Lord of The Manor
As Lord of the Manor, Winthrop was deeply involved in the management of the estate, overseeing the agricultural activities and the manor house. He eventually followed his father in practicing law in London, which would have brought him into contact with the city's business elite. He was also appointed to the county commission of the peace, a position that gave him a wider exposure among other lawyers and landowners, and a platform to advance what he saw as God's kingdom. The commission's responsibilities included overseeing countywide issues, including road and bridge maintenance, and the issuance of licenses. Some of its members were also empowered to act as local judges for minor offenses, although Winthrop was only able to exercise this authority in cases affecting his estate. The full commission met quarterly, and Winthrop forged a number of important connections through its activities.
Winthrop documented his religious life, keeping a journal beginning 1605 in which he described his religious experiences and feelings. In it, he described his failures to keep "divers vows", and sought to reform his failings by God's grace, praying that God would "give me a new heart, joy in his spirit; that he would dwell with me". Winthrop was somewhat distressed that his wife did not share the intensity of his religious feelings, but he eventually observed that "she proved after a right godly woman." He was notably more intensely religious than his father, whose diaries dealt almost exclusively with secular matters.
When his wife Mary died in 1615, Winthrop, following the custom of the time, remarried not long after. On 6 December 1615 Winthrop married for the second time, to Thomasine Clopton. She was noticeably more pious than Mary was: Winthrop wrote that she was "truly religious & industrious therein". Thomasine died on 8 December 1616 from complications of childbirth; the child also did not survive.
In approximately 1613 (records indicate it may have been earlier), Winthrop was enrolled at Gray's Inn. There he read the law, but did not advance to the Bar. His legal connections introduced him to the Tyndal family of Great Maplestead, Essex, and in 1617 he began courting Margaret Tyndal, the daughter of a chancery judge. Her family was initially opposed to the match on financial grounds; Winthrop countered by appealing to piety as a virtue that more than compensated for his modest income. The couple were married on 29 April 1618 at Great Maplestead. They continued to live at Groton, although Winthrop necessarily divided his time between Groton and London, where he eventually acquired a highly desirable post in the Court of Wards and Liveries. His eldest son John sometimes assisted Margaret with the management of the estate while he was away.
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