The Puritan Dilemma: The Story of John Winthrop

“Puritanism was a power not to be denied. It did great things for England and for America, but only by creating in the men and women it affected a tension which was at best painful and at worst unbearable.”

The dilemma in the title of The Puritan Dilemma is that it demanded people labor in the world while attempting to live up to ideals so high that they knew they would always fall short. Morgan argues here that this inner tension was difficult for Puritans to navigate, but that it was a creative tension that moved them to have a positive impact on society.

“Puritanism meant many things. But to young John Winthrop, it principally meant the problem of living in the world without taking his mind off God.”

This quotation states the Puritans’ dilemma more explicitly. For key points, such as this one, Morgan uses repetition with slightly varied wording to make his themes clear. Here, he introduces the key theme of Isolation Versus Worldly Engagement, with people like Winthrop trying to decide how best to live a godly life in an imperfect world.

“Clothworkers were unemployed, hungry but unable to pay for country produce; clothiers could not market their fabrics; farmers could not pay their rents. The cost of caring for the poor and unemployed rose steadily. Was this not a hint of God’s displeasure, a warning of worse to come?”

Morgan, as a historian, understands causation clearly but, for the sake of a tighter and more accessible narrative, condenses a lot of his knowledge into short summaries like the one here. He skims through the chain of economic consequences in which a crisis in the textile industry had ripple effects across society. The rhetorical question at the end (another technique he frequently employs) illustrates how Winthrop would have understood the crisis without Morgan weighing in on whether it is a reasonable or unreasonable interpretation.

“This was part of the same large paradox that had troubled Winthrop from the beginning, the paradox that required a man to live in the world without being of it.”

This quotation echoes the words Morgan used earlier (page 8, see quotation above) on the dilemma that Winthrop faced on how to engage the world while being primarily focused on God and godly ideals, invoking Isolation Versus Worldly Engagement. This echoing of the theme bridges between Winthrop’s private struggles to his grappling with that dilemma on a more public stage, as he considers whether or not to align himself with religious separatists and their churches.

“Just as Winthrop considered hunting with a gun a bad form of recreation because he got so little profit from it, so the move to New England was wrong unless there was a good chance that the colony would be an economic success. A man’s duty to God was to work at his calling and improve his talents like a good and faithful servant. If he could do it better in New England than in old, that was good reason for moving.”

This passage is one of many that challenges the preconception that religion is otherworldly and opposed to secular concerns. For Winthrop and the Puritans, since God was in charge of all the world, then laboring in the world was itself a religious concern and economic success a legitimate religious consideration.

“The recognition that he must live in the world had led him to the paradoxical conclusion that he should withdraw from the only part of the world he had ever known. Having learned to use the good things that God gave man, he had reached out to strike down the evils that God forbade, and in so doing found that he must save not merely Groton or Suffolk County but England herself.”

Morgan again echoes the phrase “live in the world” with the idea of dilemma or paradox to illustrate Isolation Versus Worldly Engagement. This time, he is invoking the dilemma as a key motivation for Winthrop’s decision to join the new colony.

“Looking over the beachhead to which he had brought so large and so weak a force, Winthrop saw that the colony needed backbone. On the faces of the languid men around him he read a failure of nerve.”

Morgan uses the metaphor of an army to describe the arrival of the settlers. This is part of his rhetorical toolkit that aims to keep his writing lively. The moral failure of the original settlers also serves to make Winthrop look heroic in contrast and a necessary figure for the colony to survive, foreshadowing his Moderation and Consensus in Successful Leadership.

“The people who appear in the pages of Winthrop’s journal, the good men and women who showered him with venison and partridges and fat hogs to celebrate Margaret’s arrival, the boys and girls who skipped rope on the decks of the Arbella, the men who built ships and caught fish and planted corn were all human enough.”

Morgan takes aim at drab Puritan stereotype here by repeating details from earlier in the narrative that might have been easily missed. Their repetition here works to make clear the theme of Rehabilitating the Puritans that had been woven into the narrative structure.

“Separatism might splinter the colony into a hundred earnest little Utopias, each feeding on its own special type of holiness and each breeding new types, multiplying, like earthworms, by division. Separatists could disintegrate the colony and dissolve its special commission.”

Morgan uses the metaphor of earthworms who, in popular lore, can reproduce by being cut in half and turn into two healthy (albeit shorter) worms. This image juxtaposes the high goals of the separatists with the grubby reality of how their incessant quarrels and schisms in pursuit of an unobtainable holiness could extinguish the colony, speaking to the issue of Isolation Versus Worldly Engagement.

“The history of Massachusetts during Winthrop’s lifetime is very largely the history of his efforts to meet the various dangers presented by separatism. No one could have been better equipped for the task, for Winthrop was obliged to do for Massachusetts what he had already done for himself.”

Morgan is very explicit in identifying disengagement and separatism as the wrong choice when confronted with the question of Isolation Versus Worldly Engagement. This quotation explains the emphasis in the earlier narrative about Winthrop’s own struggles with that question: They are the first step in the larger conflict that dominates the narrative.

“Winthrop, as he himself realized, had acquired a talent for command. He never grasped for authority as Dudley or Endecott might, but he did not need to: he was the kind of man upon whom authority was inevitably thrust.”

This succinct characterization of Winthrop as a leader packs in a wealth of positive attributes that Morgan uses narrative techniques to elaborate, speaking to Moderation and Consensus in Successful Leadership. This quotation implies Winthrop has self-knowledge, humility, moderation, and such obvious leadership skills and charisma that people naturally turned towards him.

“Winthrop did not believe that in extending freemanship he had transformed Massachusetts into a democracy. The legislative power was lodged not in the people but in a select group where, according to his reading of the Bible, it belonged.”

An important implicit argument in this book is the need to understand historical figures in the context of their worldviews rather than modern categories. Morgan does this in part through making this kind of careful distinction: Extending voting rights may look like a democratic move but, in reality, Biblical concerns motivated Winthrop’s actions. His religious motives are why some of his later actions seem to fail the democratic ideal.

“If Winthrop himself had such faults, the magistrates who were elected to serve with him (the deputy government and the assistants) had others of a kind most unsuitable to anyone entrusted with such extensive powers.”

This quotation offers a prime example of how Morgan balances the expectation that historians offer neutral analyses of history with holding up Winthrop as an exemplar of judicious leadership. He acknowledges a list of shortcomings that Winthrop has and admits he makes mistakes, but he also explains how the mistakes of other figures created far worse dangers.

“Yet there was a real issue here, the old issue of uncompromising purity versus charity. Winthrop, on the side of charity, sought the true course in judicial discretion rather than legislative precision.”

The word “purity” calls to mind “Puritan” and Puritans, according to the stereotype, are supposed to be inflexible, harsh, and legalistic. Morgan emphasizes that Christian charity (love) was as much part of their mindset as purity. He also states that the Puritans had rational debates about how to balance their ideals with some (such as Winthrop) arriving at moderate positions that disprove the stereotypes.

“Though he never hesitated to strike down sin, he was keenly aware that Massachusetts was endangered more by separatist zeal than by worldly wickedness. He knew too that the time to check separatism was early, before it became blind to every obstacle.”

Morgan’s use of repetition can be seen in his frequent statements that separatism was bad. This interpretation of Winthrop’s main concern is well-supported by evidence. Morgan’s emphasis on Winthrop’s attempt to fight extremism (rather than his efforts to police ordinary people’s morality) allows Morgan to subvert views of Winthrop as an authoritarian. Instead, he presents Winthrop as embodying Moderation and Consensus in Successful Leadership.

“The Great Migration was filling Massachusetts with men and women who were not afraid to take sides and not afraid to stand up against government. Among them, as it happened, was a man named Roger Williams, a charming, sweet-tempered, winning man, courageous, selfless, God-intoxicated—and stubborn—the very soul of separatism.”

Morgan frequently works to subvert expectations. The first half of this description of Williams makes him appear admirable and then, suddenly, Morgan charges him with the capital error of separatism. This playing with expectations keeps the work balanced and creates a tension in the narrative that helps propel it forward.

“Indeed they were all but bewitched with his heedless holiness, and when their minister, Samuel Skelton, died, they cast off caution and in the spring of 1635 chose Williams in his place—knowing well that the government would quickly move against them.”

This quotation illustrates the kind of stylistic devices that Morgan uses to write a lively narrative and attempt to shape the reader’s perception of historical figures, in this case painting a negative picture of Roger Williams, a man more often portrayed as admirable. The use of “bewitched” echoes contemporary attacks on him, possibly drawing on Galatians from the Bible. The use of alliteration calls attention to “heedless” and the decision “cast off caution,” both cardinal sins in a book that emphasizes Winthrop’s prudence and moderation.

“All we know about Anne Hutchinson was written by other hands than hers, for the most part by writers whose main purpose was to discredit her. Yet the force of her intelligence and character penetrate the libels and leave us angry with the writers and not with their intended victim.”

Morgan rarely allows his emotions to explicitly disrupt his writing of objective history, yet here he describes “us” as “angry.” He is acknowledging the visceral reaction that some readers may feel as they see powerful men browbeating an intelligent, independent woman. By making this acknowledgement of those readers’ emotions, he gives his account balance and may persuade them to also listen to the other side that explains Winthrop’s actions.

“What followed was the least attractive episode in Winthrop’s career. Anne Hutchinson was his intellectual superior in everything except political judgment, in everything except the sense of what was possible in the world.”

Again, Morgan here acknowledges that the Hutchinson episode does not reflect well on Winthrop. In admitting Hutchinson’s gifts, however, he subtly begins to show her weaknesses as well. This biography of Winthrop is an argument for leadership that engages with the reality of the world with flexibility and moderation; that is precisely where the last clause of the quotation says Hutchinson fails. In this narrative, she does fail as she is abandoned by most of her followers and driven away from Boston.

“God manifested His approval in other ways, too. In the spring of 1637, while Winthrop was in the process of subduing Mrs. Hutchison, the colony became involved in a war with the Pequot Indians. Through the timely warning of Roger Williams, who was corresponding regularly with Winthrop, and with the assistance of the settlers in Connecticut, who bore the brunt of the fighting, the Pequots were destroyed, virtually the whole tribe killed or captured.”

This book treats what some historians consider a genocide in a mere two sentences, presenting it as an episode of success for Winthrop, who sees it as a sign of God’s favor. This is in part the influence of older schools of American historiography that gave scant attention to the Indigenous Americans and in part a strategy to tiptoe around events that cast Winthrop in a negative light.

“Winthrop met his financial crisis as calmly as he met all difficulties. It did not sour him on New England or New Englanders.”

This book argues that Winthrop’s character is the key to understanding him and the success of Massachusetts. Events such as the financial ruin caused by his steward matter less in themselves than as moments that reveal Winthrop’s inner qualities that made him an effective leader of the colony.

“This kind of separatism wore the appearance of virtue. Just as selfishness looks virtuous when expanded into patriotism, so separatism seemed less separate when indulged in by a whole people. What is wrong in an individual sometimes appears right in a nation—at any rate in one’s own nation.”

This kind of broad moralistic statement is unusual in this narrative and suggests that Morgan believes it has importance for his audience in mid-20th-century America. It is much harder to recognize such an error when all one’s neighbors also participate in it. The final sentence sarcastically notes how easy it is to find fault in other countries but be ignorant of one’s own society’s failings.

“Winthrop saw what few men in any age have learned, that the foreign policy even of the holiest state must support one evil in order to suppress a worse one. Because it requires uncommon wisdom to recognize this fact, and still greater wisdom to choose rightly among the manifold evils of the world, foreign affairs have always suffered when exposed to the undiscriminating zeal of legislative assemblies.”

Morgan again returns to making broad statements about government and policy that seem directed as much to his own era as Winthrop’s. Here he voices suspicion of a mob mentality that either refuses to work with distasteful allies or resolutely ignores the evils that an ally does without prudent consideration of how necessary it is. He may have had in mind events from the 1940s and 1950s, such as the Allied victory in World War II involving Stalin’s USSR, or how the US then supported vicious dictators during the Cold War to thwart the spread of Communism.