In 1778, he and Joseph Brant, a Mohawk chief, led a company of Tories and Indians in the raid that culminated in the Cherry Valley Massacre. He has been blamed for the deaths of the many women and children who were killed on that occasion. He fought in the Battle of Johnstown and was killed on October 30, 1781, while retreating back to Canada in a skirmish with rebel troops (2nd Albany County Militia Regiment) and the Tryon County militia under Marinus Willett in the Mohawk Valley.