Cheeshahteaumuck, the son of a Nobnocket (West Chop) sachem, was born into the Wampanoag tribe on Martha's Vineyard and he received a formal education.

[1] He and his classmate Joel Hiacoomes were taught on the Vineyard by Peter Folger, the maternal grandfather to Benjamin Franklin.

This short letter, addressed to "most honored benefactors," contains references to Greek mythology, Greco-Roman philosophers, and Puritan theology.

[2] In 1674, Daniel Gookin, writing about American Indians in New England, described Cheeshahteaumuck's death and how "Caleb, not long after he took his degree of bachelor of art at Cambridge in New England, died of a consumption at Charlestown, where he was placed by Thomas Danforth, who had inspection over him, under the care of a physician in order to his health; where he wanted not for the best means the country could afford, both of food and physic; but God denied the blessing, and put a period to his days.

"[7] The Harvard Foundation unveiled a portrait of Cheeshahteaumuck on December 16, 2010, in the Annenberg Hall,[8] painted by Stephen E. Coit.