He left Amesbury in 1659 after years of conflict with local Puritan leaders, including being fined 30 shillings for providing shelter to Quakers during a rainstorm in 1657. He was among the first group of European settlers to establish his family on the island of Nantucket (then a part of the colony of New York); he, Tristram Coffin and other settlers purchased the land from the Native Americans. In 1671, Macy and Coffin were selected as spokesmen for the settlers, going to New York in 1671 to meet with Francis Lovelace and secure their claim to Nantucket. Macy ultimately rose to the position of Chief Magistrate. The island soon became a haven for Quakers, and many of Macy's descendants were raised in the Quaker faith (his wife Sarah converted to the faith following his death). Macy became the subject of a poem by the 19th-century Quaker poet John Greenleaf Whittier entitled "The Exiles", depicting the plight of Quakers in the religiously intolerant Puritan society of colonial Massachusetts.
Entrepreneur R. H. Macy and actor William H. Macy are among his descendants.
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