Born in 1616, Wenepoykin was the youngest son of Nanapashemet and Squaw Sachem. At a very young age he was installed as Sachem of Naumkeag, or in the present-day areas of Danvers, Andover, and south to Spot Pond. It appears an uncle or other family member helped him rule until he came of age.
Wenepoykin had a tumultuous relationship with the English. They named him Sagamore George. Wenepoykin brought several lawsuits before the court over land and other issues aurrounding the growing English settlements. The courts continually stalled his cases and he never received satisfaction.
He married the daughter of Poquannum who was a sub-sachem in the area known as Nahant. Her name was Ahawayet. They had three daughters and their beauty was legendary. It is believed Wenepoykin's name translated as feather, and his daughters were known as Wenepanaquin, or the plumed ones.
Unlike his brothers, Wenepoykin survived the smallpox outbreak of 1633. Sadly, though, it is believed the terrible ulcers left him disfigured and many referred to him as No-Nose from that point forward. After his brothers died from smallpox, Wenepoykin took control of their domains.
When his mother passed away in 1650, Wenepoykin then took over as Great Sachem of the Massachuset -- and he controlled much of the remaining Indian land north of the Charles River, west to Concord, and north to Andover. His reign would be encumbered by frustration, however, having lost all ability to control the growing English presence on his land.
After years of lost land claims all over his family's domain, and cases stalled in court for years, Wenepoykin joined with Metacomet (King Philip) in the war for Mother Earth. He was the only known descendant of Squaw Sachem to fight with the Indians in King Philip's War. Other family members were known to have helped the English in that bloody, and defining, conflict.
He was taken prisoner in 1675, sold into slavery, and shipped to Barbados. There he spent eight years enslaved. Eventually he was returned to Natick, Massachusetts -- a broken 68-year-old man -- in 1684. He died a few months later at Natick with his sister Yawate by his side.