George Washington Spy Master and the Agent Who Didn’t Make it

General George Washington was a firm believer in the value of military intelligence.  He had to be.  He was constantly opposed by British forces superior in numbers, equipment and training.  Just keeping the rag-tag Continental Army out of the clutches of the superior force and somehow in the field required reliable knowledge of the Redcoats’ dispositions and movements.  Washington ran his own fairly sophisticated intelligence operation complete with cloak and dagger missions, secret codes and disappearing ink. 

During the dark days of the Battle of Long Island in September 1776, Washington dispatched a volunteer, 21 year old Captain Nathan Hale, to go behind the lines in civilian attire to gain critical information of British troop movements.  After the fall of New York Hale was discovered and condemned to as a spy on September 21, 1777.

Hale was born June 6, 1755 in Coventry, Connecticut to a respectable family.  At the age of 14 he entered Yale College, the epicenter of orthodoxy for members of the New England Standing Order (Congregationalists) uncomfortable with the growing liberalism at Harvard.  He graduated with honors in 1773 and took up teaching first in East Haddam and later in New London.

When the Revolution broke out Hale was elected a Lieutenant of the Connecticut Militia and served with them at the Siege of Boston.  When the British withdrew from Boston, to Militia returned home, but Hale stayed and enlisted in the new regular Continental Army in the Connecticut Line.  In July 1776 he was promoted to Captain and commanded a small unit in Col. Thomas Knowlton’s Rangers assigned to the defense of New York.  He drew command attention by leading a party that captured a much needed cargo of arms, shot, and shell from a British ship at moor.

It was undoubtedly that act of daring-do that led Washington to ask him to slip behind lines in mufti.  The night of September 12 Hale was ferried across the East River from Long Island to a point in Manhattan above the city to which he made his way on foot.  On September 15 the City fell to the British and Washington’s army was forced to retreat to Harlem Heights.  On September 19 about a quarter of the city was burned in a fire that may or may not have been set by American agents.  The fire “flushed” several patriots in the city, including Hale.

By some accounts he was lured into making incriminating statements by the famous Major Robert Rogers of the Queen’s Rangers (Roger’s Rangers) who encountered Hale in a Tavern.  Other evidence suggests that he was turned in by a Loyalist relative.  Perhaps both stories are true. 

At any rate, Hale was arrested near Flushing Bay, in Queens as he attempted to flee.  On September 21 he was brought before the British Commander General William Howe at his headquarters in rural Manhattan and closely questioned.  Damming documents were found on his person.  As a spy he was condemned to death without court martial.  He was held overnight in a greenhouse and denied the comforts of both a Bible and clergy.

The next morning Hale was marched along the Post Road to the Park of Artillery next to the Dove Tavern.  A rope was tied around his neck and thrown over a sturdy tree limb.  Hale was allowed to make a final statement, which witnesses unanimously report was both dignified and brave.  He was then hoisted off of his feet and left to slowly strangle.

After Hale’s death Captain John Montresor, a British engineering officer, sent his last letter to his family and an account of the execution, which moved the Captain greatly, under a white flag across the lines where they were received by Captain William Hull.  In the letter Montresor recounted Hale’s last words as “I only regret that I have but one life to lose for my country.”  Another account, published in 1781 rendered the words, “I am so satisfied with the cause in which I have engaged that my only regret is that I have not more lives than one to offer in its service.”  Other accounts suggest similar sentiments.  But no one will likely ever know the exact words.

Hull’s publication of Monresor’s account led to Hale’s position in the growing mythology of the American Revolution in the early 19th Century.  Poems and songs were written about his sacrifice.  And two notable standing statues commemorate the event—by Frederick William MacMonnies, erected in 1890 at New York’s City Hall Park and by Bela Lyon Pratt at Yale with copies at the Phillips Academy in Andover, Massachusetts; the Nathan Hale Homestead in Coventry; the Connecticut Governor's Mansion in Hartford; Fort Nathan Hale in New Haven, the Department of Justice in Washington, D.C.; Tribune Tower in Chicago; and at Central Intelligence Agency Headquarters in Langley, Virginia.