During King William’s War, in 1689, when he was nine years of age, John Gyles was living with his family at Fort Charles. On 2 August, while labouring with his father Thomas near the new fort, he was taken prisoner by Maliseets in the Siege of Pemaquid (1689). His father was killed, one brother was taken by the Penobscot, and only one brother escaped. John was conveyed up the Penobscot River, across portages to the Chiputneticook Lakes, and on to the main Maliseet village Meductic.
For six years, Gyles was a slave to the Maliseets. He was forced to serve as drudge to one of the many small hunting parties that moved as far north as Gaspésie and endured harsh treatment.

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