The Spy Ring’s Methodology: Scouting Missions vs Embedded Spies
From early on, there was a difference of opinions between general Charles Scott, whom Washington had appointed to oversee intelligence gathering, and his subordinate, major Benjamin Tallmadge, who actually ran day to day operations. Scott believed in sending scouts in single shot missions, sneaking across enemy lines into British held territory to gather information and return with their findings.
Tallmadge thought that was inefficient and too risky, as illustrated by the fate of lieutenant Nathan Hale, who had been caught and hanged as a spy without accomplishing anything. Instead, Tallmadge wanted to recruit spies who were already living behind lines, who would not arouse suspicion by their mere presence. Those spies would remain embedded in place, and rather than risk sneaking back and forth across enemy lines, transmit their information to base via secure lines of communications, such as couriers experienced in slipping through the lines.
In September of 1778, Scott’s methodology led to the capture of 3 out of 5 spies sent on missions to New York City, and that convinced Washington to give Tallmadge’s methodology a try. In late October, Scott was pushed out and made to resign his position as head of intelligence, and Tallmadge was appointed in his place as chief spymaster.
Tallmadge abandoned Scott’s strategy of dispatching scouts into enemy territory, and he and Abraham Woodhull set up a network of embedded agents, operating from their homes in New York City, Long Island, and Connecticut. They collected intelligence, then waited for couriers to collect what they had gathered and deliver it to the Patriots. The contrast between the effectiveness of Scott’s and Tallmadge’s methodologies was stark: while numerous scouts had been captured during Scott’s single shot missions, not a single one of Tallmadge’s embedded spies was captured during the war.