The Penobscot lands, lying east of Penobscot River, were a part of Acadia, which was given back to France in 1667 by the Treaty of Breda, though the English claimed that the country between the Penobscot and the St. Croix River was included in the Duke of York's patent. The Indians were brought under French influence by Jean-Vincent d'Abbadie de Saint-Castin, known as Castin in the New England Chronicles. Castin settled among them, and married a daughter of Madockawando.
When King Philip's confederacy rose against Plymouth Colony, the eastern Indians and the English settlers in Maine and New Hampshire became involved in war. The Penobscots were the first to treat for peace among the Indian tribes, and offered to enter into an alliance with the English. Articles were drawn and subscribed at Boston on 6 November 1676, and the peace was ratified by Madockawando. The English, however, found a pretext for renewing hostilities. The Indians were successful, and destroyed all the English settlements in that part of Maine.
In 1678 a treaty was made at Casco whereby the English were permitted to return to their farms on the condition of paying rent to the Indians. The peace was kept until the territorial dispute with France was brought to an issue in 1688 by Gov. Edmund Andros, who arrived among the Penobscots in a frigate, plundered Castin's house, and destroyed his fort. The Indian chiefs took up the quarrel, being abundantly supplied with arms by Castin, attacked the white settlements, and thus began King William's War. Madockawando took a prominent part in the atrocities of this war.
When the English built Fort William Henry at Pemaquid he hastened to Quebec to carry the intelligence to Frontenac, but divulged it to John Nelson, whose messengers warned the authorities in Boston of Iberville's expedition. In 1693 the English gained Madockawando's consent to a treaty of peace, yet he was unable to persuade the chiefs who were under the influence of French Jesuit emissaries, and was compelled to recommence hostilities. The Indian war continued for more than a year after the Peace of Ryswick had been concluded between France and England, until by the Treaty of Casco of 7 January 1699 the Penobscots acknowledged subjection to the crown of England. In the later operations Castin was their leader, Madockawando having been, perhaps, one of the chiefs treacherously slain by Capt. Pascho Chubb at a conference at Pemaquid in February 1696.
In Castine, Maine, there was a plaque on Dyce Head Lighthouse Rd. that read:
UPON THESE HEIGHTS, in 1692, James [Thomas?] Giles [brother of John Gyles], a boy, and an Englishman, taken at Casco (Battle of Falmouth (1690)?), held in slavery by MADDOCKAWANDO for attempting to escape, were tortured by fire, compelled to eat their noses and ears and then burned to death at the stake. 
- This article incorporates text from a publication now in the public domain: Wilson, James Grant; Fiske, John, eds. (1900). "Madockawando". Appletons' Cyclopædia of American Biography. New York: D. Appleton.
- Madockawando: Chief and Shaman (Jud Hartmann Gallery website; visited December 30, 2009)