The Puritan Dilemma: The Story of John Winthrop

Winthrop had faults. He was intelligent, especially in practical matters, without being brilliant or original. He was quick to look down on those who came to grief after disagreeing with him. The short temper of Endecott and Dudley’s inflexibility in interpretating scripture and law posed more challenges to judicious use of the government’s nearly absolute power. Dudley and Winthrop increasingly found themselves at odds, beginning with the decision to relocate headquarters from Cambridge to Boston. Winthrop tore down his house and moved, while Dudley remained and felt rejected as a neighbor. 

Dudley deplored Winthrop’s moderation on matters ranging from giving special permission for a new fish weir to allowing expelled settlers weeks or months to relocate. For Winthrop, a new settlement required leniency and flexibility to grow; for Dudley, stricter laws were essential for a Puritan community. In 1632, Dudley openly accused Winthrop of abusing his authority to pander to the people and challenged the source of his authority. If it came from the election of the people, then arguably Winthrop had violated the royal charter; if it came from the company charter, then Dudley doubted the governor had any more authority than the assistants. Winthrop tried to dodge the question at first, then said the charter supported him.