The second chapter of 1491 is a mix of historical research and commentary; this amalgam presents a narrative and argues for its validity. The author uses the frame of an ancestor, John Billington, to ground some of the historical context. John Billington is one of the Pilgrims whose survival was aided by the "friendly Indian" Squanto. This chapter attempts to deconstruct the legend of Squanto by presenting historical and cultural context for his meeting with and aiding the Pilgrims, as well as biographical information from his life.

The first story tells of Squanto’s origins among the Pawtuxet people, his early life, his alignment with the Wampanoag tribe, and his eventual aiding of European settlers. Beginning with the full name, Tisquantum, which translates roughly to "wrath of the divine," the bulk of Squanto’s life falls outside of the popular story about him. Raised and trained to be an advisor and personal guard of the sachem, or chief, Tisquantum was kidnapped in 1614 by English sailors and sold into slavery in Spain. Soon escaping, he returned to Pawtuxet lands (near present-day Cape Cod), to find his tribe lost to disease. Having learned English from his European captors, he enlists his aid with the Wampanoag as a translator, diplomat, and liaison.