Forces, however, began to work against Winthrop. For instance, Deputy Governor Dudley, perturbed by Winthrop's gubernatorial policies and fearful of Winthrop's new vision for taking control of the government, provoked the freemen to dissent against him. They eventually voted Winthrop out of office in 1634. John Cotton, in a show of support for the stability of Winthrop's government and in an effort to gain votes for him, delivered an election day sermon on his behalf. Despite Cotton's efforts, Winthrop lost the election because of the ire the freemen felt over certain improprieties on the part of Winthrop. They were primarily annoyed at Winthrop because he persistently tried to subject them to his authority and because they feared his creation of lifetime tenure. In addition, the freemen were annoyed by ostensible acts of nepotism when Winthrop appointed his son a member of the magistrates. With the aid of his son's vote, Winthrop had been able to secure his power.
Along with assuring his status as Governor, Winthrop gained recognition for his entrepreneurial skills, as his Papers suggest, when he began trading various commodities during the first four years of the settlement. He sold iron, flannel, figs, rags, canvas, shoes, boots, lead, currants, raisins, corn, cattle, and stockings to the new mass of emigrants and to the London Port Company. Winthrop's son-in-law James Downing and brother Emmanuel were part of this London operation. The freemen and the citizens provided Winthrop with a market to sell English goods while England was furnished with furs delivered by the Massachusetts Bay Company. Despite being voted out of office for two years,
1634-35, Winthrop's business was conducted without interruption. And before the end of 1637 he was reelected to the governorship. Shortly thereafter, he was voted a life term as magistrate of Massachusetts, a position which he rotated with Endicott and Dudley.
