Before he ran George Washington’s secret intelligence network, Benjamin Tallmadge was a Yale graduate and close friend of Nathan Hale who served as superintendent of a high school in Wethersfield, Connecticut. This episode follows his unlikely leap from the classroom to the Continental Light Dragoons and into the shadow world of Revolutionary War espionage.

We break down how Tallmadge built the Culper Ring with dead drops, numeric codes, invisible ink, and a compartmentalized courier chain across Long Island Sound, his role in exposing Benedict Arnold’s treason after the capture of Major John Andre, and his daring 1780 raid that burned 300 tons of British hay. Then we trace his second life as a banker, postmaster, and congressman.

• How Nathan Hale’s failed mission shaped Tallmadge’s approach to spycraft
• The tradecraft of the Culper Ring and its route from Manhattan to Connecticut
• How Tallmadge suspected Benedict Arnold when others followed the chain of command
• Why destroying 300 tons of hay crippled British mobility before winter
• Tallmadge’s legacy, from Congress to Tallmadge Hall at Fort Huachuca, home of Army intelligence