Behind the Culper Spy Ring: Abraham Woodhull and Caleb Brewster

by | Mar 27, 2018 | Heidi's Updates

So glad you could join us as we continue our mini-series exploration of the Culper Spy Ring members, how they each play into the hit series Turn: Washington’s Spies (AMC), and what part the members play in my upcoming release, The Hidden Side.

Today we’re going to look at Abraham Woodhull and Caleb Brewster, two important members of the ring.

Abraham Woodhull, Code Name: Samuel Culper

Childhood friend and schoolmate of Benjamin Tallmadge, Abraham was fairly content to stay out of the politics raging through the colonies. He kept to himself for the most part, but living beneath the occupation of the King’s Army must have bothered him, for he did take his friend Benjamin up on his offer to help General Washington obtain information.

No doubt Major Tallmadge turned to Abraham because they already shared a bond of trust. Spying was not an honorable business, and in a field where double agents abounded, Benjamin would have wanted someone he could trust— someone who already had an excuse for being in enemy-occupied Manhattan.

(Photo above from American Gallery by Vance Locke. Depicts Abraham Woodhull (left) and Caleb Brewster exchanging information. I love how Locke conveys their unique personalities so well in the painting.)

Abraham was an unmarried farmer at the time of the Revolution. He was small and frail. His older brother had died, and Abraham had taken over the family farm, two ailing parents and two sisters depending on him.

So why did Abraham choose to risk so much?

We’re not sure, but certainly there are some important considerations to give us a clue or two. Remember, the Long Islanders had been living beneath the King’s Army for nearly two years now. The soldiers lived in their houses, took their beds and fuel and food as they saw fit. Certainly Abraham’s farm had seen its fair share of harm done by the occupation.

The death of his cousin, General Nathaniel Woodhull, may have been another reason for his espionage activities. Nathaniel had fought at the Battle of Long Island, but was later mistreated by the King’s Army and left to languish, abused, in a prison weeks before he finally died.

Certainly these are adequate motivation for Abraham, but being asked by one of his closest friends to help General Washington? Abraham no doubt thought it a worthy way to contribute to the freedom of the colonies.

Already making regular trips to Manhattan to bring food to the army, Abraham also had a sister who owned a boardinghouse in the city with her husband. He had plenty of reason for being in the city. Why not try to help the cause of the Continental Army while he was at it?

In TURN: I appreciate Abraham’s character in TURN. I have a feeling he’s portrayed with a bit more courage than he actually may have had (which makes the show all the more exciting!). In TURN, he is often at odds with his father, who is a Loyalist. There is no evidence of this in actual history, but it contributes to the conflict and tension of the show. Another conflict that TURN introduces is a marriage and child, and intense feelings of Abraham for Anna Smith Strong (more to come on her in a later post). In actuality, Abraham did not marry until nearly the end of the war, and there is no evidence that Anna was ever more to him than a neighbor.

In The Hidden SideI have tried to remain as true as I could to Abraham’s actual character. In my book, Abraham is good friends with my historical heroine, Mercy Howard. Mercy feels guilt over her Uncle’s role in leading General Howe through Jamaica Pass to successfully defeat General Nathaniel Woodhull in the Battle of Brooklyn. 

(Photo to the right is courtesy of Three Village Historical Society.)

Caleb Brewster

Another childhood friend of Benjamin and Abraham, this fierce man was a former whaleboatman who was said to have a quick wit and a rather rude sense of humor. It was likely he who took Abraham’s messages of intelligence across the Sound to Patriot-occupied Connecticut.

Interestingly, he was the only member of the ring who refused to take an alias. He was also one of the first who spoke about his espionage role in the war after it was over.

In TURN: As far as I can tell, it seems this character is one that is played incredibly close to his actual role in history. The writers of TURN show Caleb as he was—bold, daring, lively, and willing to go to great lengths, not only for his friends, but for the freedom of the colonies from oppression by the redcoats.

In The Hidden Side: Alas, as much as I love Caleb’s feisty personality, he is only mentioned in passing in my story. My contemporary characters, however, live on a real street named after him called Brewster Court in East Setauket, NY.

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