Nathan Hale was born in Coventry, Connecticut, and educated at Yale. He volunteered for service at the outbreak of the War of Independence, participated in the siege of Boston and was promoted to the rank of captain.
Following the Continental Army`s ouster from Long Island, a pressing need was felt for information about British activities in New York City. In mid-September 1776, Hale volunteered to attempt to secure that intelligence.
Poor planning almost guaranteed the mission`s failure from the beginning. Hale was to act alone rather than as one of several spies dispatched for the same purpose; a multiple effort would have helped to ensure that some member of the team would return to headquarters with the desired intelligence. Further, Hale was handicapped by the absence of Patriot contacts in the city, the failure to plan an effective avenue of escape and by the total lack of reliable communication channels with the American army.