The most fruitful way to explore the similarities and differences between Squanto and Powhatan is to examine their attitudes toward the English settlers each encountered.
By the time Squanto experienced the settlers in Plymouth, he had already spent time among other English settlers. This prior encounter shaped his attitude toward English settlers in general. By the time Squanto came into contact with the Plymouth Colony, he already spoke English fluently, accelerating his acceptance among the settlers. For this reason, he did not exhibit a great deal of distrust toward the colonists. In addition to the varieties of game in the area, he introduced the Separatists to new crops, showing them how to successfully cultivate them. Over time, Squanto's influence among the settlers and the tribes in the area went to his head. Seeing their fear of the settlers, Squanto even went so far as to extract tribute from the area tribes, threatening to have the English unleash the plague on them or promising to keep them in the good favor of the colonists. The ultimately led to his fall from grace, as both the tribes and the colonists discovered his treachery.
Unlike Squanto, who began his relations with the settlers in Plymouth from a position of trust, Powhatan made his initial distrust of the Jamestown settlers very clear. Like Squanto, Powhatan had encountered English settlers before. Fearing that the settlers were merely adventurers out to make their fortunes, Powhatan went so far as to head small-scale raids against the settlement's fortifications, more to learn about the colonists. Powhatan's distrust eventually began to soften, even going so far as to permit members of his immediately family to move freely to and from the settlement at Jamestown. The evidence suggests that Powhatan's attitude toward the English settlers changed little, if at all, despite continuous blunders on the part of the colonists.