He used his cross-cultural knowledge largely for personal economic and political gain, but at the end of his life he also turned it to the benefit of his Nipmuc kin.

He was deeply enmeshed in the economic and political workings of the English empire, particularly the land market; he was one of the few American Indians to study at Harvard College during the seventeenth century; he was one of the first American Indians to work as a commercial transatlantic sailor, a vocation that enabled him to sail to London at least twice and obtain an audience with King Charles II.

Eliot recorded insightful questions that Wompooas's wife asked during his teaching sessions, as well as the speech she gave her children before her death, and he reported that Wampooas urged his fellow Christian Indians to prepare to settle and establish a Native congregation at Natick, "that there the Lord might rule over you, that you might make a Church, and have the Ordinance of God among you.

Wompas became fluent in English as he assisted the Heaths in their farm labor, participated in daily religious observance, and attended church on Sundays.

He was also one of a handful of Nipmuc and Massachusett Indians who attended the Roxbury grammar school run by Daniel Weld.

[2] John's early education in Nipmuc Country prepared him for his adult role in the community, including hunting, fishing, tracking animals, wayfinding by the stars, and learning the religion and traditions of his people.

He learned to speak, read, and write in English, Latin, and Greek, and he later improved those skills by transferring to the Cambridge Grammar School, whose instructor, Elijah Corlett, was proficient in teaching Native students.

[17] Wompas quickly began selling some of this land to English investors, and his profits may have funded his purchase of a house near Boston Common in 1667.

Nineteenth-century antiquarians liked to point out that this house, the present site of St. Paul's Episcopal Church, was the only structure in seventeenth-century Boston owned and occupied by Indians.

While Wompas did take steps toward that end, including initiating a lawsuit against an English squatter in Nipmuc Country, he also took the opportunity to line his own pockets by selling some of the land he was supposed to protect.

[22] Such actions created legal tangles that prevented English claimants from securing these land parcels for nearly fifty years after Wompas's death.

[24] This decision probably also made him one of the most highly educated common sailors in the Atlantic World, one "who could recite and read Latin and Greek, along with a smattering of Syrian, Chaldaic, and Hebrew.

[26][27] His life as a sailor connected Wompas to a transatlantic sailing community in places such as Boston and New York in the colonies and the London suburbs of Ratcliffe and Stepney in England.

They brought with them two literate, Christianized Nipmuc boys to counter complaints that the colony had abused Native people.

[33] The situation for American Indians had also deteriorated drastically in Wompas's absence; the fighting of King Philip's War between English and Native people in New England led to widespread suspicion of Indians, including those allied with the English, and restrictions on where Natives could live, travel, and do business.

[41] The king wrote another letter on Wompas's behalf, proclaiming that "not only the Petitioner but all such Indians of New England as are his subjects and submit peaceably and quietly to his Majesty's Government, shall likewise participate in his Royall Protection," and sent it to the governor of Connecticut on March 28, 1679.

While he left a large amount of land to English colleagues, he specifically reserved all of Hassanamesit for his Nipmuc kinsmen John Awassamog, Norwaruunt, and Pomhammell.