Jacob Woolley, a Delaware, was one of Wheelock's first two Indian students. He was the cousin of Wheelock's third student, Joseph Woolley. John Brainerd sent Jacob Woolley, along with John Pumshire, to Wheelock late in 1754. While Pumshire died in 1757, Jacob continued studying with Wheelock and entered the College of New Jersey in 1759. He studied there until 1762, when he was expelled for failing his studies and abusing alcohol. It is also likely that there was a woman involved. In 1763, Jacob briefly returned to College before running away and enlisting in the army. Joseph Woolley met a man in Sheffield who described someone like Jacob Woolley teaching there in the fall of 1764, but this identification is not definite. Jacob never seems to have been very invested in becoming a missionary. Especially after his expulsion from the College of New Jersey, he expressed doubts about Wheelock's plans for him and struggled with alcohol. It is likely that he ran away primarily because Wheelock was non-responsive to these concerns.

Eleazar Wheelock was a New Light Congregationalist minister who founded Dartmouth College. He was born into a very typical Congregationalist family, and began studying at Yale in 1729, where he fell in with the emerging New Light clique. The evangelical network that he built in college propelled him to fame as an itinerant minister during the First Great Awakening and gave him many of the contacts that he later drew on to support his charity school for Native Americans. Wheelock’s time as an itinerant minister indirectly brought about his charity school. When the Colony of Connecticut retroactively punished itinerant preaching in 1743, Wheelock was among those who lost his salary. Thus, in 1743, he began operating a grammar school to support himself. He was joined that December by Samson Occom, a Mohegan Indian, who sought out an education in hopes of becoming a teacher among his people. Occom’s academic success inspired Wheelock to train Native Americans as missionaries. To that end, he opened Moor’s Indian Charity School in 1754 (where he continued to train Anglo-American students who paid their own way as well as students who functionally indentured themselves to Wheelock as missionaries in exchange for an education). Between 1754 and 1769, when he relocated to New Hampshire, Wheelock trained approximately 60 male and female Native American students from nearby Algonquian tribes and from the Haudenosaunee (Iroquois) of central New York. At the same time, he navigated the complicated politics of missionary societies by setting up his own board of the Society in Scotland for Propagating Christian Knowledge, although he continued to feud with the Boston Board of the SSPCK and the London Commissioners in Boston (more colloquially called the New England Company). By the late 1760s, Wheelock had become disillusioned with the idea of Native American education. He was increasingly convinced that educating Native Americans was futile (several of his students had failed to conform to his confusing and contradictory standards), and, in late 1768, he lost his connection to the Haudenosaunee. With his inclination and ability to sponsor Native American missionaries largely depleted, Wheelock sought instead to fulfill his ultimate ambition of obtaining a charter and opening a college, which he did in 1769. To fund this new enterprise, Wheelock drew on the £12,000 that Samson Occom had raised for Moor’s Indian Charity School during a two-and-a-half year tour of Great Britain (1765 to 1768). Much of this money went towards clearing land and erecting buildings in New Hampshire for the Charity School’s relocation — infrastructure that also happened to benefit Dartmouth. Many of Wheelock’s contemporaries were outraged by what they saw as misuse of the money, as it was clear that Dartmouth College was not intended for Indians and that Moor’s had become a side project. Although Wheelock tried to maintain at least some commitment to Native American education by recruiting students from Canadian communities, the move did a great deal of damage to his public image. The last decade of Wheelock’s life was not easy. In addition to the problems of trying to set up a college far away from any Anglo-American urban center, Wheelock experienced the loss of relationships with two of his most famous and successful students, Samson Occom and Samuel Kirkland (an Anglo-American protégé). He also went into debt for Dartmouth College, especially after the fund raised in Britain was exhausted.