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America’s journey to independence was significantly aided by the Culper spy ring. This group consisted of a few dedicated Long Island patriots, who played a crucial role in preventing multiple assassination attempts on George Washington.
One of the group’s members, a childhood friend of the North Shore participants, managed to uncover Benedict Arnold’s betrayal by infiltrating British leadership during a time when Long Island was largely under British control.
“British officers believed Washington wasn’t just better than them; he truly was,” commented Brian Kilmeade, a Fox News host and author of “George Washington’s Secret 6: The Spy Ring That Saved the American Revolution.” He added, “If you ask the CIA today, they’ll probably agree.”
Kilmeade emphasized that Washington, having commanded British troops during the French and Indian War, recognized the immense value of intelligence and insisted that his agencies outsmart the British.
Despite the challenges, the swift capture of colonial spy Nathan Hale in 1776 highlighted the dangers of deploying moles in enemy territory, although at least one spy managed to deliver valuable intelligence.
America’s early leaders relied on trusted officers to build a secret network. Benjamin Tallmadge, from Setauket, was instrumental as part of an elite unit known as the 2nd Light Dragoon Regiment.
His area was filled with British forces prepared to imprison or harm anyone leaning towards independence. Experts suggest that Tallmadge often had to decline numerous eager recruits to protect himself, only accepting those few childhood friends he could trust absolutely.
According to Kimberly Fife, community engagement manager at the Three Villages Historical Society and Museum in Setauket, those involved were not trained soldiers but rather ordinary civilians—farmers, housewives—who felt it was their patriotic obligation to contribute to the fight for freedom. The museum dedicated to this spy ring is located in the home of Abraham Woodhull, another member.
In addition to Woodhull, Tallmadge enlisted locals like Anna Smith-Strong, Caleb Brewster, Austin Law, and Robert Townsend from nearby Oyster Bay. There’s also a mysterious figure known only as “Lady,” whose identity remains lost to time.
Fife speculates that “Lady” could refer to multiple individuals, given the scant references in historical documents.
She noted that these spies managed to gather intelligence that disrupted at least four British plans to assassinate Washington, some of which involved individuals close to her own circle.
Tallmadge also discovered that the traitor Arnold had schemed to weaken West Point’s defenses in 1780 to facilitate its sale to British Major John Andre.
“The goal was to capture General Washington at West Point, but thankfully, the Culper spy ring prevented that,” Fife remarked.
For years, Washington’s spies effectively operated within the British-held regions of Long Island and New York against King George III’s forces.
Smith-Strong, for example, would communicate with Brewster by signaling through the color of her laundry.
Reportedly, Townsend aimed to write for a Loyalist publication, casually conversing with British soldiers who visited his store in Manhattan, effectively extracting military secrets.
Experts indicate that information was exchanged using dead drops, coded messages, and letters addressed to fictitious figures like Samuel Culper and Samuel Culper Jr., the cover names for Woodhull and Townsend.
Kilmeade noted that they even utilized invisible ink within their communications, ensuring a robust system of protection for the spy network if one of its members was compromised.
The Culpers also played a role in foiling a British plan to undermine the colonial economy with counterfeit currency and in facilitating the safe arrival of French troops in Newport, Rhode Island.
“The British were aware of the French troops’ arrival, and the spy ring gathered crucial information,” Kilmeade shared.
“They orchestrated a fake invasion of New York to keep British troops occupied and safeguard New York from an invasion that ultimately didn’t occur.”
Interestingly, Townsend remained anonymous even from Washington for hundreds of years until his role was unveiled in the 1930s when historian Morton Pennypacker examined documents from his family’s residence in Oyster Bay.
New discoveries about the Culper family have surfaced recently, including letters found on Long Island in 2019 and 2020.
One letter was discovered by someone stuck in a chimney during renovations in Port Jefferson, near Setauket.
Fife’s museum offers walking and kayaking tours of the Setauket waterfront, which was used by the spy ring and was integral to many significant battles in the area.
“People might still have old letters stowed away in attics or basements,” she noted. “They might not even realize the treasures of family history they have.”
One thing remains clear: the ring’s bravery in the face of danger is undeniably part of our history. Kilmeade summed it up well: “The Founding Fathers, especially Washington, would surely say, ‘I wouldn’t be here without these individuals.’”
“Long Island should never have fallen under British occupation,” he concluded.
