The Puritan Dilemma: The Story of John Winthrop

The Puritan Dilemma: The Story of John Winthrop (1958) is a work of history by Edmund S. Morgan. The Puritan Dilemma is a biographical study of the first governor of colonial Massachusetts, John Winthrop. Morgan examines Winthrop’s work and life, presenting him as a man of high ideals who understood how to lead as a model of moderation and practical flexibility. Though many Puritans chose to withdraw from the world into little cells of self-righteousness, he consistently chose to engage with the world and help others. His talents helped him unite a colony filled with prickly characters, with a few dramatic exceptions. The Puritan Dilemma offers an accessible early example of the work that would earn Morgan a Pulitzer Prize and the National Humanities Medal.

This guide uses the 1958 hardback edition by Little, Brown, and Company.

Summary

John Winthrop’s grandfather, Adam, was a prosperous English cloth merchant when King Henry VIII decided to join the Protestant Reformation and remove English Christianity from the Catholic church. Adam Winthrop acquired the estate of Groton from the king when the monarch seized the lands of the Catholic monastery there. John, as the heir, grew up in a privileged family of country gentry that served as local leaders. 

As a young man, John Winthrop embraced the fiery Puritan movement. Puritanism believed that the English Reformation had not gone far enough in rejecting Catholicism or in building a moral, godly society. They preached a more extreme Calvinist theology of predestination, in which each person is helpless and utterly dependent on God’s action in achieving salvation—and God only chose a few elect to save. Those who hoped that they were numbered among the predestined elected saints sought signs of God’s favor in their ability to live a mostly holy life (though still knowing all people sin) and in the profits they accrued through hard work. They believed the nation would receive God’s blessing and prosper if it enforced God’s law, but would be punished otherwise.

Winthrop’s early life focused on managing his estates well and learning how to live in accordance with these ideals. He settled on a policy of moderation: He would enjoy the gifts God gave the world and work hard for himself and his neighbor, but avoid overindulgence and always keep his eternal hope with God at the forefront of his mind. He married, was widowed, married again, was widowed again, and finally married a third time to Margaret Tyndal, a woman of similar faith and spirit. He also became involved in government by utilizing his partial education in law.

Meanwhile, England (in Puritan eyes) went downhill. The official Church of England seemed enchanted with bishops and theology that seemed halfway between Catholic and Protestant Christianity. King Charles I had little interest in the strict enforcement of commandments required for God’s blessings. Puritans at least had a voice in Parliament, but then the king decided to dismiss it and rule alone. More and more Puritans separated themselves from the Church of England or fled overseas to create enclaves of their preferred faith. 

Winthrop, though troubled by contemporary trends, saw the separatists as abandoning the Christian call for charity to one’s neighbor. He initially rejected the prospect of going overseas, but became intrigued by the Puritan vision behind the Massachusetts Bay Company. Through a clever manipulation of its royal charter, it would be practically self-governing and a perfect chance to experiment with building a Puritan society. Success would pioneer a path that might inspire the corrupt church back home. After a torturous internal debate, Winthrop decided to join the endeavor. The company selected him as the colony’s governor in 1629.

The first year in Massachusetts proved exceptionally harsh. The company had settled Salem earlier, which proved a difficult spot with indifferent farmland. The harsh winter killed 200 settlers and sent an equal number fleeing back to England. Winthrop, however, never despaired and energetically worked to solve problems. He relocated to Boston Bay, negotiated with local Indigenous Americans, scouted new farmland, and encouraged the settlers in starting their crops and expanding into the fish and timber industries. Fueled by an influx of immigrants and supplies procured by Winthrop, the colony soon began to thrive.

Winthrop and the other officers in the company made a key political decision within two years of arriving. Applying the Old Testament idea of a government founded on a covenant with the people to early modern English traditions, they made all male church members in the colony eligible to vote in elections. Within a few years, these “freemen” gained additional powers and representation. Winthrop opposed some of this expansion of democracy, fearing it cut into the necessary powers for leaders (who answered to God) to appropriately shepherd the young colony during its crucial formative years. This opposition, along with charges that he showed too much leniency to sinners, led to his first time losing the election for governor. He remained very influential in the colony and returned to the governorship three years later.

The absence of Winthrop’s moderating influence in government became apparent in the Roger Williams affair. Roger Williams, a charismatic young preacher, preached a radical separatism, even questioning the validity of the colony’s royal charter from a sinful king. Winthrop had managed to defuse crises such as this through rational dialogue and patience. Now, the hardline government and the stubborn minister refused to compromise. In the end, Massachusetts exiled Williams. Williams founded a new colony in Rhode Island. While there he eventually gave up on his utopian perfectionism and, in an abrupt shift, became a champion of religious freedom. 

A similar crisis came with Anne Hutchinson, an original and talented theologian whose views also became a basis for separatism in the colony. This time Winthrop, poisoned by the misogyny of his era, participated in the effort to silence and banish her. She also fled to Rhode Island and also evolved from her condemnation of other churches to a position of religious tolerance.

Winthrop returned to the position of governor for most of his final years. The trend towards greater democracy and a formalized code of rights progressed despite his doubts, but he adapted to the situation and remained a trusted leader. A larger challenge came with the events leading to the outbreak of the English Civil War. Despite the eagerness of some Puritans to join Parliament in challenging the king, Winthrop remained committed to a policy of neutrality. He wanted to continue to develop the experiment of Massachusetts in peace, without interference from England. Through astute diplomacy, he succeeded. 

The war, however, dramatically reduced the influx of settlers on which the colony relied. Winthrop worked to make the colony more self-sufficient, beginning to build profitable connections with other colonies and foreign trade partners. He died as governor in the midst of this work in 1649.