Cutshamekin was the brother of sachems Chickatawbut and Obtakiest[2] who both died in 1633 during a smallpox outbreak which decimated many of the Native Americans in the area.
[4] In 1643/44, Cutshamekin agreed that he and four other sachems from as far away as Mount Wachusett would sign a formal treaty with Governor John Winthrop submitting to the Massachusetts Bay Colony's authority in return for defense from their enemies.
[5][6] In 1646 the missionary John Eliot preached his first missionary sermon to Cutshamekin and his followers at their wigwam near Israel Stoughton's grist mill and Richard Callicott's trading post near what is now Dorchester, Lower Mills.
[8] Cutshamekin died in 1654 and was buried on his remaining 40 acres of land in Dorchester "in a ceremony fitting a sachem: on tree branches around his mound grave were draped his wealth of furs.
[1] Some historians theorize that "Jamaica Plain" was named after Cutshamekin and that "Jamaica", though a different letter "A" pronunciation, is an Anglicization of the name of Kuchamakin, who was regent for the young Chickatawbut, sachem (chief) of the Massachusett tribe.