Winthrop wrestled with the decisions but each time decided that fleeing was the only available answer. Charles's men were arresting Puritans in increasing numbers. The societal corruption might contaminate the younger generations, ending any hope of salvation. Besides, the Puritans could continue God's work and try to convert the American Indians. His friends in the new venture wooed him by saying that he would be one of the few leaders in the New World and would get to help shape the new colony. One final trick by the company's founders helped assure its success. Because of the confusion surrounding the end of Parliament, they had been able to sneak the colony's charter past the king without the common clause saying the new company would be headquartered in London–allowing them to conduct their business in the New World and giving them wider autonomy from the crown. On August 26, Winthrop signed a contract with eleven other Puritan leaders that stated they would be ready to leave for New England the following spring. And on October 20, the Massachusetts Bay Company unanimously selected Winthrop as governor of the new colony from a slate of four candidates.
From this point, everything began happening quickly. When Margaret Tyndal, Winthrop's wife, became pregnant, the family decided that it would be best for her to remain behind in England for at least a little while. Winthrop frantically organized the expedition, gathering everything from ships to horses to provisions to colonists. He tried to restrict the passengers to only the most god-fearing, but he quickly realized the colony would need a wide range of skilled workers. The trip was incredibly expensive for the average family. Some paid in advance, others–mostly tradesmen–were to get land in the new land, and some traveled as indentured servants who would work off their fare at a rate of three shillings a day. Finally, Winthrop needed to arrange some sort of industry for the new colony so it could reward its shareholders back in England. He was able to delay that decision by promising that profits would be distributed at the end of seven years, although it became clear long before then the new colony would never be profitable.
As winter ended Winthrop and a thousand fellow travelers gathered in Southampton to travel to the New World.