John Cotton Jr.'s maiden voyage to Martha's Vineyard in 1665 must have been a time of soul searching and low expectations. Two years earlier, this Harvard-educated son of a Puritan divine was run out of the Wethersfield, Connecticut, pastorate for sexual indiscretion and a sharp tongue. To rehabilitate his name, Cotton had to perform good Christian service while behaving himself; so some time later, when the opportunity arose to proselytize the Vineyard Wampanoags, reluctantly he accepted the position. One imagines Cotton sailing toward his destination, eyes fixed on the shrinking mainland shoreline, reflecting on his fall from an elite family, college, and pulpit, to become a poorly compensated missionary on a remote island responsible for filling “poor ignorant savages” with a sense of God.

Cotton spent the next year preparing for his work by studying the notoriously complex Wampanoag tongue, but this was hardly enough training, as he discovered when he finally met with an Indian audience at Chappaquiddick on March 6, 1666. He plodded through his inaugural Native-language sermon, and then perhaps breathed a sigh of relief assuming the hard work was done, only to have the Wampanoags shower him with a volley of questions sharpened by two decades of Christian education: “How conscience came to be asleepe or silent in a man at any time?” “Whether Judas was saved or damned?” And perhaps most surprisingly: “Whether John Baptist onely sprinkled christs face with water or plunged him under water?”