What helped Winthrop more as governor, his law training or learning to run the family estate?
More than anything, Winthrop's training at the estate allowed him to manage the colony as it grew. Although his law training helped lay the groundwork of the colony and the colonial government, he could not have worked out the logistics of the colony and balanced the needs of so many different tradesmen without overseeing the manor at Groton.
Was it true that Puritans never had any fun?
Winthrop realized that recreation was an important part of one's life. The Puritan faith, to him, was more about balancing aspects of one's life rather than restricting it. In order for a pastime to be worthwhile, one had to balance the effort with the reward. For instance, hunting for him was forbidden because it took so much time to gather the implements, stalk, kill, and clean an animal–the mental reward was not equal. However, something like a big meal was fine as long as he did not allow it to interfere with his post-meal plans.
Was John Winthrop a benevolent despot?
As much as his detractors tried to convince settlers otherwise, Winthrop ran Massachusetts Bay kindly and generously. His many repeat terms as governor had less to do with his aspirations of glory and power than they had to do with his willingness to give the colony his all. He paid to keep the colony running, paid for families to emigrate, and defended the colony from both physical and spiritual assailants. Likewise, his repeated attempts to limit the power of the "freemen" was primarily because he understood the advantages of a despotism–decisions could be made and executed faster, and in the fledgling colony, that was crucial.