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Squanto has a unique background, beyond being the only surviving resident of Patuxet. He had been already been captured twice by Europeans and sent across the Atlantic, learning English and the ways of the Europeans. Returning home, he arrived at his native village to find it deserted after the plague. Unfortunately for Squanto, after this string of experiences Massasoit didn't trust him and viewed him as a threat. He viewed the Pilgrims as an opportunity to get away from Massasoit and join a community that needed his experience.
His role as the primary communicator between the Pilgrims and the Native Americans gave him power - and he quickly started playing the two sides against each other. In the words of Governor Bradford:
Squanto sought his own ends and played his own game, by putting the Indians in fear and drawing gifts from them to enrich himself, making them believe he could stir up war against whom he would, and make peace for whom he would. Yea, he made them believe they kept the plague buried in the ground, and could send it amongst whom they would, which did much terrify the Indians and made them depend more on him, and seek more to him, than to Massasoit. Which procured him envy and had like to have cost him his life; for after the discovery of his practices, Massasoit sought it both privately and openly, which caused him to stick close to the English, and never durst go from them till he died.
Once Massasoit learned that Squanto was manipulating the situation for his own gain, he ordered the Pilgrims to hand him over (for execution). This placed them in a difficult spot - Massasoit was a critical ally, but Squanto was an critical supporter - between teaching them how to live off the land and helping communicate with other natives. The Pilgrims stalled until they had an opportunity to trun down the request - and Massasoit let the matter drop.
Squanto did not survive very long after that. While returning from a meeting with the Wampanoag, he started bleeding from his nose. Shortly thereafter, he died. Many historians suspect he was poisoned by Massasoit's people.
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