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Michael Kenway was an American soldier and later bandit born in Connecticut in 1848. A member of the Kenway family, Michael was the son of a mercenary that was killed during the American Civil War. Michael spent his teenage years training with his uncle, who was also a U.S soldier. Upon coming of age, Michael joined the United States Army in 1871 and first saw combat during a border dispute in Dakota. After another engagement with criminals that left Michael wounded in 1873, he deserted the Army and returned to Connecticut, where he fell in with a gang of mercenary pirates, most of whom were veterans of the Civil War. The pirates raided several merchant ships for over two years as they traveled along the continental coast. The group eventually encountered a battle off the coast of southern Alaska with the U.S Navy that left their ship destroyed. Michael was one of only seven survivors. What remained of the privateers traveled on horseback through the mountains until they reached the midwest, where they began operating as bandits.

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