All in Our Historical Family: The Story of an Outlaw

The Rye Historical Society has started a new blog, “Stories of Rye,” featuring little-known stories about interesting, famous  — and infamous — people who lived in Rye.

The Rye Historical Society has started a new blog, “Stories of Rye,” featuring little-known stories about interesting, famous  — and infamous — people who lived in Rye.


Here is the first of the tales researched and penned by Alison Cupp Relyea, a freelance writer and marketing professional who lives in Rye with her husband and three children.


“There’s one in every family.” We have all heard that saying before, and can think of a relative, distant or close, who brings some element of character to our lineage.


Within the family tree of a prominent colonial family, the Merritts, originally from England and settling in Rye and the surrounding area, there is one family member who stands out from the rest. At the time of the Revolutionary War, the Merritt name was known in Rye, White Plains, and parts of Connecticut. They were property owners and community members, some were Loyalists and some were fighting for American freedom, and one was an outlaw: the legendary Shubael Merritt.


When we think of outlaws, images of the Wild West come to mind. The same is often true when we hear the word cowboy. Long before Americans headed west, however, when the town of Rye was positioned at the center of the much-conflicted Neutral Ground during the Revolutionary War, cowboys and outlaws roamed in our own backyards.


Throughout the war years, lower Westchester County shifted from British occupation to American occupation, but for much of the time was unoccupied. Rye was miles from American lines or British lines, and the unprotected farms, homes, and daily lives of the inhabitants were in constant threat. A group of Loyalists known as the Cow-boys earned their name by chasing farmers off their land and stealing their cows, while another group with American ties, known as Skinners, stole from the enemies along British lines. Beyond these two groups were other individuals who operated outside of the law, outside of any organized group and showed loyalty to no one. They cheated, plundered and murdered, seemingly for fun. These were the outlaws, the most feared men in Revolutionary Rye, and the most memorable of these was Shubael Merritt.


Shubael Merritt’s name conjured up fear for many people in Rye, and his stories, factual or exaggerated, have made their way into Rye legend. With little regard for his family members and even less for strangers, he went about stealing and cheating his way through life and right into death. In a time when laws of the land were just beginning to form and crime and punishment were handled differently than today, many believed that in the end, Shubael got what he deserved.


In one famous example of Shubael’s outrageous behavior, he chased two Frenchmen who were carrying a large amount of gold down King Street, shooting one of them in an attempt to rob them of the money. While he was gathering gold from his victim, the other man escaped across a field and into a nearby home on King Street. Despite the language barrier, the Frenchman explained to the family that he was being chased, and the family hid the man in the cellar. Only moments later, Shubael arrived at their door. Not wanting to seem suspicious, they deny seeing anyone but invite Shubael in for dinner, during which time he grew increasingly agitated at not having found the second man. They managed to stay calm and Shubael left to continue his search, never discovering his target was hidden right below him.


In another Shubael Merritt story, he is said to have put his grandfather, a shoemaker, down a well and leave him there until he promised to give Shubael shoe buckles. While a story like this one may seem slightly humorous, the dark reality of Shubael’s callousness was anything but funny to his family and neighbors. Unfortunately, he found others who were willing to participate in his evil, thug-like games.


As legend has it, one day Shubael was playing a game of cards with another outlaw when they spotted a man and his young son plowing in a field. Shubael challenged the man that whoever lost the game should go into the field and shoot the father. Shubael lost and accepted the challenge and proceeded to shoot the father, an act of cruelty that went beyond the limits of the imagination, even in a time of widespread war crimes and murders.


Many years down the road, when the war was over and Shubael had a long history of terrorizing the town, a young man is said to have tracked Shubael down, shot, and killed him. That young man was the son of the farmer, seeking revenge. The lawmakers and townspeople never sought punishment for the young man’s actions, believing wholeheartedly that the man’s killing of Shubael was justified. While we all know two wrongs do not make a right, in the case of Shubael Merritt, the punishment seems to fit the crime.


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