Born: October 18, 1595/Droitwich, Worcester, England
Died: May 8, 1655/At sea between Hispaniola and Jamaica

“A fit man to be employed in our present affairs in England, both in regard of his abilities of presence, speech, courage, and understanding…”
John Winthrop, November 1646

Edward Winslow was born in 1595 in Droitwich England. The eldest son of a relatively prosperous family in his youth, he attended the King’s School at Worcester Cathedral before being apprenticed to John Beale, a stationer and printer in London. Before his apprenticeship was concluded, however, Winslow left London around 1617 when in his early twenties and moved to Leiden where he joined with the Separatist church. Here, Winslow married his first wife, Elizabeth Barker. The Winslows and other members of the Leiden congregation would later become Plymouth colonists.

While in Leiden, Winslow worked with the Elder William Brewster to print religious tracts that would be illegal in England at the time. One of those tracts, Perth Assembly, which criticized the King and his bishops resulted in King James issuing an order for Brewster’s arrest, causing him to go into hiding. This political and religious danger likely strongly influenced Winslow’s decision to leave Europe with the other Mayflower passengers. He was deeply involved in planning for the voyage and assisted in writing the various letters attempting to secure funding for the voyage.

After arriving In Plymouth, Winslow lost his wife Elizabeth to sickness during the winter of 1621. On May 12th, he married the recently widowed Susanna White in a civil ceremony, Plymouth’s first wedding.

Though only in his 20s, Winslow soon became the colony’s principal diplomat. He was the first colonist to meet with the Massasoit and shortly afterward was the first to travel to Ousamequin’s home. When Ousamequin fell ill in 1623, Winslow went to Pokanoket and helped him recover, establishing a special bond with the Wampanoag leader that helped cement their alliance.

Winslow was a gifted writer and highly observant. He wrote or contributed to at least six publications about the colonies in New England, the best-known of which is likely Good Newes from New England, published in 1624. In his works he presented historical events in the early colony, Indigenous culture (as he understood it), and reflections on religion and the efforts to colonize the region. His accounts of early Plymouth include many details of Indigenous life. Unlike many other colonists, Winslow established personal connections with some Wampanoag allies.

Winslow served as assistant magistrate (1632-1646) and was elected Governor of Plymouth Colony three times (1633, 1636, 1644). Beginning in 1623, he regularly traveled back and forth to England as an agent to promote the Colony’s interests, secure supplies and financial support, and find markets for goods that the colonists were exporting to England. In 1627, Winslow was made one of the undertakers of the Plymouth Colony debt, making him responsible in part for the trade with Indigenous communities around the colony and the profits from furs and other goods.

Because of complaints made against the colony, Edward Winslow was appointed as agent and sent to England in 1646 to handle the colony’s defense. He did not return to New England after 1646 and never reunited with his wife Susanna in Plymouth.

His talents came to the attention of the new Puritan government established after the English Civil War. In 1655, Oliver Cromwell appointed Winslow a joint head of the expeditionary force that captured Jamaica in 1655. He died of an unknown illness on his return and was buried at sea somewhere in the Caribbean in May of 1655.