Masconomet survived an epidemic of hepatitis that wiped out ninety percent of the Pennacook population (Rattigan). In an attempt to combat the conditions and life without a tribe, the Sagamore formed a friendly relationship with the Puritans and Governor John Winthrop, where he was welcomed into the colonial society (Waters). Not less than a year later, Masconomet was forced from the colonists’ houses, banished from the community due to his need to antagonize another tribe called the Tarrantines, a feared tribe that was known for creating chaos and destruction within colonies (Waters). In a desperate attempt to assimilate into European culture in the colonies, Masconomet sold his land, stretching across Cape Ann, for 20 pounds in the hopes of gaining the ability to trade with the colonists for tools of monetary usefulness (Waters). Unable to succeed on his own, Masconomet went to the General Court in 1643 for protection. Along with five other groups, he was granted this protection from the Tarrantines as long as he followed Christian law (Waters). He was given a six acre plot where he spent the rest of his life (Waters). There is minimal information about Masconomet and his life; Native Americans did not have a written language, mostly conveying information based on pictures, which is difficult for historians to decipher. All facts on Masconomet are based on European recounts of history and discussions with Masconomet, so the truth of his life and how Masconomet conducted himself is truly a mystery. 

After Masconomet passed away, he was buried with his rifle, tomahawk, and other artifacts; when his wife passed, she was buried next to his grave (Waters). However, in March of 1659, Robert Cross dug up his grave, carried his skull on a stick, and paraded it through the streets of Ipswich. Cross was imprisoned, fined, and forced to put the bones back in the grave (Harris). In Native American culture, it is believed that once a grave is disturbed the spirit will wander around until a proper ceremony is performed by members of their tribe (Harris). A ritual was finally done in 1933, and Masconomet grave is now on a road past the Sagamore Hill Solar Radar Observatory, and, in 1910, a stone and plaque were placed on the hill as a memorial (Waters, Harris). The only objects that can be left there are traditional native offerings, which include prayer bundles, sage, and tobacco (Harris). 

There are not any portraits of chief Masconomet that were painted in his lifetime; all current portraits are based on descriptions given by English settlers and their ancestors, often including incorrect depictions (Hauck 4). Many of the paintings showed Masconomet wearing a War Bonnet, a headdress that was not worn by Native Americans who lived in the New England area (Waters).