When the insurrection, instigated by the French revolutionists, broke out in the eastern part of the island, Jack hastened to join the insurgents, and was cordially received by Fedon, who intrusted him with an important mission, which he executed with such adroitness as to gain the confidence of the chief, who appointed him to a high command in the army.

Jack was one of Fedon's most efficient officers, and signalized himself by his bitter hatred to the whites, and the zeal with which he abetted his chief in the horrid scenes of cruelty that were enacted.
When the insurrection was quelled, Jack Shadow, although wounded, made his escape, with some others of the most obnoxious rebels, to the woods and mountains in the interior of the island.

They endeavored to conceal themselves from the pursuit of the whites, but in the course of one or two years were all, with the exception of Jack, ferreted out and shot when apprehended, or taken to jail, tried, and hanged.
Jack, however, remained in the mountains.

A large reward was offered for him, dead or alive; and parties of armed men often scoured the woods, hoping to find his lair and shoot or capture the rebel chief.

But though it was known he was hid in a certain part of the island, he eluded all endeavors to arrest him for ten or twelve years, and might perhaps have died of old age, had he not been betrayed by his wife.
It was subsequently ascertained that Jack had erected a hut by the side of a ledge of rocks, which was almost inaccessible to a stranger; and this hut, being surrounded with bushes and undergrowth, and covered with vines, could not be recognized as a habitation by any one unacquainted with the fact.