TWIH: Enoch Crosby, Spy

A little-known Revolutionary War Spy.

At about this time in 1750, Enoch Crosby is born in Massachusetts. Crosby would go on to be a Patriot soldier, then a spy, during the American Revolution.

When the Revolution began, Crosby was quick to sign up for military service, and he participated in the invasion of Canada in 1775. Afterwards, possibly because of ill health, he returned home for a period of time to recover. But in August 1776, Crosby decided to return to the army.

His path back took him through the so-called neutral ground in New York. It was there that he “fell in company with a stranger,” as Crosby later wrote in a deposition. That stranger mistook Crosby for a Tory. Crosby was “willing to encourage that misapprehension & turn it to the best advantage.” He was introduced to more Loyalists, and gleaned some information about a Tory militia unit then being formed. Then he left his new acquaintances, allegedly to meet up with British forces.

In reality, he headed to the house of Squire Young, a member of a Committee of Safety. He told Young what he had learned.

Young soon introduced Crosby to a committee led by John Jay. Today, Jay is best remembered for being the first Chief Justice of the United States. But back in 1776, he was the chair of a counterintelligence committee just beginning in the State of New York.

Jay and his committee asked Crosby to continue posing as a Tory. He’d be far more useful as a spy! Thus, Crosby was “imprisoned,” and an escape was staged so he could return to the neutral ground without suspicion.

During the ensuing months, Crosby would allow himself to be captured by American forces on many occasions. Usually, his American captors genuinely believed that he was a Tory or were arresting him with other Tories—these Tories were being arrested because Crosby had given them away, of course. It was up to Jay and the committee to help Crosby escape later.

Several stories have been told about his repeated captures and escapes, although some of these stories come from an overly dramatic account of his life, given in an 1828 book. Crosby was alive when the book was published and may have helped the author. But do the stories need to be taken with a grain of salt?

Crosby may have once made an escape with an American sentry, not knowing his true loyalties, firing shots at him. He may have once made his escape because a housemaid drugged his American captors. On another occasion, he may have been seen by someone he knew while in captivity. Shocked and disappointed, that person told Crosby’s family what he’d seen. Crosby’s family spent months believing that he was a Loyalist and a traitor to the American cause.

How awful to know that your family thinks such a thing of you—when the opposite is true! And to be able to do nothing about it.

After several months, life in the neutral ground became too dangerous for Crosby. He was becoming too easily recognized. His usefulness was waning. Crosby conducted his last operation and finally returned home, where he was able to tell his family about his true allegiance. Unfortunately, it seems that he really couldn’t stay there, either. Too many Loyalists hated him. He returned to the army, where he served as a soldier for the rest of the war.

Happily, Crosby was able to retire after the Revolution. He lived out his life as a farmer in Connecticut.

Sources can always be found on my website, here.