Tallmadge
Nathan Hale and Tallmadge were close friends at Yale, and Tallmadge's entry into the secret world was not accidental, nor did it begin with the Culper Ring in 1778. As early as 1777, Tallmadge acted as the operative John Clark's contact in Connecticut when Clark was based on Long Island. Before that, he worked for the spymaster Nathaniel Sackett, who was later fired.
Read more about this topic: Culper Ring