Famed Tory outlaw Claudius Smith meets his end on the gallows on January 22, 1779 in Goshen, New York. In the wake of his death, Patriot civilians hope for relief from guerilla warfare in upstate New York.

Born in Brookhaven, New York, in 1736, Smith moved with his family to Orange County, New York, in 1741. Thought to have fought with Mohawk leader Joseph Brandt as a Tory defender of the crown during the New York campaign of 1777, Smith earned the label “Cowboy of the Ramapos” for his use of guerrilla tactics against Patriot civilians. Smith and his cohorts stole livestock and ambushed travelers on the Orange Turnpike between Canada and New York from the cave now memorialized as “Claudius Smith’s Den” in Orange County’s Harriman State Park.

Smith managed to escape justice until his gang murdered Patriot Major Nathaniel Strong in the course of a robbery. Patriot Governor George Clinton then issued a warrant for his arrest, offering a $1,200 reward for the capture of Smith, who was described as “7 feet tall” in his wanted poster. Captured on British-controlled Long Island by vigilantes in October, he and other members of his gang, including one of his sons, were returned to Patriot territory and hung near their home turf in Goshen.

Despite his less than savory exploits, Smith earned a reputation as a “robin hood” because he targeted the wealthy but was said to be generous with the poor. Because his mother reputedly warned him that, unless he reformed, he would “die with his boots on,” Smith removed his footwear before he was hanged. Two of Smith’s three sons belonged to his gang—one was hanged with his father; another took over the gang upon his death.

Legend has it that Claudius Smith’s skull was filled with mortar and included in the edifice of the Goshen Court House.