Originally, the charter of the Massachusetts Bay Company called for 18 assistants to serve as officers in the new colony to assist the governor. They were to meet monthly in the Court of Assistants to offer advice. Winthrop and the other first officers of the colony changed their role to a combination of legislature and judiciary, with assistants elected annually by the freemen.

A colony is an overseas territory controlled by another country. European monarchs claimed the right to award land in the Americas to European settlers, usually without regard to Indigenous American claims. In England, the monarch awarded charters assigning territory to companies. Winthrop’s colony in Massachusetts was one such colonial enterprise.

The freemen of Massachusetts demanded that the General Court include two representatives from each town in addition to the assistants (who represented the colony as a whole). These local representatives were called deputies.