The Puritan Dilemma: The Story of John Winthrop

The title of this book, The Puritan Dilemma, refers to the central problem that John Winthrop and the Puritans faced in their personal lives, religion, and politics: “[T]he paradox that required a man to live in the world without being of it” (31). Winthrop and other Puritans recognized that the world and its inhabitants are inevitably imperfect, yet their religion gave them an ideal of a better world, one which—though they would not see it fully realized until after death—they could at least try to imitate on earth. Their dilemma was whether to give up on those who did not share the same high ideals and withdraw into a separate, holier community, or instead to engage with the world despite its corruption. Morgan suggests that it is a dilemma shared by idealists everywhere and that, as Winthrop shows, normally the best answer is to work within an imperfect system rather than renounce one’s neighbors to pursue an elusive utopia.

Those Puritans who favored withdrawal became Separatists—the religious movement to leave the Church of England to create tiny “true” Christian churches. The Separatists posed the main threat that Winthrop combatted throughout his career. For Winthrop, separatism had three problems. First, its proponents failed the test of the foundational Christian virtue of charity because they renounced the chance to help their neighbors. Second, it fractured community, which would be especially dangerous in a small colony like Massachusetts. Third, it was unrealistic, since all people are flawed. Roger Williams’s separatism, for example, first caused division and resentment within Massachusetts, and ended with Williams deciding that even his followers in Rhode Island were too degenerate. Williams found himself in communion only with his wife and then, realizing the ridiculousness of the situation just as Winthrop had foretold, abandoned separatism for complete religious toleration. 

For Winthrop, this stark reversal of an untenable position still represented an unhealthy withdrawal from the world because the liberal Williams seemed to have given up on helping his neighbors improve. Winthrop instead always focused on trying to bring people together, persuading them, and focusing on fighting political and social battles that could realistically be won. His own writings make clear that he went to New England to pursue an alternative strategy of engaging in the world, hoping to help England as a whole. Winthrop’s policies as a colonial leader followed this pattern of engagement in external policy as well. He insisted on not angering the king of England and negotiated with Indigenous Americans. As the English Civil War disrupted trade with their homeland, he encouraged colonial trade with other countries of different religions.

Thus, for Winthrop, withdrawal from the world was an abdication of responsibility. Instead, he believed that a good person ought to engage with the world in all its imperfection in personal, economic, religious, social, and political spheres. In Morgan’s view, it was this willingness to engage and compromise that ultimately secured the colony’s survival.