The only portrait of any Mayflower passenger is of Edward Winslow, painted on one of his extended stays in England. In it, he holds a letter which is signed by his “beloved wife, Susannah.” Edward’s “beloved wife” raised her six children mostly alone; Edward was chosen to conduct business with the King in England for the colony. He died while on a mission to the West Indies to retrieve some British ships.1

Edward was a member of the Leyden congregation in exile in Holland, and was “associated with” (apprenticed to?) William Brewster when Brewster was a commercial printer there.302 As William Bradford (Mills ancestor) was Brewster’s ward and close companion, Bradford and Edward must have known each other well for yaers before they came to America, which may be one of the reasons the two seemed to support each other in their ongoing leadership roles in the colony.133

FREEMAN: As governor, appears at head of "1633" list of Plymouth freemen. In list of Plymouth Colony freemen of 7 March 1636/7. In Plymouth section of 1639 Plymouth Colony list of freemen, then erased and entered in Marshfield section of same list.
EDUCATION: He had a hand in writing Mourt's Relation and also authored three other important pamphlets: Good Newes from new England, or A Relation of Things Remarkable in That Plantation (1624), Hypocrisie Unmasked (1646) and New England's Salamander (1647).
OFFICES: Governor, 1 January 1633, 5 January 1636, 5 June 1644. Assistant, 1 January 1634, 1 January 1635, 3 January 1637, 6 March 1638, 2 March 1641, 1 March 1642, 7 March 1643, 4 June 1645, 1 June 1647, 7 June 1648, 4 June 1650. In Marshfield section of 1643 Plymouth Colony list of men able to bear arms.
ESTATE: In the 1623 Plymouth division of land Edward Winslow was granted four acres as a passenger on the Mayflower. In the 1627 Plymouth division of cattle Edward Winslow, Susanna Winslow, Edward Winslow and John Winslow were the sixth through the ninth persons in the third company.
In the 25 March 1633 Plymouth tax list "Edward Wynslow, Gov[erno]r," was assessed £2 5s., and the same amount in the list of 27 March 1634.
In his will, dated 18 December 1654 and proved 16 October 1655, "Edward Winslowe of a voyage to sea in the service of the commonwealth," bequeathed to "Josia my only son" the entire estate "he allowing to my wife a full third part thereof for her life"; to "the poor of the Church of Plymouth in New England £10 and to the poor of Marsh~field where the chiefest of my estate lies £10"; "my linen which I carry with me to sea to my daughter Elizabeth"; residue to "my son Josias, he giving to each of my brothers a suit of apparell"; "son Josias my executor"; "my four friends Dr. Edmond Wilson, Mr. John Arthur, Mr. James Shirley & Mr. Richard Floyd" overseers "for the rest of my personal estate in England.”138

Edward Winslow was a valued agent for Plymouth Colony, as is evident from the pages of Bradford's history, and for Massachusetts Bay Colony as well. He was in the service of Cromwell's Commonwealth when he died in the West Indies.
No attempt is made in these sketches to trace all the activities of the four Winslow brothers who remained in Plymouth Colony,for they were among the most prolific creators of records in that period. The available literature on these men is scattered, and Edward, at least, deserves a full-scale biography.138

Edward Winslow was twenty-five years old when he arrived at Plymouth in 1620, and he was thirty-seven when he became governor some twelve years later. One of only two men to alternate as governor with Bradford (the other being Thomas Prence) during the 1630s and 1640s, he was probably the most aristocratic of the Mayflower passengers in upbringing, and certainly in outlook (his correspondence with Bay Governor Winthrop shows a thorough underlying belief that some by birth were intended to govern). Following the disabling mistrust engendered by Allerton's questionable dealings, Winslow became the colony's main emissary to England, and he engaged in numerous diplomatic and trade negotiations with the other New England colonies. In 1646 he was chosen by Governor Winthrop and the Bay Colony magistrates to go to England as their representative to defend the Bay General Court from the charges being made to Parliament by [Mills ancestor] William Vassall and Robert Child. In this he was successful, but his presence in England coincided with the height of the Puritan Revolution in England, and people of his experience and competence were needed. After performing various tasks for the Parliamentarians, Winslow was assigned a joint command of the 1655 English expedition which won Jamaica from the Spanish, his fellow commanders being Robert Venables and Sir William Pen (father of the Quaker founder of Pennsylvania). Winslow died during the expedition. At the time Bradford ended his History, Edward Winslow was still alive in England, and the last words of the History are "So as he [Winslow] hath now bene absente this 4 years, which hath been much to the weakning of this govermente, without whose consente he tooke these imployments [that is, Parliamentarian service] upon him," a double lament.303

In July 1621 Edward traveled with Stephen Hopkins and Tisquantum (Squanto) forty miles to Pokanoket to visit Massasoit. On a subsequent journey in 1623 he cured Massasoit of a serious illness, earning his “lasting gratitude and affection.” When Edward returned to Plymouth from England on the Charity in 1624 he brought with him three heifers and a bull, the first cattle in the land.140

“Edward Winslow was a man ‘courtly, learned and fit for lofty emprise.’ ...[H[e was ‘more gentle and lovable than most of his contemporaries.’ He wa snot strictly a religionist, being a tolerant man as evidenced by his friendship for Roger Willimas. He had a strong sense of humor and a gentle cheerfulness which won him friends and made him so invaluable to the colony and its relations to the Indians....He was not only a man of action and affairs, but a student, and a voluminous writer. Next to Bradford, Winslow is the man to whom Plymouth Colony owes most.”140

The WInslows’ home in Marshfield was called “Careswell” in memory of Edward’s English home, and part of their land later became home to Daniel Webster.140

As sad as any of the facts of Plymouth’s desertion of the original principles of its founding, is the defection of Edward Winslow from the ideals of his early associates — Bradford, Brewster, Carver and Robinson. He was the youngest of the Pilgrim fathers and his radiant personality shines from the pages of Of Plimouth Plantation and Mourt’s Relation with the freshness which defies the passage of time. In this strange land he formed a wonderful friendship with the native inhabitants and his colorful descriptions of the rough times he experienced in his diplomatic conferences with Plymouth’s neighboring Chieftain, Massassoit, are a precious part of our country’s history. He seemed able to get along with everyone, everywhere, and certainly the success of that first New England colony was greatly due to this ability of his, an ability which would be employed by Winthrop and by the English Parliament later on. We believe that we know Winslow’s excuse for deserting the Plymouth Colony for the Bay Colony, and we understand it. He had caught the fever of the Massachusetts Puritan leaders to form a separate “nation” free of all restraints from the mother country, and was willing to work for this, even though it meant giving up some of the original ideas of freedom held by the Pilgrims. As an able diplomat he was often sent to England on the business of Plymouth Colony. And while he was there he must have seen that the wind was blowing towards a strong independent colony, which Massachusetts Bay alone seemed capable of controlling. Finally, in 1646, he went to England in behalf of the Puritans at the Bay, petitioning Parliament to refuse the right of appeal from dissatisfied colonists. He was successful, but, ironically, he won his plea on the basis of the tolerance of Robinson’s Plymouth Colony, a tolerance that had almost disappeared — and had never characterized the Bay Colony which he was defending. Winslow never went back to New England, perhaps aware of disservice he had done to the New World in not revealing the true nature of the Puritan rule.304

“Baron Steele of London, took a lively interest in the settlement and progress of the colonies, and was the active President of the first corporation or society, organized in 1649."to aid in publishing the Gospel among the Indians in New England." In the formation and success of this society, Winslow of the Plymouth colony, when in England, was a most zealous and efficient agent.”246

See “William Vassall: A Biographical Sketch” for the interplay of Vassall, Bradford, and Winslow: http://www.millsgen.com/gen/hist/vassall_preface.html

Educated at the cathedral school at Worcester, later moving to Leyden to take up printing with William Brewster.137

In addition to his original shares in the Plymouth enterprise, he invested £60 to obtain ten additional shares.137 This, in addition to his education and career, indicates he may have been one of the wealthier Separatists.

Died the spring after the first winter in Plymouth Colony137