Governor Massachusetts Bay Colony: 1629-1630, 1644-1645, 1649-1650, 1651-1654, 1655-1665
Unlike the Pilgrims who didn't know what to expect in the "New World," the first Governor of the Massachusetts Bay Colony had a good idea of where he was going. When the Colony sent its first ships to what would become the Massachusetts Bay Colony, they were led by Governor John Endicott who had helped lead the Dorchester Bay Company's settlement on Cape Anne in the 1620s.
Endicott and the settlers wintered with the remainder of the Dorchester Colony in Salem. Then in June and July of 1630, they welcomed eleven ships bringing over 1,000 better-equipped Puritan settlers. Together the settlers set off with the Colony's new leader, John Winthrop, who had arrived with them.
Though Endicott was replaced by Winthrop, he had earned the respect of the colonists who benefited from his knowledge and strong leadership during that first winter. He remained an active voice in the Colony's politics. Over a decade later, he would be elected Governor again, serving almost continuously from 1644 to his death in 1665.
With survival no longer an issue, Endicott's stern leadership focused on suppressing religious dissent. Today, he is most often recalled for advocating the torture and execution of Quakers, most notably Mary Dyer. Today, Dyer is memorialized in front of the State House.