggles with balancing the need for recreation and profitable work with duty to God while avoiding the temptation to excessive pleasure. The result was a commitment to moderation and practical flexibility while keeping the ideals of religion always in mind. 

The term “moderation” and its synonyms constantly appear throughout the rest of the narrative to remind the reader of Winthrop’s central characteristic. Winthrop’s strength and patience in enduring hardships is not made quite as explicit, but Morgan makes these traits plain through his description of how Winthrop weathered the first terrible winter in New England without losing hope. He also emphasizes how Winthrop humbly accepted his first removal from office without complaint.

In describing the characteristics of Massachusetts’ early leaders, Morgan explicitly lists some of Winthrop’s flaws. Winthrop had an excellent practical intellect but was not an original thinker or brilliant theologian. He took too much satisfaction when others failed after ignoring his advice. In confronting Anne Hutchinson, he let the misogyny of his culture shape his actions and judgment. Morgan argues that Winthrop was not perfect, but that he still served as the capable, rational leader that the early colony needed.

John Winthrop had four wives, three of whom are practical nonentities in this narrative. Margaret Tyndal is the exception. She became John’s third wife and the one who lived with him the longest. She and he developed a close relationship based on love, respect, and shared religious convictions. Morgan introduces her as a “very womanly woman, one of the most appealing in American history” (13). Though he does not explicitly define what that characterization means, context suggests that what made her feminine and attractive in Morgan’s eyes are her tenderness, her gracious attitude towards others, her unwavering support for her husband, and her lively writing style.

Her writing style is known because of the correspondence between Margaret and John that survives, both from their days in England and when John went first to Massachusetts. Travel in the 1600s took time and letters bridged the gap. When John went to London to discharge his duties at the Court of Wards, for example, he and Margaret wrote letters to each other expressing their longing to be together. These letters show not only their love, but the kinds of spiritual reflection on God’s word and its application to their lives that both loved. 

Ironically, we know more of Margaret when she and John were apart (since they had to write) than the considerable influence she must have had on him as they lived together. Presumably due to this issue of evidence, Margaret disappears from the narrative between her arrival in Massachusetts and her death over a decade later. This effacement of an important woman in Winthrop’s life speaks indirectly to the differing roles allotted to men and women in their culture.

Thomas Dudley became Winthrop’s main political rival in Massachusetts. Dudley embodied the stereotypical Puritan: Strict, self-righteous, and legalistic. Those characteristics Morgan states explicitly. He also suggests that greed and envy ruled Dudley. The first thing Morgan tells us of Dudley is that he, as steward to an earl in England, raised rents on tenants there. He also took advantage of his neighbors in the colony to make a profit using techniques that Winthrop considered to reflect the sin of usury. In his next appearance in the narrative, he becomes annoyed when Winthrop leaves him behind in Cambridge to move to Boston. Morgan raises the possibility that Dudley lacked the money to start over in the new town and resented Winthrop’s financial success.

When Dudley publicly turned against Winthrop though, it was on the question of law rather than greed. He accused Winthrop in 1632 before the General Court of bending the law and showing undue leniency to sinners. Without rebuke, in Dudley’s view, sin would flourish and the colony would fail. Dudley failed in his initial confrontation but remained a champion of hardline Puritan government. When the colonists disagreed with Winthrop, Dudley became their preferred candidate. They elected him governor in 1634. Thanks to the backing of the clergy, he returned in 1640 and again in 1645. His uncompromising approach contributed to the crisis with Roger Williams.

Roger Williams is the main figure of Chapter 9. He thrusts the colony into an existential crisis by challenging its godly self-conception. He and his opponents are the example of the good-intentioned men operating without moderation and without a moderate leader like Winthrop to restrain them. Morgan introduces him as a “charming, sweet-tempered, winning man, courageous, selfless, God-intoxicated—and stubborn—the very soul of separatism” (116). The point of Williams is that he is a good, gifted man, but he has no sense of moderation in his enthusiasm for the godly life and is too stubborn to adapt to the advice of the people around him. His talent for winning people over is apparent in almost every situation. Indeed, Morgan suggests that his exile from Massachusetts happened in part because he was ill during some critical events and unable to exercise his personal charisma. Winthrop clearly liked him and continued to correspond with him even after Williams left the colony.

Williams was an early supporter of the Massachusetts Bay Company. As a separatist in England, he was eager to depart and came to Boston a year after Winthrop. His passion for purity and desire to break cleanly from the Church of England put him in conflict with other settlers. He moved from Boston to Plymouth to Salem seeking a “pure” congregation. Eventually his extreme stances led to the General Court condemning and banishing him. He and some followers left to found the colony of Providence, Rhode Island, where he ultimately embraced religious freedom and also cultivated friendly relationships with the Indigenous peoples of the area.

Anne Hutchinson was like Williams in many ways: An intelligent, charismatic religious leader whose stubborn adherence to her principles and desire for godliness put her and her followers at odds with the rest of the colony. Her dissent eventually led to her banishment to Rhode Island. There was one obvious difference that affected how others treated her: She was a woman. Winthrop, despite not being her intellectual equal in Morgan’s estimation, never warmed to her the way he did to Williams or gave her similar respect. 

Hutchinson, as a woman, never had an official position as a minister either, though she taught dozens of people at a time in her own home and her followers were able to propose her brother-in-law as a minister to preach her doctrine. She taught that leading a good life was not a sign of election to heaven. She asserted that most of the colonists, including their ministers, were still effectively believing in a doctrine of salvation through one’s works or deeds. The core of the Protestant Reformation was that only grace mattered, not a person’s works, so this was an explosive charge. She also believed that the Holy Spirit dwelled in the saved elect and guided them directly, opening up the possibility of private revelation and thereby reducing the centrality of the Bible. This latter doctrine proved the breaking point for many of the colony’s Christians.

Hutchinson immigrated to Massachusetts with her husband (a minor figure in this narrative) in 1634. Though not originally a separatist, she had a strict sense of proper preaching and believed most ministers failed to push the full message of grace and predestination. When John Cotton, her minister in England, left for Boston to find a more receptive community, she and her husband followed. Her theological discussions in her home eventually made her a pivotal figure in the Boston church, and many of its members subscribed to her theology. When this caused conflict with other church members (including Winthrop) and the rest of the colony (whom her theology condemned), the authorities intervened. After attempts at negotiation, first her brother-in-law and then Hutchinson were condemned by the General Court and exiled to Rhode Island.