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At age 15 he entered Trinity College, Cambridge. At age 17 he married the first of his four wives—Mary Forth, daughter of an Essex squire—and the next year the first of his 16 children was born. Like many members of his class, Winthrop studied law, served as justice of the peace, and obtained a Government office; from 1627 to 1629 he was an attorney at the Court of Wards and Liveries. For more than 20 years Winthrop was primarily a country squire at Groton, with no discernible interest in overseas colonization.
He was an ardently religious person. From his early teens Winthrop threw himself into scriptural study and prayers, and gradually he trained himself into a full-fledged Puritan, convinced that God had elected him to salvation—or, in Puritan terms, to “sainthood.” His religious experience reinforced his elitist outlook, but it also made him a social activist. Like other prominent Puritans, Winthrop dedicated himself to remaking, as far as possible, the wicked world as he saw it, arguing that “the life which is most exercised with tryalls and temptations is the sweetest, and will prove the safeste.”
During the late 1620s, Winthrop felt increasingly trapped by the economic slump that reduced his landed income and by Charles I’s belligerent anti-Puritan policy, which cost him his court post in 1629. When, in 1629, the Massachusetts BAY Company obtained a royal charter to plant a colony in New England Winthrop joined the company, pledging to sell his English estate and take his family to Massachusetts if the company government and charter were also transferred to America. The other members agreed to these terms and elected him governor (October 20).