Last night I went to the monthly meeting of the Winthrop Improvement and Historical Association on the grounds of the Deane Winthrop House to hear John Winthrop Sears speak about his ancestral uncle. Deane² Winthrop (1623–1704) was Governor John¹ Winthrop’s sixth son (the third son by the Governor’s third marriage), and he long outlived his full and half-siblings. He did so in one of the oldest wood-framed houses in the Commonwealth, one continuously occupied since the seventeenth century, on Pulling Point – now the City of Winthrop.

As John pointed out in his remarks, the Winthrops were peculiarly rich in lands, and it seems that Deane was inclined to leave Pulling Point in 1647 to join his half-brother John² Winthrop in Connecticut. Directing his letter to “his very Louing Brother Mr. John Winthrop … at his hous in Pequod,” Deane noted that “I thought tell todeay that I should haue presented my persin to you in sted of these lines but I could by [no] menes persweade Goodman Willi nor Goodman Lathem to helpe driue my Catell nor your hogds which is the reson that I now doe not com. I proffered them twenty shillings to hellpe driue my catill besides what you would haue Giuen them for driuing your hogds. Pray will you reserve that 40s of Goodman Lathum which he owes me. He is to pay it in commodities in shoues and stockiness or cloth at the [same] prise as he bies them here… Your hogds I feare will be lost; thay doe more herme than thay be worth. So I rest Your louing brother Deane Winthrop.” (Winthrop Papers, vol. 5, pp. 162–63)

A year later, Deane was still pondering the land in Connecticut “which was laide out for me” and asking John² to look after it. He offered John a service in return: “Sir I understand that you ded send me your gon but the pinnice that should haue brogt it ded returne backe again: if you plese you may [keep] it for I haue got me one: or if it wants mending if you will sende it I will get it don for you and send it you agin.” (Ibid., p. 278)

Deane Winthrop was a beneficiary when his infant half-brother Joshua² Winthrop (b. 1648) died in 1651. Following their father’s death, the Massachusetts General Court had granted a third of £200 to Deane and another third to his brother Samuel, they “yett having had no portions out of the late Governors Estate nor like to have.” (Vol. 6, p. 103)

During the summer of 1652, John Haynes wrote John² Winthrop noting the welcome arrival of the Rev. Jonathan Mitchell in Hartford “above A weeke since. Wee enquiring after the wellfare of our Frinds in the [Massachusetts] Bay understand by him, That the former Calamity of the fluxe and vomiting breakes oute sadely of late in severall Townes ther, and some have sodeinly dyed of it, and amongst the rest (which I am sorry to relate) the Lord has taken away your Brother Mr. Adam Winthropp who lay sicke but 3 dayes, befor hee went to his perpetuall rest. Mr. Deane Winthrop is alsoe ill of the same disease. The Lord helpe you to beare your losse (for may hee not doe with his owne what hee please) in moderating your soerrowes and cause you withall to rejoice in his gaine.” (Ibid., p. 220)

In the event, Deane recovered from his illness and lived on quietly on Pulling Point. Following John’s death in 1676, he was the last surviving child of Governor John Winthrop. He died in 1704; his widow died in Boston in 1716.