After Nathan Hale’s execution and other failed missions, George Washington needed reliable intelligence from British-occupied New York. Benjamin Tallmadge built the Culper Ring around trusted civilians, starting with his childhood friend Abraham Woodhull, a farmer from Setauket, Long Island, who took the alias Samuel Culper.

This episode covers the ring’s courier chain from Austin Roe’s dead drops to Caleb Brewster’s whaleboats across Long Island Sound, Anna Strong’s clothesline signals, and the dangerous raid that injured Woodhull’s father. We also look at Robert Townsend, known as Culper Junior, the codebooks and invisible ink, and the intelligence that helped uncover Benedict Arnold’s plot to hand over West Point.

• Why embedded civilians worked better than soldiers sent on one-time missions
• How a black petticoat and white handkerchiefs coordinated secret pickups
• Tallmadge’s number codebook and the sympathetic stain invisible ink
• Agent 355, Hercules Mulligan, and Cato’s role in stopping a plot against Washington
• How the ring exposed British counterfeiting plans and why Townsend’s identity stayed hidden until 1929