At some point in the late 1830s American author Samuel G. Drake either theorized, or encountered someone else's theory, that these names are all derived from words for "child" and "bear" - he made the claim for the first time in the 1841 8th edition of his Indian Biographies.

One of the key native figures in the colonial history of Massachusetts, New Hampshire, and Maine, he is believed to have been born between 1550 and 1570, and had died by 1669 (his birth and death dates are imprecise, and reckoning is skewed by the claim of one reporter, who says that he met Passaconaway when the latter was 120 years old).

During his lifetime English colonial settlement in New England began in earnest, intersecting with an ongoing series of socio-political and demographic changes arising from warfare over the fur trade and the introduction of Eurasian diseases.

He was a powerful and widely respected powow (a ritual expert and mediator between humans and spirits similar to a shaman); English accounts by figures like Thomas Morton and John [Eliot?]

[6] Prior to, and during the early period of, colonial encroachment Passaconaway presumably followed traditional New England Native lifeways[7] in the Pennacook territories around the Merrimack River, moving among established village sites like Amoskeag and Pawtucket seasonally, which accounts for his historical association with several places in New Hampshire and Massachusetts.

Passaconaway was one of the first native chieftains to lease land to English settlers in New England, and the 1629 Wheelwright Deed (the authenticity of which is debated, but which is generally accepted as legitimate) specifies that Passaconaway and other sachems were willing to sell territory to the English for the explicit purpose of making alliances against the Tarrantines (an exonym given to a confederation of Native groups in today's Maine which made a habit of attacking the groups in southeast New England) and the Mohawks.

Passaconaway voluntarily abdicated in approximately 1660 and designated his second son Wonalancet as next sachem of the Pennacook (a position he actively held no later than 1664), which announcement was part of a larger speech he delivered urging his people to always keep peace with the English colonists.

[9] In October 1665, Passaconaway's daughter, Bess (wife of Nobb How), sold the Pennacook territory called Augumtoocooke (present-day Dracut, Massachusetts) to Captain John Evered, for the sum of four yards of "Duffill" and one pound of tobacco.

Legend says that after the preacher died suddenly from an illness, Passaconaway decided to step down from his position of authority, announcing before an enormous crowd at the yearly native gathering that his son Wonalancet was now sachem of the Pennacook.

The other most frequently presented image of Passaconaway is a drawing that first appeared in Potter's History of Manchester, and has a somewhat better connection to period-accurate clothing, but the conspicuously displayed bearskin was almost certainly included due to the folk etymology of his name (discussed above).

Anglo-American legends about Passaconaway's death say that his body was buried in a cave in the sacred native mountain Agamenticus in southern Maine, and that at least one member of his people saw his spirit carried up to the Great Spirit's earthly abode of Agiocochook (Mount Washington) atop a sled pulled by wolves and covered with hundreds of animal skins given to him by his people and his fellow sachems.

Shortly before his death, Passaconaway was granted extensive tracks of land on both sides of the Merrimack as far north as the Souhegan River (although others, like Potter, have claimed without evidence that he settled in present-day Concord).

[13] Mount Passaconaway, a 4,043-foot (1,232 m) summit in the Sandwich Range of the White Mountains lying between the village of Wonalancet and the Kancamagus Highway, bears the sachem's name.

[14] The Daniel Webster Council of the Boy Scouts of America, which serves most of New Hampshire, honors Passaconaway by naming their Order of the Arrow lodge for the sachem.