Turn: The Mystery of the Culper Ring

This article originally ran in April of 2014. We’ve dusted it off in honor of the Turn Season 3 premiere.

In wartime intelligence-gathering, there are three big challenges: obtaining information that your enemy wants to keep secret, transmitting it to your own side, and not getting caught.

The Culper Ring, the Revolutionary War spies who inspired AMC’s drama Turn, managed to do all three. In fact, the central members of that network weren’t identified until the 20th century. They stayed hidden through assumed names, codes, invisible ink, various other subterfuges—and modesty. Those men lived for decades after the war, well into the period when they would have been safe from any retaliation, but never sought public credit for their secret service.

Maj. Benjamin Tallmadge (1754-1835), the Continental Army officer who set up the ring among acquaintances on Long Island, wrote a private memoir about the war for his family. In 1858 his proud family published it for everyone else. But even in that document Tallmadge had guarded his sources’ identity with vague language. In 1778, he recalled, “I opened a private correspondence with some persons in New York (for Gen. Washington) which lasted through the war…I kept one or more boats continually employed in crossing the Sound on this business.”

Tallmadge described going into New York in the summer of 1783, after it was clear the British would pull out. He wrote:

“I found it necessary to take some steps to insure the safety of several persons within the enemy’s lines, who had served us faithfully and with intelligence during the war. As some of these were considered to be of the Tory character, who would be very obnoxious [i.e., unpopular] when the British army should depart, I suggested to Gen. Washington the propriety of my being permitted to go to New York, under the cover of a flag…While at New York, I saw and secured all who had been friendly to us through the war, and especially our emissaries, so that not one instance occurred of any abuse, after we took possession of the city, where protection was given or engaged.”

Tallmadge’s private papers, now owned by the Litchfield (Connecticut) Historical Society, reveal a few clues about the Culper Ring, such as a draft of his letter to Gen. Washington explaining a code system he designed in 1779. A copy of that codebook survives in Washington’s own papers at the Library of Congress, along with reports sent to “John Bolton”—Tallmadge’s code name. But those documents still don’t name Tallmadge’s “emissaries” in New York.

Historians knew that Lt. Caleb Brewster (1747-1827) was part of the network, commanding one of those boats crossing Long Island Sound. Brewster signed his own name to reports describing his missions. But most of the letters he ferried to Tallmadge came from people calling themselves “Samuel Culper, Sr.” and “Samuel Culper, Jr.” When decoded, those letters contained hints of British plans, stories about nearly being caught, warnings that they might soon quit spying—a lot of dramatic detail. But their authors remained a mystery.

The first editor of Washington’s papers, Jared Sparks, quizzed people on Long Island for information about the “Culpers” and came up empty. In the late 1800s a note found in the files of British general Henry Clinton made Nathaniel Ruggles the chief suspect, but he was actually from Guilford, Connecticut, on the wrong side of the Sound.

Then in the early 1900s a local historian and genealogist with the I’m-not-making-this-up name of Morton Pennypacker noticed similarities between the handwritings of the “Culpers” and those of a couple of Long Island businessmen whose papers he was studying: Abraham Woodhull (1750-1826) and Robert Townsend (1753-1838).

Pennypacker began to investigate further. He amassed more evidence about Woodhull, Townsend, and a courier named Austin Roe (1748-1830). Those men never took credit for spying during the war, but their activities matched details in the Culper letters. Pennypacker published his findings first in The Two Spies, Nathan Hale and Robert Townsend in 1930, and then in the much thicker General Washington’s Spies on Long Island and in New York in 1939. The main members of the Culper Ring had been unmasked at last.

Since then there have been more investigations of the Culper Ring within general studies of Revolutionary War espionage. For Washington’s Spies (2006), Alexander Rose took a new look at all the evidence, disagreeing with some of Pennypacker’s conclusions but confirming the basic work of Woodhull, Townsend, Roe, Brewster, and their allies. (Corey Ford’s A Peculiar Service from 1965 and Brian Kilmeade and Don Yaeger’s George Washington’s Secret Six from 2013 present themselves as nonfiction accounts of the Culpers but offer lots of invented scenes and dialogue.)

There are still historical mysteries and debates about the Culper Ring. Was the Tory printer James Rivington, whose delightfully nasty newspaper dispatches harried the Continental cause for years, actually in league with Townsend? Did Tallmadge receive advance information about Gen. Benedict Arnold’s treachery? Who was the “lady” that one Culper dispatch describes as helping to conceal the ring’s activities?

Turn won’t supply reliable answers to those questions—it’s designed only to entertain, and already it’s well off the historical chronology. But there’s plenty of real-life drama in the saga of the Culper Ring.

J L Bell is the author of The Road to Concord: How Four Stolen Cannon Ignited the Revolutionary War (Westholme, 2016). In 2012 he completed a study of Gen. George Washington’s first campaign of the Revolutionary War, which included new findings about the commander-in-chief’s first successes and failures in espionage.

Bell maintains the Boston 1775 blog, which offers daily doses of history, analysis, and unabashed gossip about the start of the American Revolution in New England. He is also an associate editor of the Journal of the American Revolution and an assistant editor of the Colonial Comics anthologies (Fulcrum).

Keep up with all our Turn coverage here.