Twenty-one years after Henry Hudson discovered Manhattan Island, John Wintrop, and his fleet of five ships, depart Yarmouth, Isle of Wight, on April 8, 1930. Onboard the flagship Arbella, the English lawyer leads a group of nearly 1,000 Puritans on their one-way journey to America. Overcome by the religious persecution and economic challenges of England, these settlers undertake the arduous voyage in hopes of finding freedom and prosperity in America.

Either prior to or during the voyage, Winthrop delivers a prophetic sermon to his crew titled A Model of Christian Charity (commonly known as A City on a Hill). Within his address, critical details shape the foundation of America, emphasized in the following excerpt:

GOD ALMIGHTY in his most holy and wise providence… thus stands the cause between God and us. We are entered into Covenant with Him for this work… The Lord will be our God, and delight to dwell among us, as his one people, and will command a blessing upon us in all our ways. So that we shall see much more of his wisdom, power, goodness and truth, than formerly we have been acquainted with. We shall find that the God of Israel is among us, when ten of us shall be able to resist a thousand of our enemies; when he shall make us a praise and glory that men shall say of succeeding plantations, "the Lord make it likely that of New England."

For we must consider that we shall be as a city upon a hill. The eyes of all people are upon us. So that if we shall deal falsely with our God in this work we have undertaken, and so cause him to withdraw his present help from us, we shall be made a story and a by-word through the world. We shall open the mouths of enemies to speak evil of the ways of God, and all professors for God's sake. We shall shame the faces of many of God's worthy servants, and cause their prayers to be turned into curses upon us till we be consumed out of the good land whither we are a going.

Entering into the forementioned covenant (a solemn promise between two or more parties to perform certain actions), the English convoy arrives at Salem, Massachusetts, in June of 1630. By September, these colonists establish the City of Boston. In time, they dedicate a coastal island, known today as Governor's Island, to John Winthrop. Like Henry Hudson, these pioneers have no way of foretelling the shocking story that will arise from this island 371 years later.