The Puritan Dilemma: The Story of John Winthrop

Winthrop considered his immigration to America to be a positive engagement with the world rather than the kind of withdrawal advocated by separatists. How convincing are his arguments that he was not acting like a separatist? In what ways did his leadership of the colony reinforce, or diverge from, this commitment to engagement?

Morgan insists that historians should understand people’s motivations within the context of their own time periods rather than imposing modern concepts on them. How do Winthrop’s ideals of democracy, separation of church and state, and/or religious freedom differ from 21st-century conceptions? In what ways, if any, are they similar?

Compare and contrast the success of the Massachusetts colony with those that struggled or failed. Which factors seem to have led to these successes and failures? Are there factors besides leadership that Morgan may have downplayed or overlooked?

The Puritans who settled Massachusetts saw their work as a “godly experiment.” How does The Puritan Dilemma explore the nature of their religious motivations, and the success and limitations of their religious aims?

Compare The Puritan Dilemma to another one of Morgan’s studies of the Puritans, such as The Puritan Family. What key themes and ideas do the two works share in common? How is Morgan’s presentation of the Puritans similar or different in each text?

Analyze how Morgan explores the tensions between separatism and engagement in the text. How does he characterize each impulse? What rhetorical strategies does he use to present one as superior to the other?

Morgan implies that later American society owes a debt to Winthrop and the Puritans. What was their legacy? What was positive about their contributions, and what were the drawbacks?

Analyze the role of women in this book, including Margaret Tyndal Winthrop and Anne Hutchinson. What can you infer about gender roles, particularly restrictions and opportunities for Puritan women?