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Massasoit was the leader of the Wampanoag. Though he is not mentioned by name in any English accounts prior to 1621, he and his brother Quadequina are undoubtedly the "two Kings, attended with a guard of fiftie armed men" that met Captain Thomas Dermer at Pokanoket in May 1619, when he was returning Tisquantum ("Squanto") to his homeland.

On March 22, 1620/1, Massasoit decided to pay a visit to the Plantation at the invitation of Tisquantum who had first visited with the Pilgrims shortly before. In an almost identical scenerio as that of Thomas Dermer a year earlier, he and his brother along with 60 armed men came and stood at the top of the hill overlooking the Colony. Edward Winslow was sent to him with some knives and a copper jewel chain as gifts--and Massasoit was told that the Pilgrims only desired peace and trading. Massasoit was told that King James of England saluted him with love and peace, and accepted him as a friend and ally. Massasoit liked what he heard, because the English would make powerful allies against his enemies in the region. The Pilgrims wanted a peace treaty, and so he willingly undertook the negotiations.

At the peace negotiation, he was met at the river by Captain Myles Standish and William Brewster. They saluted one another and he was taken to William Bradford's house for the negotiations with Governor John Carver. Massasoit was given some liquor, fresh meat, and some biscuits. For the peace treaty he agreed that none of his Indians would harm the Pilgrims--and if they did he would send them to the Pilgrims for punishment. And if anyone did unjust war against them, or against the Pilgrims, they would come to each other's aid. They also agreed that when trading, the Indians would not bring their bows and arrows and the Pilgrims would not bring their guns.

In 1621, Edward Winslow described Massasoit as follows:

In his person he is a very lusty man, in his best years, an able body, grave of countenance, and spare of speech. In his attire little or nothing differing from the rest of his followers, only in a great chain of white bone beads about his neck, and at it behind his neck hangs a little bag of tobacco, which he drank and gave us to drink; his face was painted with a sad red like murry, and oiled both head and face, that he looked greasily. All his followers likewise, were in their faces, in part or in whole painted, some black, some red, some yellow, and some white, some with crosses, and other antic works; some had skins on them, and some naked, all strong, tall, all men of appearance . . . [he] had in his bosom hanging in a string, a great long knife; he marvelled much at our trumpet, and some of his men would sound it as well as they could.

In September 1623, Emmanual Altham described Massasoit in a letter:

And now to speak somewhat of Massasoit's stature. He is as proper a man as ever was seen in this country, and very courageous. He is very subtle for a savage, and he goes like the rest of his men, all naked but only a black wolf skin he wears upon his shoulder. And about the breadth of a span he wears beads about his middle.

Massasoit is listed in 100 Native Americans Who Shaped American History.