 Cutshamekin was the brother of sachems Chickatawbut and Obtakiest who both died in 1633 during a smallpox outbreak which decimated many of the Native Americans in the area.In the 1630s, Cutshamekin sold much of the tribal land that he controlled around the Neponset River, including deeding what is now Milton, Massachusetts to Richard Callicott, with the exception of 40 acres reserved near the Neponset River near Dorchester Mills including what is now Dorchester Park and the Ventura Playground in the Neponset River Reservation.By selling much of the tribe's land, Cutshamekin isolated many of his followers.